You would think that after two decades in business, and writing a book about how to run a business well, that I’ve got it all figured out and don’t make mistakes anymore.
Sadly, that’s not the case.
There are always new mistakes to make, and old ones to repeat. What does change is how quickly you recognize them—and how fast you recover.
Experience gives you pattern recognition, not immunity. You still say yes when you shouldn’t. You still underestimate timelines. You still convince yourself this project will be different, even when all the warning signs are there.
The difference is that you now know the cost. And you likely know how to fix it.
Early in my career, bad decisions felt educational and expensive from a financial standpoint. Now, they feel expensive in a different way—in time, energy, and opportunity. And that’s not failure. That’s awareness.
One of the biggest myths about long-term self-employment is that you eventually “figure it out” and stop struggling. In reality, you just struggle with more complex problems. The fundamentals—pricing clearly, setting boundaries, protecting your time, communicating effectively—don’t go away. They quietly wait for the moment you decide to ignore them.
I’ve recently had a project start to go sideways (I’ll share the story another time) because I wasn’t being as diligent as I should have been with communication. 15 years ago, I wouldn’t have known how to handle it and course-correct, but now I do. The mistake was another valuable reminder that even when I’m overloaded, I still need to pay attention to the underlying tasks that make a business run well.
Revisiting basic business principles still matters, no matter how long you’ve been in business. Not because you forgot them—but because you’re human, and it’s easy to take them for granted and let them slip.
In Good Work!, I talk a lot about recognizing patterns instead of chasing perfection. Good business owners aren’t the ones who never make mistakes. They’re the ones who don’t let the same mistake derail them when they make it again (and again).
Experience doesn’t eliminate bad decisions, but it does shorten their lifespan.