The conversation that changed everything for me

Why creatives need an entrance strategy, not an exit strategy.

I was sitting next to a Hood River winemaker on a press tour last summer. He and his wife were serial entrepreneurs, the kind of people who spin off businesses like other people eat potato chips. We were talking about businesses — how they start, how they thrive — when I asked him what his advice was to all entrepreneurs.

“Well, what’s the first thing on your business plan?” he asked.

Radio silence.

Other people at the time clinked wine glasses.

“Your product?” I said, more a question than an answer.

“Wrong,” he said, kindly. “Exit strategy.”

“Exit strategy?” I said.

“Like, how are you going to sell the business to someone else.”


“Yes. And what’s the second thing on your business plan?” he asked me.

“Product,” I said, more sure of myself.

“Wrong,” he said. “Exit strategy.”

“Again?” I said.

“Yes, again,” he said, and he picked up his fork.

Nothing has done more to change how I look at my work in the past year than this conversation. I went home deep in thought about how I was going about my work and how I view the business of writing and media creation.

I didn’t have an exit strategy.

I was selling off my works one at a time, on a freelance basis, to clients who pay me once.

What was I supposed to do, sell my brain when I was done doing this work? Was I supposed to sell my worldview, my talents, my distinct writing voice? What? What did I have at the end of my life to show for all this work except for the stuff I bought?

Writers need an exit strategy, I thought. But most writers aren’t going to stop writing. They aren’t going to retire (that’s the great thing about writing), and they can’t sell their brains at the end of their lives.

So what could I do?

This website I am building right now emerged directly from this conversation. I realized while talking to the winemaker that even though I have an invoicing system, relationships with clients, and products I create, I wasn’t building my business. I was selling off my brain and talents one little bit at a time. I was living on the thrill of attaching my name to other peoples’ empires without building my own.

Here’s the thing. I know I have a lot to offer people — years of experience writing, reporting, editing, creating great content, teaching others how to do the same, but when I was only freelance, readers didn’t connect with me. They connected with someone else’s brand. Someone else’s business. Someone else’s big, beautiful project.

There is certainly no problem with supporting others in their creativity and goals, but that isn’t a way to build a life as a creative.

So that’s where I am. I’m developing products for you. I’m figuring out how to connect directly with readers (that’s the fun part anyway!) and really be of value to other people — not just the magazines and outlets I write for, but direct relationships.

I’m not calling it an exit strategy, though. I don’t intend to ever stop doing this work. I’m calling it an entrance strategy. A way to have my own real estate in this work I love.

What’s your entrance strategy?

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