Your greatest work can happen when you don't try as hard

This is a newsletter about how to become more optimistic and resilient, and how to turn moments of change into great opportunity. Ready to seize tomorrow? Subscribe here — and to hear me debunk today's greatest fears about change, check out my podcast*

I’m going to try something different today, and then I'll recommend you do the same. It might help you better connect with others. It might help you gain clarity on what you do and why you do it. It might help you feel less anchored to what you think you need to do, and liberate you to just try new things.

I’ll explain it in a moment. But first, hi:

That’s me, right now. I stopped typing, took a selfie, and then got back to typing. I am writing this from upstairs in my wife Jen’s grandfather’s home outside of Cleveland, where we are visiting for Thanksgiving. It is Thursday. Downstairs, the kids are playing — but one of them is napping, which is the time Jen and I agreed I can retreat and do some work.

Yes, even on Thanksgiving. Yes, maybe that’s a little sad. No, I’m not personally sad about it. Because yes, I will feel more relaxed at dinner if I know I checked a few more things off my to-do list. No, this does not work for everyone. Yes, I realize the irony of sharing this after my previous newsletter about the glories of Calendar Zero. Because yes, we contain multitudes.

Anyway…

To get here, Jen and I undertook the great gauntlet familiar to any parent of young children: We somehow got two kids through an airport without losing a single one of them. At one point, the boys started fighting in the middle of the terminal and Jen went to break it up. Meanwhile, in a move that I realize will not earn me the Dad Of The Year Award, I did not immediately step in to help — but instead, I whipped out my phone and took this photo:

Then I posted it on social media, where I got a flood of sympathetic responses like:

And

And

Unlike a lot of my work, this was the result of something I spent 30 seconds thinking about. I did not polish. I did not consider, then reconsider, then reconsider again. I did not edit. I just did it.

Which is similar to how I’m writing this newsletter. We’re just going, folks! A boulder rolling down a hill!

Why?

A moment ago, I said I’m going to try something a little different today. Now you’re seeing it. Or at least a part of it.

Time to really explain.

Every journalist has a story that goes like this:

They spent six months on a story. It consumed every waking thought. They are proud of it. Deeply proud. And they should be: It is damn, damn good. It is art. Then they put it out into the world and… crickets. Nobody cares.

A little while later, they have a silly idea and dash it off. Maybe they spend 30 minutes writing. They hit publish. It goes bonkers. People talk about it for weeks. Forevermore, when people Google their name, this is the story that comes up first. It is their defining work.

Everyone on social media has surely experienced some version of this too. Every entrepreneur as well — when their carefully crafted marketing plan went plop and then some raw and kooky idea just nailed it.

Why is this? Why does this happen?

LinkedIn editor in chief Daniel Roth has an answer: “Effort doesn't always equal engagement," he recently wrote in his newsletter. He’s spot on. Effort is what we did, but people did not ask for our effort to be directed in any specific way. They do not owe us something because we put effort in. “The key is to start with a clear vision of who you want to engage with and for what purpose,” Daniel writes.

This is great advice — and not just for content. It’s great advice in general, no matter what we do or where we are, because it pushes us to be aware of others’ needs instead of our own. To think about how to connect with them. And to strip away some of the layers that we have built between us and them.

On social media, for example, I have found that when I capture something in the moment — when it just happens, when I just grab it, when I reveal something that I’m thinking or seeing or feeling right now — it is raw and relatable and in the moment. It pulls the curtain back. People feel closer to me, and, when they reply, I feel closer to them.

I’ve found this on virtual presentations too. Remember that viral (pre-pandemic) clip on the BBC, when a guest was frozen in terror because his kids came marching into the room?

I used to feel that way too. Then the pandemic happened. And then my kids came bursting in the door during meetings and keynotes and webinars and whatever. At first I tried to convince them to leave. Then I just embraced it and put them on my lap, introduced them to the audience, and kept going. I found that people loved it. It became their favorite moment of the day. The kids weren’t an interruption; they were an asset. They were the raw, unfiltered, un-planned-for element that people wanted and craved and got and loved.

I’m not saying to be raw every time. We must be considered. We owe people our very best. But every so often, create the space for togetherness. Let the guard down. Try out the half-baked idea. Take a risk. Let people see you for you. The thing we edit out may be the thing people remember the most.

So anyway. Here I am, on Thanksgiving, writing an edition of a newsletter that I usually spend quite a bit of time polishing, but today I am not doing that. Today I’m just bangin’ it out. And I will be so, so curious to hear what you think of this.

Maybe you think it’s garbage. Or maybe you think: This was real. And I feel like I know this guy a little better now. You should tell me. And if you liked it, maybe you should do some version of this yourself for the people in your life you’re trying to reach.

My wife just walked into the room. “Still working?” she said. Turns out our kid’s nap is over. So this is done. Here, I’ll take another photo.

And now we’re done.

Have a great weekend!

P.S. Want to know what's funny about having a podcast that releases on the last Thursday of every month? It means that, on Thanksgiving, I dropped an episode about the benefits of sex robots. I kept imagining people being with their families and then seeing this thing pop up on their phone. Surprise!!!

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