How Michelle Penczak and Squared Away Are Empowering Military Spouses Through Entrepreneurship and Community Support

In a world where military families quietly carry the burden of constant relocation, disrupted careers, and emotional strain, Michelle Penczak has built a company that flips that script.

On this episode of the Security Halt! Podcast, host Deny Caballero sits down with Michelle Penczak, the powerhouse entrepreneur and founder of Squared Away, to explore how she turned personal frustration into a mission-driven business that provides military spouses with meaningful careers, financial stability, and—perhaps most importantly—fulfillment and identity.

From Frustration to Leadership: Michelle Penczak’s Military Spouse Entrepreneurial Journey

The military lifestyle often demands that spouses put their careers on hold. Michelle knows this firsthand. After being rejected from countless jobs simply for being a military spouse, she realized she wasn’t alone in this struggle.

Despite being highly qualified, potential employers viewed her as temporary—a liability due to frequent family transitions and relocations. But instead of accepting that narrative, Michelle wrote her own.

She began working as a virtual assistant, honed her skills in business operations and talent management, and eventually launched her own LLC while her husband was deployed and she was pregnant. Even after moving across the world to Hawaii with a newborn, Michelle continued to scale her growing business.

The Birth of Squared Away: Empowerment Through Remote Work and Community

The turning point came when Michelle realized the issue wasn’t hers alone—it was systemic.

Military spouses across the country were facing the same career barriers. That spark led to the creation of Squared Away, a company that now matches military spouses with remote work opportunities tailored to their unique lifestyles and professional talents.

“I knew we didn’t need a handout—we needed a chance,” Michelle shares.

Squared Away isn't just a business scaling tool for clients. It’s a community support initiative. It connects highly capable, often-overlooked individuals with companies that need skilled virtual assistance, creating a win-win for both.

By tapping into a demographic that includes former teachers, bookkeepers, nurses, and project managers, Squared Away offers American businesses a smarter alternative to outsourcing overseas.

More Than a Paycheck: Reclaiming Identity and Purpose for Military Spouses

One of the most powerful themes in this episode is empowerment. For many military spouses, frequent moves and childcare challenges make maintaining a traditional job almost impossible. Michelle’s model addresses both the economic and emotional toll this takes.

One spouse told her,

“You gave me back a piece of me I didn’t know was missing.”

This isn’t just about income—it’s about identity, leadership, and purpose. Squared Away helps military spouses reclaim their voice, pursue their passions, and contribute professionally without sacrificing family life.

Community, Collaboration, and the Future of Military Entrepreneurship

Michelle’s journey is a shining example of resilience, collaboration, and the power of entrepreneurship within the military community. Rather than viewing spouses as charity cases or “dependents,” her model acknowledges them as highly talented professionals eager for opportunity.

Squared Away is also leading the way in how companies can recruit and retain dedicated, adaptable talent—while contributing to military family wellness and community empowerment.

As host Deny Caballero, a Green Beret and advocate for veteran support, points out during the episode:

“Entrepreneurship and leadership within the military community is about building solutions, not waiting for one.”

Listen, Watch, and Support the Mission

🎧 Listen on Apple Podcasts:https://podcasts.apple.com/us/podcast/security-halt/id1651691745

🎧 Listen on Spotify:https://open.spotify.com/show/2HqBOP3SF0VPPxsgdZZSuM?si=c04f6a449ab2429a

📺 Watch on YouTube:https://www.youtube.com/channel/UC45ILXVe5hMcs3A5k9Ln-cg

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