Most of Your Ideas Are Bad Ideas.

Earlier this week, I found a notebook from my BuzzFeed days, and inside, a few pages in, found an idea for a newsletter that I never seriously considered launching.

The idea was for a joke newsletter, one I called “the Apocalypse newsletter.” On the page, I drew the landing page for the newsletter, with a big headline: “When the world ends, you’ll be the first to know!”

The idea first came, maybe a decade ago, during a series of conversations about breaking news alerts. It felt like so many other organizations sent breaking news alerts for the tiniest things. I felt like breaking news should be reserved for stuff that you couldn’t leave your house without knowing. And then I took it a step too far: What if we created a breaking news alert that was only sent if the world was truly ending?

What would we send the rest of the time? An occasional email highlighting stories that proved — jokingly, of course — that the end of the world was near.

This newsletter never went further than the piece of paper I drew it on. I never had a serious conversation about it.

There are a lot of ideas in that notebook. Some were real ideas that turned into really good newsletter products, like our lineup of Courses. Some were silly ideas that we launched and turned out well, like This Week in Cats. Some never got off the ground (an idea for a British TV-focused email). There are far more bad ideas in there than good.

And that’s OK.

Even the bad ideas get your wheels turning. It’s easy to draw a line between that joke idea — One breaking news alert, sent at the end of the world! — and a real conversation, one I’ve had many times over the years, about what really constitutes breaking news. Even the bad ideas still led to deeper thinking.

Let the bad ideas come. Jot them down. Give them consideration.

You never know when that truly bad idea might lead you to something worth pursuing.


That’s the sketch of the Apocalypse newsletter landing page. A bad idea, yes, but so are most of my ideas.

It Never Gets Easier.

There’s this lie I’ve been telling myself for the past decade: Once I get through this next stretch, things will get easier.

But I know what’s going to happen. After this stretch of work, after this stretch of travel, after this stretch of busyness, things aren’t going to slow down. Things aren’t going to stop.

There’s always going to be more.

Things don’t magically get easier at the end of these stretches. There will be new challenges, new problems.

There’s always more.

But the good news is: Even though it doesn’t get easier, that doesn’t mean it’ll get harder. You’re always learning and figuring out new ways to solve problems. New obstacles appear, but you’re also learning more about how to get past them.

No, it never gets easier. But you’ve gotten through hard things before. You’ll get through these, too.


That photo of a boulder comes via Callum Parker for Unsplash.

Invest in What’s Next.

A bronze bull sculpture stands proudly on Wall Street, representing the resilience and power of the financial markets. This iconic symbol serves as a reminder of the bullish optimism that drives the world of finance.

At age 30, in my annual Things I Believe post, I wrote:

You don’t need to be able to predict the future — but it helps if you can see what’s coming around the corner.

I certainly don’t know what the future holds. But I think I can see certain pieces that will matter in the decade ahead. I think small, curated, in-person events will matter. I think relationships will matter. I think expertise will matter. I think that there will still be a desire to learn new skills — that will matter.

And so I’m starting to make investments in what’s next: Dinners, writing, workshops, partnerships.

You should do the same. Try to identify what’s coming in the next month or the next year or the next decade, and start to make moves to invest in things that will help you in whatever comes next. 

Maybe that means starting to have conversations with others who operate in the space you want to move into.

Maybe that means finding ways to level up your skills in a certain area.

Maybe that means making a little time to work on the ideas you have.

Maybe that means launching something small to start to carve out your niche.

Maybe that means finding partners to work on these ideas.

Whatever’s next is coming. Time to make your investments now.


That’s the eye of the famous bull on Wall Street. This post isn’t about that type of investing, but it still seemed like a nice fit for this blog post. The photo was taken by Redd F for Unsplash.

Busy vs. Occupied.

I was talking with a friend the other day, and he told me that something was annoying him. He’d been talking to his parents, who are both retired. He’d asked if they could help him with this big task, but they said they couldn’t — they were too busy.

“I don’t get it,” he told me. “They’re having lunch or dinner out every day, they’re playing pickleball, they have volunteer projects. That’s all stuff they’re choosing to do! But I’ve got work and family stuff. I’m the one who’s really busy!”

They’re not busy, I told him — just occupied. (Too occupied to take on this one task, unfortunately for him.) But it’s easy to confuse “busy” and “occupied.”

And it reminded me of something I used to do — or, if I’m being fully honest, that I occasionally still do — when I want to feel busy. I’d collect a bunch of small tasks and put them on my to-do list. And I’d cross them off. At the end of the day, I’d feel like I’d accomplished something — look at all the tasks I’d completed!

But then I’d look at the bottom of the list, and there would be one big task still on my list. It’d been the one thing I had to accomplish, and I hadn’t even started it. Deep down, I knew that I was only taking on all these other tasks to try to make myself feel better about avoiding the big task.

But occupied and busy aren’t the same thing. And sometimes, you have to stop what you’re doing and just do the work.

Might as well do it now.


A pickleball photo seemed appropriate for this post. That one was taken by Patrick Hodskins for Unsplash.

Two Bets for 2023.

At the start of the year, I made two small bets with Inbox Collective.

The first was on Dine & Deliver, this dinner series I’m co-hosting with the team at Who Sponsors Stuff. The bet here was simple: Could we start to bring small communities together, in person, in cities all around the world, to talk about newsletters?

The second was on the Inbox Collective website. Could we start to build an audience, on the web, to read great stories and guides about email?

Neither of these are short-term investments. I think Dine & Deliver has the potential to grow into a much bigger series of events in 2024 and beyond; I’ve already seen the web traffic to double in 2023, and I think we can double again by the end of the year. There’s so much room for growth here — and like with Dine & Deliver, growth should unlock opportunities for revenue: Sponsorship, affiliate revenue, and consulting work.

I don’t expect an immediate return on either of these bets. My goal for 2023 was to break even on both, and I will.

In 2024, I might be able to bet even bigger on the future of the business.


That’s a photo of me leading the discussion at a Dine & Deliver dinner in Washington, D.C., earlier this year.

The Hardest Questions to Answer.

That's sunrise over Puerto Rico in May 2023. Birds fly through the sky as the sun comes up

Sometimes, the simplest questions are the hardest to answer.

What does success look like?

What do I want to do next?

Is now the right time to try something big?

Do I know enough to start?

Am I ready for whatever’s next?

These are questions that are going to take time to answer. But they’re also worth putting in the work to answer.


I was thinking about a few of these questions while watching sunrise over Puerto Rico this morning. Not a bad place to think about big questions.

Get the First Win.

This is a photo of white golf balls and red, white, and blue golf tees on a driving range.

I went to the driving range once and found myself next to a couple that was playing golf for the first time. They had an instructor with them, and within the first minutes of the lesson, he was walking them through the complex biomechanics of the swing. He was telling them that there were more than three dozen different parts of the swing, all of which had to work together. He was giving them tips from professional golfers. He was getting into the mental side of the game.

In the hour alongside them, I didn’t see either of them swing the club a single time. The entire lesson was on golf theory.

And I remember thinking: These people will never come back and try to play again — because they never had that first win.

Golf can be a frustrating game, and yes, a really good swing is a complex thing, but the reason you come back is because of the feeling that happens when you hit a really good shot. That feeling — the sound off of the club, the whoosh of the ball in the air, seeing the ball fly — is what every golfer chases. You come back to try to recreate that feeling, over and over again. Those first-time golfers weren’t going to hit a drive 250 yards or experience a perfect wedge shot, but they never even got the chance to try.

With anything you’re doing for the first time, you’re chasing that first win.

Maybe that first win is the first time someone compliments your work.

Maybe it’s the first dollar you make.

Maybe it’s the first time a lesson starts to click.

The goal is to get that first win as soon as you can. Because once you’ve gotten that first win, you’ve experienced a taste of what the work is for — and can decide whether you want to come back for more.


That’s a photo of golf balls and tees at a driving range. It was taken by Robert Ruggiero for Unsplash.

Let Everyone In.

Here's a photo I took during “Born to Run” at the Bruce Springsteen & The E Street Band show on April 9, 2023, at UBS Arena. The house lights are up, and you can see the entire crowd dance and sing during the performance.

We saw Bruce Springsteen & The E Street Band last week, and there’s a cool moment in the encore that Bruce and the band do at every show. Throughout the concert, the house lights are down, with just the spotlights on the band. But right as they break into “Born to Run,” the house lights go up — suddenly, you can see every single person in the arena.

And since the song is “Born to Run,” every person in the arena loses their damn mind. People spill out into the aisles, singing and dancing along. If you want to understand the concept of “dancing like no one’s watching,” go to a Springsteen show and wait for the lights to come up. You’ll see 20,000 people leaning into that mantra.

What I love most about it, though, is that it shifts the perspective of the show. For 2+ hours, you’re standing in darkness, watching Springsteen and the band perform. And when the lights come up, it all changes: Suddenly, the crowd is part of the show. Their dancing, their singing — it’s part of the performance. And as the crowd gets into their role, you can see people around the arena starting to loosen up. Seeing so many others dance freely and sing at the top of their lungs gives them permission to do the same.

Would “Born to Run” be the same if the house lights stayed down? It’d still be a great moment during the show, but it’d be different — it wouldn’t be a shared performance. What makes it special is that everyone gets to be part of it.

There are moments when you want others to join in. There are moments that you want to share with the crowd. Recognize them. Turn the lights up.

Let everyone in.


That’s a photo I took of the crowd at UBS Arena, on April 9, 2023, during the performance of “Born to Run” at the Bruce Springsteen & The E Street Band show.

Change Can Be the Right Thing.

This is a photo of me, ready for takeoff back to New York

When I first started Inbox Collective, I thought most of my job would involve projects and travel.

I’d do an audit for a newsroom, then travel to their office to lead a workshop. I’d take the lead on a big project, where I’d get into a client’s email platform to build something for them. I’d do talks in person. I’d speak at conferences in front of big rooms.

And the job changed when the pandemic hit. I wasn’t traveling for work anymore, which meant more calls and presentations on Zoom. A lot of friends told me they hated Zoom — I found that I loved it. I could actually work with more teams and help a lot more people since I wasn’t spending all my time on planes. I could work with newsrooms and writers in far-off parts of the world, and do so on my schedule.

And at the same time, I started to realize that I didn’t love project work. It took up a lot of time and was full of frustration — exactly the stuff that made me want to go solo in the first place.

So the job changed. I shifted towards the work I liked most: Coaching, writing, and IRL work that involves lots of 1-to-1 time. I took on some audits, but only occasionally. I farmed out work that I wasn’t enthusiastic about to other consultants or agencies.

This week, I traveled to LA for work for an on-site with a client and a Dine & Deliver dinner. I was in LA for 36 hours. I landed just before 2 a.m. in California. I got home the next day after midnight.

And I loved the work I did on site, but it was a reminder of how happy I am with the job I’ve created for myself. It’s definitely not the job I thought I’d have four years ago.

It’s better.


That’s me on the flight back from LA. I might not have been smiling if I’d realized that I’d get home at 12:30 a.m.

It’s OK.

It’s OK if you don’t know what’s next.

It’s OK if you don’t have all the answers.

It’s OK if you don’t get everything done today that you wanted to do today.

It’s OK if you’re stuck.

It’s OK if everything needs to change.

It’s OK if you have to wait to do the thing you really want to do.

It’s OK if you have to accept “good enough” now, even if you want to do something great one day.

It’s OK, and it’s just what you’re dealing with today. It won’t be like this forever.

Tomorrow, you get another chance to do better.


I took that photo in Utah, in fall 2020, at a moment when I didn’t have a lot of answers about the future. Things turned out more than OK in the long run.