27: The Age When Your Past Catches Up With Your Future
The Quiet Crisis of Self-Reflection in Your Late Twenties
27: The Age When Your Past Catches Up With Your Future
At 26, closing in on 27, I found myself in a fog—a feeling that, as I discovered, wasn’t unique to me. My friends were in the same boat. It hit me hard after listening to the Lex Friedman podcast featuring Pieter Levels (aka LevelsIo), where he talked about the inevitable low points in life. Turns out, we weren’t as special as we thought.
Levels described how life changes when you slip into a 9-to-5 routine. Weekdays are spoken for, and weekends are for socialising—if you’re lucky enough to have the energy. This wasn’t his idea of a good life, so he bailed. Enter “the Saturn return”—an astrological excuse for your life falling apart at 27. Levels didn’t exactly buy it, but the timing was too perfect to ignore.
For him, 27 was a crisis. The idea of living a suburban life in Holland made him claustrophobic. So he did what a lot of us dream about: packed his bags and headed to Asia as a digital nomad. But here’s the twist—freedom wasn’t as liberating as advertised. He ended up alone, broke, and with nothing but questions while his friends back home climbed the traditional ladder.
Things went from bad to worse. His income shrank to $500 a month. He was 27 and feeling like a total failure. But instead of wallowing, his dad’s blunt advice gave him a jolt: “If you’re depressed, do something. You can’t sit still.” And just like that, he threw himself into a crazy project—12 startups in 12 months. Desperation, it turns out, breeds creativity.
This whole saga? It’s the quarter-life crisis in a nutshell. The life you were raised to expect doesn’t match the life you’re actually living. For Levels, entrepreneurship wasn’t the solution to everything—it was just a way to keep moving. A life raft, not a yacht.
And here’s the thing: whether or not Saturn is real, people freak out in their late twenties for a reason. By then, you’ve lived enough to know if the road you’re on is the one you really want.
You’ve travelled, seen how other people live, and compared your life to theirs. That gives you perspective—some of it useful, some of it just exhausting. You’ve been working long enough to know what you’re good at, and more importantly, what you can’t stand. You’ve seen managers come and go, navigated office politics, and tasted both success and failure. You’ve been praised, ignored, and probably micromanaged all in the same week.
But there's a larger context at play, one that's been sneaking up on us for a while. The world we live in—especially for those in their 20s—isn't designed for clarity. It’s built on noise. The never-ending barrage of social media, the endless streams of curated lives, the constant reinforcement of what we should be doing but never enough reflection on what we want to be doing. We’re comparing ourselves not just to our peers but to an entire world of people we’ve never met, and that can leave even the most confident person feeling inadequate.
Your social life? It’s no longer the endless party it used to be. Friends are settling down—buying homes, planning families, posting engagement pics. Others are still trying to stretch their weekends into mini-vacations from reality. You’ve felt the highs of new love and the gut-punch of breakups. And if you’ve done any online dating, you know the drill: swiping, ghosting, and the awkward guessing game that is modern romance.
That big friend group you once had? It’s shrinking. Big hangouts have been replaced by tight-knit circles. You miss the ones who moved away, or the ones who simply drifted. It’s just how life works.
Then there’s that moment—the one where you notice your parents aren’t as young as they used to be. They’re slowing down, and for the first time, you’re struck by the fact that they won’t be around forever. Time with them suddenly feels more precious.
All of this—the shrinking circles, the career highs and lows, the existential questions—it piles up at 27, forcing you to confront the big one: “What do I really want?” Spoiler: there’s no easy answer.
Decisions are looming. Should you commit to buying a home or stick with renting? Put down roots or keep your options open? Is it time to take the next step in your relationship, or are you not ready? Maybe it’s time for a career pivot, which raises another question: is going back to school worth it?
Meanwhile, everyone—your parents, your friends, society—has an opinion on what you should do. But in the end, these decisions are yours, and they’re going to shape the next decade of your life. No pressure, right?
But here’s where it gets interesting. Being in your 20s today is nothing like it was for your parents. Global instability, rising costs, inflation—it’s a mess. Feeling lost is practically a rite of passage. The old rules don’t apply anymore, and no one’s handing out a new playbook.
So, what do you do?
First, you need to figure out what you want, not what everyone else thinks you should want. Society pushes you one way, but your life isn’t theirs to live. Draw some lines. Sure, it’ll cause some friction, especially with family, but they’ll adjust. They always do.
Then there’s this golden window—your late twenties. You’ve got enough experience to know how to make money, probably don’t spend too much, and still have some flexibility. You’re in the best shape you’ll ever be in. You could quit your job, take two years off, come back broke, and still be fine. If you don’t use this time wisely, it’ll slip through your fingers.
The real trick? Turn up the risk.
Here’s where most people go wrong—they’re terrified of risk. Risk is energy, risk is excitement. You’re going to fail, you’re going to get rejected—that’s the point. There’s something exhilarating about betting on yourself and walking into the unknown. So take the shot. Start something risky. And if it crashes and burns? Who cares? Just don’t make a big deal about it.
The reality is, no one has the answers. Not you, not your parents, not your friends. The trick is realising that everyone’s wigging it—some are just better at hiding the cracks. But here’s the good news: you don’t need to have everything figured out. Life isn’t a puzzle you solve by 30. It’s more like a game you keep playing, and the rules change as you go. Some people find stability, while others thrive in chaos. The key is to stop measuring your progress against everyone else’s and start embracing the uncertainty.
Because here’s the kicker: even if you do fail, even if the risks don’t pan out, you’ll still be ahead of the game. You’ll have lived. You’ll have tried. You’ll have a story to tell. So for those who read this and make the changes, I say “Hit it with pace.” In the end, that’s what really counts.
If you liked this post please leave a comment or give it a like!
Talk to you again soon,
Miles
What I Read This Week
Masters of Love
Science says lasting relationships come down to—you guessed it—kindness and generosity.
This one is worth re-reading a couple of times per year. Alternative Link below:
There is some great practical advice here at the end.
Books I am Re-Reading
The ONE Thing: The Surprisingly Simple Truth Behind Extraordinary
One of my favourite all-time books.
Blog post coming soon on this stay tuned!
Audiobook I am listening to
The Happiness Trap
I've recently started a weight cut and am feeling the effects. With low energy from a calorie deficit, constant hunger, and intense training, I've been feeling down most of the time. This book has helped me manage my thoughts and not let them drag me down further. I've become accustomed to these repetitive feelings and thoughts, and now they don't bother me—they're just the same old, boring patterns. Sometimes I even think, "Can my brain come up with something new?" You can't fight how you feel; you just have to accept it. Given my diet, it's natural to feel this way, and that's okay!
Anchoring is great practical advice to separate yourself from thoughts, alongside meditation. These two skills together is a superpower.
What I Watched This Week
Caution this wigged me out a bit haha