Author: Dan Oshinsky

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Two Bets for 2023.

At the start of the year, I made two small bets with Inbox Collective.

The first was on Dine & Deliver, this dinner series I’m co-hosting with the team at Who Sponsors Stuff. The bet here was simple: Could we start to bring small communities together, in person, in cities all around the world, to talk about newsletters?

The second was on the Inbox Collective website. Could we start to build an audience, on the web, to read great stories and guides about email?

Neither of these are short-term investments. I think Dine & Deliver has the potential to grow into a much bigger series of events in 2024 and beyond; I’ve already seen the web traffic to inboxcollective.com double in 2023, and I think we can double again by the end of the year. There’s so much room for growth here — and like with Dine & Deliver, growth should unlock opportunities for revenue: Sponsorship, affiliate revenue, and consulting work.

I don’t expect an immediate return on either of these bets. My goal for 2023 was to break even on both, and I will.

In 2024, I might be able to bet even bigger on the future of the business.

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That’s a photo of me leading the discussion at a Dine & Deliver dinner in Washington, D.C., earlier this year.

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The Hardest Questions to Answer.

That's sunrise over Puerto Rico in May 2023. Birds fly through the sky as the sun comes up

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.

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Get the First Win.

This is a photo of white golf balls and red, white, and blue golf tees on a driving range.

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.

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Let Everyone In.

Here's a photo I took during “Born to Run” at the Bruce Springsteen & The E Street Band show on April 9, 2023, at UBS Arena. The house lights are up, and you can see the entire crowd dance and sing during the performance.

We saw Bruce Springsteen & The E Street Band last week, and there’s a cool moment in the encore that Bruce and the band do at every show. Throughout the concert, the house lights are down, with just the spotlights on the band. But right as they break into “Born to Run,” the house lights go up — suddenly, you can see every single person in the arena.

And since the song is “Born to Run,” every person in the arena loses their damn mind. People spill out into the aisles, singing and dancing along. If you want to understand the concept of “dancing like no one’s watching,” go to a Springsteen show and wait for the lights to come up. You’ll see 20,000 people leaning into that mantra.

What I love most about it, though, is that it shifts the perspective of the show. For 2+ hours, you’re standing in darkness, watching Springsteen and the band perform. And when the lights come up, it all changes: Suddenly, the crowd is part of the show. Their dancing, their singing — it’s part of the performance. And as the crowd gets into their role, you can see people around the arena starting to loosen up. Seeing so many others dance freely and sing at the top of their lungs gives them permission to do the same.

Would “Born to Run” be the same if the house lights stayed down? It’d still be a great moment during the show, but it’d be different — it wouldn’t be a shared performance. What makes it special is that everyone gets to be part of it.

There are moments when you want others to join in. There are moments that you want to share with the crowd. Recognize them. Turn the lights up.

Let everyone in.

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That’s a photo I took of the crowd at UBS Arena, on April 9, 2023, during the performance of “Born to Run” at the Bruce Springsteen & The E Street Band show.

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Change Can Be the Right Thing.

This is a photo of me, ready for takeoff back to New York

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.

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It’s OK.

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.

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Document Your Journey.

Here's an empty white spiral notebook on a brown desk.

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!

It’s Hard to Have a Big Ego When You’re Sleeping on the Floor.

I can look back at the days when I wondered if my work would bring in any money.

The Thing I Really Wanted During The Days in Biloxi In Which My Diet Was 84 Percent Tuna Fish.

I can read back through an old edition of “The Things I Believe” and remember the person I once was.

I Am 24 Years Old. This Is What I Believe.

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.

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What’s Not To Like?

This is a silver wall, with graffiti of the Facebook reactions — a like, a heart, and a smiley face — drawn on it.

There was a guy I knew growing up who used to like everything on Facebook.

That photo of your big vacation. A random status update. A comment you left on someone’s post. He left a “like” on all of it.

It was a strange thing, seeing his name show up at the bottom of every single post you left on Facebook. So one day, I finally asked him why he did it.

“What’s not to like?” he told me.

I’ve been thinking about him lately, particularly as I spend a bit more time on channels like LinkedIn. Often, I’ve been a bit of a lurker on social media — I see the things others post, but don’t always say something.

Shouldn’t I have more of my friend’s spirit?

I want to be a cheerleader for others. I want to be that person who re-shares, who celebrates, who likes.

I know that little things get noticed. And all these years later, I still think about all those likes my friend left on my post.

Turns out there was a lot to like about his social media habit. The little things make a bigger impact than you think.

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That photo comes via George Pagan III and Unsplash.

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Enjoy It While It Lasts.

Sally and I pose for a photo after Mizzou beat UCF on a buzzer-beating 3-pointer.

Sally and I went to a Mizzou basketball game earlier this year. At the time, I wasn’t quite sure what to expect from this team. They had a new coach and nine new players on the roster. I was hoping they’d be competitive; I wasn’t sure if they’d be any good.

And that day, we watched them bank in a 35-footer at the buzzer for the win.

As we walked out of the arena, I told Sally: That’s the kind of win that might make a team believe they could do something special this year.

And then they went out and did just that. They crushed rival Illinois. They beat Kentucky and Iowa State. Had another buzzer-beating win at Tennessee. As of today, they’re ranked in the Top 25 and headed to the NCAA Tournament.

But the thing is: A season like this goes by fast. A quarter of this team will graduate in the spring, and others might transfer. Next year’s team will probably have a half-dozen new players. This isn’t the pros, where you can root for one player for years and years — in college, players graduate or move on.

So I’ve been watching every game I can down the stretch. I’ve been trying to enjoy it all. I know it’ll be over soon. The NCAA Tournament is a win-or-go-home proposition. If they exceed every expectation, their season will still be over in the next two weeks.

I’m trying to enjoy it while it lasts, and share these moments with friends while it’s all still happening in the present. It’s not over yet.

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That’s us after that buzzer beater vs. UCF. I’m a pretty optimistic sports fan, but there’s no way I would’ve predicted the season Mizzou would go on to have.

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Even If You’re Working Solo, You Still Need a Team.

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.

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