Fix your roof when it’s raining.
Tis the season for overwhelm.
Often, in times like these and when being pushed to their limits, creatives will seek help and hear this age-old advice about when to adjust their processes, “Fix your roof when it’s sunny.”
This is not helpful.
Here’s the problem: Roofs don’t leak when it’s sunny. Roofs leak when they feel like it. Maybe a tornado of obligations just ripped your roof off.
No matter how prepared you think you are, life will have other plans.
The human brain simply isn’t made to deal with the amount of information we’re shoveling into it. Yes, try to fix your roof when it’s sunny. But if a storm occurs and your roof starts leaking, you should probably know how to fix it then as well.
If you’re not in a position to re-align expectations — to drop, delegate, or delete responsibilities — you may need to evaluate something less comfortable. That could mean your process (influencers hate when you do this) or your tools (minimalists hate when you do this).
Here’s where the real hack is revealed: Other people’s rain isn’t your rain. Their roof isn’t your roof. When you accept that fact, you can apply an appropriate fix. Don’t worry if it takes a while. Some live to be 90 without ever confronting their brain.
Ask for help. Ask a peer. Ask AI. Ask me.
The response will usually include a certain amount of, “let go of...”
Soon it will be the new year and everyone will want you to remake your life. That’s a predictable part of the content cycle. But it’s far more pleasurable, meaningful, and effective to break up with the things that aren’t working, rather than adding new obligations as fixes — under pressure and without introspection.
Tis the season for a break, I say.
Yes, take a break from work, but also break up with what isn’t working. Maybe the roof didn’t need fixing after all.
— CJ
P.S. AI search favors blog posts above all other forms of content. Newsletters are driving the most income for content creators. So, why do companies consider their blog and email channels to be the least important methods of posting content? 🤷 Hint: Managers value their tracking data more than ROI. Much more.
P.P.S. Big thanks to Kyle Porter for the shout out in his Normal Sport newsletter:
“The best short book I’ve read recently is CJ Chilvers’ 72-page book, Principles for Newsletters. I realize this title sounds almost stunningly boring. But I can guarantee you that anyone who is a content creator can take away something that will change the trajectory of their professional work life.”
P.P.P.S. And big thanks to guitar god John 5 for signing the very first copy of my 1999 book, The Van Halen Encyclopedia. To my knowledge, it was the first time his name was ever printed in a book. Little did we know he’d go on from being David Lee Roth’s guitar player to become a star in his right, performing in Motley Crue, Rob Zombie, Marilyn Manson, Salt ’n Peppa (really?), and countless others. His reaction to seeing his name in the old book? He smiled from ear to ear and said, “Wow, I’m famous!”

