After 30 Years, I’m Leaving My Job — And It Feels a Lot Like Being a Chicago Bears Fan
After three decades in education, I’ve decided it’s time to step away from the only professional life I’ve ever known. Thirty years of meetings, metrics, and mission statements. Thirty years of building systems, mentoring staff, sweating budgets, and putting out more fires than the Chicago Fire Department (and somehow with less overtime pay). Now, at 52, my wife and I are choosing something new: slow travel. We’re going to spend the next few years exploring the world — three months here, ninety days there — chasing meaning, rest, and maybe the best bowl of noodles in Kyoto.
And here’s the weird part: emotionally, this massive life transition doesn’t feel like a career change. It feels like being a Chicago Bears fan.
No, really. Stick with me.
If you’ve ever cheered for the Bears, you know that hope and heartbreak aren’t opposites — they’re co-stars. Every season starts with cautious optimism, usually based on something like a decent draft pick, a slightly improved offensive line, or a quarterback with charisma and exactly zero NFL snaps. You’re not delusional — you just want to believe. But then? The McCown years. The Cutler rollercoaster. The Marc Trestman era, which I still suspect was an elaborate prank. The 2006 Super Bowl, where Hester ran the opening kickoff back and then we… forgot how to football. The Trubisky experiment — bless his heart. And who could forget the Double Doink in 2018, a moment so heartbreaking and absurd that Bears fans now flinch anytime they hear two quick, consecutive metallic clinks.
The exact moment my trust issues began.
Leaving a long-term job is similar. At first, you focus on the opportunity — freedom, adventure, a chance to design life on your terms. But then doubt creeps in. Will I regret walking away? What if the money runs out? Will I still matter without a job title? It’s like watching your rookie QB throw a beautiful deep ball in preseason, only to fumble on the first snap of the real season. It’s not that you don’t believe — you’re just a little traumatized.
The truth is, I stayed in my job longer than I needed to. Just like Bears fans keep re-buying jerseys every August, I kept hoping the next school year would be “the one.” But over time, the spark faded. I didn’t want to coast to retirement out of fear. The endless Zoom meetings, Sunday scaries, inbox avalanches, and the relentless pressure to keep spinning a thousand plates finally wore me down. I didn’t want to look back at 60 and realize I had quietly accepted a life that no longer fit. That’s when I knew it was time to call an audible and run something new. Maybe even something fun.
So now, we’re preparing to sell the house, pack light, and set off on our first chapter of slow travel. Japan is likely the first stop, with France, Albania, and Morocco in the queue. Our dog’s even getting a passport — Meyli the Shih Tzu is a seasoned traveler in training, and arguably the most emotionally stable member of the household. We don’t have children, which means we can travel light, pivot quickly, and live a little unconventionally. No science fairs, no dance recitals, no mysterious PTA fundraisers. Just the open road (or train line) and a suitcase full of wrinkle-resistant pants.
Japan isn’t just a tourist stop — we actually found a way to stay for a full year. Thanks to my wife’s brilliant idea and a beautifully obscure immigration loophole known as the Cultural Activities Visa, we’ll be living in Japan while she studies traditional Japanese calligraphy. That’s right: the art of brush strokes, ink, and paper, performed with the same gravity and elegance one might reserve for writing a resignation letter to a terrible boss. She’ll be learning kanji, while I’ll be trying to learn how to order lunch without accidentally asking for a tire rotation.
We’ll be based in Osaka, or maybe Hiroshima — we’re still figuring out the details. I’ve read that Japan has the cleanest public restrooms in the world and also vending machines that sell hot corn soup. If that’s not worth a year abroad, I don’t know what is. I’m excited to explore grocery store etiquette, bowing angles, and possibly become emotionally attached to a rice cooker. Plus, Meyli is small enough to fit under a train seat and cute enough to get away with almost anything short of international espionage.
We’ve also spent hours researching travel health insurance, ATM fees, plug adapters, how to buy contact lenses abroad, and whether or not Japanese mail carriers will deliver to foreigners who look confused and wave too much. Turns out, they will — as long as you bow approximately 37% lower than you think you need to. We’ve set up our mail forwarding service, minimized our belongings, and donated enough stuff to Goodwill to open a pop-up shop.
This next chapter is both wildly new and deeply intentional. We’re not running from anything; we’re walking deliberately toward something that feels lighter, freer, and more human. I want to wake up in a place where I don’t already know how the day ends. I want to wander aimlessly on weekdays and master the art of not having a to-do list. I want to find joy in small moments — like discovering a hidden noodle shop or remembering what it’s like to sit quietly without checking Slack. I want to rediscover parts of myself that have been buried under Outlook notifications and never-ending strategic plans.
This also happens to be my very first article on Medium. I figured there’s no better way to launch a new life chapter than by sharing it — anonymously, publicly, and with just enough Bears references to alienate all non-sports readers. (Hi, Mom.) I’m excited, I’m nervous, and yes, a small part of me still checks Zillow once a week just to see if my old life is still listed at a discount. But mostly, I feel hopeful.
Because after all these years, I’ve learned that reinvention isn’t failure. It’s not disloyalty to the past — it’s courage toward the future. Being a Bears fan means learning to love the rebuilds, the restarts, and the ridiculousness. And so does being a person brave enough to say, “What if we just did it differently this time?”
And speaking of rebuilds — hope springs eternal in Chicago. The Bears hired Ben Johnson, the offensive mastermind who turned the Detroit Lions into an actual playoff threat. I mean, if Detroit can win playoff games, what even is reality anymore? We finally used real money to sign real free agents. We drafted smart. We look like, dare I say, a professional football team? I know it’s dangerous to feel this way. But as I stand on the edge of early retirement and a year in Japan, I feel the same cautious optimism I do every August: maybe this is the year.
It isn’t so bad rooting for these guys… lately.
Of course, I know it won’t all be perfect. There will be days when I’m homesick, when the yen-to-dollar math gives me a headache, or when I accidentally insult someone’s grandmother in a ramen shop. But I’ve spent decades doing hard things — and I’m finally doing something brave on my own terms. I’m ready to see who I am without a job title, without a commute, without a desk covered in sticky notes. I’m ready for the long game.
We may not know exactly what’s ahead, but for the first time in a long time, we’re not dragging ourselves through Monday mornings. We’re walking toward something that’s uncertain, yes — but also full of possibility. And if the Bears can build a real offense in 2025, then anything is possible.
If you made it this far, thank you. And if you enjoyed this, I’d love it if you’d follow me here on Medium. I’ll be sharing future pieces about early retirement, slow travel, and occasionally unhinged-but-heartfelt takes on sports, life, and whatever else I find in my carry-on. Who knows — maybe I’ll finally understand zone coverage and French cheese by the end of the year.
Go Bears. Go new beginnings.