In January I spotted this sign in a small restaurant we stopped at during our vacation. I love a good play on words, and this take on “the pursuit OF happiness” got me thinking.

For decades, the conventional career roadmap has followed a fairly predictable script: work hard, climb the ladder, and maximize your earnings so that eventually—once you finally cross the retirement finish line—you’ll be happy. We seem to be conditioned to view our working years as a long trade-off where happiness is the delayed payout. The problem is that happiness isn’t necessarily a prize waiting for you when your work concludes. As you approach the later stages of your career, the goal shouldn’t just be to reach the end; it should be to enjoy the journey. 

And a lucrative role doesn’t have to be awful to be the wrong fit. Often, it’s just fine. It’s relatively comfortable, but not exactly inspiring. At this stage, you are trading your most finite and precious resource—time—for a paycheck. This is the Destination Fallacy: the belief that once you reach retirement, you will finally be happy.  But having a “countdown to retirement” calendar for weeks, or months or even years isn’t exactly living an inspiring life. 

Choosing a phased retirement or a late-career pivot into something “interesting” or “fun” might raise an eyebrow or two, but it is actually a brilliant recalibration. When you pivot toward variety, you aren’t just looking for something different, something that keeps the mind sharp. When you pursue projects that are genuinely interesting, you enter a state of “flow” where you’re energized and your decades of experience feel fresh again. A lucrative role that offers no excitement is a slow drain on your creative battery, whereas a role that keeps you curious is a direct investment in your own long-term vitality. 

The philosophy here is simple: It is not that the pursuit leads to happiness; the pursuit IS happiness. When your workday consists of variety and curiosity, you stop living for a distant weekend or a retirement date five years away. You start finding value in the process itself—the thrill of being a “rookie” at something new while still being the expert in the room. This shift allows you to feel part of something evolving rather than something static. 

And often, when you choose the path that energizes you, the success and the community follow naturally because you’re finally working with your heart instead of just your habits. Life is far too long to spend the final stretch waiting for a “someday” that isn’t guaranteed. If the journey doesn’t make you smile, you’re on the wrong road—no matter how well-paved it is.