The Wins That Keep Us Going: A Reflection on the Small Habits That Sustain the Bigger Dream

Last night, just before bed, Rachel said something that stopped me. Since then, I haven't shaken this thought about small habits.

We’d just come off a long but meaningful day. Our friends Ben and his family were in town. Ben I first met during one of the more impactful moments of my life, living in Israel and backpacking across Europe. We were 20, wide-eyed, comically tanned, and had absolutely no idea where life would take us.

Now, two decades later, he’s living in Thailand with his wife and two kids and I'm in Vietnam with Rachel. How could we have imagined then that our lives would lead us here? That we would meet in the Old City over 25 years later to reconnect not just with each other but with parts of ourselves we once thought we had outgrown?

The Kind of Small Habit That Sneaks Up on You

It was the kind of day that drains you in the best way. The kind where your body is ready to crash but your mind is still buzzing, and you can't stop shaking your head at life, culture, and how surreal it all feels.

Rachel and I pulled back the sheets and got into bed, grateful and sun-tired. That’s when Rachel said it:

"You know, Stephen, you’ve had some real wins lately. I know it’s hard to see them sometimes because you often focus on just one kind of win."

I interrupted her immediately. “Well, that win is important. It’s practical. It’s about money coming in. That’s a real world win.”

She didn’t flinch. Just smiled and replied, “I know. I’m not saying it’s not important. It’s our livelihood and it matters. But we often miss the other wins. The ones that keep us going when things feel stuck. The wins on the road to the ‘real world wins’ that make it possible to even get there. You can’t miss those.”

It landed.

And this morning, sitting here with my coffee, I realized: she's right.

The Wins That Don’t Make It to the Metrics Dashboard

I know I’m not alone here. Most founders, creatives, and leaders I coach struggle with this same tunnel vision. We’re trained [sometimes subtly, sometimes by brute force] to focus only on the wins we can invoice for. The ones that validate our worth. That get the head nod at the SXSW conference.

But there are other wins. Like figuring out the rhythm that lets you write three days in a row without spiraling. Or saying no to a client that doesn’t align with your values. Texting your dad back. Eating lunch before 2:30 p.m. Or deciding that, today, you’re not going to be a hero. You’re just going to be human.

These aren’t the kind of wins that trigger a Slack emoji or get you quoted in Forbes. But they are the kind of wins that build something real over time. The small habits that quietly move you forward, even when nothing flashy seems to be happening.

They don’t scream. They don’t trend. But they stay. And they stack.

Final Thought On This Small Habit

I’m not saying we don’t need big wins. We do. They pay the bills and keep the lights on. But in between those? In the long stretches where the momentum slows and self-doubt creeps in? It’s the small habits that keep the fire burning.

So whatever you’re working toward, whatever feels just out of reach, don’t overlook the invisible progress. The little wins. The kind that keep you from quitting. The kind that get you back to the page, the meeting and the call and the kitchen counter...ready to try again.

If you’re in one of those seasons where the “real world win” feels far away, take stock of the small habits that are keeping you afloat. They count. They matter. They’re probably why you’re still in the game.

And if this hit a nerve or made you laugh quietly into your coffee, share it with a friend or shoot me a note. I live for those.