I spent months working on my college essay to get into my dream school, Syracuse University. I wrote an extended metaphor about baseball that explained going to this program would be my home run moment. I worked on my essay every day, incorporating careful details in the hope my hard work would help me get accepted. I needed to do something remarkable to get in. I didn’t have the SAT scores and my grades were ok, not great.
Once I sent it in, I remember rushing to the mailbox after school. I was looking for one large envelope with an orange logo. That meant acceptance. I knew anything that came in a standard size envelope was a rejection. One afternoon as I waited for the mail to come, we got a phone call at the house. This was back when people answered their phones. It was the Dean of the Creative Writing Department at Syracuse. He was calling to personally tell me he read the essay and that I was being accepted into the program. I was ecstatic. It was the first time I realized that writing would help me figure things out.
Corporate America tried to steal that joy. I spent years writing taglines, lame recruiting templates, and employer value propositions. When I took the leap to start Three Ears Media, these letters on Friday looked like most of the corporate creativity I expressed in my past life. They were filled with lists of links and buzzword bingo. But my tolerance for that boring writing didn’t last long. It was only a month or so before I trashed the Friday letter.
Months later, I went through one of those experiences that made me realize just how short life is. A friend I worked out with every day died suddenly. I wrote that day because I was trying to figure out what to do with all my grief. I needed to share it so other people realized just how beautiful his life was. The more I wrote these weekly letters, the more I saw how beautiful my life was.
For the last 7 years, these letters have been the thing I look forward to making the most each week. As much as I like rewriting recruiting, I crave seeing a light in someone’s eyes when they feel even more confident. I appreciate knowing that other people feel seen and held in this lonely world because I shared a story that feels like their own. I love to know I helped someone I might never meet figure things out. That feels like magic.
But what goes on this blog isn’t the only thing I write. I journal almost every day. In my life, I’ve had many “what the hell am I supposed to do” moments captured on those pages.I think on paper about the stuff that doesn’t always feel figured out. I still surprise myself when I’ve spent days letting worries rattle around in my mind only to see the solution so clearly the moment the pen hits the paper.
Now I want to share some of those prompts with you as an invitation to figure your things out on paper, too. I’m calling it The Next Best Step and it’s a monthly journal prompt. If you love these letters, I think you’ll love these prompts.
Here’s how it will work. Once a month, I'll send you a thoughtful journal prompt. The kind of question that helps you untangle something you've been carrying around, imagine what's possible, or see your next step a little more clearly. These aren't "What are you grateful for today?" prompts. They're the questions from my own search for answers.
It’ll take about 10–20 minutes. No homework. No community to keep up with. Just one good question each month delivered right to your inbox.
I’m really excited to be a guide and source of questions in this weird timeline we’re living through. I do know this. I have a strong feeling that if you’re willing to think on paper, writing can help you figure some things out too.
