043. Why You Must Celebrate Every Win

“I almost wish I could be more exciting, that I could match what is happening out there to me.” —Whitney Houston

Welcome to The Unconventional Founder, where we dive deep into the unpolished, real, and often wild journey of building a startup from scratch. Forget the glossy stories of Ivy League diplomas and cushy Wall Street gigs – my story is about grit, hustle, and the occasional hip-hop playlist to keep the energy high.

Today, we’re talking about something every founder—and really, everyone—needs to get better at: recognizing and celebrating progress.?

We’re wired to keep pushing forward. Always thinking about the next feature, the next hire, the next milestone. It’s like we’re in this constant hustle, chasing the future version of our startup that lives in our heads. But here’s the thing: in all that forward motion, we rarely take a beat to acknowledge the steps we’ve already taken. And if you don’t look back sometimes, how do you even know how far you’ve come?

Progress Isn’t Always Loud

In startup culture, we tend to focus on the big wins—the product launch, the funding round, the headline-grabbing partnership. But here’s the truth: most progress is quiet. It’s in the tweaks, the pivots, the lessons learned when things go sideways. Maybe it’s not headline-worthy, but that doesn’t make it any less significant.

For instance, I remember when I was starting out, I had this vision of everything going smoothly—financing secured, product ready to roll. (Spoiler: it didn’t happen that way.) Instead of launching my MVP, I hit a major roadblock with funding. At first, I was frustrated, feeling like all the planning and hard work had stalled. But that setback forced me to rethink my approach, to pivot. Every day, we adapted—new strategies, smaller steps forward. The real progress didn’t come from a massive breakthrough, but from navigating those challenges and finding a way to keep pushing forward.

The lesson? It’s the cumulative effect of small wins that actually moves the needle. Celebrating those micro-milestones keeps you and your team energized. Because let’s be real, startup life can feel like a marathon with no finish line in sight. If you’re always holding out for the next "big thing" before you celebrate, you’re missing out on all the little victories that make it possible.

Why We Don’t Celebrate Enough

If you’ve ever thought, "I’ll celebrate when I hit that next big goal," you’re not alone. We all do it. But why?

I think part of it comes from this culture of "hustle harder." You know, the idea that if you’re not working 24/7, you’re somehow failing. There’s this toxic mentality that celebrating is equivalent to getting soft, to losing focus. And it’s not. In fact, recognizing progress is crucial to staying in the game. Think of it like this: if you’re in a video game and you never level up, no extra lives, no power-ups, wouldn’t you get frustrated and quit?

The startup journey is exactly the same. If you don’t pause to appreciate what’s working, to high-five your team when you hit a milestone—big or small—you’re just burning fuel without ever refilling the tank.

Taking time to celebrate progress isn’t just feel-good fluff—it’s strategic. When you celebrate milestones, you’re creating positive reinforcement for the behaviors that lead to success. It builds momentum. And momentum is everything in a startup.

Take the time to reflect on what’s gone right. It could be something as small as your team nailing a tough client pitch, or your product finally hitting that elusive bug-free streak (well, mostly bug-free). These moments build team morale and help you stay connected to the bigger picture. You didn’t come this far to only come this far.

How to Celebrate Progress (Without Breaking the Bank)

Now, I’m not saying you need to pop champagne every time you squash a bug or send an invoice. But you can find ways to celebrate that don’t require a massive budget (or a lot of time). Here are some ideas:

• Shout-outs at team meetings: Acknowledge someone’s hard work. Be specific about what they did and why it matters.
• Take a break: Yes, you’re allowed. Sometimes just stepping away for an afternoon to recharge is the best way to celebrate a win.
• Share your wins: Post about your small victories on social media. Not only does this boost morale internally, but it also shows your community that progress is happening, even if it’s not front-page news.
• Music breaks: No joke, throw on a 90s or 2000s playlist, gather your team, and just jam out for a few minutes. It’s a fun, easy way to recharge the collective energy.

The Power of Looking Back

Remember that episode of "Fresh Prince of Bel-Air" when Uncle Phil tells Will that success is about appreciating where you came from? He wasn’t wrong. Sometimes the key to moving forward is taking a moment to look back at all the things you’ve already overcome.

Progress isn’t just about the destination, it’s about the journey. And in the startup world, that journey is full of twists, turns, and surprises. So, take a beat, celebrate your progress—big and small—and keep that momentum going.

Stay tuned, stay inspired, and let’s rewrite the startup playbook together. Subscribe now and join the journey.

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