May 27, 2025, 9 a.m.

Sometimes positioning hurts, so make it hurt good

Draft's Letters

One more about repositioning.

We often speak here about new positioning being easy to adopt, technically speaking. You change your home page, spin up a landing page, ask people if they’re interested. You put on new positioning like it’s a new outfit.

The real challenge is when you reposition after a decade of a previous positioning. That’s a fourth of your career! You’re kind of flushing it! Suddenly you’ve been boiling-frog’d into one of the most load-bearing decisions of your life.

There are ways to slow-pedal this and soften the impact. If you keep your existing portfolio of clients, and even your existing messaging and educational initiatives, you can test the new market without burning any bridges.

This took two years for us. We returned to some key watering holes where our clients like to hang out, and we hung out there. We built relationships slowly, figured out what the urgent & expensive problems are. We underpriced software work and were less discriminating in who we took on. All along the way, we kept our work up in our old positioning, even writing lessons for that group.

This has the same effect, intellectually speaking, as patting your head while rubbing your stomach at the same time. You are in fact serving two different groups of people, and you are making a slow, sometimes messy change in the process. When external factors forced our hand, we knew what had to go, and we had already spent enough time preparing for it to feel confident.

If you run the business, then it’s incumbent on you to take the five-year view on it. That involves big, emotional questions that ultimately nobody else can answer for you. Who are you serving? What urgent, expensive problems are you solving now? And what is the impact of broader change on your decisions?

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