How Hamilton and the GI Bill Got Me Through Law School at 45

Life Experience: The Unexpected Legal Superpower

Earned smugness. Author’s pic

Let’s get one thing out of the way: starting law school at 42 isn’t for the faint of heart. Graduating at 45 while maintaining a punishing writing schedule of seven articles a week and producing two video segments every seven days? That’s either the mark of madness or mission.

Somewhere between Federal Courts and editing B-roll for a Ukraine war update, I realized: I wasn’t just doing law school, I was surviving it. Thriving in it, even. But it came at a cost, one I’m now proud to talk about, and maybe even brag about a little, if only to help another non-traditional student think: Maybe I can do this too.

Life Experience: The Unexpected Legal Superpower

I didn’t come into law school as a blank slate. I’m a veteran, a journalist, a content creator, and, on most days, a barely functioning human caffeine vessel who sees a VA psychiatrist once a month. But all of that life experience? It turned out to be an absolute superpower.

When we tackled torts, I didn’t need hypotheticals. I had real-world examples from military service and field reporting. When we analyzed contracts, I had years of negotiations under my belt, not theoretical, but bone-dry real.

And while some classmates were still learning how to juggle deadlines and caffeine without melting into the floor, I had already learned to function on four hours of sleep and Rip-Its. My past life gave me context. Fact patterns weren’t abstract; they were familiar. I could see the people behind the parties. I didn’t just apply the rule, I lived the consequences.

From the Military to the Law Library: Discipline Doesn’t Retire

There’s a phrase you hear a lot in the military: “Embrace the suck.” It’s a mindset, equal parts grit and gallows humor, that trains you to press on when your body is toast and your brain checked out two hours ago. It turns out that mindset is also perfectly tailored for law school.

I served in both the U.S. Army and the U.S. Air Force. Two different branches. Two different cultures. One shared foundation: discipline.

Military life instills a kind of internal structure that doesn’t leave you, even after you hang up the uniform. We’re trained to compartmentalize chaos, execute under pressure, and stay mission-focused no matter how foggy the objective might be. That translated beautifully into law school, where the enemy wasn’t insurgents or aircraft maintenance deadlines; it was volume. Reading volume. Writing volume. Pressure volume.

I approached every week like a field operation. Monday through Sunday was mission planning, execution, and recovery. I had schedules, fallback plans, and contingencies for when life inevitably went sideways, which, in law school, is about every other day.

I was like a Goddamned General Patton, slicing up my days into 6-hour chunks: 8 AM to 2 PM school. 2 PM to 8 PM writing and consulting. 8 PM to 2 AM video work. 2 AM to 8 AM sleep and personal hygiene.

And when things got hard, and they did, I relied on that military muscle memory. You see, motivation has an expiration date, and when motivation ends, discipline must take its place. I didn’t rely on inspiration. I relied on structure. Law school is a war of attrition, and veterans know exactly how to endure.

So while my classmates were learning how to “push through,” I already had. Repeatedly. On deployments. In foreign countries. Under stress that made a civil procedure final exam feel like a mildly annoying DMV visit.

Law school didn’t just reward discipline, it demanded it. And thanks to my service, I came prepared. Boots polished. Mind sharp. Mission clear.

The Writing Gauntlet: Law School Meets Journalism

I’ve written professionally for years. But nothing, and I mean nothing, prepares you for the soul-grinding pace of maintaining a content business while briefing cases and writing memos in law school simultaneously.

Seriously… If there’s nothing else on my tombstone, let it say, “Dude could write, a lot.”

I was writing so much original content that even AI bent the knee. It’s my biggest superpower: I can put words together in my head without friction. If it’s any consolation, I’m quite bad at math. Proof, perhaps, that the universe strives for equilibrium.

Every week during law school, I pushed out seven (7) polished, reported articles and two fully produced YouTube videos. In that same week, I’d crank out case briefs, client letters, or memoranda on everything from intentional torts to zoning regulations. Deadlines didn’t just loom, they overlapped, collided, and laughed maniacally while I chugged my fourth cup of coffee, Excedrin, and Red Bull at 2 AM.

There were nights I’d finish a Substack piece at midnight and then immediately pivot to writing a 10-page analysis on whether a unilateral mistake voids a contract under Michigan law. (Spoiler: it can, but only under very specific conditions.)

But I kept going. Because that writing tempo? It wasn’t actually a burden. It was how I knew I was still alive.

Author’s pic

Hamilton: My Spirit Animal with a Quill

In my final semester, I hit a wall. I was exhausted. Not just tired, existentially depleted. And then, like a lightning bolt wrapped in colonial hip-hop, Hamilton happened.

I had somehow avoided watching Lin-Manuel Miranda’s Broadway phenomenon until my 15-year-old daughter sat me down, hit play on Disney+, and said, “Just trust me.”

I didn’t just like it, I saw myself in it.

Alexander Hamilton, the immigrant outsider who wrote like he was running out of time? The lawyer who fought in a war, helped shape a nation, and authored the bulk of The Federalist Papers before 40? That guy wasn’t just my historical crush, he was my coping mechanism.

Hamilton didn’t wait for perfect conditions. He didn’t whine about burnout. He just kept writing. And writing. And writing. It gave me a weird sense of peace. If he could churn out volumes while dodging musket balls, I could push through a durable power of attorney for finances while dodging burnout.

Whenever I felt like I was drowning in legalese and deadlines, I’d play “Non-Stop” on repeat and channel that same relentless, almost reckless, pursuit of excellence.

When the GI Bill Taps Out

Law school isn’t cheap. And unless you’ve been blessed with a fairy god-scholarship, you’re going to feel it. Hard.

The GI Bill, God bless it, was my lifeline. But like all good things, it had an expiration date. In my case, it ran out one semester too soon.

Cue the panic.

Suddenly, I was scrambling, applying for state veterans’ benefits, tapping into my savings, even selling some of my lesser-used video gear just to cover textbooks. It was humbling. I had done everything right, planned meticulously, and still got caught short.

But here’s the thing: veterans know how to adapt. We improvise, we overcome, we MacGyver our way through financial minefields.

I found the funds. Barely. I finished what I started. Because the mission doesn’t end until you walk across that stage. Or in my case, finish your last final with shaking hands and a half-eaten protein bar in your pocket.

Age Isn’t a Limitation. It’s an Edge.

Here’s what no one tells you: being a 45-year-old law student is an advantage, if you know how to wield it.

I wasn’t here to impress professors or socialize during happy hour. I was here for the law. I showed up prepared, not because I wanted a gold star, but because I had to; this was my second act, not my warm-up.

I understood nuance better. I knew how to communicate like a grown-up. And while my classmates were memorizing outlines, I was thinking three steps ahead, asking how this rule would play out in a courtroom, in front of a real client, with real consequences.

Sure, I couldn’t pull all-nighters like I did at 22. But I didn’t need to. I worked smarter. I brought discipline, perspective, and grit to a game that often rewards raw endurance.

It’s like my platoon sergeant once told me, “O’Donnell, you’re never going to be the strongest or the fastest. But you can be the toughest.”

Law school didn’t make me a lawyer.

It revealed that I already was one on the inside.

The long nights, the Hamilton binge sessions, the GI Bill hustle, the writing tempo that would scare a speed typist, it was all part of the same arc. An arc that started with a belief that maybe, just maybe, I had more to give the country.

The nation is in a bad place right now. And even though lawyers get a bad rap, it will be lawyers (and maybe a small civil war) that save the United States.

To the non-traditional students out there, the ones juggling kids, jobs, mortgages, and dreams, listen closely: you’re not behind. You’re just running a different race. And when you cross that finish line, you’ll have something your classmates don’t: scars, stories, and the kind of resilience that no bar exam can shake.

In the end, being older didn’t hold me back.

It made me dangerous.

I graduated Cum Laude, with honors, in April 2025.

And to quote Hamilton — because how could I not — “I am not throwing away my shot.”

Not then. Not now. Not ever.

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