You can plan all you want for retirement, but the change still hits you hard. If you spent two decades or more in Corporate America like I did, you get stuck in a certain routine. Someone thought you were useful enough to deserve a paycheck, and that job brings more than money: instant camaraderie, daily chats in the break room, those familiar conference calls. The routine also comes with built-in mentors and parental figures called managers.
Of course, not every manager is great—just like not every parent is. Cubicle life can be unpredictable. While you’re in it, make the best of it, but keep your eye on financial independence so you can leave the hamster wheel when the time comes. Don’t stay a corporate cog longer than you have to.
Work that’s “at-will” can be toxic, limiting, or boring, but it still eats up a big chunk of your life. Take it away and you suddenly have a huge gap to fill—roughly 45 hours a week, or about half your waking time. A few weeks into retirement, I found myself oddly romanticizing the flaws I’d left behind—even though I had a plan.
I thought getting my real estate license and shifting to full-time REALTOR would be the cure. Do I regret resigning? Not at all. But I still need to build new grooves: a fresh network of friends, colleagues, and partners.
I like the Blue Zones idea of “never retire.” I wrote years ago about Jiro Ono, who at 98 is still making world-class sushi. But working forever doesn’t mean staying under someone else’s thumb until your 80s. Corporations usually don’t keep you past your 60s—you’re more likely to be pushed out. Unless you’re in a tiny class of outliers, forget the idea of corporate work into your 60s and beyond.
Quitting a job, ditching the paycheck, managers-by-rotation, and endless meetings won’t destroy you. What will hurt is leaving one routine where you sat all day, only to replace it with another routine of doing nothing to grow or serve others. Instead of “never retire,” try “never stop being useful.”
If you can work on your own terms—like Jiro, staying useful and true to your values—that’s a life well lived. You won’t be 98 working for the company; you’ll be working for yourself.
The Arnold Schwarzenegger docuseries pushed a lot of this home for me. Arnold is nearing 80 and refuses to slow down. His simple advice: “Be useful.” He changed careers more than once—bodybuilder, actor, governor—and kept moving forward instead of dwelling on setbacks. Learn from mistakes and move on. As Ted Lasso says, be a goldfish.
Many high achievers come from difficult backgrounds, Arnold included. But he didn’t stay stuck in victimhood; he saw opportunity everywhere. That mindset helped me shape my post-retirement plan: a complete career makeover on my terms. I’m my own boss now.
Real estate—property management, investing, and sales—is work I enjoy and can pour myself into. Financial independence gave me flexibility to prioritize family and time for myself.
As a family, we’re spending more free time serving others. Volunteering together builds character in the kids and benefits the community and our mental health. I’m also able to spend more time on rental home maintenance. This year I put more cash and effort into that side hustle than ever before; it’s easier without a desk job to juggle.
I still have work to do. Old corporate grooves are deep and take time to fade, but they’re wearing down. I can be a better husband, father, son, brother, neighbor, and friend. If I use this freedom to grow—exercise more, learn, read, and yes, write—I’m hopeful I’ll avoid regrets.
I’m building a community, too. My wife and I joined a pickleball league—fun and social. I’ve got a long list of home projects I want to tackle, and I expect gardening will become a bigger part of my life.
Am I bored sometimes? Sure. Retirement boredom sneaks up on you. Starting out in real estate is tough right now: the market is slow, mortgage rates are over 7%, demand has softened, and supply is tight. But I’m using this lull to study the market, exercise, and network. No video games, no endless movies, and no sleeping past 7 a.m.
Bottom line: I’m very content with this at-will kind of work.
By the way, in this blog I define retirement as leaving at-will employment—that is, a job where you can be fired for any reason. You can still “retire” and keep working. Options are endless: volunteering, part-time work to top up Social Security, caring for family, running a small business, gardening, or even writing a blog.