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.

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?

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.

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.


One Week at a Time.

Something I’ve noticed in my conversations this month: Lots of organizations are trying to craft a long-term plan. 

It’s how we’re used to thinking about the future. You’ll sit down with your team and say: Here’s what we’re going to achieve this quarter. Here are our goals for the year ahead.

But no one knows what will happen next. We’re all making this up as we go along — so trying to craft long-term plans is a little foolish. You’re making a plan for a future that may not exist.

It’s hard to do, but if you can, focus more on the immediate future. For instance, I’ve been telling teams with newsletters: Right now, your daily email is focused on the crisis in your community — deaths, illnesses, the situation at hospitals. But next week, it might need to shift, as the crisis goes from a medical one to an economic one. In a few months, if the virus comes back in your community, you might need to pivot again. My best advice: Be willing to adjust the products on a week-to-week basis to make sure you’re serving your readers as best you can at that moment.

It’s hard for us to shift to a short-term mindset. It’s not our default position. But the organizations that think about today, tomorrow, and this week are the ones that will move nimbly and build things that truly help their audience when it’s needed most — now.


That photo comes via Unsplash and Estée Janssens.

Planting the Seeds for Whatever’s Next.

plants growing

In the past 24 hours, I stumbled upon two very similar quotes from two very different people.

The first: I was reading a New York Times essay by Christoph Niemann about a trip to Eastern Europe, and he quoted former Estonian President Lennart Meri, who in 1992, just a year after his country was granted independence from Russia, famously said: “Our situation is shit, but this is the fertilizer for our future.”

The second: J.B. Smoove of “Curb Your Enthusiasm,” went on a podcast recently to talk about his comedy career, and he said, “I like to plant seeds. I’m a seed planter. Whether that tree grows a week, a month, a year, five years, ten years from now, at some point, it’s going to grow. It’s just a matter of how fast it’s gonna grow.”

None of us really knows what things will look like a few weeks or a months down the road. We don’t know if we’re headed for a recession, a depression, a global change in the way we do business — or if this all just a blip.

But what I do know is that this is a moment for us to plant seeds. In the next few weeks, I’m going to launch a few small projects — some on my own, some with partners in the news space — to try to be helpful. I’m not focused on driving revenue with these projects. The goal is just to help, in the way I can be helpful, at a time of need.

Long term, my hope is that the help I give and the relationships I build now will lead to interesting things down the road — whenever and whatever that might be.

As the former President of Estonia and a guy on HBO both wisely noted: Now’s the moment to plant the seeds for whatever’s next.


That photo of plants growing comes via Unsplash and photographer Markus Spiske.

Be Prepared.

When I interviewed a candidate at BuzzFeed for a role on the newsletter team, I always asked the same first question: Do you subscribe to any of our newsletters?

These were candidates who’d applied specifically for a job on the newsletter team. They’d submitted resumes and cover letters for the role. We’d read through them, picked the candidates we’d liked, and set up a quick phone screener — 20 minutes on the phone to ask a few questions. Each candidate had a few days to prepare for that interview.

And yet: Probably forty percent of the candidates I interviewed immediately said “no” to my simple question: Do you subscribe to any of our newsletters?

I was always astonished by that. How could so many people know absolutely nothing about the types of work we’d done? Signing up for a newsletter was remarkably easy, and free. And yet two out of every five candidates failed to do even that.

In all the interviews I did, I can’t recall a single candidate who answered “no” and got a second interview.

I tell that story now because I’m reading “In the Land of Men,” a memoir by Adrienne Miller about her time working at GQ and Esquire. In it, she tells the story of her first day of work, walking through the office with GQ editor David Granger:

“As Granger and I spoke, it became apparent that I did have one thing going for me: I was able to talk about past issues of GQ. Later, he said that I got the job because I was the one person he’d interviewed who’d actually even bothered to open the magazine.”

“ ‘Never underestimate how unprepared most people are,’ he would later observe, correctly.”

The bar to clear in a first interview is pretty low: Show up on time, have a few questions ready to ask, and make sure you’re knowledgeable about the place you’re interviewing at. That minimum effort won’t get you the job — but it might be enough to get you to the second round of interviews.