You Don't Actually Want to Retire

Why organizing your 20s and 30s around an exit strategy is an admission of defeat

I remember working my first job out of school. 22 years old, absolutely hated it, was not at all where I wanted to be, and already thinking about 40 years in the future when I could finally retire. Despite working in Manhattan at a major financial institution, the department and team that I was on was devoid of all life, ambition, and excitement.

I spent hours reading about the FIRE movement - Financial Independence Retire Early. People obsessing over savings rates and withdrawal strategies, calculating down to the month when they could finally escape. Looking back, it’s kind of an insane way to live. Someone fresh out of school already thinking about retirement, about how to escape. That’s not a good signal.

Look, if you’ve been working for 20 or 30 years and you’re looking forward to actual retirement, I get it. You’ve earned it. But if you’re in your 20s or 30s and already organizing your life around an exit strategy decades away, that’s a different story. The thing is, many people never escape the living for the weekends and retirement daydream way of life.

Fortunately, I was not one of those people. But that was not by sheer luck or coincidence. It took intentionality from almost the moment I started that first job I hated. And now, nearly 10 years later, I no longer spend my days thinking about being 60 years old and not having to work anymore. In fact, now I enjoy working, and I’m not sure how I’d fill my days if I wasn’t building something I found meaningful.

I think most people in the same situation don’t actually want to retire. They just want to live life more on their own terms, do something meaningful, or at least somewhat interesting to them.

When people say “I can’t wait to retire,” what they really mean is “I want to do things on my own terms” or “I want to wake up each day and spend my time on things that interest me.” Look, when you think about it that way, this is not something that needs to wait until you’re 60 years old to achieve.

Now, I will say there are people who just don’t want to work at all. Period. This publication is not for those people. This publication is for people who have ambition and drive, who show initiative and want to live an intentional, meaningful life. And for those types, I don’t think you’re looking forward to retirement. You’re looking forward to waking up and spending time on something that interests you, excites you, and still pays the bills.

I think it’s incredibly depressing and an admission of defeat for people to be organizing their 20s and 30s around this destination they hope to reach when they’re 60 years old. I didn’t want to be wishing my days away. And you probably don’t either.

And honestly, this strategy is only getting worse over time. I wrote recently about how playing it safe is now actually the riskiest move you can make.

Playing It Safe Has Never Been Riskier

The safe job, climbing the corporate ladder for 20 or 30 years, saving in an index fund - I’m confident to say that is no longer a winning strategy. In fact, people are taking on a lot more risk than they want to admit.

• The CEO of Microsoft AI just said most tasks accountants, lawyers, and consultants do will be automated within 12 to 18 months.

• Baker McKenzie - one of the world’s largest law firms - just laid off nearly 700 staff, just under 10%, because of AI.

• January 2026 saw the highest layoffs to start a year since 2009.

Not only is this an admission of defeat, but it’s also becoming even more challenging to plan that far into the future. The rate of technological progression is insane.

ChatGPT launched in 2022. Claude came out in spring 2023. Google Gemini launched at the end of 2023. These technologies didn’t exist a few years ago, and now they’re totally reshaping the workforce and the way we work. It’s hard to know what technology will bring in the next 5 years, let alone 10 or 20 or 30.

I really think this idea of retirement is going to look entirely different for people my age - early 30s, late 20s, and younger. It’s a relic of the past.

So here’s the main point: if you’re already thinking about retirement, you’ve already lost.

You’re wishing away your days. What you really want is something more meaningful. The question shouldn’t be “how much do I need to retire?” or “when will I be able to retire?” The question should be: what can I change about my life today so I’m not spending the next 30 years counting down?

For me, the path to where I am today was not linear. There were lots of moments of failure. Lots of uncertainty. There still is uncertainty. But I at least know that where I am today is much better than where I was when I first started my career almost 10 years ago.

I made that shift by refusing to accept that my best option was to endure work I hated for decades. I took risks. I built skills. I changed direction when things weren’t working. I invested in myself rather than just deferring everything to some distant future.

You can do the same. Not by following my exact path, but by rejecting the premise that you should organize your life around eventual escape.

Build something you don’t need to retire from. Find work that’s actually yours in some meaningful sense. Develop skills that compound. Take calculated risks while you’re young enough that the downside is manageable and the upside is massive.

The future is too uncertain to bet everything on a far-off finish line. Technology is moving too fast. The systems are too unstable. And life is too short to spend your best years in waiting mode.

You only get one shot at this. Why spend it planning to escape?

Next week, I’ll share how I actually made this shift and how you can too.

If this resonated with you, share it with someone in their 20s or 30s who’s already counting down to retirement. I send one of these each week, so make sure to get on the list. And if you reply or comment below with what you thought about this piece, that helps me keep improving.