Your wins don't stay won.

I was cleaning out my desk last month and found an award I won fifteen years ago.

"Salesperson of the Year" back at a startup I worked for in NYC. I remember being so proud when I got it. I took a photo, probably posted it on LinkedIn, and felt like I'd finally made it.

Now it was buried under old receipts and some random cables in my desk, collecting dust.

At first, I felt a little ashamed. This thing mattered so much to me once, and now it’s buried in a junk drawer.

But then I realized that the award didn't lose its meaning because it wasn't important. It lost its meaning because the person who earned it fifteen years ago isn't the same person sitting at this desk today.

The win happened. It was real. But it didn't stick around just because I achieved it once.

It turns out, your wins don't stay won.

What you may not know about achievement

Every win feels permanent in that winning moment.

You hit the revenue goal, shipped the product, landed the client, or published the thing. And for a few days (maybe weeks or months), it feels like you'd finally arrived somewhere.

But then the feeling starts to fade.

Not because the win wasn't real or meaningful, but because wins are moments, not permanent states. They happen, they feel good, and then they're over.

And you're left thinking, "Now what?"

I see this all the time with people who hit a big milestone. They celebrate, post about it, and feel genuinely proud (as they should). Then a month later, they're back to feeling like they haven't done enough in their life, career, or whatever. Like the win didn't even count somehow.

It's not that they're ungrateful or broken. It's just that achievement doesn't work the way we think it does.

We treat it like a finish line. Like once we cross it, we get to stay on the other side forever. But the reality is, there is no other side. There's just the next thing, and the next thing after that.

When I watched my friend chase the feeling

I have a friend who sold his company two years ago for seriously life-changing money.

He'd been grinding for more than seven years to build it. Long hours, brutal decisions, the whole startup nightmare game. And when it finally sold, he was genuinely relieved, proud, and exhausted in all the best ways.

For three months, he felt incredible. He traveled, he got some well-deserved sleep, and spent time with his family without his phone glued to his hand. It was just as magical as he’d hoped.

Then one day, we're having a beer, and he says, "I don't know what to do with myself. I thought selling would feel different. I thought I'd feel...done."

But the truth is, he isn't done. He's just back at the beginning, looking for the next thing that will make him feel the way the sale made him feel for those three months.

He didn't want to start another company because he loved building companies. He wanted to start another company because he missed the feeling of winning.

But chasing the feeling is different than doing the work. One is about the destination. And the other is about the process.

What actually stays

I think the problem is we've been told that achievement is the point.

That if you work hard enough, win big enough, and hit the right milestones, you'll arrive at a place where you feel 100% satisfied for the rest of your life. Where the wins finally stick.

But it doesn't work that way.

The wins fade. The milestones eventually become fond memories. The awards collect dust.

What stays isn't the wins, but the process of pursuing them. The work itself, the problems you solve, the skills you develop, and ultimately, the person you become while you're chasing the thing.

Those are the things that compound. Those are the things that build something lasting.

Because winning once doesn't mean much. But winning repeatedly means everything. Not because you need more wins to feel satisfied. But because the process of pursuing the next thing is what keeps you engaged with your own life.

My friend who sold his company? He's building something new now. Not because the first exit wasn't enough. But because he realized sitting around celebrating an old win is not the way he wants to spend the rest of his life.

He doesn't want to continue basking in the light of the win. He wants to still be in the game.

And I think that's what I didn't understand about that award buried in my desk. Back then, I thought it represented the peak of something. But now I can see it was just one data point in a much longer arc.

The version of me that earned it was good at something a long time ago. The version of me today needs to be good at much different things. Not necessarily better. Just different. Because you evolve, the work evolves, and what lights you up changes.

What I do now

I don't chase wins the way I used to.

I used to think the goal was to hit milestones that would make me feel like I'd finally made it. Now I know there is no "making it." There's just the work, and whether or not I'm engaged with it.

So instead of asking "What will make me feel successful?" I consider, "What work do I actually want to do?" I chase problems that interest me. Projects that require me to develop new skills. Work that feels hard in a way that makes me better.

The wins come or they don't. But the process is what I'm here for.

I dusted off the frame and put it on my desk to remind myself that the feeling of an achievement fading is a OK. The journey is what builds character, skill, and experience. And those are the compounding elements of your career.

The bottom line

The unfortunate reality is that your wins are temporary. The feeling will eventually fade, and the moment will pass. When it finally does, you're left with a choice: keep moving forward or try to live off what you did yesterday.

The people I admire the most aren't the ones with one big win in their pocket. They're the folks who are still showing up, still trying new and interesting work, and still chasing the next thing (maybe something that scares them a little).

Not because they need another win to feel complete, but because the process of pursuing it is the whole point.

So here's my question:

What are you chasing right now? And are you chasing that thing because you want the win? Or because the work matters to you?

Reply and tell me. While I can't respond back to everyone, I read every response.

That's all for this week.

See you next Saturday.