30 and Not Retired

P.S. It’s not just about being retirable, but being more retirable than your neighbor.

This musing’s more unfiltered than usual, part serious, part satire — happy weekend reading :)

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For a certain kind of person with a certain kind of mindset in a certain kind of community, hitting 30 yrs old and not being retired yet is purgatory.

Well, it’s not that you need to be retired, but you need to be in a position to be able to retire—yesterday. I’m going to call this being “retirable.” (It’s not a commonly accepted word, nor is it in the dictionary, but it makes sense when you read it; I confirmed.)

By age 30, many people have peers that are retirable — they’d be able to retire if they wanted, based on their own threshold (and the generally accepted retirement bar).

Most of the time there’s a financial threshold in mind. Decades ago it was probably a number in the hundreds of thousands, more recently a single million, and nowadays often multiple millions (and for some, of course, aspirationally higher). Beyond money, there’s some life and lifestyle in mind to be afforded. And for those who are intrinsically, purposefully ambitious, there’s an impact goal too.

But back to these retirable peers. A few of them were prodigies in their youth. You knew they would do something big, but you just didn’t know when. And their day came early. But a lot of them weren’t prodigies. In fact you didn’t really think about their future much, until their future arrived. And it was simply magnificent.

Your retirable peers are reminders of paths you could have taken or should have taken, or just how you could have been less stupid or more lucky along the way.

But the truth is, people don’t wait until 30 to become retirable anymore. You don’t need to follow a predictable ‘partner track’ to get there, say by your mid-30s. If you work hard and smart, take an off-beat path or just take big swings, and you’re one of the few people that the stars align for, you can get there in your 20s itself. (These are the stories that get exalted in prestigious lists and press stories galore).

And hence there’s an even more expansive and often insufferable batch of people reminding the 30+ of the need to become retirable fast too: the 20 somethings.

The early 20 somethings are oblivious, arrogant, and often on top of the world. And why shouldn’t they be? They have all the time in the world, the majority of a decade before they face down 30. And they are the ones that the pickers want to pick. For the elite program (see Ivy League). For sending large sums of money in anticipation of future mega-returns (see venture capital). For Forbes 30 under 30 and the like (though any 30-something that’s still lamenting missing out on this list is missing a lot more perspective).

The late 20 somethings are on the cusp, and a bit of a mixed bag. They’re straddling the arrogance of still being in their 20s with years ahead of them and the fear of getting closer to losing it. It’s a pre-mid life crisis limbo that some people are keenly aware of and others are oblivious to until they’ve passed it. And a silly few are just fixated on the impending loss of the grounding number 2 from their numeric age.

The late 20 somethings are either on track for being retirable by 30 or they’re trying to re-route. Many of them aren’t in a lane they particularly enjoy, but they know it will lead to retirableness, even if at some age past 30, 35, maybe even 40, if they can just stay the course. And hence, many of them decide they’d rather just commit than having to start over in something else as a peer to the scary early 20 somethings, or worse yet, the prodigal teens.

To the 30 somethings, the early 20 somethings at this point represent an alternate reality. The early 20 somethings represent the period in time the 30+’s would run back to if they could redo the past. (I didn’t forget the special subset of people who would counter that they’d actually want to run back to their teens because they’d change something even earlier to accelerate the path to early retirable-ness.)

The late 20 somethings are reminders of the fuck-ups of a more mature youth that’s still too fresh to laugh at. Some 30-somethings still act like they’re in their late 20s because it’s a more comforting state of mind (and because time passes so fast it’s just disorienting). If you’re in one of those odd industries where career progression doesn’t follow a linear path (tech, media, and entertainment), it’s easier to buy into the time warp too—just talk, text, and dress like Gen Z for now.¹

But surely most people 30 and above aren’t retirable yet, right? Right. But the stories of those who are are sooo loud. For people who ingest these stories all day, on social media and in the group chats, it’s not that easy or tempting to remember all of the not-retirable people. For one, it puts things into perspective, and perspective isn’t helpful for the person who’s become accustomed to wallowing in what could have been and visiting woe-is-me-land all the while having more than 99% of people in the world. (I don’t say this with any claim to moral high ground, mind you.)

I could break down the psychology of someone who desperately wants to be retirable by 30, but I suspect I don’t need to. The Social Network and The Wolf of Wall Street are probably the most millennial-generation defining movies. We’re knee-deep in research on depression, burnout, chronic disease and more ills courtesy of social comparison and competition taken to extremes. (It’s not just about being retirable, but being more retirable than your neighbor.) And who hasn’t heard of the latest book “The Anxious Generation” implicating smartphones in screwing up the youngest adults of today?

I’d contend that the same pressures that existed before still exist today, but worse— because it seems that much harder to stand out when just about everyone seems to be competing hard in the same arena with virtually the same access to every resource. We’re on some edge of a timeline that’ll see the pendulum swing back towards seeking small, local wins and a charming white-picket-fence-life. “Retirable by 30” won’t be about never having to work again and traveling by yacht and jet plane, but about working on what you want, when and how you want. (I’ve written about this here, here, here, and more … so detour if you desire).

But the other truth, perhaps a harsher one, is that aging has always been a trauma to be dealt with. Aging becomes a struggle when you can't mourn the loss of options and opportunities that time inevitably takes away. In mourning the loss of opportunity, you must also mourn the death of the fantasy life you once envisioned—whether that was being retirable by 30 or something more illustrious.

The funny (and sad) thing is that this kind of realization rarely seems to strike until you’ve waded through the aforementioned phases. Except for those few young people who could have found peace and contentment in becoming a nun or non-profiteer (in good faith), everyone else finds themself in some ragged race. A race that’s hard to convince anyone to bow out of until they’re ready.

I can’t offer the definitive elixir for this pattern of human behavior, but one thing I’ve noticed: if you point out a common behavior that seems less than ideal, people will find it in themselves to explore it so as not to be “one of the masses” who fall into the median trap. So if you’re holding your breath til you’re retirable, regardless of which side of 30 you’re on, consider this me calling you out as basic. Read: maybe you’re just like everyone else, and there’s truly nothing scarier than that.

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1. In some ways, the paths that can’t be gamed or accelerated in any meaningful way are protective against this “30 and retirable” chase, e.g. becoming a doctor or consummate lawyer, i.e. some gated professional path that only lets you start earning once you reach near-30 or older (which of course brings many of it’s own challenges in tow). And there are of course life circumstances that can get in the way of pursuing the high risk, potentially high reward paths early in life too.