Life After Retiring Early
The question came from my friend Sam, who’s just quit his job.
Together, Sam and I co-founded two businesses. The first, a user research consultancy, was sold to PwC in 2014. The second, a SaaS business supporting user researchers, was sold to a private equity firm in 2021 (although we both remain minority shareholders).
Thanks to selling these two businesses, along with a few smaller startup investments that have returned 7-8 times the money I put in, I stopped working in February 2021 when I was 43 years old. Since then, I’ve done bits and pieces of consulting and governance work, but my main focus has been on being the best dad I can be to an 11- and 13-year-old (who are with me half the time).
Like me, Sam became financially independent after our business exits. But unlike me, he kept working until recently. Now, he’s pulled the trigger and retired.
Well, Sam, I dread the question.
Whenever someone asks, “What do you do?” I feel like what they’re really asking is “What’s your role in society?” And when I reply “retired,” I feel a subtle shame. It’s pretty unusual, after all—only 1% of Americans aged 40 to 44 are retired, and I suspect it’s similar in New Zealand. The label has always felt uncomfortable, like wearing a badge that says, “I’ve quit.”
Part of the problem is in the definition of retirement. When people hear that you’ve retired, they often assume you’ve stopped working entirely. That makes sense, that’s the definition after all, but it doesn’t capture the full picture. When Roger Federer retired from tennis at age 41, did anyone expect him to move to a retirement home and sit around doing nothing all day? Of course not. In fact, he describes himself as “graduating from tennis,” not retiring.
As a society, we need to broaden our definition of retirement to include a variety of activities. Perhaps we could learn from Japan, where there isn’t even a word for “retire” in the sense of permanently leaving the workforce. Or maybe a better way to define retirement is separating your finances from your work, which allows you to gain control over how much you work, who you work with, and what you do.
Anyway, given all this messiness, when the dreaded question comes up I usually say, “I’m semi-retired.” It’s a bit of a dodge, but I doubt I’m completely done with everything that could be termed “work.” Of course, all of us are more than what we do for a living, so maybe I should be saying “I’m a retired person who likes to spend a little time on my laptop, get some exercise, read, and spend evenings relaxing with family and friends—maybe with a board game and a homebrew or two.” Or, maybe the best response is to say “I’m a full-time human being,”—but I don’t want to be punched. I would punch me.
This wasn’t Sam’s only question. He went all in and asked for all of my advice on retiring early. Well, Sam, you might have been joking, but I have decided to go all in and write this playbook. I’m semi-retired—what the hell else am I going to do with my time?
Before we dive in, two points:
Advice is almost always gift-wrapped and doesn’t match the messiness of life. Nothing in life is this tidy. And advice often takes the form of someone extrapolating a general rule from a single lived experience. So, ignore the confident tone, what worked for me will not always work for you. In the words of Hunter S. Thompson when asked for advice by a close friend, “What is truth for me could be disaster for you.” So if you’ll indulge me giving you advice about receiving advice, follow what Bruce Lee said and “Absorb what is useful. Discard what is not. Add what is uniquely your own.”
I am also keenly aware of my good fortune. I did not grow up wealthy but I’ve had many privileges: race, gender, and background. I was lucky enough to attend university, do a degree in a desirable field, and graduate with only a small student loan. I have been blessed with good health and haven’t had to deal with any major financial crises. I live in New Zealand, a country with a high standard of living and solid social support systems. I know I am lucky and am grateful for where I am at.
Early retirement crept up on me.
Here’s the helicopter view of my career: In 2003, I co-founded Optimal Usability with Sam. A decade later, I stepped down as CEO, and we sold the business the following year. After that, I became the Chief Product Officer at a startup and later held an executive role at an online classifieds and marketplace business called Trade Me—much bigger than eBay in New Zealand—where I stayed for four and a half years. My last position before retiring was as the CEO of a not-for-profit called Summer of Tech, filling in for someone on maternity leave for a couple of years.
Shortly after starting at Summer of Tech, my marriage, and life, fell apart.
I vividly remember attending a job fair in Auckland, the first one of many that I’d go to, encouraging students to sign up for summertime internships. I’d give the sales pitch to student after student, and when there were lulls in the crowds I would go into the bathroom to sob. My eyes were already red from not sleeping the night before, I wondered if my colleagues thought I was stoned.
You might wonder why I didn’t quit or at least take some leave (and there were chunks of time when I was AWOL) but the truth is that Summer of Tech was a refuge. A job that was low stress, but that occupied my waking hours so I could have some relief from the chaos in my head. (Also, yay for sleeping pills, anti-depressants and a great psychologist. And friends and family, of course.)
So, I didn’t plan to retire after Summer of Tech. But given that I was newly separated, with the kids half the time, jumping back into a demanding C-level role didn’t feel right—for me or them. I didn’t want to hand the kids over to after-school care or a nanny. And my head wasn’t ready to tackle a big job. Instead, I thought I’d make up for the long hours I’d worked during the kids’ early years, spending more time with them and filling the rest of my days with consulting, advising, and board work. I did some of that, but it wasn’t enough to fill my time—not even close.
And so, without meaning to, I slipped into early retirement in February 2021. The transition was rockier than I’d expected.
Early Retirement Is Harder Than It Looks
It’s common for people transitioning to early retirement to feel loss or depression, and I was no exception.
It probably didn’t help that I retired as COVID-19 was sweeping the planet. I remember reflecting on the uncertainty of life at that time—shops and restaurants shut because their staff were isolating, there were disrupted supply chains (were we going to have empty supermarket shelves?), every big event cancelled. It was a time where it was hard to look forward to anything.
There were lots of times I felt adrift over those first uncertain couple of years, unsure of what to do with myself. Here are some thoughts I jotted down at the time:
5 May 2021 When the last time was that I was “light of heart”?
24 May 2021 I am lonely
27 May 2021 Lonely + Bored = Not good
17 June 2021 Can structure defeat boredom?
19 June 2021 I am lonely the minute the kids walk out the door
7 April 2022 I am so bored…I lack a purpose
25 May 2022 The only thing missing from my life is meaningful work
9 August 2022 I’m looking for inspiration everywhere. Books on climate change. Macabre poems. Doomscrolling LinkedIn.
In particular, I feel like I lost four big things—what I now call the Four Horsemen of the Early Retirement Apocalypse:
1. Loss of Structure and Routine
When you’re working, your days have a rhythm. Your weeks, months, quarters, and years all have a structure. Retirement takes that away. Suddenly, time becomes fluid, and your calendar becomes amorphous. No deadlines. No Tuesday morning one-on-ones. You no longer have to remind yourself, “The meetings are the job.”
2. Loss of Connection
Work gives you a built-in social network. The banter over Slack, Friday night drinks, small talk before meetings, or catching up with the person the next desk over. Not to oversell it, many workplace friendships don’t persist beyond the job after all, but even talking with the bus driver or the barista is more social interaction than you get when you are at home alone with your cat. Even if he is a very handsome cat.
3. Loss of Identity
Your career provides a sense of identity and self-worth. So when you step away from that career, then what? Shedding the professional identity you’ve built over years can be unsettling. You are no longer part of a company, an industry, or a professional community. So, away from work, who are you? Even Michael Phelps, the most decorated Olympian of all time, has said, “I thought of myself as just a swimmer and not a human being.”
4. Loss of Meaning and Purpose
Worst of all is the loss of meaning and purpose. A “big” day might involve a mountain bike ride in the morning, a trip to the supermarket, sitting in the sun to read a book, and a meeting in the afternoon before the kids burst through the door. There is no motivating force, no dream to chase, and no BHAG over the horizon. As Markus Persson put it when he sold Minecraft to Microsoft for $2.5 billion, “The problem with getting everything is you run out of reasons to keep trying.”
Much of the advice that follows is all about countering these Four Horsemen—rebuilding the structure, routine, social connections, identity, and purpose that once came from your work life. But before diving into how to counter the Four Horsemen, it’s important to understand the emotional terrain ahead.
Read Part 2 Next issue