Going Back to School at 39: My Kids Cheered From the Rafters

Oct 20

4 min read

Updated: 2 days ago

Going back to school as an adult is rarely a straight line. Mine was a scribble — here's how I finally finished.

Jessi in a blue cap and gown hugging her husband on graduation day, both smiling

One month before my 40th birthday, I walked across a stage in a cap and gown.

At the time I was carrying a full course load, a full-throttle internship, a part-time late night bartending gig, two daughters in middle school, a couple of dogs, and — of course — my husband. If that sounds like a lot, it's because it was. I basically ran a small circus and moonlighted as a college student. I didn't have a true weekend for months on end.

A crowded bar strung with lights during Jessi's part-time bartending shift

Here's the part nobody tells you about "going back to school": it's rarely a straight line. Mine was more of a scribble. Like my handwriting.

I did a year of college straight out of high school that I was absolutely not ready for. Not even a little. That's actually how I fell into hospitality — sometimes the wrong turn is the whole map. A few years later I blindly knocked out a bunch of my generals in the most tumultuous way humanly possible. And then, third time's the charm, I went back again after quitting a job that really wasn't the right fit.

The Moment I Decided to Go Back to School at 39

It didn't happen in some dramatic, movie-montage way. It happened over a regular conversation with a coworker at the company that was wrong for me. We were talking about my future there, and she came right out and encouraged me to go to school.

She was right. I was trying to jam a round peg into a square hole, and I was going to lose my mind doing it. There's no amount of trying hard that turns you into a shape you're not. That last sentence could be the thesis of my life. So I stopped trying to fit — and started over.

Jessi's lacrosse star start smiling behind her lacrosse stick in a red Lacrosse jersey on the field

As you can imagine, that decision was not casual. We had a mortgage. Two car payments. And if you've ever tried to raise two kids, you already know: children are not a discount experience. One of my girls was a lacrosse superstar, traveling the nation to play her games. Guess who her traveling companion was? Going back to school with all of that on the books felt a little reckless and a lot terrifying.

My husband was awesome about it. Every single step of the way — right there. That kind of support isn't a background detail. It's load-bearing.

Finding My Happy Place + a Thicker Skin

This time I went back for an associate's degree in Graphic Design. I've always been a natural designer; what I needed was the credentials and someone to actually teach me Adobe instead of me fumbling through YouTube tutorials at midnight.

A row of playful ostrich characters illustrated by Jessi, one showing off its fancy shoes

That two-year program was genuinely one of the best experiences of my life. I loved my classes. I adored my instructors — and a few of them were younger than me! I was doing what I loved, and there's a specific kind of energy you have when you find "the thing."

Commercial break! Free planner stickers for the Squad. Get my stickers button, with a blue Madge’s Misfits monster

A graphic design class branding project for New Glarus Brewing with letterhead, business cards, and a Spotted Cow Ale bottle

I learned a lot about myself in those two years, mostly on critique days. If you've never had one: they can be brutal. It was like standing on the American Idol stage every single time. You pour your heart into a piece for a few weeks, and then the instructor picks it apart until there's nothing left. YIKES! I walked out of those days with a thicker skin than I walked in with — and honestly, that's a credential you can't put on a diploma. Another point for going back to school at 39.

A group of design students sitting around a table in a campus lounge with laptops and snacks

The best surprise was that I wasn't the only adult in the room. There were others of us who'd taken the scenic route, and it made for a better, warmer community than I ever expected. Turns out "non-traditional student" only means you have better snacks and better stories.

Two little voices

Jessi in a blue cap and gown on graduation day standing between her two daughters, all three smiling

I hadn't planned to walk at my graduation. My mom made a really big deal out of it — like huge. So I did it for her Christmas present. And I am so glad I did. The gift was truly mine.

You know how people tell you to picture the place where you were the happiest when stuff goes south? There is one little moment from that day I now call mine.

As the president of the college read my name, two little voices rang out from the rafters of the gymnasium:

**"THAT'S MY MOM!"**

My girls were 12 and 14. I couldn't even see their little faces from where I stood — just their voices bouncing off the ceiling of that massive gym. The president leaned over and asked me, "Are those your kids?!"

"I sure hope so!"

I cry writing this, to be honest. I have never been prouder in my life. Not only of the degree — of the fact that my girls got to watch me go after something hard and finish it. I got to show them, in real time, that you chase what you want even when it's scary, even when it's inconvenient, even when you're doing it at 39 with a full load and a bartending shift that same night.