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The First Thing Isn’t The Biggest Thing.

When you’re just getting started with something new, you’re going to run into some roadblocks. You’ll start with some momentum, and suddenly, you’ll hit a snag. Your project’s just begun, and already you’re at an impasse.

The first time you get stuck like this, it’s easy to make a big deal of it — often, too big a deal of it. This is the biggest obstacle you’ve run into so far, so you think: This must be the biggest obstacle I’m ever going to face.

And that’s just not true. It’s probably just the first of many hurdles you’ll have to clear, and you can’t let this first one stop you.

I ran into this exact situation a few weeks ago. I was working on a project, and I ran into a brand new obstacle. I hadn’t run into anything like it before, and I was really upset about it. Instead of taking it head on, I spent some time replaying in my head the steps that had led to there. I fretted, I worried, and I mostly just paced around the house. For a day or two, I didn’t get anything done.

And then when I finally took on the obstacle, I found a way to get by it. It wasn’t all that big of a hurdle, it turned out — it was just the first time I’d faced an obstacle like that, so I didn’t have the right plan to take it on initially. But once I worked through the problem, I realized that I knew enough to get by it and keep going.

Don’t let the first obstacle slow you down. There’s always a way forward if you’re willing to work for the right solution.

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That illustration is by Katerina Limpitsouni for unDraw.

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One Door Opens Another.

Think about this for a moment: What’s something you’re working on right now that, a year or two ago, wasn’t even on your radar?

I remember at BuzzFeed when we launched our Royal Baby newsletter. There wasn’t a Royal Baby section at BuzzFeed, and we didn’t have many tools we could use to grow that newsletter. So that led to one big question: We tools do we actually have? What are we good at when it comes to newsletter growth?

Once we learned a few things, it led to another question: What could we get better at? So we tried a half-dozen new ways to grow our lists, and a handful worked well. We doubled down on those.

Once we had that set of tools, we had a new question: Which of these promotional levers could we automate? Was there anything we could do to save our team time to keep testing new things? So that led us down a new road with our product team.

Over time, these answers consistently led to brand new questions, and we kept searching for answers. Every time we asked a new question, we discovered there was even more to learn — often things we didn’t even realize we didn’t know until we’d reached that point!

One new door often opens another. The thing you’re going to be excited on in a year or two might not be what you’re working on today. But by being curious, by asking really good questions, and by seeking new answers, you might be able to open up that next door — and open yourself up to all sorts of new possibilities.

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That photo comes via Christian Stahl for Unsplash.

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There’s No Single Right Way.

It’s easy to get locked into a certain way of doing things. You get used to a certain way of working. You start thinking that there’s only one path forward.

Doing the work is a little like writing a song. Here’s one to consider: Neil Young’s “Helpless,” one of those songs from the 70s that’s absolutely perfect. I’ve listened to it too many times to count, and learned it on guitar. I didn’t think there was any way to do it better than the way Neil did it. It’s sparse, solemn, and beautiful:

But I stumbled on a cover version a few months ago that made me rethink Neil’s original version. It made me realize: There might be another way to approach that song and imbue it with that same sense of loneliness and despair. Give this a listen:

The lyrics are the same, and the intention is the same, but that’s not the same song. When I listen to that Angie McMahon cover, I hear a singer taking a completely different route to that same end: A song that’s sparse, solemn, and beautiful.

It’s a reminder for me: There’s no single right way to do the work. Keep trying new approaches, and keep bringing in new voices and new ideas to put their spin on the work. Listen to others. Read a lot. Keep learning. You never know when one of those new perspectives might help you find a brand new “right way” to do the work.

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One Lesson From Remote Work: You Have To Find Time To Pause.

I’m just a few months into working remotely as I grow Inbox Collective. There’s a lot I like about it. For one: I’m writing this from Utah, where I’ve been working for the past 10 days. It’s been fun getting to work in a new place (and then getting the chance to ski when I can).

But something I’ve learned about remote work: Your office is wherever you are. If you’re on a plane and there’s decent WiFi, that can be your office. If you’re on a chairlift checking your email, that’s your office. If it’s midnight, and you’re at home, on the couch, laptop open, well, that’s your office.

When you’re remote, it’s easy for the work to follow you around all day. I wake up, walk over to my desk, and often start my day by 7 a.m. But if I’m not careful, it can be 10 p.m., and I’m still there, working hard. And I’ve learned quickly that that’s not a recipe for success. If I try to work long hours every day, including weekends, I’l burn out.

So I’m trying a few things this year that are a little different to make sure I keep that balance between work and play. Here’s one: I’m pushing myself to make 90 minutes every day, in the middle of the day, for a pause. I can go to the gym, take a walk, step out for lunch, or get coffee with a friend — but I have step away from the desk for a little bit.

Here’s another: I’m going to set a time to shut down work at the end of the day. (It’ll be around 7:30-8 p.m.) I’m thinking of this as the “pencils down!” request your teacher probably gave you in high school at the end of a test. There’s always going to be more work, and I can’t just work all day. I’ve got a lot on my plate — consulting work through Inbox Collective, work on Not a Newsletter, and speaking gigs. I know I have to find time to pause.

We’ll see how this goes in 2020. I’m hoping that creating this time for breaks gives me the time to focus on the other things happening in my life — and hopefully, gives me the energy to come back and tackle bigger work projects in the long run, too.

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That illustration is by Katerina Limpitsouni for unDraw.

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Setting A Simple Goal For 2020.

In 2019, I decided to set a simple goal: I’d do 10 push-ups, every single day. I didn’t keep exact tabs on this — I added a recurring to-do to my to-do list, and tried to cross it off more often than not. I missed a few days along the way due to travel or illness, but otherwise, I did it pretty much every day. Over the course of the year, I easily did more than 3,000 push-ups — which, to be perfectly honest, was probably about 2,900 more than I’d done in the previous two years combined.

And I discovered something: I actually enjoyed doing push-ups! I plan on keeping that habit going in the new year.

But I also want to add something new to the mix in 2020. As I wrote a few months ago about my push-up goal:

It’s a simple goal, and a small goal. But by committing to the task every single day, it’s going to build to something that, by year’s end, I can be proud of.

So here’s one for 2020: I’d like to start practicing my Spanish again. I was a Spanish minor in college, and I spent six months studying abroad in Spain. But more than a decade removed from that experience, my Spanish is poor — and I’m a little embarrassed at how bad it is.

A few weeks ago, I downloaded Duolingo, and started finding a few minutes for it every day. (I recently added the Lupa app, too.) My goal for 2020 is to keeping making some time to practice — and to see how far a little work every day can take me.

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That wildly generic LED sign at top comes via Jon Tyson and Unsplash.

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A Wish For The Year Ahead.

As we wrap up 2019, and look towards the new year, I wanted to say:

In 2020, I wish you the courage to take a risk — to try something new, something big that frightens you a little. I wish you the opportunity to build a community around something you love. I wish you the freedom to be as weird or silly as you’d like. And I wish you the ability to focus, to stay in the moment, and to be able to pull yourself away from the work to make time for the people you love.

May 2020 be a year of growth, health, and good luck. 

Cheers.

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That photo was taken by Roan Lavery for Unsplash. Wherever that photo was taken, I wish to go there in the new year.

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Shit Happens. How Will You Move On?

What I’ve always known — and what this year reinforced for me — is that the road will be full of the unexpected. Things don’t just go wrong — things *will* go wrong. You’ll leave 60 minutes before that presentation, but the New York City subway system will turn a 20-minute trip into a 55-minute adventure. You’ll get stranded at the Detroit airport for, somehow, 48 hours. You’ll fry a laptop at the airport just before boarding a 13-hour flight home. (All of that really did happen this year.)

Things are going to go wrong, and no amount of prep work is going to prevent that from happening. So the big question is: When it happens, can you still find a way to make it work?

When things go wrong, I try to look for all the best possible outcomes. Stranded on the train? Well, that’s an extra 20 minutes to prep for the meeting. Stuck in Detroit? Let’s get a hotel and reschedule those meetings as video calls. Laptop’s dead? That’s OK — did you know the Duty Free store sells Mac laptops now?

Shit happened in 2019, and I’m sure 2020 will be full of many more unexpected (and unwanted) surprises. Here’s my wish for you: When it does, don’t dwell on it. Text your loved ones (“You won’t believe what happened to me THIS time!”), give yourself a minute to regroup, and then figure out what doors are still open for you. Whatever happened, I promise it’s just a speed bump along the way. If you look carefully, there’s always still a path forward.

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That’s a photo I took at the Brisbane airport back in November. I’m holding the laptop I bought at Duty Free a few minutes earlier. I wouldn’t usually recommend an impulse purchase like that, but it turns out there are circumstances that call for such a purchase!

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Never Too High, Never Too Low.

I wrote about this a few weeks ago on my annual Things I Believe post, about my work through Inbox Collective so far:

I tend to oscillate between “This is going to work!!!” and “Holy shit, what am I doing???” on a weekly basis. I’m scared and excited, but never bored, and always thrilled to be doing this work. That’s how I know I’m in the right place.

And this is true! Since I started this, I’ve traveled to Australia, Brazil, Canada, and France for work. I’ve got a great group of clients, and I’m thrilled with the work we’re doing together. I’ve learned so much about how to do this work, and every breakthrough is exciting. Things are good for the moment!

But at the same time: This business is more than a little terrifying! Things are good… for the moment. I have no idea what comes next.

I’m learning that that fear can be an incredible motivator. I’m hustling as much as I can to find clients I can work with for a long time, and to figure out ways to make this thing last. I’m loving the work right now, and I want to keep this going. I want to make this work.

What I’m starting to learn is that it’s easy to get too high or too low, and riding that roller coaster distracts from what I need to focus on. The real challenge is in staying focused on the work, and staying on that even keel. Some days are good, and some days are rough, but neither seems to last long. Every day, I try to learn a little more and to do a little better. It’s all about the road ahead.

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That image of a roundabout comes via Avi Waxman for Unsplash.

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No Regrets.

Here’s a story I’ve seen a few times now: A friend takes a job at a great company. It’s a huge, well-deserved role for them. Everyone agrees: They’ll do big things there.

And then a year or two later, that friend steps away from the role. From the outside, it seemed to be a good fit in terms of responsibility, opportunity, and salary. But the day-to-day of it was a different story. They weren’t learning or growing, or felt unhappy in their role. They decided to leave.

But when I’ve asked these friends afterwards if they regretted the decision to take the job in the first place, they’ve almost always told me: No, definitely not. Again, it’s the same story: These are people who did their homework before taking the job. They talked to people at the company, and asked as many questions as they could. The job didn’t work out, but it was OK: They’d still made the right decision at the time. And I’ve seen stories like theirs countless times — stories of people who made a decision that didn’t work out, but who still don’t regret the choice they made.

I’m thinking back to something I wrote back in 2011, in my annual “The Things I Believe” post. I wrote: 

Try not to regret bad decisions. Just make the best decisions you can with the best information you have.

Eight years later, that still holds true. You don’t always have control over what happens after you make the decision — but you have total control over the decision itself. Do your research, talk to people you trust, and make the best decision you can. Even if the choice doesn’t work out as well as you’d hoped, I’ve found that as long as you made the right decision for the moment, you’ll walk away with no regrets.

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That illustration comes via Katerina Limpitsouni and unDraw.

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I Am 32 Years Old. This Is What I Believe.

I am 32 years old, and I’ve taken the leap. Twelve months ago, I was at The New Yorker — a dream job at a dream organization — and focused on the work ahead of me. Nine months ago, I started giving regular talks about how news organizations could get more out of email, and realized that I could help those newsrooms in a more hands-on way — you know, in the future. Six months ago, I started thinking that maybe that work could happen sooner, possibly as soon as mid-2020. Three months ago, I left The New Yorker and launched a consultancy to start the work immediately.

This year moved fast.

What changed? I started asking more questions of my colleagues in other newsrooms, and really listening to what they were telling me. I heard over and over again: We need help growing our audience and turning them into subscribers or supporters, and we want to learn from the work you’ve done at BuzzFeed and The New Yorker. I realized that my moment to help was right now, and that if I wanted to serve this community, the work couldn’t wait.

So I made the leap. I’m thankful for everyone who had my back: The friends and family who offered support (and free legal aid!), the colleagues who helped me figure out how to approach consulting work, and the readers who reached out to work with me (and told their networks to do the same). This consultancy is just me, but it also feels like the biggest team I’ve ever been apart of. I feel incredibly, incredibly lucky.

This year, I’ve given talks on four continents in front of more than 100 news organizations. I’ve written more than 35,000 words about email for newsrooms and non-profits, and had nearly 3,000 readers in more than 50 countries sign up to be alerted every time I write. I’ve launched a consultancy, signed more than 20 clients, and helped launch dozens of email products.

It’s been the single most transformative year of my life, and the work’s only just begun. I don’t know what the future holds, but I’m pretty sure I can see just around the corner — and what’s coming next is exciting and terrifying all at once. I can’t wait.

Above all, I’m thankful for Sally. A year ago, the idea of leaving my job to start my own business — while she was still in school! — would have been unthinkable. But it was Sally who gave me the green light to do this. She kept telling me: “You can’t wait. You have to do this now.” I’m remarkably lucky to be married to someone so supportive, and so selfless. Doing this work meant that I would be busier than ever before, and traveling more than ever — and yet, she’s been my biggest champion. I wouldn’t have, couldn’t have done this without her. Every day, I try to do work that makes her proud.

Over the past year, there are certain things I’ve come to believe hold true. I know that my beliefs will continue to change. I know that I will change.

But here, at 32, is what I believe:

God bless Google Docs.

I tend to oscillate between “This is going to work!!!” and “Holy shit, what am I doing???” on a weekly basis. I’m scared and excited, but never bored, and always thrilled to be doing this work. That’s how I know I’m in the right place.

Nobody has everything they want. Life is about making the most of whatever you have.

Just be honest with people. If you screw up, if you don’t have the answer, if you’ve got something that needs to be known: Be open, be transparent, and be direct. It’s the best way.

Doing the right thing is usually the right thing.

Be confident but not arrogant. There’s a line there. Don’t cross it.

Keep making things better. I gave this one talk six different times this year — but every time, I learned something new, and then made the next one a little better. Just because the work is finished doesn’t mean the work is done.

Life is unexpected. One minute you’re waiting in the Brisbane airport, thinking about the giant presentation you need to put together on the flight home. The next, you’re freaking out because your water bottle leaked in your backpack and your laptop’s dead and the presentation’s in 36 hours and you’re completely, totally fucked. The next, you’re wondering why there can’t be an Apple Store inside the airport. The next, you’re walking through duty free and realizing: They sell MacBooks here — tax free! The next, you’re boarding your flight, passport in one hand, the brand new laptop you bought 20 minutes ago booting up and restoring all your files from the cloud so you can finish that presentation on the plane.

Like I said: Life is unexpected, but also pretty amazing if you’re ready for it.

New rule for traveling: Water bottles always stay outside your backpack.

Whatever it is you do, be the best at it. I’ll always be thankful to The New Yorker for teaching me that.

Less isn’t always more — but it’s enough.

When you start traveling regularly, you’ll realize that the four greatest words in the English language are: “Sir, we’ve upgraded you.”

Listen. Learn. Work. Repeat.

Right now, everything is potential — and potential is pure fucking joy.

Privilege is a tailwind, and I’ve had a strong wind at my back all these years. I know I’m lucky, and want to do the most I can with this opportunity for as long as I can.

And lastly: You don’t have to have all the answers when you start. Keep trying new things, and keep learning along the way. You’ll get there.

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