At dinner I felt like a fraud.
On giving yourself space to make big decisions where you've previously been stuck.
Welcome to issue #049 of Unsubscribe. Each week, I send one essay that helps you step off the default path to build a life you love, supported by work you enjoy.
For the last three years, I’ve gone back and forth about writing my first book.
Not a self-published book or an eBook. A traditional book. The hardback kind you see on Amazon or at Barnes & Noble with the glossy cover and my name printed on the spine.
I picture myself on podcasts talking about the book or doing the morning show circuit. The feeling of walking into a bookstore and seeing my book on the shelf. I think about how proud my mom would be. So damn proud.
Every time I imagine it, I feel this pull. Like, “Yeah, I should definitely do that. That’s the right next step.”
But over three years, I’ve done almost nothing to move it forward. I’ve talked to some agents and bestselling authors. But I’ve never written a proposal. Not even an outline.
A few weeks ago, I finally asked myself: Am I putting this decision off because I’m not ready? Or because I don’t actually want to do it?
To be honest, I genuinely don’t know yet.
About three years ago, I talked to a very successful creator who was in the process of writing his very first book (he’s since become a New York Times bestselling author).
He said something that I haven’t been able to shake since our conversation:
“Writing a book is the most stressed out I’ve ever been in my entire life for a full two years.”
Writing a book is a monster decision. A two-year minimum commitment. You hire an agent, pitch publishers, and wait for responses. If you get a deal, your publisher becomes your quasi-boss. Your editor shapes the direction, and you have deadlines you cannot move.
I haven’t had a boss in six years. The idea of giving that up for two years? I don’t know if I want to.
A few months ago, I went to an author’s dinner in New York. I was one of fourteen people invited, and it was filled with some of the biggest names in non-fiction. I was the only person there who hadn’t written a book.
When one of the authors asked what stage I was at, I fumbled for an answer about not feeling like a person who could write a book. How I’m just some guy who writes a short newsletter every week, and not a real writer like everyone else there.
I felt ridiculous when I left.
All my friends have written books. I can name ten people who’ve dealt with the stress, the deadlines, and the loss of control. They still managed to publish and move on.
And I’m still sitting here three years later, thinking about it.
The decision itself is getting heavier.
Three years ago, “Should I write a book?” was a light question I was kicking around. Now it’s this big thing I tend to avoid. When my friends publish their books, I feel this weird mix of pride and guilt.
The longer I defer it, the harder it gets. It’s no longer just a decision I haven’t made, but proof that I’m actually stuck.
And as I’ve danced around the idea, I’ve realized that I literally have no space to even act on it. I’m trying to figure this problem out while living the exact same life that’s kept me stuck for three years. I’ve got the same routines, same systems, and everything is optimized for consistency.
You can’t make a good decision about something big when there’s no space to make it.
A few weeks ago, Jennifer and I were sitting on the couch talking about how nothing big was really changing in our lives. We’re busy, sure. But we’re busy with the same things. The same work, the same schedule, the same conversations.
I said something like, “I don’t think I can figure out this book thing from here. I need to be somewhere else for a while.”
So we made a decision. What if we spent the next 3-6 months living up and down the California coast? Different time zone, different scenery, different surroundings. We’d meet new people, start new conversations, and shake up our stagnant routine.
Not because we need a vacation. But because I need space to figure out what I actually want instead of what I think I should want.
Maybe after a few months in California, the answer to the book problem becomes obvious. Maybe I realize I’m ready to commit to the two-year grind. Or maybe I realize I don’t want to do it at all, and I can finally let the idea go without feeling guilty about it.
Either way, I’d love to come to answer. And I hope that giving myself some actual room to feel it instead of just thinking about it is exactly what I need.
If you keep deferring a decision for years while sitting in the same environment, doing the same work, and having the same conversations, you’ll likely never come to an answer. You’ll just stay stuck.
But if you actually create space, if you change something significant, if you give yourself room to test what you want instead of just sitting around and analyzing it, the answer might actually show up.
I still don’t know if I’m going to write a book.
But I’m done trying to figure it out while staying exactly where I am.
If you’ve been deferring a decision for so long that you can’t remember when you first started thinking about it, the problem might not be that you don’t know the answer.
It might be that you’re trying to find it while everything stays the same.
You can’t think your way to the “a-ha moment” on something this big. You have to create the conditions where the answer might actually reveal itself to you.
So here’s my question for you:
What decision have you been stuck on for months or years? And what would actually have to change in your life for you to finally know what you want?
Reply and tell me. I read every response.
That’s all for this week.
I appreciate your time.
What decision have you been deferring for so long that you can’t even remember when you first started thinking about it?
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I had been stuck on whether to leave my job and pursue something else for the last 3 years. It paid well, was close to home, I knew all the tricks of the trade. But I wasn’t learning, wasn’t growing and there was no room to grow at the company.
I finally took the leap a couple of weeks ago and start a new role in January. Even if this doesn’t end up being the perfect fit, at least I know I’m trying something to move forward.
Thanks for your post, I hope we both have a great new year in 2026.
Great piece. A year ago I bought a radiology imaging center. I had been working on buying one for 2 years but as a side project. Then 1.5 years ago I decided it was go time and sold my shares of my prior practice and went all in on buying my own. Getting through the buying process was very difficult. Dealing with banks, lawyers, insurances, sellers, etc. I’m not sure I would have figured it all out if still had the safety net of my prior practice.