Three months in. Two solid clients. A real pipeline.

And she wanted to scrap the whole thing.

I was working with a former Fortune 100 VP last fall. Smart. Senior. She had finally landed on a positioning that didn’t make her wince when she said it out loud. Fractional COO for early stage healthtech. We spent weeks getting her brand down to one clean sentence she could actually say.

Then a friend told her she should also do fractional CTO work. A former boss said she’d be great in nonprofits. Somebody in a Slack group said operations consulting was hot.

Within a month she had added two service lines and a third industry. Her LinkedIn read like a buffet. Her inbox went quiet.

I see this constantly. People build something real. They don’t give it room to land. Then they wonder why nobody is calling.

You are the product

Here’s what I’ve learned from years running enterprise teams as a CIO, and from the work I do now with people building their own brand and identity: the market needs time to find you. Not days. Months. Sometimes a year.

A new positioning is a wet signature on paper. Keep messing with it and the ink never dries. Nobody can hand it back to you.

You probably know the feeling. You change your LinkedIn headline. Two weeks later somebody on a networking call says something that makes you nervous, so you tweak it again. Then again. Then you wonder why your calendar stays empty.

Think of it like planting tomatoes. You put the plant in the ground. Two days later you decide the soil is wrong and dig it up. Three days after that you switch to peppers. By August you’ve got dirt and no produce.

What I’ve actually watched work

Let me cut to the chase. A few things hold up over and over with the people I work with.

It takes real time for a market to register that you exist.

When you try to be everything to everyone, you become nothing to anyone. Nobody calls you for a role. Nobody books you. Nobody buys your service.

Premature optimization is a polite way to say starting over. You don’t get progress. You get motion.

There’s a buyer for almost any honest offer, if you stay in one spot long enough to be findable. The research on grit lines up with this. People who sustain effort and interest toward a single goal over years consistently outperform people with more raw talent who switch constantly (Duckworth et al., 2007).

The Rocking Horse trap

I’ve been using the phrase “Rocking Horse” with people for years. You know the toy. You sit on it. You rock back and forth. You sweat. You feel like you’re working. You’re not getting anywhere.

That’s exactly what happens when you keep repositioning before the market sees you. You’re on networking calls every morning. You’re rewriting your one liner every week. You’re busy. You look productive. You’re rocking.

This is how people convince themselves they’re working hard while quietly going nowhere.

The Burnout Connection

Running in place wears you out faster than running forward. When effort doesn’t produce results over time, and the future starts to feel unsurvivable, people slide into emotional exhaustion and cynicism. That’s the textbook burnout pattern (Maslach & Leiter, 2016).

Constant repositioning is exhausting because nothing ever pays off. Your runway shrinks. Your hope shrinks faster. One morning you can’t open your laptop.

Identity work itself is slow on purpose. Research on how professionals actually adapt to new roles shows that people build identity through observation, experimentation, and outside feedback over a long stretch, not through constant relaunches (Ibarra, 1999). If you don’t let the process run, you never get the feedback that tells you whether to stay or adjust.

Trust Your Instinct

Pick two people who could actually hire you or buy from you. Ask them this.

“What do you think you’d get from working with me?”

“What do you think I’d leave behind once the work was done?”

If the answers are scattered, vague, or wildly different from each other, your positioning hasn’t set yet. You’re not unfit. You’re hard to picture.

And if you’re still asking yourself, “Who am I, professionally?”, that is the answer. You’re doing too many things right now. Pick one. Sit with it.

If you want help getting your identity down to one sentence and staying with it long enough to see real results, you can book time with me at https://book.drdegnan.com.

Cheers, and until next week, my friend!

—Oliver

Bibliography

Duckworth, A. L., Peterson, C., Matthews, M. D., & Kelly, D. R. (2007). Grit: Perseverance and passion for long-term goals. Journal of Personality and Social Psychology, 92(6), 1087–1101. https://doi.org/10.1037/0022-3514.92.6.1087

Ibarra, H. (1999). Provisional selves: Experimenting with image and identity in professional adaptation. Administrative Science Quarterly, 44(4), 764–791. https://doi.org/10.2307/2667055

Maslach, C., & Leiter, M. P. (2016). Understanding the burnout experience: Recent research and its implications for psychiatry. World Psychiatry, 15(2), 103–111. https://doi.org/10.1002/wps.20311