If you want to stay happy as you get older, say goodbye to these 5 behaviors

Last week, I turned 44 in Singapore. No party. No celebration. Just me, a coffee, and this uncomfortable realization: I’ve been treating happiness like it’s something waiting for me in the future, rather than something I’m actively destroying in the present.

It hit me while I was editing my latest YouTube video about the guaranteed ways to be unhappy in life. The irony wasn’t lost on me—here I was, teaching others about happiness while sitting alone in my apartment, refreshing Instagram to see who’d remembered my birthday.

The truth is, we don’t suddenly become unhappy as we age. We cultivate unhappiness through behaviors so normalized we don’t even recognize them as self-sabotage. These aren’t dramatic acts of self-destruction. They’re quiet, reasonable choices that slowly suffocate joy.

After two decades of building businesses, living across cities like London, New York, Bangkok, and now Singapore, and co-creating platforms like The Vessel with Rudá Iandê, I’ve identified five behaviors that guarantee misery as we age. More importantly, I’ve learned what happens when we finally let them go.

1. Comparing your timeline to everyone else’s

I’m 44, in a relationship but without kids, watching friends and family hit conventional milestones at a different pace. During our Brown Brothers Media calls with my brothers Lachlan and Brendan, I sometimes catch myself measuring my life against theirs—different chapters, different priorities, different definitions of success. The comparison is poison, and I’ve drunk it more often than I’d like to admit.

As I shared in my YouTube video on the roadmap to unhappiness:

The constant comparison to others, especially those more “successful” in conventional terms, creates a prison where happiness becomes impossible. I learned this viscerally when I visited Richard Branson’s private island—surrounded by entrepreneurs who’d achieved everything I thought I wanted, I’d never felt smaller.

But here’s what I’m learning at 44: comparing timelines assumes we’re all running the same race. We’re not. Some of us are building families. Some are building companies. Some are building entirely new ways of being human. The moment you accept that your path isn’t delayed but different, something shifts. The anxiety loosens its grip.

2. Chasing validation through achievement

I spent years believing that if I could just build the right company, reach the right revenue milestone, get featured in the right publications, I’d finally feel legitimate. Worthy. Enough.

This is the entrepreneur’s curse—we mistake external metrics for internal worth. Every achievement becomes a hit of validation that wears off faster than the last. You need bigger wins, faster growth, more recognition just to maintain baseline contentment.

In my 30s, I ran Ideapod believing that viral growth would somehow validate my existence. We reached millions of users, but I felt emptier than ever. The validation I was chasing wasn’t actually about the business. It was about proving to my parents, my former classmates, myself, that I mattered.

The cruel joke? External validation is a moving target. There’s always someone with more followers, more revenue, more success. Richard Branson has his island, but I’m sure he looks at Bezos’s space program and feels something twist inside.

Last month, I made a decision: I stopped checking our monthly metrics first thing in the morning. I stopped comparing DMNews’s growth to other publications. I stopped treating my worth like a stock price, fluctuating based on external indicators.

The withdrawal was real. But what emerged in that space was something I hadn’t felt in years—a quiet satisfaction with simply doing good work.

3. Living in the shadow of past mistakes

At 3 AM, when Singapore sleeps and my mind won’t, I catalog my failures. The relationship I sabotaged with my emotional unavailability. The business partnership that imploded because I couldn’t communicate my needs. The years spent in cities I now look back on with fondness but treated as temporary at the time.

We tell ourselves we’re “learning from the past,” but there’s a difference between integration and rumination. Integration means extracting the lesson and moving forward. Rumination means replaying the same scene hoping for a different ending.

I’ve noticed something about people who seem genuinely content as they age: they’ve made peace with their imperfect past. Not through forced positivity or spiritual bypassing, but through genuine acceptance that they did the best they could with the consciousness they had.

A friend of mine, now in his late 60s, told me something that shifted everything: “Justin, you’re going to make mistakes until the day you die. The only question is whether you’ll make new ones or keep repeating the old ones.”

Now when those 3 AM reckonings come, I don’t fight them. I let the memories surface, acknowledge the younger version of myself who did his best, and then—this is crucial—I refuse to let him drive the car.

4. Postponing joy until conditions are “perfect”

“When I finally meet the right person…” “When the business hits seven figures…” “When I can afford that house…” “When things calm down…”

I’ve been starting sentences like this for twenty years. It’s what Rudá Iandê calls “mental masturbation” in our Out of the Box course—this constant projection into an imagined future where conditions are finally perfect enough for happiness.

But here’s what nobody tells you about getting older: the conditions never align. Life doesn’t calm down; it just changes its chaos. The perfect partner doesn’t exist; only real, flawed humans who might love you anyway. The business success you’re chasing? It comes with new problems that make you nostalgic for your current ones.

I spent my 30s believing happiness would come when I “made it.” Now in my 40s, by most metrics, I have “made it”—successful company, global reach, financial freedom. But happiness didn’t arrive with the achievement. It can’t. Because happiness isn’t a destination you reach; it’s a practice you maintain.

These days, I’m practicing something radical: enjoying my imperfect present. The coffee that’s slightly too bitter. The apartment that’s smaller than I’d like. The date that went okay but not amazing. This is it. This is life. And waiting for better conditions is just another way of saying no to what’s here.

5. Believing your inner critic’s narrative

There’s a voice in my head that’s been with me since childhood. It says things like: “You’re not smart enough,” “You’re behind,” “Everyone can see you’re faking it.” For most of my life, I treated this voice as the honest one—the voice cutting through my delusions with hard truth.

But that voice isn’t honest. It’s just loud.

The inner critic doesn’t deal in truth; it deals in fear. It takes your deepest insecurities and presents them as facts. And the older you get, the more ammunition it has. More failures to reference. More relationships that didn’t work out. More evidence for its prosecution.

What I’ve learned, partly through working with Rudá on The Vessel and partly through my own stumbling attempts at self-awareness, is that the inner critic is just one voice among many. There’s also the voice that notices beauty. The voice that feels gratitude. The voice that says, “You’ve come further than you think.”

The behavior that kills happiness isn’t having an inner critic—everyone does. It’s believing the critic is the only one telling the truth. It’s giving that voice editorial control over the story of your life.

These days, when the critic speaks, I listen briefly—sometimes it has useful data. But I no longer let it write the headline.

The uncomfortable truth about happiness and aging

Here’s what I wish someone had told me at 24, when I was a management consultant convinced that the next promotion would make me happy. Or at 34, when I was building Ideapod in New York, certain that scale would bring satisfaction. Or even at 40, when I moved to Singapore thinking a change of scenery would shift something fundamental.

Happiness isn’t something you find. It’s something you stop blocking.

Every behavior on this list—comparison, validation-seeking, rumination, postponement, self-criticism—is a wall we build between ourselves and the contentment that’s already available. We don’t need to add anything to our lives. We need to subtract these patterns that have been running unchecked for decades.

I’m 44. I don’t have it figured out. But I’m slowly learning that the path to happiness as we age isn’t about achieving more or becoming better. It’s about releasing the behaviors that made sense when we were younger but now only serve to keep us miserable.

The letting go is the work. And it’s never too late to start.