
So much for the notion that time slows down in retirement. It’s been nine months since I quit my corporate cubicle job last spring, but it doesn’t feel nearly that long.
I had a laundry list of adjustments to make leading up to my last day as an at-will employee: tweaks and such that I’ll cover here in this long-overdue post. There have also been some unanticipated adjustments. Turns out, it’s not just tactical stuff like where to invest money or make money or any of that Nerd Wallet jazz…
Cubicle FOMO Is Non-sense (Or Is It?)
I’ve discovered as a newly minted retiree (that is, retired from a career, not from being useful!) that there are significant psychological adjustments to the new routine. Kids love a good old-fashioned summer vacation to do whatever they want. Grown-ups, on the other hand, tend to get grooved in pretty hard to that nagging feeling: “Shouldn’t I be working now, and at least pretending to do something productive Monday-Friday while everyone else is at work??”
Oy…!
Although I had already set in motion my plan to get a REALTOR’s license last summer, it was still a difficult adjustment to detach from the identity I’d built up over decades of working as a (slow) ladder-climbing middle manager. I knew the remedy was to stay busy, but I didn’t want to just fill my days willy-nilly, avoiding the root problem.
Instead, I found that I need to keep chipping away at finding my purpose while looking ahead (vs. second-guessing that glorious resignation, especially when the two-week paycheck cycle rolls around and ain’t no cash popping into Wells Fargo.)
Early retirement comes with varying degrees of FOMO (fear of missing out), depending on how much of your life you’ve spent in the hamster wheel. I suspect the earlier that one retires, the less Cubicle FOMO there is. The longer one keeps slogging away, the more Cubicle FOMO, until you simply decide to never retire or get shoved out the door with a sugary sheet cake.
Remedies for Cubicle FOMO
Don’t laugh, but I’ve found a wonderful little pass-time in Pickleball. My wife got into the sport last fall and I have been playing twice a week with her and some great neighborhood friends ever since.
Pickleball competition is fierce but always friendly. I’ve sustained no injuries yet. The calories are burning and my ankles are getting the most work they’ve experienced since my high school tennis exploits. No longer a skeptic of the Pickle, I can now wholeheartedly recommend this sport.
Another solid remedy? Side-hustles! The real-estate market is still super challenging with rates hovering at 7%. There just isn’t enough volume for the legions of agents out there. And there are only so many continuing education classes I can handle before going bonkers about lead in paint.
So just within the past month, I added another feather to my cap and signed up on the Thumbtack app as a handyman. I reckon that I love houses and working on them so much, that I need to swap out toilets and narrowly avoid electrocution in the service of swapping out other peoples’ light fixtures.
After I spent the month of January rehabbing a rental property for a friend (i.e., two toilet swaps and a host of other projects later), I was ready to give it a go as a mini-general contractor and general “doer” of sorts.

Thumbtack is a pretty slick operation. They’ve been around a long time in Silicon Valley start-up years and are making good hay within the gig economy. I recommend it for anyone with chops as a handyman, TV mounter, or personal trainer. You can sign up on Thumbtack here and I’ll get a tidy little referral bonus for your efforts. Thank you!
Aside from keeping active and useful, I’ll get on 2 or 3 walks each week to our nearby Starbucks with the Mrs. to enjoy an overpriced brew and not feel the least bit guilty about it. These are nice breaks from the various projects around our own house (like adding those slick slide-out shelves in our kitchen – nice…)

About Those Tactical Adjustments?
Having a decent nest egg doesn’t automatically qualify one to retire early. I about shit a brick when I realized that our income wasn’t quite keeping up with our expenses. Part of that was just incomplete planning on yours truly. Cash flow is key when you retire, especially if assets are locked up things like real estate and employer-sponsored retirement plans.
Our Healthcare Exchange plan setup was intense, and I didn’t realize that our newly diminished income level wouldn’t reduce our premiums until 2024 (i.e., SEVEN months later). Whoopsie daisy.
As of January 1st, thankfully, our premiums are much lower. I expect they’ll go back up again with my side hustle Thumbtack and REALTOR income. Just something to keep in mind if you plan to retire mid-year and sign up for coverage via the exchanges – Don’t count on a lower premium on Day 1.
I also did a significant amount of shuffling within our gap-year post-tax Vanguard investments to move more heavily into dividend stocks. To be crystal clear, I don’t recommend relying on individual stocks for aspiring early retirees. Our total assets in this category comprise about 6% of our net worth. I still get a little panicky when 3M and Target have rocky days in the stock market.
Still, the transition to dividend stocks in concert with the lower exchange premiums boosted our monthly income enough to get us back into the operating black earlier this year. And bonus, we’re expecting a hefty IRS refund for the months I was still employed in 2023 – enough to pay for overdue exterior house projects this spring.
(Side note: Be sure to read up on tax loss harvesting before making a bunch of trades in your post-tax account. This is especially helpful if you retire in the middle of the tax year. You can deduct up to $3,000 in post-tax investment losses per year and roll any additional losses above that 3K into future years.)
A Few Parting Thoughts
Another cure for the Cubicle FOMO blues I forgot to mention: Getting together with former colleagues and staying connected. There are at least 3 or 4 peeps from my working days with whom I keep a standing monthly lunch, or simply a chat on the phone.
I mainly enjoy the camaraderie and the connection, but there’s a side benefit I hadn’t anticipated: I get reminded by my friends of how glad I am not to be stuck in that dreadful job anymore.
Until the Taylorists are sent home packing, I frankly don’t see any mental or physical health benefits from putting up with the toxicity of Fortune 500 “healthcare”.
Coming soon: A deep dive into the latest on the Airbnb Experiment. Since the “cow post” in the preceding link, the market has become saturated by legions of well-meaning hosts, creating an oversupply of rentals and a massive shortage of affordable housing in vacation towns. That’s a very real Pickle…

It’s been 8 years since I retired and it seems like 8 months at most. Time actually does fly by when you are having fun. I haven’t missed work one single day. My volunteer work makes me feel extremely useful. We split time between our house and our mountain cabin. Life is good!
Living the dream, Steve! The volunteer work is an important piece of the puzzle. We did more this past fall as a family, but I’m planning to invest more time here for sure.
Fortunately I have no cubicle FOMO, I happily walked away, refocused and never looked back. Even if I might sometimes (but very rarely) miss the cut and thrust, I certainly never miss the getting up at 5.30am on a Monday morning ! These days I’m more than happy to talk about the work rather than do any – seems a reasonable compromise !
I’m with you, Ben. Although it took me a few months to sort of “rinse off” the old identity, I’m finally quite content having the added time to focus on health, family, and earning a little side dough doing things I actually enjoy.
Those working year Monday mornings sure put a dent in our Sundays, no??
Glad you’re finding your purpose in post-corporate FIRE life, Cubert! I think, accepting that we don’t have to work just for the sake of appearing busy …takes some time. I know it took me a while but now, 4 years in, I’m pretty comfortable in my FIRE skin.
Do you have an email that I can reach out to you directly?
Hey man! Good to hear from you. Try Cubertac@abandonedcubicle.com.
I’m curious to hear how things are going 4 years in for you in more depth. It’s a psychological cash flow game now – not wanting to part with any bricks in the “nest egg wall” is a problem.
Are you still trying to be a realtor? With the new ruling on realtor fees, I wonder if you’re gonna change course. I read that this new ruling on realtor commissions will push hundreds of thousands of realtors out of business. I am a part-time agent myself, so I’m likely going to quit.
Hi CC! I actually AM a Realtor! But I know where you’re going with the question. It is not a field I’d consider with the rules about to change in a major way with respect to commissions. Being a Realtor still gives me some advantages from a tax perspective (being a real estate professional helps with expense write offs on rentals) and additionally, I have more “firepower” to fight assessments on my rentals to keep property taxes fair (typically my units are valued much higher than comps of similar quality and condition.) So there are perhaps enough “side benefits” of being a Realtor to compel me to stick with it, even if the buyer side representation is facing an uncertain future.