How the Military Kept Trying to Cancel My Career: Why I Started Squared Away

Let me set the scene.

You meet someone in uniform. He’s got the jaw, the manners, the whole thing. You fall in love. You get married. It’s all very adorable.

Then somebody hands you a binder, a base map, and a moving truck, and quietly informs you that your career is now the family’s least important asset. Congrats, you played yourself.

I’m Michelle. My husband Sean is a Marine. I have 2 boys, a frankly concerning tolerance for chaos, and a resume that used to read like a crime scene. In 2017, I started Squared Away because I was tired of watching capable women get flattened by a system that was never built for them.

Let’s talk about it.

The Milso Career Experience: A Horror Film in 3 Acts

Act 1: You get a job. You’re good at it. You’re thriving.

Act 2: The orders drop.

Act 3: You’re unpacking boxes in a state you’ve never visited, googling “jobs near me,” and explaining to a stranger why you’ve had 4 employers in 6 years. “Was it commitment issues?” No, Brenda. It was the federal government.

If you’ve lived this, you know the hits:

• You move every 2 to 3 years, so you’re permanently the new girl with no network.
• Your license or certification doesn’t transfer, so you get to pay to re-qualify for the job you already know how to do.
• Employers see “military spouse” on a resume and hear “flight risk.”
• Deployment hits, you’re suddenly solo-parenting, and a rigid 9-to-5 in an office becomes a cute little fantasy.
• And the resume gap. Oh, the resume gap. The thing you have to “explain” like you spent those months in witness protection instead of holding an entire household together with duct tape and spite.

Here’s the part that makes me genuinely feral: none of this is a talent problem. Military spouse unemployment has been parked around 20% for basically forever. Not because milsos can’t work. Because the traditional job market was built for people who stay in one zip code and have a backup parent on speed dial. That has never been us.

Meanwhile, In My Own Life

I was that woman. I had the skills. I had the drive. I also had a husband who could be told to leave the country with roughly the same notice as a brunch reservation.

I watched my own career do the slow fade. Start something, build it, pack it in a box, start over, and then do the whole thing again. Each move chipping off a little more of the person who existed before I became somebody’s “dependent.” Truly the most romantic word the military could have picked. Nothing says I love you like being officially classified as a liability.

And I kept looking around at the other spouses in my orbit. Brilliant women. Former teachers, project managers, marketers, operators. People who could run a fundraiser, a household, and a deployment at the same time without breaking eye contact. Every one of them underemployed or unemployed for the exact same dumb reason. The map kept changing.

At some point the rage curdled into an idea.

So I Built the Thing That Should Have Existed

If the job couldn’t move with us, then the job needed to be the kind that didn’t care where we were.

That’s Squared Away. I started it in 2017 on one stubborn premise: hire the people the market keeps fumbling, and give them work that survives the next set of orders.

We’re a fully remote executive assistance company, and we intentionally hire military spouses, first responder spouses, and other overlooked talent. Our assistants support founders and leaders with the real work of running a business and a life. And because we’re remote, your job comes with you. PCS to a new state? Your laptop still works. Deployment season? You’re on a team that gets it, because we are it.

That last part matters more than anything else I could say. We don’t run on the lonely-freelancer model where you sink or swim by yourself. We run on what I call the beehive. Every client gets a dedicated assistant, but that assistant is backed by a whole team. Somebody’s kid spikes a fever, somebody’s spouse comes home early, somebody’s internet dies in the middle of nowhere, and the work still gets covered. Because nobody is doing this alone. That was the entire point. Nobody should be doing this alone. I sure was.

What It Actually Fixes

Here’s the math the rest of the workforce keeps getting wrong.

The same woman juggling 3 calendars, a sick kid, a cross-country move, and a grocery list entirely in her head is the most organized, unflappable operator you will ever meet. That is not a liability you tolerate. That is a superpower you fight to hire.

At Squared Away, the resume gap is not something you apologize for. It’s proof you can manage chaos. The constant moving is not instability. It’s adaptability with a change-of-address form. The skills you thought you had to abandon every time the orders dropped? You keep them, you grow them, and you get paid for them.

Skilled support for the leaders who hire us. Real, portable careers for the spouses who power it. Everybody wins, and frankly it is about time.

If This is You

If you’re reading this in a half-unpacked house, silently rehearsing your “please explain this gap” speech for an interview you don’t even want, hear me on this:

You are not behind. You are not too much. You are not a flight risk.

You’re exactly who we built this for.

Stop justifying your life. Start leveraging your talent.

Meet Michelle

Michelle Penczak is the founder and CEO of Squared Away, a fully remote executive assistance company she launched in 2017 to build portable careers for the people the traditional job market keeps overlooking. As a Marine spouse and mom of 2 who has run a household and a business solo through deployments, she built the company she needed, one that intentionally hires military spouses, first responder spouses, and other overlooked talent as skilled executive assistants. Under her hands-on leadership, Squared Away pairs each client with a dedicated assistant backed by a full team and earned the #297 spot on the 2023 Inc. 5000 list of America’s fastest-growing private companies. Michelle and her mission have been featured on CBS Evening News, Forbes, and Inc., spotlighting her advocacy for military spouse employment and the capable talent the workforce too often counts out.