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.
Sometimes, the simplest questions are the hardest to answer.
What does success look like?
What do I want to do next?
Is now the right time to try something big?
Do I know enough to start?
Am I ready for whatever’s next?
These are questions that are going to take time to answer. But they’re also worth putting in the work to answer.
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I was thinking about a few of these questions while watching sunrise over Puerto Rico this morning. Not a bad place to think about big questions.
I went to the driving range once and found myself next to a couple that was playing golf for the first time. They had an instructor with them, and within the first minutes of the lesson, he was walking them through the complex biomechanics of the swing. He was telling them that there were more than three dozen different parts of the swing, all of which had to work together. He was giving them tips from professional golfers. He was getting into the mental side of the game.
In the hour alongside them, I didn’t see either of them swing the club a single time. The entire lesson was on golf theory.
And I remember thinking: These people will never come back and try to play again — because they never had that first win.
Golf can be a frustrating game, and yes, a really good swing is a complex thing, but the reason you come back is because of the feeling that happens when you hit a really good shot. That feeling — the sound off of the club, the whoosh of the ball in the air, seeing the ball fly — is what every golfer chases. You come back to try to recreate that feeling, over and over again. Those first-time golfers weren’t going to hit a drive 250 yards or experience a perfect wedge shot, but they never even got the chance to try.
With anything you’re doing for the first time, you’re chasing that first win.
Maybe that first win is the first time someone compliments your work.
Maybe it’s the first dollar you make.
Maybe it’s the first time a lesson starts to click.
The goal is to get that first win as soon as you can. Because once you’ve gotten that first win, you’ve experienced a taste of what the work is for — and can decide whether you want to come back for more.
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That’s a photo of golf balls and tees at a driving range. It was taken by Robert Ruggiero for Unsplash.
When I first started Inbox Collective, I thought most of my job would involve projects and travel.
I’d do an audit for a newsroom, then travel to their office to lead a workshop. I’d take the lead on a big project, where I’d get into a client’s email platform to build something for them. I’d do talks in person. I’d speak at conferences in front of big rooms.
And the job changed when the pandemic hit. I wasn’t traveling for work anymore, which meant more calls and presentations on Zoom. A lot of friends told me they hated Zoom — I found that I loved it. I could actually work with more teams and help a lot more people since I wasn’t spending all my time on planes. I could work with newsrooms and writers in far-off parts of the world, and do so on my schedule.
And at the same time, I started to realize that I didn’t love project work. It took up a lot of time and was full of frustration — exactly the stuff that made me want to go solo in the first place.
So the job changed. I shifted towards the work I liked most: Coaching, writing, and IRL work that involves lots of 1-to-1 time. I took on some audits, but only occasionally. I farmed out work that I wasn’t enthusiastic about to other consultants or agencies.
This week, I traveled to LA for work for an on-site with a client and a Dine & Deliver dinner. I was in LA for 36 hours. I landed just before 2 a.m. in California. I got home the next day after midnight.
And I loved the work I did on site, but it was a reminder of how happy I am with the job I’ve created for myself. It’s definitely not the job I thought I’d have four years ago.
It’s better.
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That’s me on the flight back from LA. I might not have been smiling if I’d realized that I’d get home at 12:30 a.m.
It’s OK if you don’t know what’s next.
It’s OK if you don’t have all the answers.
It’s OK if you don’t get everything done today that you wanted to do today.
It’s OK if you’re stuck.
It’s OK if everything needs to change.
It’s OK if you have to wait to do the thing you really want to do.
It’s OK if you have to accept “good enough” now, even if you want to do something great one day.
It’s OK, and it’s just what you’re dealing with today. It won’t be like this forever.
Tomorrow, you get another chance to do better.
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I took that photo in Utah, in fall 2020, at a moment when I didn’t have a lot of answers about the future. Things turned out more than OK in the long run.
I’m lucky to be in a place where I’ve got a career I love and a business that’s growing.
But to anyone thinking that this all happened overnight: It most certainly did not.
That’s why I’m so grateful that I’ve been documenting my journey over the years. And every time I look back upon certain entries — from a year ago, or five, or ten — I’m reminded of what I went through on the road to today.
I can look back and remember the moment when I was sleeping on a floor in Springfield, Missouri — and excited about it!
I can look back at the days when I wondered if my work would bring in any money.
I can read back through an old edition of “The Things I Believe” and remember the person I once was.
These stories are humbling. They’re a reminder of what I went through to get here.
And they’re why I’ll keep documenting my story, one day at a time. I know I’ll look back on this time, too, remembering the person I once was — and the person I’ve since become.
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That photo of a spiral notebook comes via Justin Morgan and Unsplash.
I had a few candidates take editing tests this week for a part-time editor role with Inbox Collective. (I paid them for their work — it’s only fair that they should be compensated for their time and talent.) And reading through their notes, I kept thinking: These edits are going to make these stories so much better! They pointed out all sorts of edits and structural changes I hadn’t thought of.
To put together a really great website, I know I need editors to help make my work better. My ideas are pretty good, but they’ll be sharpened by a smart editor.
I operate as a one-man operation, but I still need a team around me. I need part-time editors to help out with stories. I need freelance writers I can turn to. I need friends in the industry who I can talk to for advice. I need people I trust who I can bounce ideas off of. I need to do surveys and have lots of conversations with readers to get their feedback.
I need all this extra input and help. It’s hard to do this work alone. And recognizing that means that I can look for ways to add support around me to make sure I do the best work I can do.
I’m doing this solo, but that doesn’t mean I have to go it alone.
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That photo was taken by Hannah Busing for Unsplash.
We live in an age of copycats. When someone has success in a particular way, there’s a rush for others to copy that model.
There’s nothing wrong with learning from others. There’s no reason to make the same mistakes that others have already made. Ask good questions, listen, and learn from others. Use existing examples to make the work you do better.
But you have to find your own way, too. You have to find ways to take what you’re doing and put your own spin on it.
Only you can do what you can do. So don’t be content to copy and paste — learn from others, and find a way to make things your own.
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That image comes via Kelly Sikkema and Unsplash.
I went to see my Washington Capitals play last night. The team is in an interesting place this season: They’ve got a ton of veteran players who were part of the Stanley Cup run from 2018, several young players who’ve been impressive this year, and a few players who are coming back from injuries. The coach, Peter Laviolette, has some real choices to make when setting his lineup.
And at the game last night, everyone around me had an opinion about who should start, who should sit, and which players should be playing together. If I’d polled the fans within earshot of me, I think I would’ve gotten a dozen different answers. Everyone had an opinion, and no one was happy. (The Caps lost to the rival Philadelphia Flyers, 3-1.)
But the thing I kept telling my neighbors was: There’s a long way to go in the season. It’s not the playoffs yet, and not even the stretch run leading up to the playoffs. The season’s barely halfway done. So the team has some time to figure out the answers.
It can feel like you’re in a rush to get to an answer. But there’s no rush here — the direction you’re headed is more important than the speed at which you get there.
Try a lot of things, and see what sticks. In the end, if you’re patient, you’ll figure it out.
(The Caps, hopefully, will too.)
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That photo of a Caps game was taken by Alex Korolkoff for Unsplash.
I’ve been working with a few newsletter writers who are in a period of transition. For nearly two years, they’d been writing multiple newsletters per week. Now, they’re all trying to figure out what to do next. Should they write more, or less? Should they change the way they monetize?
And my advice, over and over, has been simple: Whatever you do choose to do next, make it work for you.
There isn’t a single way forward here. There is no one-size-fits-all answer.
Which means that the right answer, for now, is the one that works for each of these writers. It’s up to them to figure out what they want to build and how they want to build it. There’s no need to build around someone else’s constraints or rules — they’re free to do what’s best for them.
Maybe that means, as I told one writer, telling their readers that they’d be taking a month off in December so they can get ahead for 2023 and pre-write the first few months of newsletters. “I’m allowed to do that?” they asked me.
You are, I told them, because this is all about making it work for you.
Maybe it means changing up the way they monetize. One writer’s been trying to push forward with a paid subscription, but it isn’t working as well as they hoped. But they do have a fairly large, engaged audience. Advertising might be a better way forward for them.
“Can I just cancel the paid offering and switch businesses models?” they asked me.
You can, I said, because if you’re going to make this work, it first needs to work for you.
What’s the best route forward? Figure out what’s best for you , and work from there.
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That’s a photo of a Brother typewriter, in teal and black. It comes via photographer Laura Rivera and Unsplash.
As I’ve played more golf over the past year, I’ve realized something: It’s easy to make too many changes.
Every time I check YouTube or Instagram, the algorithm serves me with another video promising a quick fix to my swing. Sure, you’re playing decently, Dan, but what if you adjusted your stance? What if you stood up taller? What if you had more bend in the knee at impact? What if you moved the ball back in your stance? What if you bowed your wrist at the top of the swing? What if you tried a lower follow-through? No, wait, what if you tried a higher follow-through!
And it’s easy for all these thoughts to get in my head and screw everything up. On a normal day, I’m a decent golfer. Not great, not terrible — but the more swing thoughts I have, the worse I play.
When I go to the driving range, sometimes I’ll try to implement a small tweak to my swing, but usually, I’m impatient. If it doesn’t work right away, I’ll drop it, or move on to the next tweak.
But if you keep changing stuff before you have time to see results, how will you know if it’s working?
No matter what it is you’re doing — improving a golf swing, running an A/B test, trying out a new strategy — you have to be willing to be patient. Find things you want to try, and commit to them for a certain length of time. Often, it’s not the tactics that are wrong — it’s just that you didn’t wait long enough to see the results.
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That’s me, hitting golf balls at Chelsea Piers in New York. Not a bad view for a driving range!