squaredawayv2

I Can Do It With a Broken Heart

Wed, 01 Apr 2026 20:50:20 GMT

Frequently Asked Questions About Leadership During Hard Times

I Can Do It With a Broken Heart

By Jordan Streetman Cole - Chief Experience Officer at Squared Away

Cue the Taylor Swift song…

Leadership is often portrayed as steady and unshakeable. If you’ve ever met me, you are well aware my leadership philosophy is a little more… complex than that.

For my entire career, “people” have been my life: sales, relationship management, managing teams, learning from clients, taking feedback (on the chin, mostly), the list goes on.

I remember during COVID, incoming clients were tearfully overwhelmed trying to run businesses and keep them afloat. Many also had children they suddenly had to manage when it came to remote learning. To call it overwhelming is, honestly, an underwhelming statement.

All that to be said, sometimes leaders are quietly living through the most destabilizing moments of their lives. And your job title or status quickly loses its luster when you’re sitting in very real life moments.

For me, it was divorce.

Fifteen years in the rearview and my future waiting for me, all played out perfectly in my own vision: a house in Charleston, a family, more travel, simple nights at home, continued family holiday schedules that were already a routine, evenings sitting on the dock together, growing old. All of it wrapped up in a perfect bow with the person who made me feel safe and at home no matter the circumstances or challenges we came across.

Then…everything in my existence that felt stable completely crumbled, like a California earthquake.

There is something surreal about leading meetings, making decisions, and supporting your team and company while your personal world feels like it’s collapsing. One second you are in tears, and the next you’re wiping them away before a Zoom call and talking about metrics and strategy.

The truth is: leadership doesn’t pause for heartbreak . But that doesn’t mean you have to pretend.

So, with a large exhale just recapping my own painful moments, here are the things that helped me lead through one of the hardest seasons of my life.

Don’t Drown Yourself in Work

Work harder. Stay busy. Keep moving.

I’m going to be extremely direct…

That’s avoidance, not productivity, and people in your orbit will notice it.

There is a quote from Tyler Perry that sat in my head for a while, thanks to my social media algorithm: “All grief does is wait for you to finish.”

Whether that be the task, the distraction, the busy schedule, or focusing only on the kids, it will still be there if you don’t tackle it head-on. And if you don’t tackle it, you’re asking for exhaustion, burnout, and eventually feeling like a shell of yourself.

Work can be grounding. It was for me. It was my only steady space in that moment. But I was not the leader I needed to be unless I allowed myself to also sit in the moment I was in.

Let Your Team See the Human Moment

I learned in this season that my team can do more than I gave them credit for, especially once they knew what was happening.

They stepped up, made decisions, leaned on one another, and didn’t ask questions when I said, “I’m unavailable for the next two hours or the rest of the day.”

I’m not expecting this is everyone’s situation, but personally, my team does have more transparent communication about personal situations than most. I thank the military for that trait because, at any given time, you are forced to adjust and shift your plans in your personal world, and that does bleed into work without ego or embarrassment. It just is what it is.

Even a small bit of transparency does two important things.

First, it allows your team to step in where needed. Good teams know how to step in and handle things, they just need your trust to do so.

Second, and most importantly, it’s showing, not just telling. When leaders acknowledge their limits and boundaries during hard seasons, it creates space for your team to do the same when their own storms arrive.

Because eventually, they will.

Get Outside Within the First 20 Minutes of Waking Up

This became one of the most stabilizing habits in the moments when I almost couldn’t get out of bed.

Before emails.
Before Slack.
Before social media.
Before the world wakes up.

Step outside.

For me, I walked the dog, journaled, or sometimes just sat on the porch with a Diet Coke (IYKYK) and just felt the morning air on my face.

I’m not going to sugarcoat it, it wasn’t that simple. At first, it was forced.

Letting the quiet exist before the day starts helped reset my nervous system and gave me mental clarity. Was it effective every day? No. But being consistent about it gave me control over something that felt good for my soul.

However you want to take this, please do yourself a favor and protect one non-work ritual for yourself.

Don’t Disrupt the Team’s Flow Because Your World Shifted

If you need to step back to handle something personal, do it!

Whether you want to see it as a priority or not, the reality is that some conversations or situations outside of work demand your full attention and are equally important.

Take the call with the lawyer.
Handle the logistics on the sale of the house.
Sit with the emotion if you need to.

This was a hard lesson.

When you’re on what feels like the 100th call with a lawyer and then jump right back into work, it can feel completely unproductive. While you’re trying to re-engage and be helpful, your team has to stop what they’re doing to update you, even though they’re already ten steps ahead.

If you have a team you trust, trust that they are in their rhythm and will communicate with you when needed.

Otherwise, you’re creating more chaos than support.

So I started asking myself a simple question:

Am I helping right now, or am I reacting?

If I wasn’t in the right headspace to add value, it was better to take the extra time to regroup. Leadership isn’t about being present every second. It’s about being effective when you are.

Leadership doesn’t require isolation. Allow yourself to lower the bar for “perfection” and aim for being consistent rather than flawless.

Two things can be true at once: you can walk through grief, or navigate a season that is simply too overwhelming, and you can still be a good leader and show up for the people who rely on you.

You can do it with a broken heart.

Why Military Spouses Are the Most Underestimated Remote Workforce in America

Thu, 12 Mar 2026 16:02:17 GMT

Frequently Asked Questions About Military Spouse Employment

Why Military Spouses Are the Most Underestimated Remote Workforce in America

By Jessica Ryan - Chief People Officer at Squared Away

There is a resume sitting in someone’s inbox right now that doesn’t tell the whole story.

It shows gaps. Location changes. Job titles that don’t connect in an obvious way. Maybe some retail. Maybe some childcare. Maybe nothing for a year or two.

And somewhere, a hiring manager is moving on to the next candidate.

What that resume doesn’t show is this: the person who submitted it has built a life from scratch in places they didn’t choose, managed a household alone for months at a time, and figured out how to thrive inside a system designed around someone else’s schedule.

That’s not a liability. That’s exactly the kind of person you want on your team.

What a Military Spouse Resume Actually Reflects

Military spouses don’t have gaps in their experience. They have gaps in their geography.

Most military bases aren’t located in thriving job markets. They’re in places where the local economy runs on retail, fast food, and base support jobs. It’s not a lack of ambition that shapes that resume. It’s a zip code they didn’t choose.

And the myth that they’ll leave in two years? Consider this instead: you get someone who will train their replacement, build something real in the time they have, and if you’re smart enough to offer flexibility, they can do that job from anywhere. Almost everything can be done remotely now.

What Military Spouses Bring That Nobody Talks About

They are exceptional at change. Not just tolerant of it, skilled at it. They have built homes in places they’d never heard of, learned new systems with no manual, and figured out how to create stability inside constant instability. That’s not soft skills. That’s operational excellence.

They bring world experience. Many have lived across the country and internationally. They’ve worked alongside people from different branches, different cultures, and different backgrounds. That perspective walks in the door with them on day one.

They are chaos coordinators. When a spouse gets deployment orders with two days' notice, a military spouse reorganizes an entire life without missing a beat. Imagine what they can do with a project timeline and a real support system.

Their spouse’s deployment doesn’t make them less committed to your company. It makes them more practiced at doing hard things without a safety net.

And when you take a chance on them? They don’t forget it. Military spouses know what it feels like to be overlooked. When an employer sees them, really sees them, they show up with everything they have.

What We’re Actually Asking For

We’re not asking for special treatment. We’re asking for a fair shot.

Look past the resume and ask about the person. Ask what they’ve navigated, what they’ve built, what they’ve figured out with limited resources in unfamiliar places. The answers will surprise you.

Offer flexibility where you can. Remote work isn’t a perk for military spouses; it’s the difference between a career and a series of restarts.

And understand this: when you hire a military spouse, you aren’t just changing their life, you’re changing their family’s. You’re giving a parent presence, income, and identity beyond their military spouse title. That investment comes back to you tenfold.

A Final Word

To the military spouse reading this: you are not your resume. You are not your zip code. You are not the gap years or the lateral moves or the jobs that didn’t match your actual capability. You are someone who has done extraordinary things in ordinary circumstances, and you deserve an employer who can see that.

To the employer reading this: that person is out there right now, waiting for someone to take a chance on them.

Be that person.

Professionalism Doesn’t Require an Office

Thu, 29 Jan 2026 16:03:49 GMT

Professionalism in Remote Work: Frequently Asked Questions

Professionalism Doesn’t Require an Office

By Jessica Ryan - Chief People Officer at Squared Away

For a long time, professionalism was measured by proximity.

Were you in the office?
At your desk by 9?

Did someone see you “working”?

Did you leave before 5 without telling someone?

Remote work disrupted that model, and not always in ways that felt comfortable.

At Squared Away, we’ve spent years building and scaling a fully remote team that supports demanding, high-trust clients. The kind of work where reliability, judgment, and discretion actually matter. Over time, one thing has become very clear:

Professionalism isn’t about where you work. It’s about how you show up.

The Myth That Professionalism Requires Oversight

There’s a common belief that without an office, professionalism starts to slip. That if no one is watching, standards slip. That hasn’t been our experience. If anything, remote work tends to expose professionalism rather than dilute it.

When there’s no physical oversight, people can’t rely on optics. They rely on follow-through. On communication. On judgment. On whether the work actually moves forward. Professionalism becomes a series of conscious choices, not performative behaviors. And it becomes obvious pretty quickly.

What Professionalism Looks Like in a Remote Environment

At Squared Away, professionalism isn’t vague. It’s not “do your best” or “just be flexible.” We’re clear about what it looks like in practice.

Clear, proactive communication
Not reactive. Not last-minute. Professional communication means anticipating questions, naming roadblocks early, and closing loops without being chased.

Judgment and discretion
Our clients trust us with sensitive information and evolving priorities. Professionalism means knowing what needs escalation, what can be handled independently, and when silence is more appropriate than noise.

Ownership over outcomes
Remote professionals don’t wait for instructions at every step. They manage timelines, deliverables, and follow-through because the work is theirs to own. They respect your time and everyone else’s. That ownership shows up in how people respect time, both their own and everyone else’s. In being prepared. In keeping commitments. In understanding that flexibility only works when responsibility is shared.

None of this requires an office. All of it requires clear expectations.

Why We Don’t Micromanage

At Squared Away, trust isn’t a perk. It’s a prerequisite. We don’t manage by monitoring activity or tracking hours just to prove someone is “working.” We manage by setting clear expectations, defining outcomes, and stepping in when things get complex.

That approach only works when professionalism is non-negotiable. Remote work gives people autonomy. Professionalism determines whether that autonomy works for the individual, the team, and the client.

Flexibility and Standards Aren’t Opposites

One of the most persistent misconceptions about remote work is that flexibility comes at the expense of standards. In reality, flexibility without standards creates anxiety. And standards without flexibility create burnout. Professionalism lives in the space between the two.

It’s what allows someone to step away when needed without work stalling. It’s what allows teams to collaborate across time zones without friction. And it’s what allows clients to trust that things are handled, even when they’re not watching closely.

The Real Test of Professionalism

The true test of professionalism isn’t how someone performs when everything is predictable, well-structured, and running smoothly. It’s how they show up when priorities shift mid-process.
When the information they’re working with is incomplete, when there’s no obvious answer, and when no one is checking their work in real time.

Remote environments don’t hide those moments. They bring them to the surface. When expectations are clear remote work doesn’t weaken performance; it strengthens it.

What We’ve Learned

What we’ve seen at Squared Away is that professionalism has very little to do with being in the same place every day. It comes from clear expectations, trust, and people doing what they say they’ll do.

Remote work isn’t a workaround for us, it’s how we work. And it works because we’re honest about what it requires. When expectations are clear, we’ve found that people don’t just meet the bar, they raise it.

7 Mistakes You're Making with Executive Assistant Services (and How Military Spouse VAs Fix Them)

Thu, 08 Jan 2026 15:07:38 GMT

Executive Assistant Services: Frequently Asked Questions

Let's get something straight: you're probably doing executive assistant services all wrong .

If you've been cycling through virtual assistants like they're seasonal employees, wondering why nothing sticks, or feeling like you're still drowning in administrative tasks despite having "help" – you're making at least three of these seven critical mistakes.

Here's the truth no one wants to say: most executive assistant services fail not because the assistants aren't capable, but because leaders don't know how to work with them. You're setting both yourself and your assistant up for failure before you even start.

But here's what's different about military spouse virtual assistants – and why companies like Squared Away are seeing dramatically different results for their clients.

Mistake #1: Writing Vague Job Descriptions (Like You're Hiring a Mind Reader)

You know you're guilty of this one. Your job posting probably said something like "I need someone to handle my calendar and emails" – and then you wonder why your new assistant can't anticipate your needs.

Vague expectations create chaos. When you don't clearly define what "calendar management" means to you specifically, you get someone who books meetings without considering your energy levels, travel time, or strategic priorities.

How military spouse VAs fix this: Military families move every 2-3 years. Military spouses have learned to quickly decode what people actually need versus what they say they need. They ask the right questions upfront because they understand that clarity prevents crises.

At Squared Away, our military spouse VAs go through a comprehensive discovery process that maps out not just your tasks, but your decision-making patterns, communication style, and business rhythms. They're trained to think strategically, not just administratively.

Mistake #2: Skipping Onboarding (Because "They Should Just Figure It Out")

Expecting an executive assistant to hit the ground running without proper onboarding is like expecting someone to run a marathon without warming up. Even the most experienced remote executive assistant needs context about your business, your priorities, and your way of working.

Most leaders give their new assistant access to their calendar and email, then wonder why nothing feels seamless after week one.

How military spouse VAs fix this: Military spouses are masters of rapid integration. They've had to quickly understand new bases, new communities, new systems, and new expectations dozens of times. But they also understand that proper preparation prevents poor performance .

Our onboarding process doesn't just cover what you do – it covers how you think, what drives your decisions, and what success looks like in your specific context. Military spouse VAs ask about your non-negotiables, your pet peeves, and your vision before they touch a single task.

Mistake #3: Micromanaging Everything (While Complaining You Don't Have Time)

If you're checking every email before it goes out and approving every calendar invite, you're not delegating – you're supervising. And you're wasting both your time and theirs.

This happens because you don't trust your assistant's judgment. But here's the thing: if you can't trust their judgment, you hired the wrong person.

How military spouse VAs fix this: Military spouses are used to making decisions when their spouse is deployed, unreachable, or in high-stakes situations. They develop exceptional judgment and ownership mentality out of necessity.

When you work with a military spouse VA through Squared Away, you're getting someone who understands that your business can't wait for your approval on routine decisions. They make smart choices and keep you informed, rather than keeping you involved in every detail.

Mistake #4: Communication That's All Over the Place

Your assistant is trying to track priorities through scattered WhatsApp messages, random emails, and those "quick calls" you schedule without warning. No wonder nothing feels organized.

Poor communication creates cascading problems. When your assistant doesn't understand which fires are urgent versus which ones can wait, everything becomes urgent. When priorities change without clear communication, your entire operation feels chaotic.

How military spouse VAs fix this: Military families live by systems and protocols. Clear communication isn't just nice-to-have – it's survival.

Military spouse VAs establish communication rhythms that work: structured check-ins, priority matrices, and systems for handling changing requirements. They've learned to over-communicate important information and under-communicate routine updates. They know the difference between keeping you informed and keeping you overwhelmed.

Mistake #5: Hiring Task-Doers Instead of Strategic Thinkers

You put together a list of administrative tasks and hired someone to execute them. But you forgot that good executive assistance requires strategic thinking, not just task completion .

Your assistant should understand the "why" behind your requests, anticipate your needs, and suggest improvements to your processes. If they're just checking items off a list, you're not getting executive-level support.

How military spouse VAs fix this: Military spouses don't just follow orders – they understand mission objectives. They've learned to think several steps ahead because military life requires contingency planning and strategic thinking.

When a military spouse VA manages your calendar, they're thinking about energy management, strategic relationship building, and business development opportunities. When they handle your email, they're protecting your attention and identifying patterns that could improve your operations.

They're not just executing your vision – they're helping you refine it.

Mistake #6: Delegation That's Either Too Much or Too Little

You either dump everything on your assistant and hope for the best, or you hold onto tasks that should have been delegated months ago. Both approaches fail.

Over-delegation without proper context leads to burnout and mistakes. Under-delegation means you're paying for executive assistant services while still handling routine work that should be off your plate.

How military spouse VAs fix this: Military spouses understand capacity management and gradual responsibility transfer. They've managed household operations, family logistics, and often their own careers while supporting a military member's demanding schedule.

Our team approach at Squared Away means your dedicated military spouse VA has an entire support system behind them. If your workload spikes, you have team bandwidth. If your assistant has an emergency, your operations don't stop. You get consistency and scalability.

Mistake #7: Using Basic Tools for Complex Operations

You're trying to run executive assistant services through email chains and basic calendar apps. That's like trying to run a restaurant with a microwave.

Effective executive support requires integrated systems: task management platforms, shared calendars, document collaboration tools, and communication systems that create accountability and visibility.

How military spouse VAs fix this: Military families are early adopters of technology that makes life manageable. Military spouses have used every productivity app, communication platform, and organizational system out there – because they have to.

At Squared Away, our military spouse VAs don't just use advanced tools – they help optimize your entire operational stack. They integrate AI where it makes sense, streamline workflows, and create systems that scale with your business growth.

The Squared Away Difference: It's Not Just About Military Spouses

Here's what makes our approach different: we don't just hire military spouses – we build them into high-performing teams with integrated AI support and proven systems .

Our military spouse virtual assistants bring unmatched reliability, strategic thinking, and adaptability. But they're supported by team resources, advanced technology, and processes refined through hundreds of client relationships.

When you work with virtual assistant services that understand these seven mistakes – and how to avoid them – everything changes. Your operations become predictable. Your time becomes protected. Your business becomes scalable.

The question isn't whether you need executive assistant services. The question is whether you're ready to do it right.

Ready to see how military spouse VAs can transform your operations? Schedule a consultation and let's fix what's been broken in your approach to executive support.

Because in 2026, you can't afford to keep making these same seven mistakes.

How CEOs and Business Leaders Can Prepare for 2026 Without Drowning in To-Dos

Mon, 22 Dec 2025 18:30:50 GMT

CEO Productivity and Strategic Delegation: Frequently Asked Questions

Let’s get something straight.

2026 is not going to magically be calmer.

If you are telling yourself, “Things will slow down after this quarter,” you are lying to yourself with confidence. Ask me how I know.

Every year, CEOs and business leaders say the same thing. “I just need to get through this season.” Then another season shows up. Louder. Faster. With more Slack pings and less margin.

And suddenly you are not leading. You are reacting. You are not planning. You are putting out fires with one hand while answering emails with the other.

That is not leadership. That is survival mode.

If you want 2026 to feel different, you cannot wait until January to fix what is broken right now.

The Firehose Problem No One Talks About

Most high performers do not fail because they are bad at their jobs.

They fail because they are doing too many of them.

CEO. Operator. Project manager. Executive assistant. Household logistics coordinator. Family calendar keeper. Human reminder app. Emotional support human.

That firehose feeling does not come from a lack of ambition. It comes from a lack of infrastructure.

And here is the spicy truth.

If you do not intentionally build support into your business and personal life, growth will punish you for it.

More revenue means more decisions.
More team means more communication.
More visibility means more obligations.

2026 will demand more of you, not less.

So let’s talk about how to prepare without losing your mind.

Step One: Audit Your Life Like a CEO

Before you plan goals, launches, or growth, audit where your time actually goes.

Not where you think it goes. Where it actually goes.

Ask yourself:

What decisions am I making repeatedly that someone else could own?
What tasks drain my energy but still need to get done?
What personal responsibilities are competing with my highest-value work?
What would break if I stepped away for two weeks?

If the answer is “everything,” congratulations. You have built a business that depends on your exhaustion.

That is not sustainable leadership.

Step Two: Separate Control From Competence

This is where most leaders get stuck.

You are not holding onto tasks because no one else can do them. You are holding onto them because you are used to being the fastest, the most informed, and the most capable.

But here is the plot twist.

Being good at something does not mean you should be the one doing it.

Your job in 2026 is not to be the best doer. It is to be the best decision-maker.

That requires delegation. Real delegation. Not dumping tasks and hoping for the best.

Step Three: Build Support Before You Desperately Need It

The worst time to hire support is when you are already underwater.

That is when leaders panic hire, under-delegate, and micromanage because everything feels urgent.

The best time to build support is before the chaos hits.

That means:

Creating systems that someone else can step into
Documenting how things actually get done
Offloading operational, administrative, and personal logistics that do not require your brain
Trusting capable professionals to execute without constant oversight

This is where the right support changes everything.

Not just any support. Strategic support.

At Squared Away, we work with CEOs, founders, and high-level leaders who are done being the bottleneck in their own lives.

We do not just help you get things done. We help you reclaim your focus so you can lead.

Step Four: Stop Treating Personal Life Support as a Luxury

This is my favorite hill to die on.

Your personal life is not separate from your leadership performance.

If your calendar is chaos, your inbox is exploding, your household logistics live in your head, and you are the default parent, planner, and problem-solver, it will bleed into your business.

You cannot out-work a lack of support at home.

The most successful leaders I know do not do everything themselves. They build ecosystems of support that allow them to show up fully at work and at home.

That is not indulgent. That is intelligent.

The 2026 Question You Should Be Asking Now

Here it is.

Do you want 2026 to feel like growth with clarity, or growth with burnout?

Because the difference is not motivation. It is preparation.

If you are tired of being in reactive mode, tired of drinking from the firehose, and tired of carrying everything alone, it might be time to do leadership differently.

Let’s Talk About Support That Actually Works

If you are a CEO, business leader, or high-performing professional who knows you need support but wants it done right, our team is ready.

We help leaders delegate with confidence, build systems that scale, and reclaim time without sacrificing standards.

Chat with our team at Squared Away and let’s make sure 2026 is the year you lead with clarity instead of chaos.

Because you were never meant to do this alone.

Remote Assistants In 2025: What’s Actually Working And Why Squared Away Still Leads The Pack

Fri, 21 Nov 2025 06:17:58 GMT

Remote Assistants in 2025: Frequently Asked Questions

If you’ve been anywhere near the business side of the internet in 2025, you’ve probably noticed two things.

Everyone is “optimizing their workflow”.
Everyone is also drowning in said workflow.

And that’s exactly why remote assistants are exploding right now. Not in a “cute little admin” way, but in a “this is the only thing keeping my company from spontaneously combusting” way.

Let’s break down what’s trending, what actually matters, and where Squared Away fits into the chaos.

AI Is Loud Right Now, But Human Support Is Still Doing The Heavy Lifting

AI is everywhere this year. Every platform has a new assistant, a new integration, a new “brain”, and honestly… most founders are still using it like a calculator with glitter on it.

But here’s the truth no one wants to say out loud:
AI does not replace a high performing remote assistant. It replaces the busywork , not the brainwork .

Squared Away assistants use AI the way it was meant to be used:
To automate the repetitive tasks, speed things up, and give you your time back… not run your entire business like a rogue robot.

Our military spouse assistants are trained to integrate AI into:

Inbox systems
Meeting recaps
Light project workflows
SOP updates
Content repurposing
CRM cleanup

But they still bring the judgment, intuition, context, and professionalism that AI simply cannot replicate.

Fractional Support Is No Longer “New” — It’s Essential

The remote market right now is wild . Only a tiny percentage of jobs are fully remote, and they get flooded with applications the second they go live. Meanwhile, businesses are trying to do more with fewer full time hires.

Enter fractional support.

Instead of hiring someone 40 hours a week to “sit around and be available”, founders are turning to flexible remote assistant models. Ten hours some months. Twenty hours the next. Scale up. Scale down. No HR paperwork-induced headaches.

This is literally what Squared Away was built for.

We match you with an assistant who knows your tools, your industry, and your vibe — and you only pay for the support you actually need.

Because no one needs a full time calendar manager. You need a problem solver.

Specialized Support Is Outperforming Generalists Everywhere

The days of hiring a “virtual assistant” to do everything from booking your dentist to running your sales funnel are gone. In 2025, companies are hiring specialists.

Think:

CRM and sales support (hello HubSpot)
Operations-minded assistants who keep projects moving
Content and social support who understand trends, tone, and timing
Client experience assistants who manage gifting, onboarding, and customer relationships

Squared Away assistants aren’t generalists. They’re seasoned military spouses with real-world backgrounds in operations, marketing, client success, logistics, and yes — the kind of time management that comes from moving across the world every two years with kids, dogs, and three boxes missing.

We match clients based on actual skill, not who has the lightest calendar that day.

Security And Trust Are Front And Center

With hybrid offices and distributed teams, companies are finally tightening their access, role permissions, and data systems. Good. They should.

But it also means you can’t hire someone off the internet and hope for the best. You need someone who understands responsibility, confidentiality, and professionalism on day one.

This is where Squared Away shines.

Our assistants are trained, vetted, and supported by internal systems that actually protect your business and your peace of mind.

Military spouses take confidentiality seriously. They have to. Their entire lives depend on it. That level of integrity is exactly why our clients trust them with the heart of their business.

Why Squared Away Continues To Be The Remote Assistant Partner For Founders In 2025

If you’re reading this, chances are your inbox is overflowing, your calendar looks like a game of Tetris, and you haven’t seen the bottom of your task list since 2021.

You don’t need more hacks.
You need a right-hand human.

Squared Away assistants help you:

Run your operations smoothly
Stay organized across time zones
Move faster with AI supported systems
Keep your clients wowed
Reduce decision fatigue
Protect your time and energy like it’s gold

And because our assistants are military spouses, you’re not just getting support — you’re making an impact that directly empowers an underserved community.

Your life gets easier. Their careers stay portable.

Everybody wins.

Ready To See What A Military Spouse Assistant Can Do For You?

If you want 2026 to feel less like survival mode and more like momentum, let’s talk.

Squared Away will match you with the perfect assistant for your needs, your tools, and your growth goals.

Because remote assistants aren’t the future.

They’re the right now.

And you deserve support that keeps up.

Cut Costs, Not Support: How to Stay Steady During a Government Shutdown

Wed, 29 Oct 2025 17:21:28 GMT

Staying Financially Steady During a Government Shutdown: Frequently Asked Questions

When the world seems out of control, leaders are required to make difficult decisions. I’ve seen it all - shutdowns, recessions, the pandemic, deployments - and I will say this with absolute confidence; There is no stability in cutting people. It comes from investing with more wisdom.

The government shutdown has had ripple effects across families, businesses and entire communities. Currently, every CEO and entrepreneur faces the same question-- where can I save money yet not at the cost of cutting off the lifelines that keep us alive?

Let me be clear. Your support team is NOT where you start.

Your People Are the Plan

At Squared Away, we have survived from the 2018 shutdown crisis to the COVID-19 upheaval and countless global curveballs that pushed companies to make a sudden pivot overnight. Our mission has been the same through each crisis: keep military spouses working, empowered, and engaged, all the while keeping our companies running smoothly.

And you know what has never failed us? Our people.

Most corporate teams can never dream of adaptation from military spouses. Cross country moves, last minute deployments, childcare mishaps and time zones have been handled all with the requisite level of professionalism on a daily basis. Hiring a military spouse assistant means you’re not just buying hours of service. You’re investing in resilience, loyalty and unparalleled problem solving.

The knee jerk reaction is to cut support when leaders start cutting budgets. But that’s not cutting costs. That’s cutting capacity.

Efficiency Is the New Luxury

Rather than scaling down your support, start right-sizing your operations. Delete devices that replicate capabilities. Revisit old software subscriptions. Automate what can be automated. Streamline your workflows.

And that’s the real definition of cost cutting. So it's not about losing your team. You give them power to do more with less friction.

Our Squared Away assistants assist business owners and other executives in identifying those efficiency gaps on a daily basis. From HubSpot automation and inbox management to financial tracking and client correspondence, we help every hour you invest in support see results that can be measured.

It’s not just about delegation. It’s about optimization.

Survival Mode is Not a Strategy

Here’s a fact that many leaders don’t like to admit: When the world seems uncertain, we hold tighter. Every email. Every calendar invite. Every tiny task.

That “I’ll just do it myself” way of thinking feels safer, but it is the quickest road to burnout and bottlenecks.

Delegation isn’t a luxury for the safe-to-be reserved times. It’s your lifeline in a fog of chaos.

And when you delegate well, you set your brain to looking at the whole. Instead of getting lost in spreadsheets, you work with strategy. You lead from the perspective of clarity.

Don’trun into weariness when your support team understands adaptability like our military spouses do. Then your business doesn't simply outlast unpredictables as soon as they happen. It evolves through them.

We’ve Been Here Before and We’ll Be Here Again

When COVID-19 got in the way, whole industries ground to a halt. Companies rushed to pivot remote. Leaders panicked.

And yet Squared Away didn’t merely survive. We grew. Because business acknowledged that support wasn’t a “nice to have.” It was the only thing keeping them alive.

And our customers were leaning on their assistants, not distancing themselves from them, and they ended up stronger and leaner and more efficient.

Now, under the new uncertainty of the current government shutdown, the lesson is still here. The answer is not to cut support. It’s to double down on the people who help you make it through.

When It Matters Most, Stand Together

Government shutdowns strike our community differently. And for military families, it’s not just politics. It’s paychecks, stability, and survival.

Which is why at Squared Away, it matters. When businesses continue to hire military spouses in tough times, they’re doing more than keeping their productivity intact. They are directly supporting a family that might be dealing with that same uncertainty at home.

You’re not simply hiring a virtual assistant. You are fueling economic stability for military families who have engineered entire careers based on adaptability, loyalty and excellence, no matter what’s happening in the world.

The Bottom Line

Cut the noise. Cut the waste. Remove everything that isn’t creating value.

But never remove the humans who make your business possible.

When you protect your people, they protect your mission.

If there’s one thing we’ve seen with Squared Away, from shutdowns and pandemics, through recovery from them, it’s that once you invest in your people, your business doesn’t just survive the storm. It leads through it.

Krista Knuffke: Redefining Resilience Through Reinvention

Tue, 14 Oct 2025 17:13:03 GMT

Source:

https://www.podbean.com/media/share/pb-djyii-1992d9a

In this episode of Beyond Orders, Michelle sits down with Krista Knuffke, proud Army spouse, mom of two, and Director of Client Success at Squared Away. Krista’s journey from healthcare to operations leadership is one defined by adaptability, grit, and purpose. Together, they explore what reinvention really looks like for military spouses navigating constant change: balancing family, career, and identity while creating impact in every chapter.

From managing moves and motherhood to leading sales and client onboarding, Krista shares how she’s built a life and career that thrives beyond the boundaries of traditional work.

Tune in for an honest, uplifting conversation about growth, service, and the strength it takes to start over, again and again.

How to Support Military Families During a Government Shutdown

Wed, 08 Oct 2025 11:51:35 GMT

Government Shutdowns and Military Families: Frequently Asked Questions

When the government shuts down, the headlines talk about politics. What they don’t talk about are the families sitting at kitchen tables across military housing neighborhoods, doing math that doesn’t add up.

I’ve lived this life. My husband’s paycheck, the one we depend on for groceries, rent, and everything in between, is suddenly paused because Congress can’t agree. And like so many military spouses, I’ve stared at the calendar wondering how we’re supposed to cover the gap between duty and dollars.

But here’s the thing about military families: we don’t stop showing up.

We still make school drop-offs, prep deployment care packages, and run the household solo while our partners serve. We do it with quiet strength, but that doesn’t mean we don’t feel the strain.

So let’s talk about what a government shutdown really means for military families and how you can help.

What Happens When the Government Shuts Down

A government shutdown means federal funding lapses, and while active-duty military members are required to report for duty, their pay can be delayed. Civilian employees working on base or in support roles may be furloughed.

For many families, that can mean missed rent payments, late bills, or even choosing between gas and groceries.

And because military families often move every few years, many don’t have local support networks or a second steady income to rely on. The stress compounds fast.

How You Can Help Military Families

If you’re wondering how to make a real impact, here are a few ways:

Donate to relief fund s – Organizations like the Armed Services YMCA and Operation Homefront provide emergency financial assistance to families impacted by pay delays.
Support military spouse–owned businesses – Many spouses, like those in our Squared Away community, run businesses or freelance to keep their families afloat. Every purchase from them goes directly toward stability and independence.
Advocate for consistent military pay – Call your representatives. Remind them that military families shouldn’t be political collateral. Our service members deserve better than uncertainty.
Offer community help – If you live near a base, small gestures matter. Offer childcare swaps, share meals, or simply check in on your neighbors. Connection is often the greatest relief.

Where Squared Away Fits In

At Squared Away, our mission has always been rooted in this truth: military spouses deserve stability, opportunity, and respect.

We’ve built a company that hires, trains, and champions military spouses, not as charity, but as exceptional professionals who thrive in chaos and lead with resilience.

When shutdowns hit, our assistants don’t lose income. They keep their clients’ businesses running, they keep serving, and they keep proving that flexibility is power.

Every client who hires through Squared Away isn’t just getting a world-class assistant. They’re investing in a family’s peace of mind when the world feels uncertain.

Final Thoughts

Government shutdowns remind us of something we already know too well: systems can fail, but communities can’t.

If you’ve ever said “thank you for your service,” this is your chance to show it by supporting the families behind the uniform.

Whether that’s donating, hiring through Squared Away, or simply sharing this message, your action matters. Because when paychecks pause, military families keep serving. And we’ll keep standing behind them.

Lauren Cecora: Faith, Family, and the Postpartum Journey

Tue, 30 Sep 2025 11:15:55 GMT

Source:

https://www.podbean.com/media/share/pb-yp2fn-197d435

In this episode of Beyond Orders, I sit down with Lauren Cecora - a 16-year Air Force spouse, devoted mom of two daughters, homeschool parent, and author of Past-Partum. Lauren opens up about the challenges and triumphs of military family life, from navigating deployments to preparing for her husband’s upcoming retirement after nearly two decades of service.

We dive into her journey through postpartum struggles and how sharing her story in Past-Partum became a lifeline of hope for other mothers. Lauren also shares how faith has grounded her family, why homeschooling has been such a powerful choice for her daughters, and how embracing the 1000 Hours Outside movement has transformed the way her family connects with nature, each other, and themselves.

Lauren’s story is one of reinvention, courage, and intentional living and it’s a reminder that even in seasons of uncertainty, we can choose resilience and purpose.

Why AI Will Never Replace Virtual Assistants: The Human Nuances That Tech Can’t Touch

Fri, 12 Sep 2025 10:55:38 GMT

AI and Virtual Assistants: Frequently Asked Questions

Everywhere I turn, I hear the same question: “Won’t AI tools like ChatGPT replace virtual assistants?”

As the CEO of Squared Away , where we employ over 1,600 military spouse virtual assistants worldwide, I’ve had a front-row seat to how both technology and human talent are transforming the way leaders get support. And here’s the truth: AI will never replace great virtual assistants.

Why? Because while AI can generate information, only humans can build trust, adapt in real time, and make things happen when it counts.

1. Conversations Require Human Connection

ChatGPT and other AI platforms can generate scripts or templates in seconds. But what they can’t do is read the tone of someone’s voice on the phone, pause when emotions run high, or offer empathy in the middle of a stressful conversation.

Virtual assistants aren’t just task-doers. They’re communicators. They pick up on nuance, adjust their approach, and bring warmth to conversations that no bot can replicate. For example, when a frustrated client calls, AI can suggest what to say. A VA listens, empathizes, and builds a stronger relationship in the process.

2. Reading Between the Lines

AI follows rules. Humans read people.

A leader might say, “I need help with scheduling,” but a great VA hears the stress behind it and asks, “What’s really taking up your time?” That ability to read between the lines is how virtual assistants uncover deeper needs and provide proactive solutions.

AI can answer what is asked. A VA anticipates what’s not being said. That’s the kind of nuance that drives true value in business.

3. Negotiation and Deal-Making

Here’s where AI completely falls short: making deals happen.

AI can draft an email to a vendor. But it can’t negotiate with a staff member at the Grand Canyon to bring a wheelchair curbside for someone who otherwise couldn’t access the park. That takes empathy, persuasion, and the human ability to connect.

AI can’t convince a French event team to dump 100 pounds of ice into a rented dinghy floating in the south of France because a marketing event required it. That takes hustle, creativity, and the willingness to push boundaries politely but firmly until the job gets done.

Whether it’s rearranging a last-minute flight, securing a venue against all odds, or solving problems no one thought had a solution; deal-making requires persuasion, grit, and imagination . No algorithm can replicate that kind of human ingenuity.

4. AI + Virtual Assistants = The Future of Work

Let me be clear: I am not anti-AI. At Squared Away, our assistants use ChatGPT and other platforms every day. They use it to speed up research, create first drafts, or automate repetitive tasks.

But here’s the key: AI doesn’t replace them, it empowers them.

By letting AI handle the time-consuming, data-heavy work, our assistants have more capacity to do what only humans can do: build trust, solve problems creatively, and strengthen relationships.

Leaders don’t hire assistants because they need more data. They hire them because they need partners who can bring order to chaos, anticipate needs, and adapt when things don’t go as planned.

5. Why Human Nuance Will Always Matter

The business world moves fast, but leadership is still built on people. Clients want to feel heard. Teams want to feel supported. Decisions often require emotional intelligence, not just information.

That’s where virtual assistants shine. They embody resilience, adaptability, and empathy - especially our military spouse assistants, who know better than anyone how to navigate change, handle challenges, and get things done no matter the circumstances.

The Bottom Line

The future isn’t AI or humans. It’s AI with humans.

AI can make us faster. It can give us shortcuts. But it will never replace the value of human nuance; the conversations, the relationship-building, and the deal-making that keep businesses moving forward.

At Squared Away, we’re excited about AI because it gives our virtual assistants more leverage. But the heart of what we do, creating partnerships that last and helping leaders thrive, will always come down to people.

Because no matter how smart AI gets, it can’t pick up the phone, calm someone down, or convince a company to ice down a dinghy in the south of France. Only humans can do that.

�� Curious how a virtual assistant could support your business while leveraging AI the right way? Let’s chat.

Kerissa Frigo: Veteran Strength Meets Military Spouse Resilience

Fri, 05 Sep 2025 13:44:31 GMT

Source:

https://www.podbean.com/media/share/pb-xe5kz-1956cae

In this episode of Beyond Orders, we sit down with Kerissa Frigo. Veteran, military spouse, mom of two energetic boys, and now an Executive Assistant with Squared Away.

Kerissa shares her journey from serving five years in the Air National Guard to navigating a decade of marriage through the highs and lows of military life. She opens up about raising a child with Williams Syndrome and how that experience has reshaped her outlook on resilience, adaptability, and purpose.

Today, Kerissa brings that same strength and perspective into her role supporting leaders at Squared Away, where she helps them stay focused, organized, and ready for whatever mission comes next.

This conversation is about more than career shifts; it’s about how the challenges of service, parenting, and perseverance equip us with the skills to lead and support others in powerful ways.

Tune in to hear Kerissa’s inspiring story and discover the lessons she carries from the Air National Guard to the homefront to the clients she serves today.

Danielle Hillebrand: Piercing Through Challenges and Building Identity Beyond Orders

Mon, 25 Aug 2025 15:32:56 GMT

Source:

https://www.podbean.com/media/share/pb-haxs4-194371f

In this episode of Beyond Orders, we sit down with Danielle Hillebrand, a professional body piercer with 17 years of experience and a proud military spouse of 8 years. Danielle’s story is one of resilience, reinvention, and the relentless pursuit of identity in the face of constant transition.

Each PCS move has brought new challenges, but also new opportunities. Danielle has successfully restarted her studio, Elegant Edge, four times in four different states — proving that dedication and creativity can keep both passion and career alive no matter where military life leads. Through every relocation, Danielle has rebuilt her clientele, reestablished her business, and continued to grow her craft.

As a mom of two young kids and a business owner, Danielle balances the demands of family, entrepreneurship, and military life with grit and grace. She shares candidly about the sacrifices, lessons, and strategies that allow her to maintain peace, protect her sense of self, and continue thriving in a career she loves.

Listeners will walk away with insights on:

Navigating career reinvention through PCS moves and military life
The challenges and rewards of running a business while raising young kids
Why identity and purpose outside of the military structure are vital for spouses
How to lean into passion and perseverance to create a life that works anywhere
The resilience it takes to start over, again and again, without losing momentum

Danielle’s journey is a testament to the fact that military spouses don’t just adapt, they innovate, rebuild, and thrive. This conversation will leave you motivated to hold on to what makes you you, even in the most unpredictable seasons of life.

August 10, 2015 — The Day Everything Fell Apart

Sat, 16 Aug 2025 14:33:46 GMT

August 10, 2015, is etched into my memory. Not as a gentle turning point, but as a gut punch that knocked the wind out of me.

At the time, I was working as a manager & virtual assistant for Zirtual. My husband was deployed. I was three months pregnant. And I was in Hilton Head, finally taking a little break with my family and brand new baby niece. Life felt…steady. Predictable. Safe.

Then, at 8 a.m. on a Monday morning, I tried logging in to my work accounts. Locked out. I thought it was just a glitch. But then an email landed in my inbox from the CEO: Zirtual was shutting down. Effective immediately.

https://www.businessinsider.com/zirtual-suddenly-laid-off-400-employees-via-email-2015-8?utm_source=squaredaway.beehiiv.com&utm_medium=newsletter&utm_campaign=august-10-2015-the-day-everything-fell-apart

No warning. No severance. No “here’s how we can help you transition.” Just…done.

I remember staring at my laptop, my heart racing, thinking, How am I going to tell my clients? How am I going to pay my bills ? My phone started buzzing from clients, teammates, friends — all asking the same question: What happens now?

One of those clients was Daniel Houghton , at the time I was his right hand and remote sidekick. I called him in full-blown, hormonal hysterics; ugly crying, snotty voice, the whole thing. I blurted out that I had no idea what was going to happen next. And instead of panicking, he calmly said, “I’m not going anywhere.”

That moment changed me.

I grabbed my car keys, drove to the closest Best Buy, and bought a laptop with money I really didn’t have to spare. By mid-afternoon, I was on the phone with my other clients one by one, bracing for the worst. But every single one of them said the same thing: “We’re staying with you.”

Zirtual’s collapse wasn’t a small stumble, it was a total freefall. The company had scaled too fast, spent too much, and when the money ran out, the people were left to pick up the pieces. I was one of those people. Pregnant. Military spouse. Far from family. With a career that just evaporated overnight.

And yet, in that wreckage, something unexpected began. Without even fully realizing it, I started building the systems, values, and relationships that would one day become the basis for Squared Away .

It didn’t happen overnight. It took almost two years post-Zirtual before Squared Away officially took shape. By then, I was thriving as a mom, with my clients, and had a rhythm I had worked hard to create after moving to Hawaii. Then my now-co-founder, Shane Mac , came to me with a challenge: “I need you to help me scale.” That was the push.

In July 2017, we soft-launched Squared Away. Not as a desperate rebound from a collapse, but as a deliberate, people-first business built on everything I had learned since that August morning.

The lessons from 2015 became our foundation:

Communicate openly, even when the news isn’t pretty.
Build relationships that can weather any storm.
Make decisions with people in mind first, profit second.

Fast forward eight years, and that little post-crisis seed has grown into something far bigger than I could have imagined. We’ve employed over 1,600 military spouses , supported clients in every niche and season of life , and paid out over $30 million dollars directly to military families.

And we’ve done it all with integrity, transparency, and taking care of people as our north star.

When I think back to that August day, with all the fear, uncertainty, and countless tears, I can see now that it was the start of something extraordinary. What felt like the end was really the moment the door swung open to a bigger purpose.

Sometimes the worst day of your professional life is the day that sets the stage for the best work you’ll ever do.

Taylor Lingerfelt: Leading with Heart as a Military Spouse and Team Lead

Sat, 09 Aug 2025 15:16:05 GMT

Source:

https://www.podbean.com/media/share/pb-upwb8-192bb4e

Taylor Lingerfelt is a proud active duty Army spouse, mom of two, and Team Lead at Squared Away. She began her journey with the company in 2021 while at home with her kids, seeking a way to reconnect with her own identity. Over the years, she’s held multiple internal roles, growing her skills in leadership, client success, and remote team management. Today, Taylor is passionate about finding balance between family life and career, leading with empathy, and embracing the beautiful chaos of military life. Her story is a testament to the resilience, adaptability, and leadership that military spouses bring to the workforce.

In this episode of Beyond Orders, Taylor shares how she built a fulfilling career from home, the challenges and rewards of managing a remote team, and the lessons she’s learned about leadership, delegation, and staying grounded while life moves at military speed.

Beyond the Bar: Libby Jamison’s Fight for Military Families and Policy Reform

Mon, 04 Aug 2025 16:12:29 GMT

Source: https://www.podbean.com/media/share/pb-qawrt-1923551

This week on Beyond Orders, we sit down with Libby Jamison, a powerhouse attorney, policy strategist, and unapologetic advocate for military families. With nearly 20 years in law, government, and grassroots organizing, Libby has worked everywhere from the Department of Veterans Affairs to the West Wing, where she served as Senior Advisor to Joining Forces, Dr. Jill Biden’s initiative supporting military families, caregivers, and survivors.

As former President of the Military Spouse JD Network, Libby helped drive licensing reforms across more than 40 jurisdictions, opening professional doors for spouses nationwide. She has earned national recognition, including Military.com's Spouse Changemaker of the Year and a spot on the 2023 Mighty 25, and for good reason.

In this episode, Libby shares the behind-the-scenes truth about policymaking, the personal toll and triumph of advocacy, and why military spouses are more than just resilient. We are revolutionary!

Meagan Eskew’s Inspiring Story – Single Mom, Breast Cancer Survivor, Leader

Sun, 27 Jul 2025 16:11:55 GMT

Source: https://www.podbean.com/media/share/pb-74i8k-1917181

Meagan Eskew started as a virtual assistant with Squared Away in 2020 and worked her way up to become our Director of Client Connections. A single mom who battled, and beat, breast cancer, Meagan didn’t just climb the ladder, she built her own. Now, she’s stepping into a full-time role with a client buyout, proving what happens when grit meets opportunity.

She homeschools her kids, leads with heart, and shows exactly what betting on yourself looks like when life throws everything at you.

If you’ve ever wondered whether it’s possible to go from surviving to thriving, this episode is your answer.

Listen in and see why Meagan is one of the toughest, smartest women we know.

Military Spouses Make Great Leaders & Jessica Ryan Proves It

Mon, 21 Jul 2025 16:10:56 GMT

Source: https://www.podbean.com/media/share/pb-vzydb-190ea8c

What does it take to grow from a virtual assistant to a trusted executive leader, all while proving that military spouses are some of the strongest leaders in the workforce?

In this episode of Beyond Orders, Michelle Penczak, CEO of Squared Away, interviews Jessica Ryan, the company’s Chief People Officer. Jessica started in 2020 as a virtual assistant and steadily rose through the ranks, from Team Lead to the executive team, by leading with empathy, consistency, and quiet strength.

Jessica shares how she built trust, supported hundreds of military spouse virtual assistants, and helped shape Squared Away’s culture. Her story is proof that military spouses are not just support staff, they are leaders, innovators, and change-makers.

If you’re a military spouse ready to grow your career, step into leadership, or prove that you’re more than “just an assistant,” this episode is a must-listen.

What you’ll learn in this episode:

How to grow from support roles to leadership positions
Why military spouses make exceptional leaders
The power of empathy and consistency in building influence
How to lead without a loud voice and still be heard
Listen now to discover how you can own your story, your skills, and your seat at the table.

From Virtual Assistant to COO: Sara Brooks-Glover on Leadership, Growth & Reinvention

Mon, 14 Jul 2025 16:09:33 GMT

Source: https://www.podbean.com/media/share/pb-isw9w-190590b

In this episode of Beyond Orders, host Michelle Penczak, CEO of Squared Away and military spouse, sits down with Sara Brooks-Glover, Chief Operations Officer at Squared Away, to talk about career growth, remote leadership, and scaling systems in a mission-driven company.

Sara shares her inspiring journey from starting as a virtual assistant to rising through the ranks as Director of Finance and Compliance, leading Talent and Development, and now serving as COO. She offers insights into how she built scalable operations, aligned cross-functional teams, and leaned into reinvention every step of the way.

Whether you're managing a remote team, hiring virtual assistants, building business infrastructure, or navigating a leadership transition, this episode is packed with practical advice and lessons in resilient, empathetic leadership.

Keywords: military spouse career, remote team management, virtual assistant business, leadership development, female COO, career growth, business operations, hiring systems, delegation strategies, Squared Away, Michelle Penczak, Sara Brooks-Glover, Beyond Orders Podcast

Subscribe for more interviews with military spouses, remote leaders, and professionals redefining what’s possible.

From Grief to Grace: Tiffany McCawley’s Story

Sun, 06 Jul 2025 16:07:49 GMT

Source: https://www.podbean.com/media/share/pb-7jg8q-18f82eb

In this deeply moving episode of Beyond Orders, host Michelle Penczak sits down with Tiffany McCawley, a military spouse and mother of five whose faith and resilience leave a lasting impression. Tiffany became part of the Squared Away team in 2020, but her journey began long before that.

In 2015, Tiffany endured every parent’s worst nightmare; the loss of two of her children in a tragic accident. What followed was not a neatly wrapped healing journey but a raw, honest walk through grief, anchored by her faith and a quiet strength developed through lived experience.

Tiffany shares how she moved from surviving to thriving, how her work brought renewed meaning, and how her belief in God gave her the courage to keep going when nothing made sense. She speaks candidly about the causes close to her heart, including Let Them Live, supporting foster and at-risk youth; While We’re Waiting, empowering women facing unexpected pregnancy; Backpack Friends, feeding food-insecure children; and Ride Safe Foundation, striving to reduce underage drinking and increase safe rides for teens.

To learn more about Tiffany’s journey, visit her blog: theclanmccawley.blogspot.com.

Some causes that are important to the McCawley Family:

https://ridesafefoundation.org/
https://www.backpackfriends.org/
https://whilewerewaiting.org/donate/a

Beyond the Resume: Leadership, Life Lessons, and Starting Over

Tue, 01 Jul 2025 16:06:25 GMT

In this episode of Beyond Orders, host Michelle Penczak speaks with Rachel Hornbeck, the Director of Talent and Development at Squared Away, about her journey from being a stay-at-home mom to a leadership role within the company. They discuss the supportive culture at Squared Away, the challenges of imposter syndrome, the importance of community, and the personal stories of adoption that have shaped their lives. Rachel shares her insights on leadership, accountability, and the hiring process, culminating in a reflection on the theme of reinvention and personal growth.

Real leadership starts when we stop waiting for permission to grow.
The culture at Squared Away empowers individuals to thrive.
Imposter syndrome is a common challenge for many leaders.
Supportive communities can foster personal and professional growth.
Heart and caring mentality are essential in leadership roles.
Being open to feedback is crucial for success.
Accountability is key to building trust within teams.
The hiring process at Squared Away is thorough and thoughtful.
Personal stories of adoption can create deep connections.
Reinvention involves being brave enough to outgrow comfort zones.

Rooted at Last: How Squared Away Became Jordan’s Steady Ground

Sat, 21 Jun 2025 16:04:58 GMT

In the inaugural episode of Beyond Orders, host Michelle Penczak sits down with Jordan Streetman Cole, Chief Experience Officer at Squared Away, for a powerful conversation about the realities of military spouse life and the unexpected opportunities that can come from uncertainty.

Together, they unpack Jordan’s journey from applying to Squared Away out of sheer desperation to growing into a key leadership role within the company. Along the way, they explore themes of reinvention, resilience, and the deep need for stability in a life shaped by constant change.

This episode dives into the unique strengths military spouses bring to the workforce, the transformative power of meaningful assistant-client partnerships, and why building community and trust is at the heart of it all. Whether you’re navigating career transitions, PCS chaos, or simply looking for a story that reminds you you’re not alone, this one’s for you.

Because while military orders may move us, they don’t have to define us.

Jordan's book reference - Time, Talent, Energy

The podcast aims to empower military spouses to rewrite the rules of their careers.
Desperation often drives military spouses to seek new opportunities.
Stability in employment is crucial for military spouses facing frequent relocations.
Resiliency is a key trait of the Squared Away team.
Building a community among military spouses enhances support and connection.
Successful client-assistant matches require time and investment in understanding each other.
Celebrating wins, both big and small, is essential for motivation.
Reframing opportunities for military spouses can change perceptions in the workforce.
Reinvention is about honoring one's potential and evolving into the best version of oneself.
Leadership is about empowering others and leading by example.

Mastering the Back-to-School Season: How an Executive Assistant Can Help You Thrive

Tue, 20 Aug 2024 11:20:40 GMT

Back-to-School Productivity and Executive Support: Frequently Asked Questions

The Back-to-School Rush

The whirlwind of back-to-school season is here — are you ready? As summer winds down, the shift to a more structured routine can feel overwhelming. Between managing your professional responsibilities, coordinating family schedules, and tackling a seemingly endless list of school-related tasks, it’s easy to feel stretched thin. But what if you didn’t have to do it all on your own?

Imagine having a dedicated professional by your side, someone who can seamlessly manage the details and keep everything running smoothly. An executive assistant can be your secret weapon, helping you navigate the chaos of the back-to-school season with ease, ensuring that you and your family are set up for success. In this post, we’ll explore how an executive assistant can take the stress out of this busy time, allowing you to focus on what matters most.

Managing the Chaos: How an Executive Assistant Streamlines Back-to-School Tasks

The back-to-school season often feels like a juggling act with countless tasks and deadlines to manage. From organizing schedules to making sure everyone has the right supplies, it can be challenging to keep everything in order. This is where an executive assistant can step in to bring structure and calm to the chaos.

Organizing School Schedules

One of the most overwhelming aspects of back-to-school is managing multiple schedules — school events, sports practices, extracurricular activities, and more. An executive assistant can take the lead in setting up and syncing these schedules across all your devices, ensuring that every family member is on the same page. Whether it’s school orientations, early dismissals, or parent-teacher conferences, your assistant will make sure nothing falls through the cracks.

Handling Supplies and Shopping

The annual back-to-school shopping spree can be time-consuming and stressful. An executive assistant can streamline this process by creating a detailed shopping list based on your children’s needs and preferences. They can handle everything from online ordering and delivery coordination to in-store pickups. By delegating these tasks, you save time and ensure your kids have everything they need for a successful school year.

With an executive assistant managing these crucial back-to-school tasks, you can focus on being present for your family and maintaining your professional responsibilities without the added stress of logistical details.

Work-Life Balance: Keeping Professional Life on Track

As the back-to-school season kicks into high gear, the demands of work don’t simply pause. Balancing a busy professional life with the added responsibilities at home can be challenging. However, with the support of an executive assistant, you can maintain that delicate balance and ensure your work life stays on track, even during this hectic time.

Prioritizing Work Responsibilities

When your plate is overflowing with both work and family obligations, it’s easy to feel overwhelmed. An executive assistant can help you stay organized by prioritizing your work tasks, ensuring that your most critical responsibilities are handled efficiently. They can manage your calendar, flagging high-priority meetings, and tasks while rescheduling or delegating less urgent items. This way, you can focus on what truly matters, knowing that your assistant has everything else under control.

Delegating to Stay Focused

Distractions are inevitable during the back-to-school season, but an executive assistant can help you stay focused by taking on administrative tasks that might otherwise pull you away from your core work. From managing your inbox and scheduling meetings to preparing documents and handling communications, your assistant ensures that you remain productive and focused on high-impact activities. This delegation not only keeps your workday running smoothly but also frees up mental space, allowing you to be more present in both your professional and personal life.

With your executive assistant handling the day-to-day details, you can maintain a clear mind and continue to excel in your career, even as you navigate the demands of a busy school season. This support ensures that your work life remains steady, enabling you to juggle both worlds effectively.

Family Support: Beyond the School Day

The school day might end in the afternoon, but the responsibilities of parenting and managing a household continue well into the evening. Juggling after-school activities, meal prep, and transportation logistics can quickly become overwhelming. An executive assistant can provide invaluable support by taking charge of these tasks, ensuring that your family’s needs are met seamlessly.

Meal Planning and Prep

One of the most time-consuming aspects of daily family life is meal planning and preparation. An executive assistant can take this burden off your shoulders by coordinating weekly meal plans tailored to your family’s dietary preferences and nutritional needs. They can manage grocery shopping, either by placing online orders for delivery or arranging in-store pickups. If you prefer home-cooked meals but lack the time to prepare them, your assistant can organize meal prep services or schedule meal delivery from your favorite restaurants. With these tasks handled, you can enjoy healthy, stress-free dinners with your family every night.

Transportation and Logistics

After-school activities often involve a complex web of transportation needs, from soccer practice to piano lessons. An executive assistant can simplify these logistics by coordinating carpools with other parents, scheduling rides with trusted services, or arranging for family members to be where they need to be, when they need to be there. Whether it’s getting the kids to their activities or ensuring they’re safely home afterward, your assistant will ensure all the details are covered, giving you peace of mind.

By entrusting these essential but time-consuming tasks to an executive assistant, you can reclaim your evenings and weekends. This support allows you to focus on spending quality time with your family, rather than being consumed by the constant demands of managing daily life.

Make This School Year Your Best Yet

As the back-to-school season ramps up, it’s easy to feel overwhelmed by the sheer volume of tasks on your to-do list. From managing family schedules and school supplies to balancing work responsibilities and self-care, it can all feel like too much to handle alone. But with the support of an executive assistant, you don’t have to.

By streamlining your schedules, handling the logistics, and ensuring that both your professional and personal lives remain in harmony, an executive assistant can transform this busy season from stressful to seamless. They provide the organizational backbone that allows you to focus on what matters most — being present for your family and excelling in your career.

So why face the back-to-school rush alone? Consider how an executive assistant can help you maintain balance and thrive, not just in these hectic weeks, but throughout the entire school year. With the right support, you can start the school year with confidence, knowing you have everything you need to make it your best one yet!

Top Tools and Technologies for Efficient Assistance: Boosting Productivity with Modern Solutions

Wed, 31 Jul 2024 11:20:39 GMT

Productivity Tools for Executive and Remote Assistants: Frequently Asked Questions

Efficiency and productivity are crucial in today’s fast-paced world, especially when working with a personal or professional assistant. Leveraging modern tools and technologies can make a significant difference in managing workloads and achieving goals. At Squared Away, we integrate advanced technologies to enhance the assistant-client relationship. Here are some tips and platforms we utilize.

Key Tools for Efficient Assistance

In the realm of modern assistance, leveraging the right tools is crucial for maximizing efficiency and productivity. At Squared Away, we utilize a suite of platforms that streamline communication, task management, and collaboration. Here are some essential tools that our assistants rely on to provide top-notch support:

Communication Platforms: Slack, Microsoft Teams, Zoom

Effective communication is the backbone of any successful working relationship. Platforms like Slack, Microsoft Teams, and Zoom facilitate seamless and instant communication between clients and assistants. These tools enable quick messaging, video calls, and collaborative discussions, ensuring that everyone stays connected and informed. Whether it’s a quick check-in or a detailed project discussion, these communication platforms make interaction smooth and efficient.

Task Management Tools: Asana, Trello, Monday.com

Keeping track of tasks and deadlines can be daunting without the right tools. Task management applications such as Asana, Trello, and Monday.com help our assistants organize, prioritize, and monitor tasks efficiently. These tools offer features like to-do lists, project timelines, and progress tracking, making it easier to manage workloads and ensure that nothing falls through the cracks. With visual boards and automated reminders, staying on top of tasks becomes a breeze.

Calendar and Scheduling Apps: Google Calendar, Calendly

Scheduling meetings and managing appointments can be time-consuming. Tools like Google Calendar and Calendly simplify this process by allowing easy scheduling, rescheduling, and reminders. Google Calendar integrates seamlessly with other Google Workspace tools, providing a unified experience for managing events and tasks. Calendly, on the other hand, automates meeting scheduling by allowing clients to book available time slots, reducing back-and-forth communication and optimizing time management.

Document Collaboration: Google Workspace, Microsoft Office 365

Collaboration on documents and files is a key aspect of many professional tasks. Google Workspace and Microsoft Office 365 offer robust solutions for real-time document collaboration. Google Docs, Sheets, and Slides, along with their Microsoft counterparts, enable multiple users to work on the same document simultaneously. This real-time editing capability enhances productivity, reduces errors, and ensures that everyone is on the same page. Additionally, cloud storage solutions provided by these platforms ensure that documents are accessible from anywhere at any time.

These essential tools form the backbone of our efficient assistance services at Squared Away. By leveraging these technologies, we ensure that our clients receive the highest level of support, allowing them to focus on their business and free up their time.

Spotlight on Squared Away’s Unique Technology: The Delegation Assistant

At Squared Away, we pride ourselves on staying at the forefront of innovation to better serve our clients. One of our most groundbreaking tools is the Delegation Assistant, a custom ChatGPT application designed to streamline and enhance the delegation process. This unique tool helps clients identify tasks that can be effectively delegated to their Squared Away assistant, ensuring that nothing is overlooked. By providing tailored suggestions based on the client’s specific field, job, or company, the Delegation Assistant enables clients to maximize efficiency and focus on high-priority activities. It’s like having a personal delegation strategist at your fingertips, guiding you through optimizing your workflow.

The Delegation Assistant not only simplifies the delegation process but also encourages creativity and customization. It understands the nuances of different industries and roles, offering insights that are both relevant and actionable. For example, a marketing manager might receive suggestions for delegating social media management, content creation, and data analysis, while an entrepreneur could get recommendations for administrative tasks, research, and customer outreach. This tailored approach ensures that clients can delegate with confidence, knowing that their assistants are equipped to handle the tasks effectively. With the Delegation Assistant, Squared Away clients can transform their work habits, making their professional lives more manageable and productive.

Interested in the delegation assistant? Find it here: https://chatgpt.com/g/g-5VC42XNCZ-squared-away-delegation-assistant

Meal Planning and Prep

The Benefits of Using Advanced Tools in Assistance

Utilizing advanced tools in assistance significantly boosts productivity and efficiency by streamlining processes that otherwise consume valuable time. Communication platforms, task management applications, and scheduling apps automate routine tasks and facilitate real-time collaboration, freeing up time for more strategic work. These tools enhance communication and collaboration, ensuring alignment and reducing errors. Platforms like Slack and Microsoft Teams foster clear communication, while task management tools like Asana and Trello provide transparency in project progress. Document collaboration tools like Google Workspace and Microsoft Office 365 promote teamwork and innovation. By leveraging these technologies, clients and assistants can work together seamlessly, making remote work more effective and productive.

The Future of Assistance Technology

The future of assistance technology is poised to bring even more innovations that will further transform how we delegate and manage tasks. Emerging trends such as artificial intelligence, machine learning, and advanced automation are set to enhance the capabilities of personal and professional assistants. At Squared Away, we are committed to staying ahead of these trends and integrating new technologies that can offer even greater efficiency and customization for our clients. By continually adopting cutting-edge solutions, we aim to provide the most effective and forward-thinking assistance services, ensuring that our clients can leverage the best tools available to achieve their goals and streamline their workflows.

Conclusion

Leveraging modern tools and technologies is essential for maximizing efficiency and productivity in today’s fast-paced world. At Squared Away, we integrate advanced solutions like our unique Delegation Assistant alongside industry-standard tools for communication, task management, and collaboration to provide unparalleled support to our clients. By embracing these innovations, clients can streamline their workflows, enhance their productivity, and focus on what truly matters. We invite you to explore Squared Away’s services and discover how our advanced tools can help you achieve your goals with ease and confidence. Contact us today to learn more about transforming your work habits with our expert assistance.

The Importance of Trust in Virtual Relationships: Building and Maintaining Trust Remotely

Wed, 26 Jun 2024 11:20:38 GMT

Building Trust in Remote Teams: Frequently Asked Questions

Since COVID, the workforce has embraced remote work at an unprecedented rate, bringing up the importance of trust in virtual relationships. As teams and individuals collaborate across cities, countries, and even continents, the ability to build and maintain trust within a remote team or team member has become a critical component for success. Building trust remotely can be challenging when there isn’t opportunity for things like break room chats or popping by someones desk to ask about their weekend plans or upcoming trips become a lot harder to happen organically. Interactions like these are important in building relationships between team members and help in building trust. Trust serves as the foundation of any successful relationship, and this holds true even in virtual settings. In the absence of physical presence, establishing and nurturing trust can seem daunting, yet in these situations, it is more important than ever to get it right.

Understanding Trust in Virtual Relationships

Trust, at its core, is the belief in the reliability, truth, and ability of someone or something. In virtual relationships, it means having confidence that team members will fulfill their responsibilities, communicate honestly, and support each other despite physical distances. In virtual settings, feeling assured that colleagues are committed to the team’s goals and will act with integrity and transparency is the foundation of a trusting relationship. When trust is present, it fosters open communication, encourages collaboration, and boosts overall team morale. Team members are more likely to share ideas, provide constructive feedback, and work towards common goals when they feel trusted and trust others. Conversely, a lack of trust can lead to miscommunication, decreased productivity, and a fragmented team dynamic. In remote work environments, where face-to-face interactions are limited, building and maintaining trust is crucial to ensuring that teams remain cohesive, motivated, and productive.

Challenges of Building Trust Remotely

Building trust remotely comes with a unique set of challenges. The lack of face-to-face interactions, like being able to pop over to someone’s desk to chat through something, can lead to miscommunications and misunderstandings. Non-verbal cues are often missed in virtual conversations and can lead to confusion when things aren’t clearly articulated. Dependence on digital communication tools can also create barriers, especially when technical issues arise and disrupt the flow of information and collaboration. While working across different time zones and cultural backgrounds can complicate coordination and inclusivity, making it harder to establish a unified team dynamic. These challenges highlight the importance of being intentional and proactive in fostering trust in virtual relationships, requiring clear communication, reliability, and a solid commitment to inclusivity and understanding.

Strategies for Building Trust in Virtual Relationships

One of the biggest foundations to trust in a virtual relationship is open and consistent communication. Regular check-in, updates, and timely replies help keep everyone on the same page and reduces the chances of misunderstandings. Having your communication channels established and ensuring everyone is comfortable using them will make the transfer of important information easy for the whole team. It’s also vital to set clear expectations from the start, defining roles, responsibilities, and deadlines. Establishing norms for virtual interactions, such as response times and availability, can further help in aligning team members and preventing miscommunications.

Demonstrating reliability and competence is another crucial aspect of building trust remotely. Delivering on promises, meeting deadlines, and producing quality work consistently show team members that they can depend on each other. Encouraging social interactions, even in a virtual setting, can strengthen relationships and build trust. Virtual team-building activities and informal virtual gatherings can create opportunities for team members to connect on a personal level, fostering a sense of camaraderie and mutual respect that often comes with the break room chats when in person. These strategies can help teams overcome the inherent challenges of remote work by building strong, trust-based relationships with their team from the start.

Maintaining Trust Over Time

A big part of maintaining trust over time is making sure team members feel heard and valued by everyone. This can be achieved through periodic performance reviews and constructive feedback sessions, which provide opportunities to address any issues and make necessary adjustments. It’s important to be open to feedback and willing to adapt communication strategies based on team members’ needs and preferences. Maintaining an ongoing dialogue helps keep everyone aligned and reinforces the trust that has been established.

Company culture is often what keeps people around, so fostering a positive virtual culture will be crucial for long-term success. Celebrating achievements and milestones, whether big or small, helps to build a sense of community and recognition. Promoting a culture of appreciation and acknowledgment makes team members feel valued and motivated. While addressing issues immediately and maintaining a problem-solving attitude are vital for sustaining trust. Being proactive in resolving conflicts and demonstrating a commitment to finding solutions helps to maintain a healthy and productive team dynamic. By focusing on these aspects, remote teams can ensure that the trust they have built remains strong and enduring.

Conclusion

Trust is the cornerstone of successful virtual relationships. In a world where remote work is becoming increasingly common, building and maintaining trust among team members is essential for effective communication, collaboration, and productivity. Despite the challenges of limited face-to-face interactions, technological barriers, and diverse working environments, trust can be cultivated through consistent and transparent communication, clear expectations, demonstrated reliability, and encouraging social interactions.

Maintaining trust over time requires ongoing communication, regular feedback, and a positive virtual culture that celebrates achievements and addresses issues promptly. By prioritizing these strategies, remote teams can foster strong, trust-based relationships that enhance cohesion, motivation, and overall success. As we continue to navigate the evolving landscape of remote work, investing in trust will be the key to thriving in virtual environments.

Celebrating Military Spouse Appreciation Day

Wed, 08 May 2024 11:20:36 GMT

Each year, Military Spouse Appreciation Day is something we at Square Away love to honor. Recognizing the invaluable contributions and sacrifices made by military spouses is something we do every day, but on this very special day, we want to make some extra noise around it. Established by President Ronald Reagan in 1984, this day is set aside each year on the Friday before Mother’s Day. It acknowledges the critical support role military spouses play in maintaining the morale and readiness of our armed forces.

The Squared Away team knows the unique challenges of being part of a military family. We recognize the resilience and strength of military spouses — from managing households, handling deployment seasons, and building community while often pursuing their own professional and personal ambitions. Today, we want to honor their contributions and shine a light on the vital role they play both within the military community and in our society at large.

The Life of a Military Spouse

Every day, military spouses across the globe navigate a unique set of challenges that test their resilience. The reality of military life can often mean unpredictable changes are thrown their way, yet through these, they often discover their incredible capacity for strength and adaptability.

One of our assistants, Ashley Orians, shares a snapshot of her life when, unexpectedly, she had to adapt to solo parenting two young children. “Little did we know, that only 6 days after welcoming our sweet girl Kinsey into the world he was going to be deployed for 10 months, leaving me to solo parent 2 babies under two ALONE,” she recalls. Ashley found solace in establishing routines despite the overwhelming demands, her days filled with “love, patience, and copious amounts of coffee.” Her story is a testament to finding strength in the toughest times, remarking on the bittersweet reunion, “What a strange feeling that he left this baby when she was 6 days old…and then met her again when she was already 10 months old; she was like a whole little person already!”

Lawson Brandon’s experience highlights a different facet of military spousal life — dealing with significant life events during deployment. Lawson recounts the emotional rollercoaster of learning she was finally pregnant right before her husband’s deployment, a moment they had awaited through years of challenges. “We struggled to get pregnant for a few years and suffered through many doctors appointments, so this was the news we had been waiting for,” she explains, underscoring the mixed feelings of joy shadowed by her husband’s absence. Things looked up in her situation when her husband returned just in time for the birth, a poignant reminder of the sacrifices made by military families. “He might’ve missed the pregnancy, but our strength during that scary deployment was rewarded by his perfectly timed arrival and our son’s debut 4 days after his daddy got home.”

These personal stories underscore the complex reality military spouses face — managing solo parenting and dealing with critical family moments in the absence of their partners. They navigate these trials with grace and fortitude, turning challenges into opportunities for growth and deepening family bonds. Their experiences enrich the tapestry of the military community, highlighting why recognition on Military Spouse Appreciation Day is both warranted and deeply necessary.

Supporting Military Spouses

Anyone who has been a military spouse can tell you that support and a network you can rely on give you the power to handle the unique challenges of military life. Things like the programs that allow military families to go to college no matter where they live via online courses and scholarships mean they don’t have to put their ambitions on hold when signing up for military life. Career assistance programs, such as resume-building services, networking events, and job placement programs designed for people with busy lives, are very helpful for keeping and advancing professional careers. While online and in-person counseling services offer important emotional and mental support that helps military spouses deal with the stresses of deployments and moving around a lot.

The public and military institutions can both do a lot to help military spouses get more help. People can get involved by supporting and taking part in community programs that help military families, like local job programs or housing programs that take into account the specific needs of military families. Military institutions can do a better job if they make sure that policies are open to all military families and change as the needs of military families change. They can do this by making it easier for military families to keep learning and find work and by offering more family support services.

How Squared Away Supports Military Spouses

We’ve been military spouses’ number one fan for a while. Founded by Michelle Penzcak, a military spouse herself, she recognized the talent and potential within this community to do great things. By actively seeking to hire them into our dynamic team, we are committed to creating career opportunities that are both flexible and rewarding and can accommodate the unique lifestyle of military families. Our company not only offers remote positions that allow military spouses to work from anywhere but also ensures stability and continuity in their careers despite frequent relocations. By focusing on the strengths and adaptability that military spouses bring to the workforce, Squared Away is dedicated to providing meaningful employment that supports their professional aspirations and personal commitments.

To further foster this commitment to military spouses, Squared Away has also established specific programs aimed at fostering their professional development and personal growth. Our mentorship program pairs less experienced spouses with seasoned professionals within the company, facilitating knowledge transfer and skill enhancement in a supportive environment. We also offer specialized training programs that focus on leadership development, technical skills, and business management, ensuring that our team members are equipped to excel in their roles and advance in their careers. Through these initiatives, Squared Away not only aids in the professional journey of military spouses but also contributes to their sense of purpose and community.

Conclusion

As we honor Military Spouse Appreciation Day, it’s good to recognize the resilience, strength, and essential contributions of military spouses. From their roles in enhancing military and community morale to their professional achievements despite numerous challenges, military spouses embody a spirit of dedication and adaptability. At Squared Away, we proudly support these incredible individuals through targeted hiring practices and empowering initiatives aimed at professional and personal growth. We encourage everyone to acknowledge and participate in this special day by attending local events, supporting military spouse-owned businesses, or advocating for policies that aid their welfare. Let’s come together to celebrate and support the vital role military spouses play in our communities and nation.

Hiring a Remote Assistant: What Businesses Need to Know

Tue, 02 Apr 2024 11:20:35 GMT

Hiring a Remote Assistant: Frequently Asked Questions

The shift towards remote work is transforming the modern workforce, presenting businesses with unprecedented advantages, from heightened productivity to access to a global talent pool. At the heart of this transformation is the role of the remote assistant, a game-changer for companies seeking to leverage this new paradigm. Squared Away leads this charge by harnessing the unique skills and unwavering dedication of military spouses, making them the ideal candidates for businesses aiming to scale and thrive in today’s competitive landscape. Hiring a remote assistant not only offers logistical benefits but, through Squared Away, also provides the opportunity to contribute to a meaningful mission, highlighting the extraordinary capabilities of an often-undervalued segment of the workforce.

The Rise of Remote Work

The shift toward remote work is reshaping the workplace, leading to increased productivity, reduced operational costs, and better work-life balance. This change offers numerous benefits, from lower office expenses to access to global talent, and contributes to environmental sustainability by cutting down on commuting. Remote assistants play a key role in this transformation, providing flexibility and support across various tasks. Their contribution is essential for businesses looking to maintain agility and drive growth, making them invaluable assets in the evolving landscape of work.

Why Military Spouses Make Exceptional Remote Assistants

Military spouses are a distinct talent pool whose professional capabilities are forged in the unique challenges of military life, including resilience, adaptability, and commitment. At Squared Away, we harness these attributes by connecting businesses with remote assistants who excel in navigating the fluid dynamics of the remote workspace. Their exceptional organizational skills and ability to manage change are invaluable for teams seeking to boost efficiency and adaptability. Supported by Squared Away’s specialized training, these military spouses are not just prepared to meet immediate tasks but are also equipped to evolve with the company, showcasing their potential to adapt to changing business landscapes.

What Businesses Need to Consider Before Hiring a Remote Assistant

Before hiring a remote assistant, businesses need to carefully consider several key factors to ensure they embark on a fruitful partnership. Identifying the specific skills and expertise required is the first step. This depends on the tasks you plan to delegate, such as administrative duties, customer service, or specialized projects. Knowing exactly what you need allows you to match with an assistant whose capabilities align with your business objectives.

Determining the tasks to be assigned is crucial. Outline the responsibilities and projects your remote assistant will handle. This clarity ensures you select someone with the right experience and also sets the stage for effective task management.

Management and communication strategy form the backbone of this relationship. Decide on the communication channels and project management tools you’ll use to ensure tasks are completed efficiently and effectively. Options might include email, video conferencing, or platforms like Slack and Asana for day-to-day communication and task tracking. Regular check-ins will keep both you and your assistant aligned and provide opportunities for feedback and adjustments.

Considering these aspects — skills and experience needed, tasks to be delegated, and your management approach — will guide you in finding and effectively working with a remote assistant, ensuring a successful and productive partnership.

Simplifying Your Search with Squared Away

Squared Away streamlines the hiring process by expertly matching businesses with executive assistants. This service prioritizes the perfect alignment of skills and company culture, ensuring a seamless integration and a productive partnership.

The Squared Away Process

Skillset Alignment: Squared Away evaluates your business needs to connect you with an assistant who excels in the specific tasks and responsibilities you require, from administrative support to project management.
Assistant Experience: Our matching mechanism goes beyond mere skill alignment. We recognize the value of experience, which is why assistants with a longer tenure and proven track record within our team are acknowledged through higher compensation packages. This approach ensures you’re connected with not just any assistant, but one whose experience and skill depth are poised to meet and exceed your expectations.

Why Choose Squared Away

Quality Matches: Through a meticulous vetting process, Squared Away guarantees highly qualified, dedicated military spouses known for their resilience and adaptability.
Supporting a Mission: Partnering with Squared Away means more than just finding the right assistant; it’s about supporting the empowerment and employment of military spouses contributing to a meaningful cause.

In essence, Squared Away finds you the ideal remote assistant and supports a larger mission, providing a skilled professional ready to contribute to your success while fostering community support.

Maximizing the Potential of Your Remote Assistant

Once you’ve initiated a partnership with a remote assistant through Squared Away, laying a robust foundation for this collaboration is crucial, encompassing clear communication, routine check-ins, and mutual goals and expectations. A structured approach that incorporates consistent feedback and open dialogue ensures efficient task completion and quick issue resolution, fostering a trust-based rapport with your assistant. Furthermore, promoting your remote assistant’s professional growth by offering learning and development opportunities not only keeps them motivated and abreast of the latest industry trends and technologies but also bolsters your business’s success and capacity for innovation. A valued and supported remote assistant is more inclined to excel, pushing boundaries to contribute to your company’s enduring prosperity.

Conclusion

The power of hiring a remote assistant offers unparalleled flexibility, efficiency, and strategic support, marking a significant step toward business growth and innovation. This evolving dynamic provides access to a global pool of talent, transforming the traditional workspace into a more productive and agile environment. Such partnerships transcend typical task delegation, fostering relationships built on trust, mutual respect, and a collective drive for excellence. Incorporating the approaches discussed here can revolutionize operations and boost productivity for any business. Unique among these opportunities is Squared Away’s approach, which connects companies with highly skilled military spouses. This not only supports business objectives but also contributes meaningfully to the lives of military families, making Squared Away a distinctive choice in the remote assistant marketplace. Choosing Squared Away means gaining a partner who is genuinely invested in your success and ready to support your journey toward innovation and leadership. Step forward with a remote assistant who brings more than skills to the table — someone who shares your commitment to excellence and growth and is ready to help your business soar.

The Evolution of the Executive Assistant: How the role has changed in the digital age.

Tue, 02 Apr 2024 11:20:34 GMT

The Modern Executive Assistant Role: Frequently Asked Questions

In the digital age, the role of the executive assistant (EA) has evolved from traditional administrative support to a dynamic position that intertwines technological proficiency with strategic partnership. At Squared Away, we’ve recognized the shift towards a more complex, tech-driven business environment. This evolution reflects not just a change in tools and workflows but a significant redefinition of the EA’s role, marking a transition towards strategic insight and adaptability.

As advocates for innovation and excellence, Squared Away is committed to embracing the opportunities this digital revolution presents. By understanding the journey from the EA’s traditional roots to their current, multifaceted role, we aim to empower our team and readers alike, highlighting the profound impact of technology on executive support and the indispensable value EAs bring to their organizations in this new era.

The Traditional Role of the Executive Assistant

The traditional role of the executive assistant was once defined by a clear set of administrative tasks — managing calendars, answering phones, and maintaining office efficiency. These foundational responsibilities laid the groundwork for what was largely perceived as a support role, vital yet circumscribed by the physical boundaries of the office space. However, the essence of this role has always been about facilitating the executive’s ability to lead effectively, a core purpose that remains unchanged even as the surrounding tasks and technologies have evolved.

With the advent of the digital age, the scope of the EA’s role has expanded dramatically. The introduction of sophisticated digital tools and platforms has transformed the way EAs manage information, communicate, and organize workflows. This technological shift has not only enhanced efficiency but also broadened the EA’s involvement in strategic planning and decision-making processes. Today, EAs are expected to navigate a suite of digital tools, from CRM systems to advanced scheduling software, embodying a shift towards a more proactive, strategic role that leverages technology to drive organizational success.

The Emergence of the Digital Age and Its Initial Impact

As we ventured deeper into the digital age, the executive assistant’s role began to morph, integrating advanced technology that reshaped their daily tasks and overall contributions to their executives and organizations. This era introduced a plethora of digital tools — CRM systems, sophisticated scheduling platforms, and virtual meeting software — each serving to streamline operations and enhance productivity. The proficiency in these technologies became a new benchmark for excellence, pushing EAs to adapt and thrive in an increasingly virtual workspace. This shift was not merely about adopting new tools; it represented a fundamental change in the EA’s role, from administrative support to becoming a pivotal part of the executive’s strategic toolkit.

The Rise of Specialized Roles

The digital age has also led to the emergence of specialized roles within the executive assistant domain, reflecting the diversification and specialization of their responsibilities. Niches such as project management, digital marketing assistance, and even social media management have become more common, enabling EAs to tailor their careers to specific areas of interest and expertise. This trend towards specialization not only highlights the expanding scope of the EA role but also emphasizes the unique value they bring to their organizations. By developing specialized skills, executive assistants can contribute more strategically to their teams, further cementing their status as indispensable members of the executive support structure.

The Rise of Remote Work and Virtual Assistance

The pandemic accelerated a trend that was already visible on the horizon: the shift towards remote work and the necessity for virtual assistance. While this transition marked a significant change in where and how executive assistants work for many, emphasizing the need for digital proficiency and effective online communication skills, Squared Away was ahead of the curve. Having built a solid foundation in remote operations from the outset, there was no shift or transition for us — instead, the global changes underscored and expanded upon our well-established practices. Our executive assistants were already experts in managing virtual offices, coordinating online meetings, and ensuring seamless communication across distributed teams. This existing adaptation allowed Squared Away to not just continue but thrive and expand our capabilities, leveraging our robust online foundation to enhance flexibility and efficiency without the need to navigate the learning curve that the rest of the world faced.

The Impact of AI and Automation on Executive Support

The rapid advancement of AI and automation technologies presents both opportunities and challenges for executive assistants. AI tools have begun to take over routine tasks such as scheduling, email management, and even basic decision-making processes, freeing EAs to focus on more strategic aspects of their role. However, this shift also requires EAs to continuously update their skill set to stay ahead of the curve, understanding how to leverage AI to enhance their effectiveness without being overshadowed by it. This evolution underscores the importance of adaptability and lifelong learning, ensuring that executive assistants remain indispensable by complementing technological advancements with human insight and expertise.

The Continued Importance of Soft Skills in a Digital Age

Despite the significant impact of technological advancements, the value of soft skills — such as communication, empathy, and problem-solving — remains paramount for executive assistants. In a digital age where human connection can sometimes be diluted by screens and virtual interfaces, EAs stand out by providing personalized support and maintaining strong relationships with colleagues, clients, and stakeholders. These skills ensure that executive assistants can navigate the nuances of digital communication, manage complex interpersonal dynamics, and provide the kind of intuitive support that technology alone cannot replicate. As the role of the executive assistant evolves, the combination of tech-savviness and strong interpersonal skills becomes the hallmark of truly effective executive support.

Conclusion

As we reflect on the journey of the executive assistant through the digital age, it’s evident that this role has undergone a profound transformation, evolving from a primarily administrative position to a multifaceted, strategic partnership with executives. The integration of advanced technology, the expansion of skill sets and responsibilities, and the emergence of specialized roles have all contributed to redefining what it means to be an executive assistant in today’s fast-paced, tech-driven business environment.

At Squared Away, we recognize the incredible value and potential that modern executive assistants bring to their organizations. Their adaptability, tech-savviness, and strategic insight are indispensable in navigating the complexities of the digital age. As we look to the future, it’s clear that the role of the executive assistant will continue to evolve, shaped by ongoing technological advancements and changing workplace dynamics. Embracing continuous learning, leveraging technology, and honing interpersonal skills will be key for executive assistants aiming to stay at the forefront of their profession. In this era of constant change, the executive assistant’s role stands as a testament to the power of adaptability and the enduring importance of human insight and connection in the world of business.

The Untapped Talent of Military Spouses: Exploring the Skills and Resilience of Military Spouses in the Workforce

Fri, 19 Jan 2024 11:20:33 GMT

Military Spouse Employment and Workforce Impact: Frequently Asked Questions

Often hidden in plain sight, the exceptional talents of military spouses represent a startling oversight in today’s workforce narrative. At Squared Away, we’re challenging the status quo by spotlighting the resilience and adaptability of these remarkable individuals. Their journey, marked by constant change and uncertainty, forges a unique set of professional skills that remains grossly underutilized. Join us as we delve into this untapped reservoir of potential, advocating for a paradigm shift that fully recognizes and leverages the diverse capabilities of military spouses in the workforce.

The Dual Challenge: Mobility and Employment

Military spouses confront a striking employment paradox, defined by their mobility and the consequent challenges in the labor market. Despite often being highly educated, they face an unemployment rate of 24% and underemployment ranging between 31% to 51%. These figures starkly contrast the national averages and underscore the systemic employment barriers these individuals encounter due to their transient lifestyles [ source ]. This mobility, while enriching, poses significant hurdles in career consistency and progression, leading to a workforce segment rich in skills and experience yet significantly underutilized.

This resilience in the face of career and mobility challenges is where the potential of military spouses truly shines. Their ability to start anew, build networks from scratch, and quickly adapt to diverse work environments is not just commendable, it’s a competitive advantage in today’s fast-paced business world. Employers are beginning to realize that the skills honed through the unique experiences of military life — quick assimilation of new information, adaptability to change, and creating order from chaos — are invaluable in any professional setting. Military spouses, often perceived through the lens of their challenges, are, in fact, a rich source of untapped talent, ready to make significant contributions to the workforce when given the right opportunities.

Key Strengths of Military Spouses: A Rich Tapestry of Skills

Military spouses, in navigating the unique challenges of their lifestyle, develop a comprehensive skill set that is highly valuable in the workforce. Their adaptability is unparalleled, allowing them to thrive in constantly changing environments, a trait that is crucial in today’s dynamic business landscape. They are masters of organization, adept in managing logistics, budgeting, and scheduling, honed by running households often single-handedly during deployments. This organizational prowess seamlessly translates to project management skills in a professional setting. Their life experiences also foster exceptional cross-cultural communication abilities, making them adept at navigating diverse work environments. Additionally, their resilience and problem-solving skills are well-developed, enabling them to approach challenges with innovative solutions and a strong work ethic.

With their constant relocations, military spouses often take on community leadership roles, developing robust leadership and interpersonal skills. They are skilled in crisis management, handling emergencies with calm and efficiency, and are proficient at multitasking, juggling multiple responsibilities seamlessly. Their ability to build and maintain networks in frequently changing communities is a testament to their strong networking skills. Empathy, another critical strength, allows them to understand and relate to a wide range of perspectives, enhancing team dynamics and customer relations. Additionally, their flexibility in adjusting to changing demands, coupled with digital literacy for managing long-distance communications and efficient time management, makes them ideal candidates for a variety of roles in any organization. These diverse skills, born out of their unique experiences, position military spouses not just as capable employees but as valuable assets, bringing a rich tapestry of abilities and experiences to the workplace.

A Solution to Military Spouse Employment

Squared Away’s inception is a direct response to the military spouse employment challenge, born out of the personal experience of our founder, Michelle Penczak. As a military spouse herself, Michelle intimately understood the employment barriers faced by her peers. Fueled by her firsthand experiences and driven by a desire to make a tangible difference, Michelle crafted a mission for Squared Away to offer flexible, fulfilling roles as executive assistants specifically tailored for military spouses. Her vision was to harness the unique skills and talents of this demographic, offering a platform where their talents as executive assistants are fully valued and utilized. Michelle’s journey with Squared Away not only stands as a testament to her entrepreneurial spirit but also highlights a successful model of how businesses can effectively address and solve the issue of military spouse underemployment.

Impact and Future Aspirations

Since its inception, Squared Away has significantly addressed the employment needs of military spouses by creating a supportive environment where they excel as executive assistants. This role perfectly aligns with their inherent strengths, offering them not just employment but a path to professional growth. As executive assistants, they bring their unique skills to the forefront, demonstrating the significant contributions they can make in the corporate world. Looking to the future, we have committed to expanding our reach and continuing to champion the employment of military spouses. This endeavor is not just about job creation; it’s a movement towards a more inclusive and diverse workforce, recognizing and embracing the exceptional abilities of military spouses in various industries.

Conclusion

In conclusion, the journey of military spouses in the workforce is one of untapped potential, resilience, and remarkable skill sets. Through the inspiring example of Squared Away and our founder, Michelle Penczak, we see a powerful model for how businesses can tap into this extraordinary talent pool. As we continue to advocate for and leverage the unique strengths of military spouses, we not only enhance the fabric of our workforce but also uphold a commitment to inclusivity and diversity. The story of military spouses in the workforce is not just about overcoming challenges; it’s about recognizing and harnessing a wealth of skills and perspectives that can drive innovation and success in any organization.

Maximizing Your Productivity: Leveraging the Power of ChatGPT as You Get Squared Away

Thu, 27 Apr 2023 11:20:32 GMT

Using ChatGPT to Improve Executive Assistant Productivity: Frequently Asked Questions

As Chief Executive Assistants at Squared Away, we are always looking for ways to optimize our workflow, improve our productivity, and better serve our clients while working remotely. One tool that can be extremely helpful in achieving these goals is ChatGPT, a powerful AI language model that can assist us in a variety of ways.

Here are some of the ways that ChatGPT can be a great tool to implement with your assistant:

Automated Responses: With ChatGPT, you can easily create automated responses to common client inquiries, saving you time and allowing you to focus on more complex tasks. For example, if a client asks about your services, you can share a saved blurb automatically. To take this a step further, consider adding basic automations into your business, such as automated email replies, social media messages, and hiring processes.

Content Creation: ChatGPT can also be used to create content for social media, blog posts, and other marketing materials. Simply input a prompt or topic, and ChatGPT will generate a response that you can edit and refine as needed (by your assistant!) . This can be particularly helpful if you’re working with a in a niche industry and need to quickly create content that speaks to the target audience.

Research Assistance: Another great use case for ChatGPT is as a research assistant. If you need to quickly find information on a specific topic, you can input your query into ChatGPT and receive a response that provides relevant information and sources. Your assistant can dig deeper into this topic through the use of ChatGPT; send them your intial findings and let them handle the rest. This can save you time and allow you to provide more value to those you serve.

Language Translation: ChatGPT is capable of translating text from one language to another, which can be extremely helpful if you’re working with people who speak different languages. You can input a message in one language and receive a translated response; we recommend looping your assistant into email threads where differing languages are in play and they can summarize the email content for you in your preferred language.

To sum this all up — ChatGPT can be a great tool for your assistant to optimize their workflow, improve their productivity, and better serve you, our clients. Give it a try and see how it can help you take your assistant relationship to the next level!

Save Money on Support During a Recession

Fri, 02 Dec 2022 11:20:29 GMT

Outsourcing and Fractional Support During a Recession: Frequently Asked Questions

We’ve all been seeing and hearing the dreaded whispers of an economic recession. Preparing ahead of time is the best way to ensure that you and your business are fully supported, even amidst the scariest economic episodes.

Fractional support such as finance, human resources, and executive assistants are some of the best ways to keep your business costs lean. Not only are you avoiding the financial burden of hiring an employee, but you are gaining more flexibility and options when it comes to these roles.

Benefits to Outsourcing:

Gain the support you need without the burden of employee salaries and benefits
Avoid layoffs on your team
Stress less about providing options for your core team

Do Your Homework:

Make sure you look into highly-rated and recommended fractional support
Know your asks — outline the role and be prepared to answer clarifying questions
Ask about their company recession plans; how do they plan to support their internal team without impacting you as a customer?

What to Outsource:

Admin support
Accounting
HR & Payroll
Personal tasks (ie grocery shopping)

During rough economic times, we tend to take on more as individuals because we think: 1) I can do it better and faster 2) this will save me money in the long run. However, the biggest questions we should be asking ourselves are ‘what is my time worth?’ and ‘what is the value-add of me delegating ___?”

A recession oftentimes leads to personal burnout, added stress, and an overall depressing attitude. Outsourcing is your first line of defense to protect you & your company so that you can operate long term not short term.

How to Support a Military Spouse

Fri, 11 Mar 2022 11:20:28 GMT

How to Support a Military Spouse FAQs

Have you ever wondered why military spouses are some of the toughest, most resilient people you know? Furthermore, have you wondered why they may be that way? We’re here to pull back the curtain and share what the wave of deployment emotions look like for many of our fellow military spouses.

We want to help with the understanding of what this cycle may look like so we can bridge the gap between wanting to be supportive and not knowing the best way to do so.

Let’s start with an honest fact, as Military Spouses, we know the good intentions that come with asking us what our spouses are doing, but please avoid doing so. If we feel like sharing, we will, but most of the time we won’t.

As a military spouse, compartmentalization is how we get through each day. If we’re at work, we want to focus on work, not the fact that our spouse is gone, and if we’re spending time with friends, we likely want to distract ourselves from all that is going on with our spouses (especially because we likely don’t know where they are at the time). We will take time to process what we are experiencing, but we often prefer to do that alone or with people who get it (our military spouse sisters and brothers).

An Honest Look at the Emotional Cycle of Deployments

These are the phases that many military spouses go through when their spouses deploy. A deployment is a period of time when a service member is sent to another location to serve their country. It is common for this location to be a potentially dangerous place, and a place where we will have little contact with them throughout the extent of their deployment; we’re often lucky if they can connect to WiFi or make a phone call while deployed.

Stage 1: Anticipation

This hits wen our servicemember is notified that they are deploying; they receive orders to deploy. This means that our service members have an appximate day and time that they will be deployed along with a relative location.
This can cause tension at home with some feelings of resentment. As a means of protecting ourselves emotionally, we tend to start distancing ourselves from each other.

These feelings can be especially taxing if our spouse is deploying with hours or a day’s notice; the first 3 stages are happening in a short period of time, causing emotional exhaustion.

Please don’t ask when they’re leaving, this is confidential information that can impact OPSEC (Operational Security), remember the phrase “Loose Lips Sink Ships?” This is what it’s relating to, we can’t share dates or locations of troop movements.

Stage 2: Detachment/Withdrawal

Leading up to the deployment, our service member is usually very busy preparing to leave and isn’t around much. Many people feel ready to, “just get it started” or “rip the band-aid off” as a means of starting the deployment so they can begin the countdown to homecoming.

This is a hectic time and it also impacts children in their ways, we generally see them acting out because of the confusion and changes they are facing.

Stage 3: Dark Day

The day the service member leaves is usually the day where it all hits the spouse; many spouses choose to take a day to feel sad and grieve the lost time with their spouse and allow all of their emotions to hit them.

It feels like a release of emotions when they leave because the figurative band-aid has been ripped off and they have finally left. The lead-up to them leaving is a high-stress time and we often don’t take time to stop and process what we’re feeling .

Stage 4: Finding a New Normal

The first month+ of deployment is when the spouse and family hit a wall that is known as emotional disorganization, which is a massive disruption to your family’s routine causing emotions to be everywhere.

As the spouse managing the homefront, we naturally have more responsibilities to handle, and our children sometimes regress in their progress with any milestones for their age (such as sleep schedules).

This first month or so sets new routines as our family finds our new norms. We ask that you give us grace as we work through this new routine.

Stage 5: New Routine Setting

Once the first month (or so) has passed, and we have begun to find our new normal, it’s often the time when we feel we’ve hit our confident and independent stage. It takes some trial and error, but we often surprise ourselves with how well we’re managing things at home.
It may take our kids a bit more time to adjust (and vice versa). Everyone deserves to give themselves and others grace through this period of time.

While we may look like we have it all figured out, it is not uncommon for us to have setbacks during the new routine setting stage, there will be difficult days, especially if we hear an update on the news that may pertain to our spouse, or if we don’t hear from our spouse for a few weeks.

Please refrain from asking where our spouse is or how they are. We know you mean well, but this can bring up a range of emotions. If we want to share how we’re feeling, we will reach out.

Stage 6: Prepping for Homecoming

Usually about a month before the anticipated end of the deployment, we begin preparing for homecoming. There is usually a wide range of emotions that come through this phase; from excitement to anxiety and some fear about what it will be like when they’re home. We are usually feeling anticipation and potential hesitation for what reintegration will look like. Reintegration is when our spouse is home from deployment and we’re working through finding our family’s new norm.

Our kiddos usually look to us (as spouses) for emotional cues. If we have young kids, it’s common for us to not discuss that we’re expecting our spouse home soon as a means of keeping the “norm” going as long as possible. Every family knows what’s best for them.

There are times when homecoming is pushed out until an unknown date due to the needs of the deployment changing. When they’re home, we will let you know when we’re ready. Please don’t ask what the date is, we likely don’t know, and even if we do, it’s going to change multiple times. They’re not home until they’re in our arms again.

Stage 7: Homecoming

This date will likely change several times, and once a date is finalized, the timing will likely also change many times.
The first 24 hours/couple of days generally feels like a honeymoon where the excitement of them returning has emotions running high, and we’re physically relieved to just have them back in our home again.
During the initial hours and days of homecoming, our kiddos may be apprehensive and unsure about their parent returning, it may take them longer to warm up to their parent being home. If you see/interact with our kids during this time, please know that they’ll find their new bond with their service member parent in time.

Stage 8: Reintegration

This relates to finding a new normal at the beginning of deployment. Now that our servicemember is home, our family’s responsibilities need to be re-divided; this can cause some friction. Generally after a few weeks to a month, our family’s new normal is found. This is a normal part of the process of our service member returning.
This can be stressful because we have all become accustomed to our spouse not being home. While we are happy they are home, this is a massive adjustment for both ourselves, our service members, and our family. It’s not uncommon for military spouses to take a period of time off or be a bit more split-minded during this reintegration period. It will end soon, and if we’re putting more focus on our family during this time, know that it’s for the best long-term.

We share these phases of deployment to identify the range of responsibilities, emotions, and experiences military spouses and service members face. This is usually occurring in conjunction with our jobs and any other life responsibilities we have. Please give us grace and know that if we need time off/time to process/are going to be slow to respond that day, we will let you know.

How Can You Support a Military Spouse?

We understand that there are curiosities about how we can provide support to military spouses and what you can do to support them. Holding space for us, sharing that you’re here for us, and giving us grace is one of the best ways to support us . Oftentimes we just need to be reminded that we don’t need to have it all together all the time.

If you’d like to do something a bit more tangible for a military spouse, here are a few ways you can provide support:

Sending a meal gift card (Doordash, Ubereats, Starbucks, etc)
Sending flowers with an encouraging message
Sending gift cards (self-care often goes to the wayside when we’re in the thick of deployment)
A handwritten letter/card letting the spouse know that you are thinking of them
Sending a personalized gift (think Etsy type items i.e. candle, card, water bottle)
Send a childcare voucher/gift card or set up childcare (if you know the spouse in this capacity) so they can have a few hours to themselves
Offer to have them (and their children) over for dinner one night, but ensure they know they can postpone it if they don’t feel up for it that day. Deployments can change at a moment’s notice and there may be times when we need to just focus on getting through the day.

The bottom line is, just be there the way you likely already are. Please leave it up to us to let you know if we’d like to talk about it, and know that we’re doing our best if we’re in a deployment season, so a little grace goes a long way.

Squared Away’s 2021 Holiday Gift Guide

Wed, 01 Dec 2021 11:20:27 GMT

Honoring Our Veterans

Thu, 11 Nov 2021 11:20:26 GMT

Squared Away is committed to employing Military Spouses and Veterans. Our core mission is to employ military spouses while giving people their time back. We are honored to highlight Veterans who are clients and teammates of Squared Away.

Squared Away Clients

Andrew Weins, Army Veteran

Andy Weins has built a reputation through his no-holds-barred teaching style, which inspires immediate and transformational action. No frills, no fluff. This business has grown from a two-man backyard operation to a nationally renowned multi-faceted enterprise at a rapid pace. As an adviser and public speaker, he has helped thousands of leaders and entrepreneurs unleash their full potential and achieve unparalleled success. A proud US Army Veteran, military career counselor, and Master Resiliency Trainer, Andy brings his battle-tested experience and expertise to business leaders and professionals everywhere.

Andrew Lundquist, Air Force Veteran

Andrew Lundquist is the CTO of Never Settle ( neversettle.it ) a Marketing and Web Development Agency.

Andrew graduated from the US Air Force Academy in 1999 and served in the Air Force until 2005.

Squared Away Chief Executive Assistants

Megan King, Air Force Veteran

Megan served in the Air Force as an Air Traffic Controller, she is now a Chief Executive Assistant with Squared Away.

Brianna Arcediano, Navy Veteran

Brianna served in the Navy as a U.S. Navy Hospital Corpsman for 7 years. Brianna is now a member of the Squared Away team as a Chief Executive Asssitant.

Kristi Santiago, Air Force Veteran

Kristi is based out of Ocean Springs, MS. She has three kids, 14, 10, and 6. Kristi joined the Air Force after graduating high school. She was a dental hygienist and loved her job! Kristi separated from the Air Force once she became a mom. She then married into the Air Force, and her husband is now retired. Kristi used her GI Bill to get a couple of Associates Degrees and her Bachelor’s degree. Kristi shared, “I love working for Squared Away and the love and focus they put on military spouses and veterans!” Kristi is now a member of the Squared Away team as a Chief Executive Assistant.

Morganne Cook, Army Veteran

Morganne served as a Logistics Officer with 3rd ID stationed out of Fort Stewart, GA. Morganne shared, “Happy Veteran’s Day to all my brothers and sisters in arms!” Morganne is now the Training and Transition Team Manager and a Chief Executive Assistant within Squared Away.