The short answer: you don’t. And that’s the point.
The lesson I keep learning is that no matter how much you plan, things will always turn out different than you expected. Which is why it’s actually better to give yourself less time to plan—so you can test, learn, and reset faster.
The Trouble With “Fail Forward”
I’ve always hated the phrase “fail forward.” Because here’s the truth: I’m a Black man in a country that doesn’t give people like me the same room to fail. My whole life I’ve felt I had to be twice as good just to get the same opportunities.
So I studied hard. I worked hard. I did everything “right.” And it paid off in my career as a creative director.
But entrepreneurship? That’s a whole different ballgame.
Entrepreneurship = Experiments
I once had a conversation with my friend Chris Guillebeau, and he helped me see this clearly:
Entrepreneurship is just a series of experiments.
Failure isn’t the enemy—it’s a gift. Every test teaches you something new. And when you start thinking about your ideas as rough drafts or tiny experiments, it becomes so much easier to separate your self-worth from the outcome of any single launch.
That’s a blessing for the perfectionist in me who still shows up now and then. Because if an idea doesn’t land, it’s not me that failed—it’s just that idea. And I can relaunch it over and over until I get it right.
What Really Might Be “Off”
Most of the time, it’s not even the idea itself that’s the problem. It could be:
- The audience
- The messaging
- The positioning
Those are all things you can change.
From Home Runs to Base Hits
For a long time, I thought I had to hit a home run every single time. But now I know the real goal is just to get to the next base. And if I strike out? That’s fine too. Tomorrow, or next week, or next month—I’ll step up to the plate again.
Because every swing is another chance to learn.
So, how do you know if your idea is good enough to launch?
You don’t. You just launch it anyway.
