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 ask myself this a few times a quarter when projects start to pile up: I’ve got a lots of things to tackle. Where should I start?
And the truth is: You can start anywhere — as long as you start.
I know I can find myself paralyzed by all those choices. Instead of getting stuff done, I end up worrying about all the stuff I have to get done. (And then I find myself with a lot less time to actually do the things I need to do!)
Don’t worry about finding the perfect starting place. The end result is far more important than where you start.
Start somewhere, and go from there.
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That’s a photo of an American Airlines jet taking off, with pink flowers blurred in the foreground and the moon behind. It was taken by Sachin Amjhad for Unsplash.
I’ve never played Talking Stick Golf Club, in Arizona, but I’m fascinated by one of the golf holes on their course. The hole, no. 2 on their O’odham Course, measures 500+ yards, and at first glance, the hole appears to be unusually straightforward. The hole is flat and straight, with just two bunkers near the green. It looks more like a driving range than a golf hole.
The catch is that there’s a fence on the left side of the hole, and any shot that goes left of the fence is out of bounds. Hit it over the fence, and you’ll take a penalty stroke. It’s possible to play well to the right to avoid the fence — but eventually, as you get closer to the green, you’ll have to hit a shot with out of bounds lurking behind. The hole has one interesting feature — you can’t go left — but that constraint makes this a fascinating hole to play.
It’s a great reminder that simple constraints can be powerful. When you’re planning a new project, sometimes it helps to give yourself some limitations. Maybe you’re operating on a limited budget or a limited timeframe. Or maybe you’re intentionally giving yourself a restriction to see how it impacts creativity. I remember seeing a songwriter once who told me that he played a game on tour: He’d give everyone on the tour bus a song title, and they’d all have a day to write a song with that title. The song could be in any style and about any topic — as long as it had that title. There’s still room for creativity, but you do have to write with that restriction in mind.
I don’t think constraints are a bad thing. I know I can get a bit carried away when I’m dreaming up a new project. Sometimes, a rule or two can be what I need to focus on the elements that matter most.
Here’s a little trick I use to decide if I actually want to work on a project:
Let’s say I’ve got an idea, and I get really excited about it. I buy a domain for the website for the project, and start jotting down notes. I’m convinced that this is my next big idea!
The next step’s been a game changer for me: I go and add a note to my to-do list — one month in the future. I remind myself to revisit the idea then.
And then I do nothing — at least for 30 days.
Often, a month later, I look at the idea and go: Why was I so excited about this? That’s not a bad thing, I think — I’ve just saved myself a bunch of time and effort on an idea I wasn’t all that excited about!
But if I’m still excited about the idea a month later, that’s how I know it’s worth the investment, and that’s when I actually start to work on it.
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I like to use Domainr to come up with domain names. But I don’t think yournextnewsletteridea.com is my next project!
In the spring of 2019, I was starting to think about leaving the New Yorker to start Inbox Collective. But I was still nervous about it. Was it the right time to leave? Was I ready to take on the responsibility of building a new business?
And that’s around the time a recruiter reached out to ask about a job.
It was a good job with a big title at a major news organization, making more money than I’d ever made it my life. I wasn’t looking for another job, but I interviewed anyway. It was the kind of offer I had to at least consider. I wasn’t sure what to expect.
Within 20 minutes of the first interview, I knew what I wanted to do next.
I wasn’t excited about the idea of taking another job. I still loved my job at the New Yorker.
But more than anything else, I felt excited about the idea of starting my own consulting business — well, equal parts excited and nervous. Whenever I feel nervous, that’s usually a good thing. It’s a signal that I really care about something.
So I started to ask myself: Why, exactly, am I still doing the same old thing if I’m ready for what’s next?
By the end of the month, I told my bosses that I was leaving to start Inbox Collective.
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That’s a photo of me talking to a group of newsrooms in Sydney in fall 2019, a few months after starting Inbox Collective.
I had a moment last night with my newsletter. I wasn’t sure what to do about the intro section — I knew there should be an intro, but I wasn’t sure what I should say. And I felt stupid for not knowing: People pay me every week to help them figure out stuff like this! Why couldn’t I figure it out on my own?
And then I thought about a conversation I’d had with a client earlier in the week. They were feeling a little down, so I gave them a pep talk. It seemed to help.
And I thought: Could that be the intro?
So I wrote it up last night, but didn’t schedule the email. I wanted to read it again this morning.
This morning, it still made sense. It gave the newsletter something it didn’t have before — a bit of life, a bit of personality. It made it sound more like me.
I think I figured this one piece of the puzzle out today. And I know there’s a lot more to figure out.
But just figuring that one thing out made me feel a little lighter — the weight of this one task, however small, has been lifted.
Four years ago this week, I left The New Yorker to launch Inbox Collective. I kept things simple at the start.
I launched Not a Newsletter as a Google Doc so I wouldn’t have to build a website. It was enough to start.
I set up my email list with TinyLetter, not something more sophisticated, so I could launch faster. It was enough to start.
I set up my company’s website as a set of Google Slides, again so I could get something live as quickly as I could. It was enough to start.
I didn’t spend money on a logo or business cards. I realized: Why would I need those on Day 1? I just needed enough to start.
Four years later, a lot has changed. I’ve switched email platforms (twice, actually), built a real website, and brought on freelancers and contractors to help with some Inbox Collective work. I still don’t have a logo or business cards, though — maybe one day, but that day isn’t today.
The question for you is, and always should be: What do you need when you start? Figure out the stuff that’s worth spending time and money on right away. The rest can come later — or, as the work progresses, you may find you might never need it at all.
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Above, the original Inbox Collective “website” was just a public set of Google Slides.
It’s hard to make time for everything you want to do. I know I’ve got a big list of things I’d love to do one day — new projects, new adventures. I don’t have time for it all.
So it always comes back to this big question:
What is it you really want to do?
• Do you want to read more? • Do you want to learn a new skill? • Do you want to run that first 5k or 10k? • Do you want to launch a new project?
You can’t do all of it. You can’t choose everything.
But you can make time for some of the stuff you want to do. Maybe it’s not as much time as you’d like — maybe it’s just 20 minutes a day. Maybe it’s an hour or two a week.
A client had a question recently about something I’d worked on at BuzzFeed, so I went back into my email archives to try to find an answer. And what I found, unexpectedly, was this email:
It’s from the end of year 1 of my work at BuzzFeed. It said:
Monday marks 1 year since we really launched the newsletter program here at BuzzFeed. Quick numbers for you:
January 2013 5 newsletters — all automated, with about 20,000 total subscribers Newsletters drove 46,000 clicks to BuzzFeed Newsletters were the 28th biggest referrer of traffic to the site
January 2014 14 newsletters — all hand-curated, with more than 125,000 total subscribers Newsletters drove over 650,000 clicks to BuzzFeed Newsletters are the 8th biggest referrer of traffic to the site
I’ll be honest: I knew I did a lot of work that year — I just didn’t remember how much work!
Looking back, I know I was motivated to prove that newsletters could be a great tool for BuzzFeed, and I remember working long hours to keep the newsletter strategy moving forward. I was making stuff up as I went along, and I didn’t really have many resources at my disposal. I was lucky to have a few wonderful supporters in my corner who helped me stay on track. But even now, looking back at this email — which I wrote — I’m stunned at those results from year 1.
Did I really do that?
I know I can be dismissive of some of the work I’ve done in the past. I know I’m better at this now than I was a decade ago. I don’t always want to talk about the mistakes or lessons I learned along the way.
But I don’t get the chance to build Inbox Collective without that work I put in ten years ago at BuzzFeed. I’m grateful for that work, and I’m proud of it.
So here’s how a response to a welcome email led to one of the best things I’ve done in my three years of running Inbox Collective.
In October 2019, I get an email from Jan Birkemose, who runs the Danish media website Medietrends. He got my welcome email and wrote back, telling me a little about his business. We start trading notes back and forth. He tells me about these courses he’s running, including a two-day class all about email.
A few months later, Jan invites me to speak as part of that course. It goes well. He invites me back for another session later that year.
And then two more in 2021.
In December 2021, I happen to find myself in Denmark after Mette Will invites me to speak at Email Summit DK. (Thanks again, Mette!) On my last night in town, Jan and I meet in person for the first time. He asks if I’d be interested in hosting an email workshop of my own in Denmark in 2022.
Yes, I most certainly would.
I’d been wanting to do one of these for a while. I’d built up a series of workshop session that I do with individual newsrooms, but I’d never done them with several different orgs in a single room. Only thing had stopped me: Planning the event itself. Booking a space, coordinating with all the different teams, scheduling lunches for a big group — that part seemed intimidating to me.
But Jan had done these sorts of workshops dozens of times already. If I was going to take the leap on something like this, I needed a partner like him.
Fast forward to mid-September. It’s the end of a beautiful fall week in Copenhagen, and we’ve got 20 participants from 16 organizations (who came from four different countries) in the room together. They’ve learned a lot of the past three days (and, thanks to Jan’s planning, been fed every day!), and are telling me about what they’re going to do next.
They’ve got ideas: For surveys to run, and growth tactics they want to implement, and newsletters they want to launch. There’s a lot of excitement in the room, and a lot more work to do, but this group is ready to take it on.
Now that it’s all over, I’m feeling grateful for the opportunity to share what I’ve learned, and grateful for partners like Jan, who believed in this workshop idea and gave me the chance to lead it.
(And thanks for writing back to that welcome email, Jan! It’s amazing to think about the doors that a single email reply can open.)
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That’s me with the group at the end of the workshop. What a week!
College athletics are in flux right now. Teams are changing conferences (Rutgers vs. UCLA and Oklahoma vs. Kentucky will soon be in-conference matchups), and Name, Image, and Likeness rules mean that some athletes are now (legally) collecting checks from sponsors. Greg Sankey, commissioner of the Southeastern Conference, addressed all these changes this week at the conference’s annual media days for football. “It’s never going to be the same,” he said, “but it doesn’t have to be the way that it is”
The same could be said for many businesses. It’s certainly the case for the news world, where I come from. Are we going back to the days when local newspapers employed hundreds of journalists? Probably not. But it’s up to us to build something new moving forward. Just this week, I’ve talked with local news outlets investing in solutions journalism, digital outlets building out new models for revenue sharing with writers, and individual writers who are building an entire business through their own newsletters or podcasts.
Everything changes, and that’s OK. We can fight it, or we can accept it and try to figure out how to build the best possible future for ourselves. The choice is ours.
