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.

Be Willing to Let Things Go.

When I think back on my time at BuzzFeed, there was a lot that made us successful. We hired a talented, diverse group of creators. We invested in learning and development programs so staff could continue to grow in their roles. We built strong product and data teams to provide the resources so we could try things that no other media company could do.

But we also were willing to let a lot of things go.

There’s a long list of BuzzFeed projects that launched — some to significant fanfare — that didn’t work.

There aren’t many who still remember projects like BuzzFeed University (a program to encourage advertisers to build their own sponsored content), (a dashboard tracking the biggest stories on the internet), or (a social network that allowed you remix content). We launched these, and quickly realized that they weren’t working.

Sometimes, BuzzFeed launched projects that flopped — but showed a few signs of promise. Often, someone on staff would latch onto those projects and try to figure out how to take what had worked and turn it into something new.

But with certain projects, we knew early on that there wasn’t an audience for the thing we’d built. So instead of compounding our error and continuing to funnel resources and staff into a failure, we let it go, and moved on to whatever was next. There was always another idea that was worth trying.

No one wants to see a project fail. But it happens. Anytime you launch something new, make sure you know in advance how you’ll measure success for this new thing — if you do that, you’ll be able to see clearly when a project works, and when it doesn’t.

When it doesn’t, you may have to let it go. If there isn’t an audience or a need for the project, no amount of tinkering or investing is going to help. Better to quickly move on to the next idea than to lose more time trying to fix what doesn’t work.


That’s a screenshot of the BuzzFeed homepage on October 23, 2013. As you can tell from the list of stories here: It wasn’t nearly as useful to readers as we hoped it would be.

Something To Look Forward To.

By the end of January, I had my calendar for the entire year pretty much set.

I knew where I was going to give talks this year, and had the flights planned out. I knew which weddings I’d be going to. I had some vacation days penciled in.

Then Covid-19 hit here in the U.S., and all of that changed.

I used to have a nice balance of remote work and in-person work. Now, like everyone else, my work’s shifted entirely online. I’m not sure when I’ll fly next or when I’ll travel again for work.

And that’s OK! I’m lucky to be the position that I’m in. Inbox Collective is doing well, and I’ve got my hands full with work. I feel incredibly grateful for the opportunities that I have.

Still, I’m realizing how much I miss being able to look forward to the next thing: The next trip, the next birthday party, the next night out. Zoom is such a useful app, but it’s not the same as being there with friends or clients.

Here’s the closest thing I’ve found to life before Covid-19: This past weekend, my wife and I decided to get out of town for a few days. We rented a car and drove upstate. We didn’t do much — we ate, we drank, and we saw a few friends from a distance — but just knowing that we had something like that on the calendar lifted both of our moods for an entire week.

Going forward, I’m going to try to keep putting something on the calendar to look forward to. It could be small (setting aside some time to meet a friend in the park) or big (a road trip somewhere). I’m not going back to the pace I had a year ago, and that’s alright by me. Just knowing that something’s coming up is enough to keep me moving forward.


That’s a screenshot of Flighty, the app I use to track my travel. That’s what my travel schedule looked like from March through June. (Obviously, it all changed.)

Keep Moving.

There is so much we need to accomplish. It can feel overwhelming at times to look at the to-do list and see what still needs to be done. The tasks ahead can feel endless.

But the work doesn’t happen all once. Change happens incrementally. You point yourself in the right direction and slowly start moving there, step by step. It’s only through persistence and time that you’re able to move things forward.

The most important thing is to keep making progress. You won’t always go as fast as you want, and you won’t always get where you’re going as quickly as you want. Even when you reach that destination, you may find that things have shifted — there may be new goals and new milestones ahead. Good.

Keep pushing forward.

Keep trying to make things a little better every single day.

Keep moving.


That photo comes via Zac Ong and Unsplash.

A Thought on My 33rd Birthday.

I turn 33 today. A year ago, I was just thinking about leaving The New Yorker. I didn’t know that in the year ahead, I’d get to work with clients across the country and across the world. I didn’t know how much this business would grow. (I’m not sure I even realized that I was building a business!) I didn’t know that I’d have the chance to give talks to teams on four continents. I didn’t realize how familiar I’d get with Zoom. I didn’t know I’d get to spend so much with Sally in such wonderful places: Rio, Salt Lake, Surf City. I didn’t know how much I would learn.

I don’t know what 33 will bring. This year’s been unexpected, eye-opening, and full of opportunity. I hope I get to do it all again, and more, in the year ahead.


Do It Again. Make It a Little Better.

A few weeks ago, we tried making pizza at home for the first time. It wasn’t even close to being from scratch — the pizza dough was purchased at the local market, and the tomato sauce was from the jar — but we broke out the pizza stone and a bunch of toppings and gave it a go. The result? Not bad!

But there was room for improvement. The cheese was nice and bubbly, but the crust was a little soft on the bottom.

So we decided to try again, really trying to get the crust right. This time, we rolled out the dough a little thinner, and put it on the pizza stone for about seven minutes before adding on the toppings and cheese. An improvement — but still not perfect!

So we started asking around to friends who do this: What’s your secret? How do you get the crust right?

And one friend suggested: Have you tried putting the stone in the oven in advance for 30 minutes first to get it nice and hot, and then adding the pizza to it?

We’d never thought about that before.

So we’re going to keep trying. Every time we make this thing, we’re trying to make it a little better. A small tweak here, a slight adjustment there. It’s never going to be perfect, but we’re going to keep working to do better.

It could be pizza, it could be your work. Just keep working to make things a little better, bit by bit, until you get it right.


That’s a photo of our first pizza — not bad for a first attempt!