Why Chasing Happiness Is Making You Miserable (and What to Do Instead)

For most of our lives, we’ve been taught a pretty simple formula: Work hard. Make and save money. Retire. That’s the formula for happiness.

It sounds right. After all, that’s what we’re all aiming for.

However, the older I get and the more wealthy people I meet, the more I begin to realize that something isn’t right. That formula doesn’t work the way we think it does.

This is something my friend Derek Coburn understands better than most. As a financial advisor, he served ultra-wealthy clients for nearly 20 years, eventually selling his business and making his way out of the industry. As a bestselling author and founder of the Cadre mastermind, he has seen what happens after people reach financial success firsthand.

What he has seen is eye-opening. He wasn’t really concerned with retirement planning, investing, or lifestyle design.

Rather, it was about meaning and purpose. As such, he explains why trying to achieve happiness constantly can make you ill, unfulfilled, and burned out.

The Surprising Science Behind Happiness vs. Meaning

Derek shared a study from researcher Barbara Fredrickson with me that I was floored by.

Participants were divided into two groups in the study:

• Personal happiness was prioritized in the first group.
• Those in the second group prioritized a sense of meaning and purpose, contributing to something greater than themselves.

The researchers tracked physical markers such as inflammation, immune response, and overall health. The results were nothing short of shocking.

There was a higher prevalence of inflammation, weakened immune systems, and greater susceptibility to illness and early death among people who focused primarily on happiness.

In contrast, the group focused on purpose had lower inflammation, a stronger immune system, and better long-term health outcomes.

Let that sink in.

People become less healthy by trying to be happy — directly and obsessively.

But living with meaning? It strengthens people.

The takeaway was simple but profound: If you want happiness, stop chasing it.

Therefore, it’s time to pursue your purpose.

Why Retirement Often Backfires

In real life, I’ve seen similar results repeatedly.

A person retires, financially free, without obligations, with all of the time in the world, and then something strange happens. Physically, mentally, and emotionally, they decline.

Everyone has heard the stories: retired people decline in health or pass away within a few years. This is not a coincidence.

Whenever people feel disconnected, meaningless, and unconnected, their bodies respond in kind. It’s for this reason that we’re seeing an increased movement toward “un-retirement”. Approximately 30% of retirees return to work. It’s not that they need the money, but they miss being useful.

After all, our bodies and minds are wired to contribute. And when we stop doing that entirely, something inside us shuts down.

Winning the Financial Game—Then Choosing a Different One

Derek’s story resonated deeply with me.

Over the course of his career, he built a successful financial advisory practice, which he sold in 2019. Financially, he won. As a result, he has enough money to take a step back, reassess, and decide how he actually wants to live.

That’s the real win.

It’s not about maximizing income forever or grinding forever. It’s about getting to a point where your decisions aren’t dictated by money.

After that, Derek chose not to travel endlessly or take a permanent vacation. Particularly with his family, he was intentional about being present.

The $50,000 Bedtime Story Lesson

Derek shared a powerful moment involving his children.

When his boys were younger, he found himself rushing through bedtime routines to get back to his inbox or watching Netflix. His life changed when he had a thought experiment.

He imagined a future where a time machine allowed him to relive one single bedtime moment with his child.

What would that be worth? Without hesitation, he answered $50,000.

As a result, he began treating those moments like they were worth $50,000.

The routine and time were the same. However, the presence was radically different.

That’s lifestyle investing in action.

Investing attention in the moments that matter most now is more important than just investing money for future freedom.

Rethinking Retirement Altogether

In traditional retirement planning, the assumption that work ends is one of the biggest mistakes. In fact, most financial plans begin with the same question: “What age do you want to retire? ”

Most people, however, never ask: “Are you even interested in retiring? ”

Many people don’t want to stop working — they just want to stop doing work they dread.

This is perfectly illustrated by Derek’s example.

Let’s say a 45-year-old earns $150,000 a year and has $150,000 saved. For them to have enough money to retire at 65, they will need to save over $2,400 per month.

However, if they simply extend their working years to 75, they will only have to save about $110 a month.

That’s a 96% reduction.

Why?

• More years of earning.
• Compounding time is increased.
• There are fewer years when withdrawals are required.

Ultimately, in both financial and emotional terms, purpose creates flexibility.

Money Doesn’t Create Happiness or fulfillment—Meaning Does

It’s a shocking truth that many high achievers find hard to believe: Money solves money problems. But it doesn’t solve fulfillment problems.

I’ve seen it firsthand. Big exits. Passive income. Financial freedom.

There’s a real satisfaction spike, but it’s temporary.

Then the question comes back: “What’s next?”

In the aftermath of financial success, most people crave:

• Connection
• Contribution
• Growth
• Alignment with their values

That’s why people who anchor their identity solely to wealth often feel lost once they’ve “made it.” In other words, people need meaning instead of money to motivate them.

Faith, Stillness, and Fertile Soil

Faith is important to both Derek and me.

By stepping away from the constant hustle, Derek became more intentional about his spiritual life — praying more, reflecting more, and getting in touch with God.

His perspective was reshaped by the Parable of the Sower. It describes how most seeds don’t take root. However, fertile soil allows them to produce exponentially.

As a result, he doesn’t put his focus on long-term goals anymore. He focuses on cultivating the right daily habits that will enable him to be grounded, healthy, and open to guidance on a daily basis.

I found that deeply moving.

When you’re exhausted, stressed, and disconnected, it’s hard to hear anything else. Stillness, however, creates clarity.

Why Community Accelerates Happiness

The importance of community is one last thread I would like to highlight.

Derek founded Cadre, a highly curated mastermind centered on contribution, not extraction. Using similar principles, I built the Lifestyle Investor Mastermind.

What we’ve learned is that your peer group will shape your future more than anything else. Having people around you who value growth, integrity, generosity, and purpose changes how you think and live.

Simply put, the right community doesn’t just help you make more money. You become a better human as a result.

Final Thought: Design a Life You Don’t Need to Escape From

Happiness is fleeting. But purpose? That endures.

Achieving financial freedom isn’t about stopping — it’s about choosing.

In particular, it is about choosing meaningful work, contributing to the community, and being present.

By designing your life around purpose instead of escape, you will never need to retire.

And ironically? When that happens, happiness tends to show up on its own.

Key Takeaways

• Stop chasing happiness. Build meaning. Purpose tends to lead to happiness, not the other way around.
• Retirement isn’t the goal. The majority of people don’t want to stop working; they want to stop doing work that drains them.
• Working longer (by choice) buys flexibility. Financial pressure can be dramatically reduced even with a modest income later in life.
• Money creates options, not fulfillment. Money problems can be solved by it, but meaning can only be found through intentional life design.
• Presence pays the highest return. When you’re fully present, the moments that matter most to you become your most treasured memories.
• Your habits shape your clarity. Grinding harder isn’t as important as energy, health, and stillness.
• Community compounds. If you surround yourself with the right people, you’ll raise your standards, sharpen your thinking, and expand your horizons.

Featured Image Credit: Magda Ehlers; Pexels: Thank you!