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.
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.
A J-school student told me a few weeks ago that she’s worried she’s behind when it comes to her career. Her peers have more experience or have won more awards than she has. She sees college journalists at other schools who seem to be a few steps ahead of her professionally.
“Am I behind?” she asked. “Should I be worried?”
I told her that I remembered feeling the same way in college. Back in 2005, I remember watching ESPN and seeing a headline-making interview that NFL wide receiver Terrell Owens had done with a college sophomore at Syracuse. I’d always thought I was a little ahead of the pack: I’d been published in The Boston Globe, had written for a few different papers at that point, and was in journalism school at Mizzou. I’d won a national award for high school journalists. I was doing pretty well!
And then I watched that ESPN interview and thought, There’s someone else ahead of me! I’m falling behind!
How were they “ahead,” exactly? They’d done something different — something pretty exceptional — and it scared me to think that there were others doing great work, too.
But a few years later, I started to look back and wonder why I’d been so nervous in the first place. I wrote:
I get jealous, sometimes, when I see 25 year olds who are way ahead of where I am. I get competitive. How’d that person pull off a book deal at 25? How’d they get a movie done? How’d they make their first million already?
But then I remember that this isn’t a 400-meter race. We’re not all shooting for the same end goal.
We’re all on different paths. We’re all running our own races at our own speeds.
It’s tough to tell where each of us is going now. It’s only with time — a decade, maybe more — that we’ll start to understand where we’ve been going.
In the meantime, what really matters is that we keep going.
That’s what I reminded that J-school student: There is no race. There is no ahead, or behind. There’s only the path you take, at the speed that suits you best. Keep moving forward — launch things, try things, keep learning. It doesn’t matter what you’ve done at 20, 30, or 70. There’s always more road ahead of you, and new opportunities. It doesn’t matter what you’ve done today — your best work is still ahead.
Watch this video of Stevie Ray Vaughan, the legendary guitarist, on “Austin City Limits” back in 1989. You’re about to see something extraordinary: About 30 seconds in, one of Stevie Ray’s guitar strings is going to break. He’s playing live, in the middle of a guitar solo. He’s recording for TV.
And he doesn’t miss a note:
Somehow, he plays through it, signals to his guitar tech for a new guitar, switches to the new instrument, and continues playing — like it’s no big deal.
Maybe because to a guitarist like Stevie Ray — someone with decades of experience on stage and in front of the cameras — it simply wasn’t.
All those hours of practice, all those hours on stage — they’re not just about helping you gain experience. They’re also preparation for all of the tricky situations that inevitably arise along the way.
There’s really only way to learn how to make things work when things go wrong: By screwing up, over and over again. The more things break in key situations, the more you learn how to handle it, and how to prepare for the next time.
That video of Stevie Ray? That wasn’t the first time — or probably even the hundredth — that he’d broken a string on stage. He’d been through it before, and so had his crew. They knew their roles.
On Saturday, I was in midtown for a Cycle for Survival ride. (If you’ve got the chance to be a part of one, I can’t recommend it highly enough. It was SO inspiring.) I heard some incredible speeches that day — including one from Olympic gold medal-winning gymnast Nastia Liukin.
She told this great story. She said that when she was a kid, she’d come home after a bad day and try to quit gymnastics, but her mom wouldn’t let her. “You can quit,” her mom would say, “but you can’t quit until after you’ve had a good day.” (Both of her parents were gymnasts, so they may have known a thing or two about tough days at the gym.)
So she’d go back to the gym day after day, until she finally had a good day. And on that good day, she’d come home, and her mom would see the smile on her face. ”OK,” her mom would ask her. “Do you still want to quit now?”
I listened to that story and nodded along the whole time. You’ve probably experienced it, too: Things are never as quite bad as they seem on your worst days, and never quite as good as they feel on your best days. But sometimes, when you’re in a lull, you find little ways to dig yourself out and get back to a better place. It’s easy to want to give up when things are bad. It’s much harder to be resilient enough to keep pushing through with the work you need to do.
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That very shaky GIF was the view from my bike at last week’s Cycle ride.
I’m watching college basketball last Saturday. Clark Kellogg, who’s been doing games for CBS for 20+ years now, is on the call. It’s the Missouri-Florida game, and Mizzou’s on offense. There’s a mismatch: One of the Florida guards is matched up in the post against a Missouri player who has seven inches and probably 70 lbs. on him.
The ball goes into the post, but the Florida defender doesn’t give an inch. So the Mizzou forward kicks the ball out, then reestablishes position on the inside. He gets the ball back, turns, and hits the shot.
“It’s not always easy,” Kellogg says, the replay playing over his commentary, “but it certainly isn’t complicated.”
I’d never heard anyone say something like that before — it really clicked for me. So I paused the game, grabbed a notebook, and drew this up:
Most of the things I work on fall into one of the two categories on the left: Easy + simple or Hard + simple:
Easy + simple — This is the category for things like A/B tests on a subject line, or small tweaks to a newsletter.
Hard + simple — This is for the projects that don’t seem like they should be all that hard — for instance, changing a CTA on our website — but might require a handful of engineers and a complicated series of steps to execute.
A smaller percentage of work falls into the two categories on the right:
Hard + complicated — These are the big picture projects that involve multiple teams and ambitious goals or testing. If we’re launching a new newsletter; moving our email operations onto a new piece of technology; or attempting to shift to a new roadmap, we’re probably operating in this quadrant.
Easy + complicated — There aren’t a lot of things that fall under this heading, but here’s one: Having a really tough conversation with a co-worker, or attempting to get buy-in from your team. Those things seem simple on paper, but once you attempt to factor in all of the relationships, opinions, and egos on a team, things can get complicated quickly.
As your grow in a role, you’ll find that your work tends to shift from the left half of the graph to the right half. You’ll take on bigger projects, with larger goals and more on the line. But there will always be left-half types of projects to maintain. The challenge for all of us: Figuring out ways to handle the little things quickly so that you can stay focused on the big picture.
A co-worker asked me this week: How busy are you these days?
I’ve been at this job for four months, and my co-worker knows that we have a thousand things to do. We have to improve the way we drive newsletter growth. We have to launch new products. We have to improve our existing products. We have to work more closely with our sales and marketing teams to serve their needs. We have to improve the types of data we collect, and find and build better tools to work with.
That’s why my response seemed to catch my co-worker by surprise: I have a list a mile long of things to do… but I’m not crazy busy.
Yes, there’s a lot to do. And yes, I want to get these things done as quickly as I can.
But I can’t make all these things happen at once. I don’t have the team in place yet to take on all these projects, and I’m still getting buy-in from other teams in the office that we’ll need to work with.
Sure, I could try to run through walls to try to get stuff done. But I know I can’t get past those walls by myself. The only way to get through them is with time, teamwork, and money. But I don’t have those things yet — and if I push too hard, too fast, I’m going to drive myself insane.
“Direction is more important than speed. It doesn’t matter how fast you’re going if you’re headed the wrong way.”
Building something new is going to take time. For now, the best thing I can do is help point the team in the right direction. I’m spending a lot of time meeting with other stakeholders, figuring out what they want and how it lines up with what I want. I’m spending a lot of time asking questions, and a lot of time listening.
We’re not moving as fast as I want to, but that’s OK. We’re starting to move in the right direction, and it’s OK to take slow steps towards progress. If we’re heading the right way, and if we’re working with the right people and tools, we’ll build up speed over time.
