4 Questions I Ask When Worried About "Something" [WRAP 214]

Hey Reader,

I spent most of this week dealing with a fever and sore throat (Sunday morning update, it’s strep!). One of those bouts of sickness that old-me would have pushed straight through—same hours, workouts, schedule—because I was worried about falling behind on something.

I could never really articulate what that something was. Just a vague, low-grade dread that if I stopped, I’d lose ground I couldn’t get back.

As I write this, I realize I still may have done too much… it did become strep, after all. But in between naps and gargling salt water, here’s what I was thinking about.

💡 One Big Idea: Play Your Own Game, pt 2

Last week I talked about trying to beat a guy who didn’t exist. A version of me who’s fully rested, didn’t spend the week sharing a twin bed with a 7-year-old who’s afraid of the dark, and didn’t stay out until midnight playing senior beer league softball (ok, that last one’s all me).

But the real problem wasn’t the imaginary guy. It was the vague “something”. This undefined thing I was supposedly falling behind on. And when something stays vague, it stays scary. It lives in the background like a tab you never close.

Tim Ferriss calls this fear-setting. It’s the idea that most of our anxieties lose their power the moment we force them to be specific. I’ve done a video on this, and it’s one of those concepts I keep coming back to. Austin Kleon references an Ingmar Bergman line that I love: “The demons hate fresh air.” Same idea. Drag the vague fear out into the open and it shrinks.

So this week, sick on the couch and unable to outrun it, I sat down and actually interrogated it. Just a simple personal Q&A:

What are you (supposedly) falling behind on? Earning enough money for my family.

Ok, let’s check the bank. Do you have enough for now? Yes — 3 months of expenses saved and 3 more months of booked revenue.

Great. So then what is it really? I’m not making as many YouTube videos as I want.

Do you want to record videos with a sore throat and fever chills, or can you start back up next week? Next week is fine.

That’s it. The monster under the bed turned out to be a mild scheduling delay.

Now here’s the thing I want you to try. Next time you feel that creeping sense of falling behind, pull out a notebook and write down the answers:

1. What am I “falling behind” on?
2. Is it actually urgent, or does it just feel that way?
3. If I check the facts—the bank account, the calendar, the actual numbers—what’s the real situation?
4. What’s the smallest next step, and when can I realistically do it?

You might be surprised how often the “something” dissolves the second you make it specific. Mark Twain put it well:

Your version might not be as clean as mine was this week. Some weeks the questions will surface something bigger—an actual problem that needs solving. That’s good too. At least now you know what you’re dealing with instead of fighting a shadow.

But most of the time? You’ll find out you’re worrying about a “something” that was never actually there. Give the demons some fresh air. Close the tab.

📹 Video to Watch: Andy Weir on writing The Martian​

Andy Weir wanted to be a writer since he was a kid. But he also wanted regular meals and to not sleep on a park bench—so he became a computer programmer. While working he wrote two books that he says were "really bad". Then he started serializing The Martian to his email list of about 3,000 people, just because he loved the idea. No agent, no publisher, no timeline. He played his own game, on his own schedule, and gave himself permission to be bad at it for a long time before he got good.

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📚 Books I’m Reading: DCC Book 8 & Barclay’s Commentaries on Matthew

I’ve had quite the reading list while being sick! The newest Dungeon Crawler Carl book, Parade of Horribles came out on Tuesday and I’ll be done with it in a couple days. And a heads up—all the DCC books are on Kindle Unlimited, so you could pay for a couple months and binge all the books.

We’re going through the book of Matthew at my church and I picked up William Barclay’s Commentaries (parts one and two) at my favorite local bookstore. Really interesting to read more about the history, context, and detail of what was going on in the Bible.

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Thanks for reading the WRAP!

Matt Ragland