by James A. Whittaker
‘You’re retired?’ It’s a refrain I often experience when I greet customers at one of my bars. They recognize me from my years in tech and are generally surprised to have me pour their beer or deliver their meal. Beyond the surprise, the question is tinged with disbelief and, I fancy, some disapproval. I like to assume that it is because I am relatively young but lately I have been questioning why so many find it so surprising that I should choose to give up tech.
Upon reflection, I realize that surprise is merited. Given that my former peers, managers and skip-levels are, almost to a person, still working, stepping away from tech at my age is rare. Tech is a difficult skin to shed.
Of course, there is nothing wrong with that. There are no rules about when or under what circumstances to retire. Generations of Americans have traditionally worked as long as they are able.
However, my former colleagues and I can hardly be compared to those prior generations. None of us work to put food on the table. Not to put too fine a point on it, but our careers made us rich as fuck. Unless my colleagues have 7 to 8-figure financial needs I am unaware of, remaining in the workforce is a choice, not a necessity. And yet nearly all of them have made that choice.
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It’s a choice that clogs the advancement pipeline for younger people still in need of employment. It’s a choice that prevents newer, fresher ideas and perspectives from reaching positions of influence. It’s a choice that concentrates wealth where it isn’t needed.
I can’t delve into the minds of people who work beyond need or the specifics of their personal lives that make spending 40–60 hours a week away from said personal lives a desirable choice. I can only look to my own motives in choosing to retire in my mid-50s and reflect on my regrets. Perhaps the excuses I made to convince myself to retire are the same excuses that convince others to stay put.
The ‘I love my work’ excuse
When I retired I did so on the tail-end of an illness that put my life and my future into perspective. Being on sick leave for months did for me what COVID-19 did for many others. It brought attention to all the onerous aspects of work: the commute, the stress, office politics, death march projects, and the large amount of time I spent with people I wouldn’t otherwise choose to spend time with. A year before the pandemic began, I started questioning why I was doing what I was doing.
The truth is, I did love many aspects of my job: Wrapping my head around the mind-bogglingly complex problems tech has to offer; pondering human motivations, desires and lifestyles that rapid tech advancement had changed for better or worse; tackling problems that brought a significant amount of pride when I solved them, and so forth. My work made me feel proud of myself and gave my life purpose.
But it turns out, I didn’t have to leave any of that behind when I retired. I can still work with smart people on problems of epic proportions. Retirement didn’t change that, it just meant doing it without financial compensation. Retirement doesn’t mean giving up the work, just the pay. So I lost the first excuse I believe many of my colleagues use when they choose to stay employed. You can still love your work independently of someone paying you to do it.
Publicly bleating about how much we love our jobs is our way of convincing ourselves that sacrificing love, adventure and self fulfillment is actually worth it. It’s self deception with the purpose of keeping us in the game.
When people tell you they love their job, don’t believe them. It’s the work they love. The job isn’t a necessary part of loving the work.
The ‘why walk away from all that money’ excuse
Growing up poor has made me appreciate being wealthy. Frankly, the path to my personal pot of gold was a rush. I know it isn’t socially acceptable to admit this but making money feels really good. No one can tell me that a 7-figure bonus doesn’t improve one’s mood or snap one out of a bout of melancholy. It most certainly fucking does. We’ve all seen lottery winners wagging their tails over a life-changing windfall and the gambler’s elation at a big haul. There are gambling addiction centers for a reason: making money is right up there with orgasms and psychedelics when it comes to making one feel good.
Tech execs enjoy such climaxes every year and, believe me, it never gets old. It takes some willpower to walk away from this annual adrenaline rush. Making money is addictive and turning your back on it is not easy. Amassing wealth, whether you spend it or not, is the hobby to end all hobbies. Just ask Warren Buffett. His simple lifestyle makes all but a tiny portion of his fortune unnecessary, yet he keeps working to accumulate more.
In a tech landscape of unemployment, lack of advancement opportunities, and a general industry-wide belt-tightening, the kinder course of action is to retire and make way for others who still need to work.
I believe this is why, when money doesn’t matter, so many choose to still earn it. It isn’t greed for the green. It’s greed for the feeling the green brings. Shopaholics don’t shop for the goods. They shop for the feeling they get when acquiring the goods. Making money falls in that same category of a rush without a real purpose other than the rush.
The problem is that no one wants to say this out loud because it makes you sound like a douche. But I believe it is the number one reason most people who can retire don’t. It is the one thing I miss most in my post-work life. But I will also say that, like any addiction, it can be beat. It took about 3 years, but I am now at peace with the gradual decline of my bank balance without ready replenishment.
The ‘I still have a lot to offer’ excuse
Short answer: no you don’t.
I spent a lifetime honing my skills. At multiple points in my career, I was recognized as among the top minds in the world in one subject or another. Indeed, not long after I retired the thing that I was best at, artificial intelligence, suddenly popped to the forefront of tech. If I was still in the game, I would be crushing it.
But would it matter? Truth is, the industry seems to be humming along just fine without my daily involvement or constant bleating on social media. Any idea I have or have had about AI is well covered by others still active in the field. My ego tells me how important my voice is, but the absence of my voice doesn’t seem to be holding the industry back.
The ritual of performance reviews, I believe, is at the heart of these oversized tech egos. Writing performance reviews forces us to sing our praises and identify things for which we can claim credit. There is no way to get to the top of companies like Microsoft and Google without being good at taking credit for shit.
Compounding this problem is that success brings the respect and envy of masses of folks still trying to climb the ladder. On campus, envious whispers follow you wherever you go. In meetings, your opinion matters, even when it should not. So many careers depend on your goodwill that everyone is on their best behavior around you. This is where the dystopia that starts with performance reviews gets amplified. The respect for the title becomes a surrogate for respect for the individual. The two become so intertwined that you can be a private laughingstock even while your title is publicly respected. What other career allows charisma-challenged nerds to be admired like rock stars?
Retiring is the one way you find out whether it was you or your title that gets credit for all that respect. Retirement strips away the title and what’s left after it’s gone is, potentially, the life of a nobody. This is a mental mind-fuck. Coming to terms with the fact that you are optional, replaceable, and even forgettable is a lot to take on. Switching careers to something you might not be good at is a huge risk to one’s ego. Waking up years later and realizing that anyone could have done your job and the world would be no worse off is hard. The bigger one’s ego, the harder it is to put aside.
I got used to being good at tech. With my new career, I am making mistakes like a 20-something fresh out of school. I often miss being good at shit.
All these excuses make up a powerful psychological dynamic that keeps us pinned to our desks long after our sell-by date. Walking away from the rush of financial windfalls, yielding all that prestige and importance to someone else, and coming to terms with the myth of one’s actual contribution demands a level of honesty and character that has to be summoned over time. I had the benefit of a long illness that slow-rolled me into retirement. Not sure I could have ripped that bandaid off any faster.
I ultimately decided that retirement is the more honorable path. In a tech landscape of unemployment, lack of advancement opportunities, and a general industry-wide belt-tightening, the kinder course of action is to retire and make way for others who still need to work. Now I spend my time ignoring all my prior strengths and trying to develop new ones. I often miss being good at shit. I have to study and think instead of acting on the reflex of experience. I have to find my purpose and self-worth without a corporation doing it for me.
To my former peers, managers and skip-levels I say only this: it’s ok to call-in rich. Don’t doubt your ability to pivot to a new specialty and find new ways to be valued. Something you had deep inside you made you successful the first time. Retirement is the one way to find out if that something is still there.