So much for the idea that time slows down in retirement. It’s been nine months since I left my corporate cubicle job last spring, but it doesn’t feel that long at all.
I had a long list of practical tasks to handle before my last day—some of which I’ll cover in this overdue post. There have also been unexpected adjustments. It turns out it’s not just tactical things like where to invest or how to make money (no, not just the NerdWallet stuff)…
As a newly minted retiree (retired from a career, not from being useful!), I’ve found there are real psychological shifts to get used to. Kids love the freedom of summer vacation. Adults, though, often get stuck with a nagging question: “Shouldn’t I be working now? Shouldn’t I at least look busy Monday–Friday like everyone else?”
Oy.
Even though I’d already started the process of getting my real estate license last summer, it was still hard to let go of the identity I’d built over decades as a slow-climbing middle manager. I knew staying busy was part of the cure, but I didn’t want to fill my days aimlessly just to avoid the root issue.
Instead, I learned I need to keep working toward a sense of purpose and look forward—rather than second-guessing that glorious resignation, especially when the paycheck rhythm disappears and the bank balance doesn’t instantly refill.
Early retirement brings varying levels of Cubicle FOMO (fear of missing out), depending on how long you’ve been on the hamster wheel. I suspect the younger you are when you retire, the less FOMO you feel. The longer you slog away, the more FOMO builds—until you either decide never to retire or you get pushed out with a sheet cake.
Don’t laugh, but I’ve found a great hobby in pickleball. My wife got into it last fall, and I’ve been playing twice a week with her and some neighborhood friends ever since. Competition is real but friendly. No injuries yet. I’m burning calories and giving my ankles the most workout they’ve had since high school tennis. Once a skeptic, now a convert—I can wholeheartedly recommend it.
Another good fix: side hustles. The real estate market is still tough with rates around 7%. There aren’t enough deals for all the agents out there, and only so many continuing-ed classes I can sit through before I lose my mind about lead paint.
So last month I added a new string to my bow and signed up on Thumbtack as a handyman. I love houses and working on them, so why not swap toilets and dodge sparks while changing people’s light fixtures? After spending January rehabbing a friend’s rental (two toilet swaps plus a stack of other projects), I felt ready to try being a mini-general contractor and general “doer.”
Thumbtack is a slick platform. They’ve been around long enough to feel established and they fit the gig economy well. I’d recommend it for anyone handy with tools, TV mounting, or personal training. If you sign up through my referral link, I’ll get a small bonus. Thanks!
To stay active and useful, my wife and I take two or three walks a week to our nearby Starbucks for an overpriced coffee—and I don’t feel guilty about it. Those stops are nice breaks from projects at home (like the new slide-out kitchen shelves—very satisfying).
Having a decent nest egg doesn’t automatically mean you can retire early. I nearly freaked out when I realized our income wasn’t keeping pace with expenses. Part of that was my own incomplete planning. Cash flow matters a lot in retirement, especially if assets are tied up in real estate or employer retirement plans.
Dealing with health insurance on the exchange was intense. I didn’t realize our lower income wouldn’t lower our premiums until 2024—seven months later. Whoops. Thankfully, as of January 1 our premiums dropped. I expect they might rise again once I start earning on Thumbtack and from real estate. If you plan to retire mid-year and get coverage through the exchanges, don’t count on lower premiums right away.
I also shifted some of our post-tax Vanguard investments into dividend stocks. To be clear: I don’t advise early retirees to rely on individual stocks. These holdings are only about 6% of our net worth, and I still get nervous when big names have a rough day. But moving toward dividend payers plus the lower exchange premiums boosted our monthly cash flow enough to put us back in the black earlier this year. We’re also expecting a sizable IRS refund for the months I was still employed in 2023—enough to cover some overdue exterior house projects this spring.
Quick tax tip: read about tax-loss harvesting before you start trading in your post-tax account. If you retire mid-year, it’s especially useful. You can deduct up to $3,000 in post-tax investment losses per year and carry any extra forward to future years.
One cure for Cubicle FOMO I almost forgot: staying in touch with former coworkers. I have three or four people from my working days with whom I keep monthly lunches or phone calls. I enjoy the camaraderie, and they remind me how glad I am not to be stuck in that old job.
Until the company Taylorists are shown the door, I honestly don’t see any mental or physical upside to enduring the toxicity of big corporate “healthcare.”
Coming soon: a deep dive into the latest on the Airbnb experiment. Since my last post, the market has become flooded with well-meaning hosts, creating an oversupply of rentals and a shortage of affordable housing in vacation towns. That’s a real pickle.