From Grief to Grace: Tiffany McCawley’s Story

July 6, 2025

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


How to Support Military Families During a Government Shutdown
By Michelle Penczak October 8, 2025
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.
Lauren Cecora: Faith, Family, and the Postpartum Journey
By Michelle Penczak September 30, 2025
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.
Why AI Will Never Replace Virtual Assistants
By Michelle Penczak September 12, 2025
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.
Kerissa Frigo: Veteran Strength Meets Military Spouse Resilience
September 5, 2025
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.
August 25, 2025
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.
August 10, 2015 — The Day Everything Fell Apart | SquaredAway
By Michelle Penczak August 16, 2025
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.
Taylor Lingerfelt: Leading with Heart as a Military Spouse and Team Lead
August 9, 2025
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
August 4, 2025
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
July 27, 2025
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.
Military Spouses Make Great Leaders & Jessica Ryan Proves It
July 21, 2025
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.