Read this next time your newsletter feels like a chore...

Most of the time, when a writer starts to feel bored, it’s because they’re writing what they think they should write, rather than what they’re actually interested in.

Led by obligation, rather than curiosity.

We got some experience with this at Trends. People paid $300 per year for the newsletter, and we felt pressure to deliver the same kind of newsletter every week. But you can’t pull business opportunities out of thin air just to fill space.

So over time, we developed a rule: If we’re struggling to fill a segment, cut it, and see if people scream.

It’s a concept I got from Andy Rachleff, the man who coined the term ‘product-market fit.’

“At the end of your free trial, you should pull the trial,” he said. “If the customer doesn’t scream, you don’t have PMF.”

If we were struggling to fill a segment we thought needed to be there, we’d cut the segment entirely, and see if readers screamed.

If they did – if they wrote in asking where such-and-such was – we would put it back the following week, and make sure to prioritize it in the future. That’s how you know you’re making something people care about.

But often, they didn’t complain at all. Because cutting a “meh” segment gave us time to focus on stories we actually cared about, and made the newsletter better overall.

Your readers don’t need you to deliver the same format every week. They need you to deliver the same feeling. Your authentic voice will typically do that better than something you feel obligated to write, even if it ends up being much shorter.

My favorite example of this comes from The Hustle…

A daily writer once called out sick, and all of a sudden, Sam needed to get the newsletter shipped on his own.

What did he do? Cancel all his meetings, and draft a perfect email?

Not quite.

This is what he sent that day…

That’s it. That’s the whole thing.

People loved it.

It’s honest, in a surprising way. Because the truth is that he was busy and he needed to get back to work on other things. But more importantly, he didn’t try to fake interest in a bunch of random news stories and force himself to write a typical email.

He took an authentic emotion, and turned it into something he could share with his audience.

I think of this often.

My newsletter always feels like work. That’s because writing’s hard. It should feel like work, in the same way that going to the gym feels like work. Work you enjoy.

But if it ever feels too much like an obligation, I take that as a signal that there’s a gap between what I’m writing and what I actually care about at the time.

To close the gap, I’ll sometimes spend a few minutes free-writing. Either I’ll write about what’s making me mad right now (no stopping, no edits) or I’ll just set a timer and write non-stop for ten or fifteen minutes about whatever goes through my mind.

Usually, one of those gives me a thread I can pull. It’s hard to write for ten minutes straight without tripping over a thought you’re genuinely interested in.

“Excited curiosity [is] both the engine and the rudder of great work,” Paul Graham once wrote. “It will not only drive you, but if you let it have its way, will also show you what to work on.”

So if your newsletter’s feeling like a chore, rather than something you can sit down and enjoy making, stop for a second and ask yourself what you’re actually excited or curious (or mad) about these days.

Write about that.

To hell with your typical format. Just make sure you’re in it.