See If It Works. Then Build It Yourself.

When I’m working with a team on a project, one of the first questions I’ll ask is: How do we start as quickly as possible?

Let’s say we’re working on a new design for an email. Instead of hiring someone to do coding — on a concept that may or may not work! — I’ll use an email builder that allows us to build an email that’s pretty close to what we want. Will it be exactly what we want? No, probably not. But we’ll get 80% of what we want in 20% of the time.

Once we’ve got that built, we can test it out, see how it goes, and make additional tweaks and changes. Maybe we’ve got a winning concept, and if that’s the case, that’s when we’ll go to the designers to get it to 100%. Maybe we don’t, and we’ve got to keep testing. The good news is, we won’t have wasted valuable resources on a concept that didn’t work.

There are so many tools out there that allow you to test and iterate quickly. Instead of building your own stuff, or wasting time on ideas that might not work, utilize those tools, and see if you can get something live that allows you to collect feedback, learn, and move forward.

First, just see if it works. You can always keep building from there.


That photo of a construction site comes via Unsplash and Shivendu Shukla.

Don’t Worry About That First Step. It’s Often a Doozy.

When you take the first step on any big project, you might step in it. You might start off on the wrong path, or make the wrong hire, or ask the wrong questions.

It happens. It happens to all of us.

One misstep doesn’t doom a project to failure. It might shake your confidence, but keep moving. Keep asking questions, keep trying to find your way back. Don’t let a bad first step send you permanently off course.

There’s More to Do.

There’s a tendency at a moment like this — whether you’ve just completed an election, like we did in America this week, or whether you’ve completed a big project at work — to have a sense that things are over. You put in the work, you did the work, and now you’re done.

But the truth is: There’s always more work to do. New doors are going to open, new opportunities are going to become clear. The work is never really done.

Enjoy this moment, for just a moment, and then keep moving onward.


That photo of a George Washington figuring comes via Ben Noble and Unsplash.

The Four Obstacles: Time, Money, Stress, Failure

here's a talk I gave in Sydney in 2019

Inbox Collective is my second attempt at starting a business — a decade ago, was my first. I know more this time around, I’ve better organized a network of supporters around me, and this time, I’ve built an audience to support my work. I learned so much from, and it’s put me in a far better place to succeed with Inbox Collective.

But even with all that knowledge, I’ve found that there are still obstacles in my way. I believe that these four obstacles exist for everyone who starts something — no matter how ambitious the project or how prepared the team is behind it:

Time — There’s never enough time to do all the things you want to do. In a business like mine, it’s so hard to strike the right balance between doing the work that pays the bills and building the relationships that will lead to paying work down the road. If there were twice the number of hours in the day, I still don’t think it’d be enough. It means that I need to prioritize certain work and say yes to only the things that are most important to me — even though sometimes, I have to say no to stuff I’d really love to be able to do.

Money — This was the big question when I launched: Would anyone actually pay me to do this? The answer’s been a resounding yes, and I feel so grateful for that. But now there’s pressure to keep this thing going. 2020 changed everything — no work-related travel or talks, but lots of remote projects. Could I keep that up for another year or three if I had to? So many of my 2020 projects came from meeting people at conferences and events back in 2019, and if my business stays remote for the foreseeable future, I wonder if I’ll be able to keep this going. I know I can do it, but that fear is still going to be a small weight on my shoulders. Even when things are going well, I’m always going to be looking ahead and trying to plan for what’s next.

Stress — Anytime time and money get involved, there’s going to be a certain amount of stress, too. Inbox Collective is my work, and mine alone. If it succeeds, if it fails, it’s on me. I like the pressure of it, and I’d gladly take this work — even when it’s stressful — over the frustrations of working within a larger organization. (And that might change down the road — that’s just how I feel today!) But it doesn’t change the fact that this job applies real pressure on my life, and it’s up to me to manage that stress. It’s something I’ll always have to deal with.

Failure — At the end of the day, there’s always the chance that Inbox Collective fails. I might not be able to do the work, I might lose clients, I might have to change careers or fields. Now that things are working, there’s pressure to keep this business going, and to keep learning so I can continue to grow Inbox Collective.

I don’t know what Inbox Collective will look like in a year or five. I certainly have no idea whether it’ll be around in 10 years, or beyond that. But I know that as long as I work on this, those four pressures — time, money, stress, and failure — will weigh on me. That’s just part of the job.


At top, that’s a photo taken of me giving a talk in 2019.

Now’s No Time to Stop.

At the start of the year, I had a revenue goal in mind for Inbox Collective. Revenue isn’t the only metric that matters to me, but it’s certainly an important measuring stick for a consultancy like mine.

This week, I broke my revenue goal for 2020 — with two months to go in the year.

But I’ve still had this odd feeling all week. Work is good, I’m as busy as ever, and thrilled about the clients I’m working with. I just hit a big goal, despite all of the obstacles that 2020’s thrown my way!

And yet, there’s this nagging fear: What if this all goes away? What if the business hits a rough patch? What if my clients leave?

What I’m recognizing is this sense of paranoia that I’ve seen in several founders I look up to. It’s a sense that you can’t get complacent, even when business is good. I know I have to keep learning and keep creating new ways to help my community. I know I need to think about new revenue streams. I know I have to start thinking about big choices for 2021 — where I might expand my work, and ways for me to better serve the clients I have.

I feel like I can see around the corner to what’s coming next, and I’m excited about what lies ahead. But I’m still nervous. None of this is guaranteed, and I know I have to keep working to move this business forward. I still have a lot more to learn.

Yes, I’m taking some time to celebrate the little victories — that’s so important! — but I can’t get too comfortable just yet. There’s so much more work to do, and it’s up to me to keep moving.


That stock photo — of a motorcycle going through the mud, which, honestly, doesn’t have anything to do with this post — comes via Gabriel Sanchez and Unsplash.

Ask, Optimize, Improve.

Mere Creek Golf Course, in Brunswick, ME

I’ve been playing a lot of golf lately. That’s not a sentence I expected to type in 2020. I played some as a kid, but stopped after college. Since I moved to New York, I think I’ve picked up a golf club twice in eight years.

But earlier this summer, a friend — who also happens to be pretty tall — asked if I wanted his old set of clubs.

So I started playing again.

Golf’s a frustrating sport, even for experienced, talented players. (And I am not one of those.) The first few times I played this year, I realized that I’d forgotten how lousy I was at the sport to begin with. I suppose I’d been hoping that watching The Masters every year had magically made me into a talented golfer.

But I’m trying to get better. I know certain skills (like hitting a driver) might take years to master. So I’m starting with a big question for 2020: What are the basics I need to get right? Every time I’m on the driving range or playing 18 holes, I’m coming into it with something I need to learn. How can I best hit that shot from 60 yards out? How can I improve the way I chip around the greens? Am I putting the right way? It’s the same strategy I use when I’m working on a project: Start with the big questions, and then drill into the specific tactics to optimize and improve. 

Some days, it feels great. Most days, I walk away thinking about how much work I still have to do. I’m never going to be a pro, and never going to be guy who regularly shoots par. If I could break 90 most rounds, I’d be thrilled. But I’m trying to get a little smarter every time I play. I like playing golf, it turns out, and I know that I suck at it for now, but I don’t want to suck at it forever.

So I’m going to keep asking questions, and keep testing. Over time, I should — I hope! — get a little better.


That’s Mere Creek Golf Course, in Brunswick, Maine. I played there a few weeks ago.

Here’s to Another Year.

I left The New Yorker a year ago today. Leaving a place as special as that to start a consulting business is a true leap, and I’m lucky to have had so many amazing people supporting me on this journey.

To everyone who offered words of encouragement, advice, introductions; to everyone who shared my Google Doc with their friends; to every client who believed in me and decided to take a chance to work with a one-man newsletter operation:

Thank you.

And, of course, to Sally, for encouraging me to take the leap. I could not have done this without her.

Here’s to an amazing, unexpected, unforgettable first year. And here’s to wherever the road leads next.


Thanks again to Wesley Verhoeve, who took the headshots on my site. They’ve been republished here with his permission.

Be Curious.

When I left San Antonio to start, I didn’t know what I’d find in Biloxi.

When I went to Springfield and hired a staff, I didn’t know what we’d actually make.

When I took a job at BuzzFeed, I didn’t know the kinds of work we’d do over the following years.

When I started at The New Yorker, I didn’t know the projects that we’d put out into the world.

When I left that role to start Inbox Collective, I didn’t know where I’d be in a year. I didn’t know the work I’d do, the clients I’d be lucky enough to work with, or the connections I’d make.

I had no idea.

And I still don’t know what things will look like one year from now. I have a guess — I think I can see around the corner — but I truly don’t know.

When I don’t have all the answers, I’m at my most curious. This is when I’m asking questions, looking to learn and make connections, and looking for new opportunities. It’s when I’m most open to new possibilities.

Ask. Learn. Be curious. Wherever the road goes, your curiosity will lead you there. 


That photo’s one I took at Salt Lake City International Airport earlier this year. I remember thinking as I was taking that photo: Who would’ve guessed that my work would have taken me to such beautiful places?

Don’t Write The Story Until It’s Over.

Nine years ago, I attended a baseball game I’ll never forget.

It wasn’t a particularly important game: Nats-Phillies, in the middle of the 2011 season. The Nats finished that season 80-81 — out of the playoffs, again.

It was a humid night in D.C. We sat through a two-hour rain delay before the game really got going, and once it did, the Nats fell behind, 4-0. By the 7th, with a score of 4-2, my friends said they were tired and wanted to go home. I couldn’t blame them — it was late, and the game really didn’t matter.

Still, it was my last baseball game of the season — I’d be heading to Columbia, Mo., for a fellowship in a few days — and I wanted to see it through. I’d been to enough baseball games to know that if your team’s losing by a few runs that late in the game, they usually don’t come back.

But then again: You never know. And I remember from my days covering the team that you can’t finish your game story until the final out.

My friends went home, but I stayed.

In the 9th, the Nats faced Ryan Madson, the Philadelphia closer who’d only blown one save all year. But the Nats came back, stringing together a few hits to tie the game. Then came Ryan Zimermman, the third baseman and the face of the franchise. Two outs, bases loaded, bottom of the 9th, full count — and he hits a walk-off grand slam to left.

I remember texting my friends and telling them to turn on the TV. I remember their disbelief at the score. (“We…won???”) I remember how strange it felt to be truly surprised by a result like that. Up until those last moments, it seemed unlikely — even impossible — that the game could have ended the way it did.

I almost never leave games early anymore. As long as there’s still more to play, there’s more story to be written. You never know when you’ll get the chance to write a better ending.


That photo is of Nationals Park, and was taken by Sung Shin for Unsplash. The video is of the walk-off grand slam — wait until the very end.

Beware the Ground Beneath Your Feet.

In 2010, while reporting in Biloxi, Mississippi, on the anniversary of Hurricane Katrina, I stumbled upon this story:

A century earlier in Biloxi, there was a man of some renown named Walter Hunt. He didn’t go by that name, though — in town, locals called him Skeet.

Skeet was quite the figure in Biloxi. At age 26, he’d become the youngest alderman in the city’s history. He’d been the grand marshall of the Mardi Gras parade. Later in life, he’d move to Washington, D.C., and become a captain of the Capitol Police. (He’d ship up fresh seafood from the Gulf on trains when he was trying to curry favor with members of Congress.)

But in 1925, Skeet took a gamble. He’d inherited an island, twelve miles out in the Gulf of Mexico, from his grandfather, and decided to build a casino on it. He called it the Isle of Caprice — “caprice,” as in, a sudden, unpredictable series of changes.

For a few years, things went well for Skeet and his casino. Business boomed. In 1927, an estimated 40,000 visitors came to the island. Ethel Merman played the lounge.

Then in 1931, Skeet’s team went out to the island to get the casino ready for the summer season.

But the casino wasn’t there.

What must it have been like to be a member of the crew, floating out in the Gulf of Mexico, and suddenly realizing that Isle of Caprice had been built not on an island, but a sandbar? What were they thinking as they discovered that over the winter, when the sandbar moved, the casino had sunk into the Gulf?

All the staff could find was a single pipe sticking out of the water, still connected to a well that had been dug deep into the ground. Everything else was gone.

I’ve been thinking a lot lately about Skeet’s story. I’m thinking about all the things that will be different once we’ve emerged from this pandemic. Businesses will change, cities will change. We don’t know what life will look like in a few years, but things will almost certainly be different.

Right now, that once-solid ground is shifting underneath our feet. Standing still isn’t an option. It’s up to each of us to recognize that we need to move with the tides — or we will sink.


At top, that’s a postcard from the 1920s of the island. Below, a photo of Skeet from a Mardi Gras parade.