Too young to retire, too old to get hired

So. Is this retirement? Everyone says pivot, but to what?

Mar 11, 2026

It takes only one innocuous remark to disturb the foundation of something hanging in precious balance, even if you’re content with where you are in life. While the life you created may be on steady ground, it’s still one that’s built on the edge of a perch.

Lately, I’ve been trying to quiet the noise inside my head:
Maybe you should look for work.
Maybe you need another side gig.
Maybe you should quit this newsletter because too much time/ too little financial return.
Maybe you should attempt a second career as an artist.
Maybe maybe maybe.

I’m on a call with a possible new tax accountant. He keeps repeating back to me the number that I reply with when asked what our income for 2025 was because surely he was mishearing. He keeps throwing out wild assertions like, I assume you’re both pulling in a quarter of a million dollars combined, correct?

Um, what? Excuse me?

No sir, have you no other clients who are no longer earning what they used to? Who have aged out of their careers? Layed off? Had to quit for health reasons? Or how about just fucking tired of the grind. What about all of the above? Not surprisingly, he didn’t follow up as he had promised, nor did I pursue it. It was not a good match.

But by then, his remarks seeped into my thoughts and I spent the week feeling like a loser for the first time in a while. A parting gift from a half hour conversation.

There is a phase called hyperphagia that describes a period of insatiable hunger before bears hibernate. They’re constantly in search of food in a sleep deprived state because they spend 22 hours a day eating in this phase of furious accumulation. I used to tell myself that my working years were similar to this. A sleep-deprived preoccupation for getting clients, more jobs, and more money.

When I stepped away from my career two years ago, I didn’t know what my life would look like, and not knowing is a death knell to someone who is a planner. In a lot of ways, the financial part is simple. Numbers are numbers, and you can’t really fudge that. You either have enough to slow down and pull back from your career, or you don’t and you’re still working towards it.

Before I made the decision to no longer look for a full time job, I had to reconcile my relationship with money and redefine success. I began to look at it not as a measure of how much I was earning, but by my ability to support a lifestyle of my own choosing. Yes, it meant frugal living, but when I had that moment of clarity—that I didn’t need to be making a salary that I believed I should be making for someone my age with my experience, but rather what I actually needed to pay the bills—the pathway became more clear. It’s also how we approached my spouse’s windy and often turbulent path from the bottom up during his own post-career journey from being a chef and business owner to his current desk job now.

I have multiple spreadsheets that outline our finances for the next five to ten years. Everything balances on the edge of that perch, but for now this spreadsheet helps me sleep at night.

All the other factors around self-worth, ego, and identity have proven to be more fluid and complex. Even though I tell myself that I’ve earned this break from years of breadwinning during the accumulation phase, there’s still a bit of lingering shame and embarrassment for not having a “real” job.

A painting on my desk — What I’m doing instead of working a real job

When asked what I do by old acquaintances and new people I meet, I answer that I’m semi-retired. I don’t know how else to answer that question. If pressed further, I offer a simple explanation, “because of health issues.” It usually shuts down the conversation.

Some of us weren’t ready to quit our careers. Some of us had no other choice because we were forced out by layoffs and couldn’t find another job in this market. I know too many people my age in this situation right now, searching for themselves in what’s proving to be a really vulnerable stage in life. Everyone is pivoting, but pivot to what? We’re too young to retire, but too old to get hired.

The challenge, with the future being so murky, is that many of us don’t even know what to pivot to. Jobs are no longer secure and long-term career outlooks are uncertain with all this predictive doom about entire jobs getting eliminated.

The smartest thing we can do, which is something I’ve always put into practice and believed in even when I had a full time job, is to create multiple sources of income. A safety net. I know it’s easier said than done. What I thought of as side gigs back then were really second and third jobs, but it saved me so many times. And in this impossible job market, it may be our only option.

At the beginning of the year as a sort of ceremonial act, I uninstalled Slack and Figma because client work was dwindling and I no longer needed it. The other day out of curiosity, I read an opinion piece on how AI in product design in the last six months alone is changing the process at an astronomical pace because of Claude Code. I have never felt more relieved that I didn’t have to keep up with this industry anymore. It felt like closing the last chapter in a series of closed chapters in this long-winded journey of leaving a career.

It takes courage to face the system and say, no thanks. It takes willpower to stay the course. When my fears threaten to sabotage the life that I’ve finally managed to build, it takes all my mental strength to hold the line and kick those thoughts to the curb.

When I look at the ages our fathers passed away, it wasn’t much older than we are now. That’s staggering to me. When we lose our jobs, we not only lose our identity, but we lose the structure that defines our everyday. That loss can create a feeling of being unmoored. But while the risk of retirement might be the lack of purpose, the far greater risk is assuming we have many more years and good health to live a life we didn’t have time for while working and raising families.

I feel incredibly fortunate to be able to land where I am now, to prioritize my health, to be able to write every week, to draw, to read, to take walks in the middle of a weekday. To have support of a spouse who is taking over the breadwinning reigns for the first time. I have figured out how to fill my days, and life is fulfilling despite the fact that I barely earn an income.

So, why do I fall back into self doubt? Just one little thought, one remark, one comparison that invades my psyche like a dagger.

I guess because life keeps getting more expensive? Because HVACs need replacing and college tuition keeps rising and that container of yogurt I’ve been buying every week for years is on the precipice of crossing the $5 mark for a quart. The money isn’t moneying anymore.

So…is this retirement? Are all the things I’m filling my days with retirement hobbies or am I pivoting once again? If I’m still trying to brainstorm streams of income, am I really retired? The grind looks different, but I’m wondering if it truly ever ends.

Thank you for reading.
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Some interesting links and art

To watch:

This short animated film called “Retirement Plan” by John Kelly has been making the rounds (hat tip to Andy Adams for introducing me to it). The pacing, the music, the humor, and the sentiment is so overwhelmingly human that it makes you melancholy to watch it. And at this age, I can see the myself and my mom in the narrative.

To read:

‘I am never off the clock’: inside the booming world of gen Z side hustles (The Guardian)
Speaking of side hustles and multiple income streams, apparently 57% of Gen Z Americans have one. I really do think that this is the way!
“Gen Z is thinking in terms of what I call a ‘portfolio of careers’ – not just one path, but a bunch of different things that bring them fulfilment,” …“They saw their parents struggle and concluded they’d rather have more balance. They don’t believe they can achieve the same financial success as previous generations, so they’re refocusing on their goals.”
Were You Born to Love Music? How you respond to art—from poetry, to visual art, to music—may be partly written in your DNA (Nautilus)
This is an interesting thesis. New research may suggest that our emotional response to music and art is partly genetic.
Meet the Researchers Who Can Engineer Your Dreams (The Walrus)
“Dreaming was its own kind of freedom of thought and expression. The nine-year-old kid in me is still in complete wonder of the dreams that sleep offers.”
It’s fascinating to think that our dreams might be controllable by external stimuli at just the right moment, but apparently humans have been doing this in ritualistic practice for thousands of years. Scientists are now interested in influencing dreams in a controlled environment to study the mind, memory, and creativity. But, is it ethical?
Can the Dictionary Keep Up? (The Nation)
How the dictionary came to be, how it’s adapts and adds new words, and a little bit of drama between the Webster and Mirriam families.
Film is in its own crisis, Timothée (Vulture)
You probably heard about Timothée Chalamet’s dismissal on ballet and opera by now. Such a disappointing take from a Laguardia High School grad (the “Fame” school) whose building is literally right next door to The Met. The same Met Opera that is struggling right now. So, maybe he spoke an uncomfortable truth out loud. But as a former parent of a kid who went to that same high school, I can attest that those students form a boundless appreciation and support for their fellow classmates of every artistic discipline, and that’s why his comment was so disappointing. This article does have a point, though. Film may not be immune to the existential crises that is facing the broader arts. Timothée probably knows that.

On the internets:

I love this thread.

An exhibit I recently saw in NYC:

William Eggleston: The Last Dyes
The last batch of Eggleston’s dye-tranfer prints. Images from the American South, which apparently was described in the 70s as “perfectly banal.” Read more about the exhibit here.
As an aside, I encourage anyone to go see an exhibit of film photos in print. The saturation and richness in color can’t compare to how we usually view images through a screen.
Is this where Shake Shack got it’s name??