Have you already surprised yourself?

A lesson learned, again. / Issue 1,527

Oh, hi friends!

This week, Chicago Cubs field reporter Taylor McGregor held an event for aspiring broadcasters at Wrigley Field.

The proceeds benefited Project Main Street, supporting those living with ALS.

Taylor asked if she could give the college students copies of my journals Do It For Yourself, Do It Today, and Do It (or Don’t).

YES!

I love that these students already know what they want — broadcasting!

She posted an IG video of the event...

taylor_mcgregor

A post shared by @taylor_mcgregor

And seeing these students (umm, class of 2025 — how is that possible?!) plot out their futures made me realize something…

I’ve surprised myself so many times in my life.

Sometimes I forget about the journals. I wrote the first one as a side project while editing at Money and starting the BMI Workshop. The other two were written alongside editing gigs, short musicals, and freelance assignments.

Now they feel like creative diaries — essays on my beloved Grandpa, bird-watching, why I write “thank yous” to my rejections.

But usually they sit on a shelf while I’m staring ahead, kicking myself for “wasting time” or <insert creative anxiety spiral>.

But Taylor’s event sparked me to open Do It Today.

Flipping through the last chapter, I realized: it’s really good?!

I worked hard on it.

Opening it reminds me of that effort.

The same thing is true for the drafts on my desktop and the proposals never bought and the songs you’ve never heard.

I surprised myself every time I made something, regardless of where it ended up.

The same thing is true for all of your drafts and your dreams and your chapters.

You’ve surprised yourself so many times in your life, with your persistence or creativity or innovation.

The proof is everywhere.

Reminding yourself what you’ve already done…

Maybe that’s how you find the audacity to go after what’s next.

P.S. — Stuck on a project? Launch the Plane is back and open through August. Let’s get moving together.

P.P.S. — My new micro-project — Open Skies Day — are free 15-minute brainstorming slots held once a month. We’re booked for July and August! If you want a heads-up when future dates open, get on the list here.