How would you know if you'd already won?
A friend asked me a question this week and I haven't been able to shake it.
So here's the setup. I'm about a year out from leaving my old career. And honestly, dude... I'm living the dream. I keep saying yes to opportunities, I'm doing work I actually love, I'm working from home with my kids watching Bluey in the background. Full integration.
But I told him something that I think a lot of you are feeling too.
The jump was the hardest part. Getting here was the hard part. And now that I'm here, it's like, okay... now what? I just want to keep building. And I never want to be complacent.
BUT.
I can't just keep pursuing for pursuing's sake. I need to know what ENOUGH is.
So he asked me the question. And I want to ask it to you.
Not "what does winning look like?" That's the easy version. The real question is: how would you know if you had already won?
Read that again. Because most of us are on a treadmill and we don't even realize it. We set a number, we hit the number, and then we immediately want a bigger number. That's not a character flaw, that's just... natural. I know that if I say "I want to gross a million with high margins" then the second I get there, I'm going to want more.
So here's how I'm trying to think about it. Three layers.
Layer one: the ecosystem. What's the portfolio of things I want to be able to point at and say "that's mine"? For me it's owning my own little world of businesses and content and community. Not a job. A system.
Layer two: the number. Yeah, there's an income number in there. There has to be. But the number comes FROM the ecosystem, not the other way around. If you chase the number first, you'll just build a bigger treadmill.
Layer three: the North Star. This is the one that actually matters. I've got a front row seat to someone who has built exactly what I want. And the thing that stands out isn't the revenue. It's that he's very intentional about pulling himself OUT of the business so he can spend more time with his family. The team runs it. He sits down, creates, makes the big decisions... and then goes and lives his life.
That's the whole game. Not "how big can this get." It's "at what point does this thing work FOR me instead of me working for it?"
And here's the part I didn't expect. My friend pointed out that when you're the entrepreneur, you're infinitely optimistic and high agency. Your spouse trusts you... but they don't necessarily share that optimism. So having a basic plan that says "here's what winning looks like, and here's how we'd know" isn't just for you. It's for the people riding the wave with you.
My wife is a bookkeeper by trade. She's the numbers person in our house. And the fact that someone who lives in spreadsheets trusted me to make this jump... that means even more.
So I'm going to actually sit down and do this. Define enough. Define the win condition. Not so I can stop, because I don't want to stop. But so I have FREEDOM beyond that point instead of murky stress.
Here's your homework. Grab a napkin. Write down three things:
- What's the ecosystem? What would you want to own?
- What's the number that falls out of that?
- What does your life look like on a random Tuesday when it's working?
If you can't answer number three, you don't have a goal yet. You have a treadmill.
What is enough is a lifetime question. But you have to start asking it.
Stay in the fight, Kevin