I’m Dan Oshinsky, and I run Inbox Collective, an email consultancy. I'm here to share what I've learned about doing great work and building amazing teams.
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.
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.
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!
It’s been a decade since I graduated from college. I thought that when I graduated — after all those years in school — that the learning would stop there.
Turns out, that was just the start.
As you go through your career, you’re always going to be working to learn new things, and discovering new ways to learn them. You’ll find that you can:
What are you good at? Think about it for a moment. What skills do you bring to the table? What are your best qualities or habits?
Then think about your team at work. What is your team best at? What are your collective strengths?
Lastly, think about your entire workplace. What is your organization great at? What do you do well?
Give yourself a second, and really think about your strengths.
Now think about your weaknesses. Think about yourself, your team, and your organization. What do you do poorly? What do you need to improve on?
Now let’s consider one more thing: If you had an opportunity to improve one of these things — to double down on your strengths, or to better your weaknesses — which would you choose?
Many would choose to improve their weaknesses. That’s natural. People tend to focus on their own faults — I’m not good enough, I’m not smart enough, I’m not talented enough — and would love to have the chance to improve.
But my advice would be to do just the opposite: Do more of the things you already do uniquely well. Take the things you’re good at and truly master them.
Imagine for a second that you’re a Major League Baseball pitcher, pitching for a National League team. In the NL, pitchers have to hit, too, and even the best-hitting pitchers are, by any other standard, bad hitters. (Madison Bumgartner, one of the best-hitting pitchers ever, has a career .183 batting average.) Let’s say it’s the start of the offseason. You’ve got a few months to improve as a baseball player before the new season rolls around. So what would you do: Work on your hitting, and try to become a passable (but still poor) hitter? Or would you work on adding new pitches and becoming a dominant pitcher? The answer is easy: You’d work on your pitching. Baseball teams don’t need good-hitting pitchers — they need great-pitching pitchers.
It’s rare to find a true jack-of-all-trades. Most people specialize in just a few things — and that’s OK!
I started thinking about all of this a few weeks ago, when I was talking with a group of news organizations. Many of them were thinking about launching new newsletters, and trying to decide what to focus on. So I asked: What do you do uniquely well? What’s something you do that your fans fans already love? Many of them talked about their coverage of local news or sports or culture — the areas of expertise that their readers, listeners, and viewers rely on them for. That’s where to focus your attention, I told them. Invest in products to serve those audiences, and give them more of the things they already depend on you for.
There’s a great Steve Martin quote: “Be so good they can’t ignore you.” He’s right. Be so good they have to hire you. Be so good that your fans have to pay to get more of what you do. Identify your strengths — and work hard to get even better at the things you do well.
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I took that photo of San Antonio Missions pitcher Simón Castro — who later went on to pitch for the White Sox, Rockies, and As — back in 2010.
I was having a conversation the other night with a friend from college, and we were talking about how much has changed in the decade since we graduated. “Did you ever think you’d be doing the job you’re doing today?” she asked.
I didn’t. Ten years ago, my current role — being the person in charge of a newsletter program for a news organization — didn’t exist. It was six years ago this week that I launched my very first newsletter at BuzzFeed, and I remember struggling to find many other people in the industry who were working on email full time. There just weren’t that many of us around — email was usually a small part of someone’s job. Six years later, most newspapers, websites, and magazines have someone in a dedicated Newsletter Editor or Director of Newsletters role. (Often, they have an entire team devoted to email!)
I’ve been thinking about this a lot: The job I’m working in today didn’t exist five years ago. The job before that didn’t exist before I helped create it.
Which means that the job that comes next may not exist yet, either.
If you ever get worried about the future, remind yourself: There is no defined path forward. Embrace the uncertainty. Keep learning, keep reading, keep asking questions, keep working. Every day is a chance to build whatever future comes next.
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That’s a screenshot of the very first BuzzFeed Today newsletter, sent on Feb. 4, 2013.
“The show doesn’t go on because it’s ready; it goes on because it’s eleven-thirty.”
That’s what Lorne Michaels, creator and producer of “Saturday Night Live,” said about “SNL.” As Tina Fey explained a few years ago:
This is something Lorne has said often about “Saturday Night Live,” but it’s a great lesson in not being too precious about your writing. You have to try your hardest to be at the top of your game and improve every joke until the last possible second, but then you have to let it go.
I remember reading those words back when “Bossypants” came out in 2011, and they stuck with me. In 2012, I decided to make a commitment to this blog, which I’d first started in 2008, but hadn’t written for regularly. I decided I wanted to write three times a week for the blog — and somehow, despite everything I was doing with Stry.us that year, I somehow stuck to it. Then I went through a lull — just a handful of posts per month. In 2015, I made myself re-commit to writing one post a week, and have stuck with that pace ever since.
I’ll admit: Many of my blog posts aren’t great. (In fact, they’re mostly bad!) But it’s something I always do. The work happens, and then I move on. Writing for this blog has taught me so much about how to do the work even when I’m in a creative rut.
Lorne and Tina are right: Don’t be too precious with your work. Your work isn’t going to be perfect. Some of it will suck. But the show goes on at 11:30 — just get it done.
Most of my ideas are bad. Recently, I started a notebook that I’ve been filling exclusively with bad ideas: TV shows that should never get made, apps that should never be launched, products that should never be spoken of to another human being. It’s humbling to add another bad idea to the notebook. For every 100 ideas I have, 70 are incredibly bad, 20 are acceptably terrible, and maybe — if I’m lucky — 10 are decent enough to do something with.
And I think that’s a pretty good success rate.
In my time at BuzzFeed, I learned that it was OK to have ideas that didn’t work out. There was so much that we did at BuzzFeed that worked, and worked incredibly well. But for every launch that grew into something big, there were dozens of ideas that failed: BuzzFeed University (a program to get ad agencies to create their own BuzzFeed sponsored content), Star.me (a collaborative social media site that was a cross between BuzzFeed and Giphy), or Fre.sh (a leaderboard for the internet). These were the kinds of projects that, as Jonah Peretti wrote in a 2013 memo to the staff, “don’t distract from the core and have the potential to be much bigger in the medium term future.” They weren’t, but that didn’t matter. As the internet mantra goes: We failed fast, and often.
But here’s something I didn’t always understand about that saying: It’s not just about trying lots of things and seeing what sticks. The hard part is reminding yourself that it’s OK to be wrong.
I’ve never met anyone who liked being wrong. But I’ve met some who have accepted it as part of the process. You come up with ideas, or you test out a new theory, and it doesn’t work out. Then you have to admit to yourself and to your team that the thing you believed in isn’t worth pursuing anymore, or that you need to change course. (Sometimes, even when it’s painful, you’ll even have to admit to a colleague: “Yes, you were right.”) The most productive people I know have these conversations on a monthly basis — or sometimes, weekly.
In other words: If you’re doing things right, you’ll often be wrong.
It’s not easy to admit that your ideas aren’t great. It’s not easy to admit that you were wrong. It’s not easy to kill your darlings.
But it’s part of the process: Come up with lots of ideas, pick your favorites, and be willing to be wrong. Don’t get discouraged: Just because you were wrong before doesn’t mean you’ll be wrong forever. The great ideas will come soon enough.
A few weeks ago, I wrote about my Washington Capitals, and their improbable run to the Stanley Cup. “It’s OK to believe,” I wrote. And because 2018 is relentless, here’s a nearly identical story from the world of sports, this time from the World Cup. This week, England beat Colombia in a penalty shootout — the first such victory for England ever at the World Cup, after three previous heartbreaking losses in penalties. Their manager, Garrett Southgate, was part of a famous penalty shootout loss, at the 1996 Euro championships, when he missed one of the penalty shots that cost England the game.
But as manager, Southgate took that experience and tried to face it head on. The Guardian explained how in an article this week:
Make no mistake, this shootout success belongs to Gareth Southgate. He is unlike every England coach who has faced a penalty shootout in the past: the only one to have missed a penalty for England, and the only one to accept that the penalty shootout is not a lottery; that taking penalties is about performing a skill under pressure; and that penalties can be trained.
Not for him the arrogance, incompetence or fatalism of England coaches past. “You can never recreate on the training ground the circumstances of the shootout,” said Glenn Hoddle in 1998. “When it comes to the pressure we are not good,” said Sven-Göran Eriksson in 2006. “You can’t reproduce the tired legs. You can’t reproduce the pressure,” said Roy Hodgson in 2012.
Southgate turned the trauma of his own experience in 1996 into a vindication of five months’ work preparing for the prospect of a shootout. Funny how we heard similar excuses from the Spain coach Fernando Hierro — “it’s a lottery and we were unlucky” — and Denmark’s Åge Hareide — “unfortunately it was decided by a lottery” — after their shootout defeats at the weekend.
Southgate talked to his players about owning the process, and he worked on the players’ individual technique and team dynamics. He even recreated “the tired legs”, with Kieran Trippier admitting that players had “practised and practised and practised” penalties, taking spot-kicks while fatigued at the end of long sessions. Twenty-eight years of World Cup penalty hurt and all it needed was a bit of practice. Who would have thought it?
They even practiced ways to avoid screwing up the timing of their routines. Here’s one wonderful nugget:
[England goalie Jordan] Pickford also handed the ball to each England player on his way to the spot. This is owning the process, and ensured that [Colombia goalie] David Ospina would not disrupt any players’ routine by making them walk to get the ball.
England won the shootout, 4-3, and advanced to a quarterfinal game tomorrow versus Sweden.
And as much as I love the preparation that Southgate put his team through, his quote after the match was just as fantastic — and reminded me so much of what I heard from the Caps this spring:
“We’ve spoken to the players about writing their own stories. Tonight they showed they don’t have to conform to what’s gone before. They have created their own history, and I don’t want to go home yet. Missing my penalty [at Euro 96] will never be ‘off my back’, sadly. That’s something that will live with me forever. But today is a special moment for this team. It’ll hopefully give belief to the generations of players that will follow. We always have to believe in what is possible in life and not be hindered by history or expectations.”
Well said. I’ll be rooting for England tomorrow. It would be an amazing thing to watch a team defy history and win it all — again.
In the waning moments of Game 5 of the Eastern Conference Semifinals, with my Washington Capitals leading the Pittsburgh Penguins, and the team just one game away from advancing to the next round of the playoffs, Caps radio announcer John Walton said a wonderful thing on the radio:
“It’s OK to believe,” he said.
If you’re a Capitals fan, that was easier said than done. The Capitals had been around for 43 seasons. They had made the playoffs in 28 of those seasons — but prior to this season, had only made one Stanley Cup Finals. In 10 of those seasons, the Capitals had held either a 3-1 or 2-0 series lead in a playoff series — a commanding lead by hockey standards — and lost. No team in NHL history compared when it came to playoff collapses.
And yet, there was John Walton on the radio, reminding all of us: “It’s OK to believe.” I think we all needed that reminder — we’d been through so many playoff losses that the idea of a win seemed almost impossible.
The next game, Game 6, on the road, in overtime, the Capitals finally broke through and beat Pittsburgh.
In the next round, down three games to two, the Capitals won two in a row — shutting out Tampa Bay in both games — to secure a place in the Finals.
And then, after going down 1-0 to Vegas, against a team that hadn’t lost three games in a row all season, the Caps won four consecutive games to win the Stanley Cup.
