Make Time to Review.

Jon Stewart did this great interview the other day with Matthew Belloni on “The Town” podcast, and this part really stuck with me:

Jon Stewart: Post-mortem is the gift to the gods in terms of improving content and really anything.

Matthew Belloni: So Tuesday morning, it’s, “What did we do right? What did we do wrong? Did this land? Did this not?”

Jon Stewart: It‘s Monday night, and it has to be an agnostic process. It’s not a blame process. It’s always a constructive, like, “How do you feel that worked out?” You always have to be self-examining, reflective of the process, little things, because it’s the only thing that keeps you on top of it.

It’s a lesson I think more of us could apply to our work.

Running an end-of-the-year campaign? Make sure you put time on the calendar the week after the campaign ends to review everything and document lessons for next time.

Launching a new newsletter? Set up check-ins on the calendar every few months to make sure you’re meeting your goals and want to continue investing in that newsletter.

Building a new business? Make sure you hold quarterly reviews to track what’s what working, what isn’t, and what you want to do next.

It’s not enough to put the work out into the world. You also have to make space to review, reflect, and iterate.

———

That photo of Jon Stewart accepting a Peabody Award on stage in 2005 — he’s in a black suit with a dark tie and is behind a podium with a gold replica of the award — comes via the Peabody Awards and a Creative Commons license.

Just Ask The Question.

Before my son was born, I wondered how long it would take before I asked a truly stupid question.

Other friends had told me their stories about asking that first dumb question. One friend confessed that they called the pediatrician’s emergency line the first night home from the hospital because their child was crying. “Yeah, they’ll do that,” the pediatrician chuckled, and hung up. Another told me that they misinterpreted the doctor’s instructions before leaving the hospital. They called the pediatrician the day after they got home, reporting back that they child had pooped three times when the doctor had told them to make sure their newborn pooped once. “We meant at least once, not only once!” the pediatrician laughed. Every new parent, it seemed, asked something stupid.

I was a new dad who’d never changed a diaper before. The only thing I knew for certain was that I knew nothing. I knew I was going to ask something dumb — eventually, at least. 

It took me 45 seconds.

Ben was born, and the doctors called me over to a little scale where they were weighing Ben. I looked down at his tiny feet. They were black.

I hadn’t remembered reading anything about black feet in any of the parenting books.

So I asked them: Are his feet supposed to be black? Is that normal?

That’s when they held up a piece of paper with his tiny footprint on it. They’d pressed his feet in black ink to make the footprint.

It was the first of what would be many, many stupid questions.

But getting that first one out of the way really did help! With a baby, new stuff happens all the time, and I quickly became unafraid to ask, even when I knew the answer was going to be something obvious. I didn’t have to preface questions with, “I know this might be a dumb question, but….” I just asked.

I constantly remind myself: There’s so much I don’t know, and there’s no reason to pretend like I know everything.

Even when it feels like it might be a stupid question, I now just ask.

———

That photo at top is of me the night we got home from the hospital. I’d changed about five diapers at that point. I didn’t have my technique down, but hey, I got better.

Shift, Pivot, or Sunset?

The sun sets behind clouds as trees glow in the foreground.

We sometimes need to make a change with the work we do. The question is: How big a change do you need to make?

Sometimes, you just need to make a shift. The change is small — you’re refocusing on something new, but it’s within the normal scope of what you’d do already.

Sometimes, you need to pivot. You’re making a big change — taking your skills and applying them to something outside your current orbit. The skills and the work might look similar, but you’re doing it in a different space.

And sometimes, you need to sunset things. You’ve done the work, you’ve learned the skills, but you’re ready for something brand new. You’re ready to shut down what you’re doing and move into a brand new field.

For my work, for instance, a shift would be changing my focus from working with newsrooms to working exclusively with non-profits. A pivot would be moving from newsletter consulting to building an agency to help newsletters grow. And to sunset would mean shutting down Inbox Collective to focus on something new.

None of these match where I’m at right now, but maybe they will be in the future. When it comes time to make a change, the big question remains: Shift, pivot, or sunset?

———

That’s a photo of a sunset, taken by Dawid Zawiła for Unsplash.

Give Yourself a Constraint.

I’ve never played Talking Stick Golf Club, in Arizona, but I’m fascinated by one of the golf holes on their course. The hole, no. 2 on their O’odham Course, measures 500+ yards, and at first glance, the hole appears to be unusually straightforward. The hole is flat and straight, with just two bunkers near the green. It looks more like a driving range than a golf hole.

The catch is that there’s a fence on the left side of the hole, and any shot that goes left of the fence is out of bounds. Hit it over the fence, and you’ll take a penalty stroke. It’s possible to play well to the right to avoid the fence — but eventually, as you get closer to the green, you’ll have to hit a shot with out of bounds lurking behind. The hole has one interesting feature — you can’t go left — but that constraint makes this a fascinating hole to play.

It’s a great reminder that simple constraints can be powerful. When you’re planning a new project, sometimes it helps to give yourself some limitations. Maybe you’re operating on a limited budget or a limited timeframe. Or maybe you’re intentionally giving yourself a restriction to see how it impacts creativity. I remember seeing a songwriter once who told me that he played a game on tour: He’d give everyone on the tour bus a song title, and they’d all have a day to write a song with that title. The song could be in any style and about any topic — as long as it had that title. There’s still room for creativity, but you do have to write with that restriction in mind.

I don’t think constraints are a bad thing. I know I can get a bit carried away when I’m dreaming up a new project. Sometimes, a rule or two can be what I need to focus on the elements that matter most.

———

That video comes via Fried Egg Golf.

Try It. Then Figure Out What You Want to Keep.

A few years ago, I saw Adam Sandler perform live. He was recording what would become his first comedy special in decades, and honestly, I wasn’t sure what I was in for.

What I was in for, it turned out, was something both funny and unpolished.

Sandler’s set, which he’d trim down to about 70 minutes for TV, ran nearly two hours. He performed original songs and some stand-up material. Some bits worked; others didn’t. The cameras rolled the whole time.

What I discovered later was that this was Sandler’s creative process. He does the same thing with movies: He records lots of takes, lots of different ways, and then figures out which is the funniest once he gets to the editing bay. The goal when he’s recording is to capture all sorts of options — he’ll figure out what works later on.

That’s not a bad way to approach your work. Some things become hits, and others flop. You don’t really know which is which when you’re making it. You can’t always see around corners.

So instead of hoping that your first idea will be the right one, try doing a bit more than you expect. Leave yourself some alternatives. If something doesn’t work, that’s OK. You’ll have a Plan B already waiting for you.

Be Something to Someone.

The Pitchfork homepage in late February 2009.

The team at Slate put together a great oral history of Pitchfork, the music site that ran from 1996 until 2024, and there was a line in there from Chris Kaskie, Pitchfork’s former president and co-owner, that really stuck with me.

“We are not trying to be everything to everybody,” he said. “We’re trying to be something to someone.”

It’s something a lot more of us could take to heart. Whatever it is you do, your work doesn’t have to matter to everyone — just to someone.

———

At top, a screenshot of the Pitchfork homepage on a random February in 2009.

Should You Work on That Idea?

Using Domainr, I can see if a domain name is available

Here’s a little trick I use to decide if I actually want to work on a project:

Let’s say I’ve got an idea, and I get really excited about it. I buy a domain for the website for the project, and start jotting down notes. I’m convinced that this is my next big idea!

The next step’s been a game changer for me: I go and add a note to my to-do list — one month in the future. I remind myself to revisit the idea then.

And then I do nothing — at least for 30 days.

Often, a month later, I look at the idea and go: Why was I so excited about this? That’s not a bad thing, I think — I’ve just saved myself a bunch of time and effort on an idea I wasn’t all that excited about!

But if I’m still excited about the idea a month later, that’s how I know it’s worth the investment, and that’s when I actually start to work on it.

———

I like to use Domainr to come up with domain names. But I don’t think yournextnewsletteridea.com is my next project!

Every New Experience Can Be a Learning Experience.

a rainbow of colors on a bookshelf

I’m lucky to have a job where I learn new things every day.

Every new client brings me questions I haven’t had to answer before. Every new project introduces challenges I’ve never dealt with before. Every new year brings opportunities I’ve never had before.

And that’s just what happens at work. When I come home, being a new dad means I learn all sorts of new stuff every day — sometimes, a few new things a day. (Sometimes, that new stuff involves learning ways to not get peed on.)

You try, you do, you screw up, you learn. I’m not going to say I get smarter every day — I’m still working on that part! — but every new experience is a learning experience. You just have to be willing to see it that way.

———

That photo of a bookshelf comes via Jason Leung and Unsplash.

Good Advice Can Come From Anywhere.

A few weeks after Ben was born, we hired a photographer to take photos of our newly-expanded family. Midway through the photo shoot, Ben got hungry and started to fuss. I grabbed a bottle to feed him, and the photographer followed along to take a few shots of us together.

When it came time to burp Ben, I put him into the position I’d been shown at the hospital: His chest on my shoulder, with me gently patting his back. But I couldn’t get a burp out.

“Would you like me to show you how I do it with my kids?” the photographer asked. It turned out she had four young kids, so she’d had plenty of practice.

I immediately handed over Ben, and watched as she propped him up on her knee, tilted him gently forward, and placed her hand on his chest.

Before she could even pat his back, Ben let out a massive belch. Naturally, that position became my go-to any time I needed to burp my son.

It was a reminder that day: Good advice and ideas can come from anywhere. You just have to be willing to make space and listen.

———

That photo of lightbulbs comes via Unsplash and photographer Daniele Franchi.

What More Do I Really Need?

There are days when I look at what I’m doing and wonder: Shouldn’t I be doing more?

Sure, I’ve grown my email list from 0 to 10,000 subscribers — but couldn’t I have more subscribers?

Sure, I’ve built a successful consulting business — but couldn’t I bringing in more revenue?

Sure, I’ve created a profitable website — but couldn’t it get more readers?

Couldn’t I sell courses? Couldn’t I write a book? Couldn’t I give more talks? Couldn’t I charge more for each speaking engagement?

And then I have to take a few steps back to acknowledge what I’ve actually done.

I’ve built an audience, I’ve built a business. I’ve created, from nothing, the best paying and most flexible job I’ve ever had. I’ll take more time off this year than I’ve taken since college. I’m in a position where I get to pick and choose what projects I take on and who I work with.

I’m proud of the success I’ve had. Success should be enough — do I need to be excessively successful? Do I really need to do more?

I know the answer to those questions, but it’s hard to quiet the voice that wants to do more. I have to remind myself: I don’t need to do everything. This is more than enough.

———

That’s from a talk I gave in Denver in September. It went well — but yes, I still do wonder if I could’ve done better for those who attended.