She Built the Company She Wished Existed for Her (and 1,600 Other Military Spouses)

Michelle Penczak woke up on a Monday morning to no job. Seven months pregnant, managing a team at Zirtual, she discovered the entire company had vanished overnight, taking 400 jobs with it.

By noon that same day, she’d formed an LLC from her Hilton Head vacation rental countertop.

Before she started Squared Away, Michelle was a military spouse herself, moving every few years, sitting through interviews that went nowhere, watching her own career possibilities shrink with each PCS. That Monday morning, seven months pregnant with nowhere to go, she decided to build the company she wished had existed for her.

Today, Squared Away is an executive assistant platform that has employed over 1,600 military spouses. Michelle’s story shows what happens when you stop fighting constraints and start designing around them, exactly what we help people do at Please as we build the largest library that takes ideas to reality.

“What brings you to Jacksonville, North Carolina?”

Michelle knew her interview was over the moment she heard it. “Not the scenery, I assure you.” Then came the predictable pivot: “What does your husband do at the Marine Corps?” Suddenly the conversation shifted to V-22 Ospreys and deployment schedules. The callback never came.

She applied for months. Nobody wanted to hire her. Three to four years was “too temporary,” even though the average American worker stays at their job for 3.9 years. Her military spouse friends faced the same wall. The pattern repeated: great interviews, then silence.

Michelle realized nobody saw what she saw. Military spouses weren’t liabilities; they were the best problem-solvers she’d ever met. They figured out how to make things work in impossible circumstances. They built systems that traveled. They pivoted faster than anyone else because they had to.

So she built Squared Away around that truth. When clients worry their assistant might move, Michelle’s ready: “Your assistant trains your covering assistant. She’s not going off the planet. And frankly, she’s probably better at documentation and transitions than someone who’s been sitting in the same office for a decade.”

Spoken from true experience and road miles herself, having moved six times. Moving a family in itself is an incredibly complex undertaking, proving her point that “military spouses are the best figure-outers.”

You’re in Hawaii with a newborn. You have 13 East Coast clients across six nearly impossible timezones, and your husband just deployed.

For Michelle, her solution was to wake up everyday at 3am for two years straight. Living off of Venti caramel macchiatos and sheer determination, working Hawaiian predawn hours while her baby slept. Her clients never knew their assistant was emailing them from the middle of the Pacific Ocean in the dark. “Sponsored by every caffeine product out there,” she jokes, but it wasn’t funny at the time.

Here’s what those brutal mornings taught her: constraints aren’t problems to solve, they’re the design principles. She couldn’t change the time zones. She couldn’t make her husband not deployed. She couldn’t stop being a military spouse. So she built a company that worked because of those realities, not in spite of them.

Then Shane, her client-turned-co-founder, said the magic words: “I need you to scale. I need more of you.”

She was exhausted but ready. Those 3 AM Hawaii mornings had accidentally created the operating system for a global company. She made her first hire in July 2017. By December, she had 28 military spouses on the team. Today, there are 438 active assistants and more than 1,600 total who have worked for Squared Away.

Michelle has a secret talent most people don’t know about. She’s an incredible crafter who spends weekends with glue guns and glitter. Same principle every time: take chaos, make something that works.

“AI can write you beautiful itineraries and templates,” Michelle says. “But can it get on a phone and have somebody hand-walk a wheelchair out of the Grand Canyon for $20 for your friend who is paralyzed?”

AI tools could map routes and suggest vendors. They could optimize logistics and generate perfectly formatted action plans. But they couldn’t negotiate with a park ranger, read the desperation in someone’s voice, or figure out how to make impossible things happen when the official answer is “no.”

Technology handles the heavy lifting. Michelle’s team leverages every AI tool available. AI organizes scattered screenshots, builds draft plans, suggests optimizations. But clients pay for the human who knows “urgent” means different things at 9 AM versus 9 PM, who reads between the lines, who makes magic when the algorithm hits a wall.

Asked to choose between spreadsheets or sticky notes, she picks sticky notes every time.

Skip the five-year plan. Here’s how to start your next venture from your current one this weekend:

□ Find your problem
For Michelle: “This isn’t fair.” The interview question that killed her chances. The qualified spouses who couldn’t get hired. The system that punished people for serving their country.

□ Use your constraint
Make it your design principle. Michelle had time zones, deployments, constant moves. She built a company that required those things to work.

□ Start now
7 clients. A laptop. Fury. You don’t need venture capital or a perfect plan. Michelle started from a vacation rental countertop while seven months pregnant.

□ Document everything
Even if it’s ridiculous. Waking up at 3 AM in Hawaii is absurd (until it becomes your competitive advantage).

□ Find one believer
Someone who says “I need more of you.” Shane gave Michelle permission to scale. Find your Shane.

□ Build as you go
Michelle’s advice for military spouses applies to everyone: “Put a process in place. Your life will flip upside down every other day, but having a base for how you can make your career goals come to fruition is huge. You can always tweak it as you go.”

Best advice Michelle ever got: “Feedback is a gift. Don’t take it personally. Take it as a learning experience.”

Worst advice: “You need to do XYZ or you’re not going to succeed.”

Most annoying myth: “You knew what you were getting into when you got married.”

Spoiler alert: nobody knows what they’re getting into, you figure it out one impossible constraint at a time.

If Michelle could go back to that moment, seven months pregnant in a vacation rental, staring at the termination letter, she’d tell herself: “This is gonna be kick-ass moving forward.” She was right. That fire inside you never goes away, and if she had waited for better timing, 1,600 military spouses wouldn’t have meaningful work today.

At Please, we help you capture that drive the moment it hits. Screenshot the inspiration. Build the plan. Get help with the impossible parts. What problem makes you ticked off enough to build something today?

Follow Michelle here and Squared Away here.

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