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.

Do The Basics Well.

building blocks

To succeed in business in 2020 takes a great team, a strong mission, and more than a little bit of luck. But it also takes a willingness to focus on the basics — and do them well.

So let’s take news organizations for a moment, because it’s the business I know best. A few years ago, several newsrooms took part in the Knight-Temple Table Stakes project to lay out the seven basic things all news organizations needed to do to make change. To simplify things for the sake of this blog post, it all really comes down to a few key principles:

• Serve your readers
• Build relationships
• Establish trust
• Listen, learn, and engage
• Drive loyalty and habit
• Grow revenue
• Keep trying new things

The newsrooms that are doing well today do all seven things incredibly well. Some aren’t doing as well — and to get onto the right track, it requires an entire news organization working together to get these basics right.

You’ll note from the list above that the categories are broad, and intentionally so. It’s up to every part of an operation to figure out how the table stakes fit into their roles. A newsletter editor might see that list and say, “Let’s build a daily newsletter that serves readers, drives a daily reading habit, and then converts those readers to paying subscribers.” A copy editor might say, “Let’s just focus on establishing trust — how should we be transparent with our readers when we make a mistake?”

When you’re seeking to transform a business, first identify the basics. What are the things we need to be doing to be successful? Where are the areas we need to invest in? And how will each part of our operation implement these basics into their daily routine? Build from there.


That photo of a Jenga set comes via photographer Nathan Dumlao and Unsplash.

Stress vs. Frustration.

Every job comes with pressure.

When you’re working for a big corporation, that pressure often comes in the form of frustration. You’re frustrated that your company isn’t working on the things you want them to. You’re frustrated by the pace of work. You’re frustrated with the way the company is structured, by the pay, by your colleagues or bosses. Big corporate jobs are frustrating for all sorts of reasons, but they usually stem back to one thing: The lack of control you have over the work you do and the people you do it with.

When you’re working for yourself or a startup, the pressure comes in the form of stress. You’re working on the things you want to work on, but you’re stressed about doing the work well. You’re stressed about keeping things moving forward — are we still going to be able to do this work in six months? In a year? You’re stressed about money, about bringing the next client in or making the next sale. You’re stressed because there are no guarantees, no roadmap forward except the one you make — and you’re never quite sure that the path you’re on is the right one.

Every job comes with pressure. The question is: Which type of pressure will you choose?


That photo of employees working in an office building comes via Chuttersnap, a photographer who published their work on Unsplash.

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?

Just Ask.

Back in July, I created a fundraiser for my Google Doc, Not a Newsletter, and asked my readers to donate to The Marshall Project. I wasn’t sure how much money we’d raise.

In the first 24 hours, we raised $1,000. In a month, we raised more than $3,300.

I’m thrilled, and so, so grateful.

It’s a reminder for me: Put the work out into the world, and see what happens. You don’t know what will happen until you ask.


A big thank you to Givebutter, which made this fundraiser possible. I’d absolutely use their platform again.

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.

The Only Time Is Now.

The truth is, I almost didn’t leave The New Yorker when I did.

I knew that I wanted to start Inbox Collective. I knew there was a market for my services. I knew that I had an opportunity to help the journalism world.

But I wasn’t sure if the timing was right.

Sally was in nursing school. She was 18 months in, with a year of classes left. She’d graduate in Spring 2020. And my thought was simple: Sally still had a few semesters of tuition left to pay, we were a one-income household, and if Inbox Collective didn’t work, we’d be a no-income household. Leaving my job to start a consultancy was a gamble, and the safe move was to wait until Sally had graduated and gotten a job — sometime in the summer of 2020.

But Sally convinced me to take the leap anyway. She reminded me that I had momentum and a clear opportunity. There was something else, too, something we talked about a lot at the time: The window for me do this was open, and we weren’t sure how long it would stay open. There was risk in leaving my job to start something new, but also risk if I waited too long and the window closed.

Now looking back, if I’d waited, I don’t think I’d ever have left to start Inbox Collective. Taking the leap to start a business is tough enough during good times, but during a recession and a pandemic? There’s no way.

It’s a reminder that when you’ve got something you’re excited about, and something you feel ready to take on, the only time to try it is now. If you wait, the window might close, and you might miss out on that opportunity forever.


That’s a photo of me giving a talk in Sydney last year — one of many pretty amazing experiences that I couldn’t have had without taking the leap.

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.