You can build a very intelligent strategy around the wrong identity. I know because I did.
There was a stretch after Promax when I found myself quietly comparing my next chapter to what other people were building. Some were scaling firms, some were launching platforms, some were raising money and expanding teams. Even if I didn’t say it out loud, there was a steady voice underneath it all telling me I should be building something bigger, that I should capitalize on the title, that I should stay at a certain “altitude.” It wasn’t dramatic or insecure. It felt responsible… logical, even.
So I started sketching strategy around that voice. On paper it made sense. It positioned well. It aligned with what someone in my position would reasonably be expected to build next. But the more I shaped it, the more I noticed something subtle: it felt tight. Not wrong. Just slightly misaligned.
Around that time I kept coming back to a passage in John Steinbeck’s “East of Eden” about a single word that can be translated three ways: “thou shalt,” “thou shalt not,” and “thou mayest.” The difference between obligation and choice. I realized I was building from “shalt.” From what I OUGHT to do next. From what would look “correct” externally. What I hadn’t fully done yet was ask who I actually chose to be in this chapter of my career.
I took this photo recently in front of a green screen. It struck me how easy it is to change the backdrop. Much harder to change the person standing there.
That shift changes everything. When strategy is built from comparison, it carries pressure, even when it’s intelligent. When it’s built from choice, it carries energy. If you don’t anchor identity first, you end up optimizing the wrong thing. The plan might work. It just won’t feel like yours.
Before mapping the next move, I’ve learned to pause and ask a quieter question: am I choosing the backdrop… or choosing myself?
It’s worth asking yourself the same.
“Your 50” is a 50-week reflection series about realigning, activating, and expressing what comes next.