#1: Permission to be Bad

Bob Ewing
January 29, 2021

Talking Big Ideas.

“It’s not the writing part that’s hard. What’s hard is sitting down to write.”
~ Steven Pressfield, The War of Art

Today we’re in Dixon, New Mexico. It’s a beautiful winter wonderland, up in the mountains outside Taos. We are excited for 2021 and new beginnings: Maryrose is now full time with the Ewing School, I’m starting this newsletter, and Ollie is taking over all invoicing.

When I told Josh Smith from the Center for Growth and Opportunity that I am focusing on writing more, he encouraged me to read the delightful classic Bird by Bird by Anne Lamott. One of Lamott’s mantras: Write shitty first drafts.”

She’s a fantastic writer and makes a convincing case. We don’t start off amazing at things, we have to work hard to get there. We all understand this. Michael Phelps wasn’t born the best swimmer in history. He put in a ton of effort.

Yet it’s easy to forget this on a smaller scale. When we sit down to prepare for a presentation or write an article, we can get discouraged. We can find it tough to even get started.

The truth is, nobody writes like E.B. White on their first draft. Including E.B. White. It takes lots of rewriting and practice. The same applies to speaking.

I love working with my clients on big presentations they have coming up. The difference is always massive between their first baseline session and when they get on stage and crush it.

Once we begin, we’re off to the races, heading in a new direction — as I’m doing today with this newsletter.



It’s hard to get started. Giving ourselves permission to be bad at first is key.

Ask yourself: What is some communication I’ve been putting off? An email sitting in my inbox? A tough conversation, an upcoming interview, testimony, or speech?

Block off five minutes over the next week (or right now!) to sit down and begin a bad first draft. Focus on just getting things out. Try not to have any expectations.

For example, when I sat down to write this newsletter, I typed: “Once we get the boulder moving. Pat Collison from Stripe. Jim Collins Windmill analogy.” These aren’t even sentences, and it all ended up getting cut. Which is fine, it got me started.

Stop after five minutes. See what you’ve done and note how you feel.


If you try this week’s challenge, will you let me know how it went? I’d love to hear from you. My inbox is always open.

PS: Please send me your feedback & advice. How can I make the newsletter better? Do you have an idea or challenge I should include?

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