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Sponsor the next email to 200,000+ entrepreneurs → My wife and I have a friend named Carol who always wants to know exactly how everything in her life is going to unfold. I like to describe her as thinking in “10-year plans.” She wants to know where she’ll live, what she’ll be doing, and what’s going to happen in her career. She basically needs the end of the story before she gets too far into the beginning. I’m pretty similar. I’ve always liked predictability. I want to know where things are going and have some kind of plan I can follow that tells me where I’ll end up. That personality trait worked very well for the first 20 years of my career in business, because the sales career path is pretty straightforward. You become a good salesperson, manage a team, run a bigger team, become a VP, and then maybe become a Chief Revenue Officer. That’s how most corporate paths work. They give you a pretty clear idea of what progress is supposed to look like. When I started working for myself back in 2019, for the first time, all of that certainty went away. I could make a decision that felt totally reasonable based on what was happening and still have no idea what kind of career it was helping create. Over time, I had to become more comfortable making smaller decisions as I learned more instead of trying to figure out the whole story in advance. The individual decisions could make sense even when the larger career was still impossible to see. That kind of path can feel pretty illegible while you’re living inside of it. Some of the decisions I made led to things that became critical parts of my business. Others led to things that lasted a few months, and then I’d pivot once I could tell they weren’t working. And some bombed pretty fast. Good luck trying to find Tales from the SaaS Whiteboard, my 2017 failed YouTube series! Whether a decision succeeded or failed, each one gave me a little piece of information I could use. Early on, healthcare consulting taught me what customers would pay me to solve and how to position my expertise. It also taught me that I needed to start writing online to get more customers. Writing online taught me that a huge group of my readers wanted to learn about writing on social media, not healthcare. That led me to build courses about social media growth. Selling courses on social media growth taught me how to increase my income through eCommerce. The lessons piled up as I made more and more decisions. At the time, I had no clue where those decisions were taking my career. They just made sense based on what I knew right then. And I hoped that they would leave me a little better informed for the next decision. Your career doesn’t need to make sense in advance to make sense in hindsight. When I started working for myself, making decisions without knowing where they would lead made me deeply uncomfortable. Seven years later, I’m much more comfortable making the next decision based on what I know today. I still understand why Carol wants a 10-year plan. But I have seven years of evidence that I probably don’t need one. Do you?
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