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.