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.
My son loves going to Costco, and for a funny reason: He loves the checkout process.
At Costco, you get your receipt from the cashier and then hand it to an employee at the exit. They look at the items on the receipt and then cross-reference it with what’s in your cart.
But when you’ve got a toddler with you, the Costco employee will also turn the receipt over, draw a smiley face on the back, and hand it to your child.
My son absolutely loves the smiley face drawings. When we go to other grocery stores, he always wants to know: “Can they draw a happy face for me?”
When it comes to serving your audience, it’s not always about the big things. The little things matter, too.
A funny thing I’ve noticed lately: I’ll be chatting with a friend and mention something that I was able to make time for — going skiing, spending time with the kiddo, reading books. And they’ll say, “Oh, I wish I had time for something like that!”
But when you probe a little deeper, you find that they often do have the time. We’ve all met people who are willing to wake up at 6 so they can squeeze in a workout before work, but who can’t seem to find the time to cook dinner.
And I get it: We’re all busy, and there’s never enough time for everything. But if there’s something you really value, there’s often a way to make space for it.
For me, one of those things is getting outside. I was feeling a little sluggish the other day, and I had a break between calls. I sat down, ate some lunch, and watched crappy TV on the couch for an hour. Weirdly, lying down on the couch didn’t particularly help with that sluggishness!
And as I went downstairs to go on my calls, I found myself asking: Why didn’t I get outside for a 20-minute walk to clear my head?
Yes, I’m busy. No, I don’t have time for everything. And no, I don’t need to fill every minute of the day with something.
But I have 20 minutes for a walk. I have time to read before bed. I can move things around so I can do the stuff I want.
I do have the the time if I want it.
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That’s a photo I took last summer of the kiddo and I on a little hike together here in the mountains.
About a decade ago, I made a commitment to start writing more on danoshinsky.com. It was a small thing — the goal, at first, was just to have a place to write. I was in a job at the time that involved a lot of technical writing (subject lines, captions, stuff for SEO), but I wanted a place where I could do my own thing and share what I was learning.
So I made a commitment to write once a week.
And one of things you learn when you start writing once a week is that some posts are good, some are great, and some are lousy.
But you also learn: By taking more swings, you have more chances for success.
Let’s lean into the baseball analogy here. Let’s say I hit .300 on my posts — three out of every 10 posts is something I’m super proud of. More swings means more opportunities for success.
A hit rate of .300 on 12 posts means I’d have four hit posts a year.
But by writing weekly, I’ve got 52 posts — which means a hit rate of 17 posts.
Could I go further? Maybe I could up my outage of posts. If I somehow wrote 365 posts — and I feel dizzy just thinking about writing that much — I’d have 109 hits in a year. (Though honestly, if I wrote that much, I wonder if my hit rate would naturally go down. More output doesn’t mean I’d be consistent with the quality of my writing.)
But the point is: It’s a good thing to take more swings. Not everything is a hit, and that’s OK. But every time I take a swing, I’ve got a chance to do something great.
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I took that photo at a San Antonio Missions minor league baseball game back in May 2010. The pitcher is Simon Castro, who went on to pitch parts of three seasons in the majors with the Chicago White Sox, Colorado Rockies, and Oakland Athletics.
Last summer, I set a weird business goal for the year ahead: I wanted to try to play golf or go skiing at least 50 times over the course of the calendar year, starting September 1st.
And you might be thinking, “Dan, that’s not a business goal! That sounds like a personal thing!” But for me, it represented an evolution of my business. I love doing this work because it gives me flexibility to do the things that I love outside of work. But if I’m not actually doing the stuff that I love, it means I’m taking on too much with Inbox Collective.
So it’s the end of the summer, and it’s been a year. How’d I do?
This year I hit 25 days of skiing, and 22 days of golf.
(I tracked everything in a Google Sheet, if you’re curious.)
Yes, I came a little short: 47 days, not 50. But I’m still so happy with that number — it’s more skiing and golf than I’ve ever done in a single year! Plus, I’ve got a kid (who isn’t quite old enough to go skiing or play golf with me, though he did come out a few times to help “drive” the golf cart), so maybe in a year or two, getting to 50 days will be easier.
It’s not easy to make time for big things like this — even once a week was a challenge! But getting so close to the goal means I’m on the right track.
Here’s to more time outside of work, more time for yourself, and more time doing the things that you love.
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That’s Sally and I at lunch at Alta on a spring ski day. Nothing quite like skiing on a Monday instead of working!
I set a big goal for 2025 — something I’ve never set in the six years I’ve run my business.
My big goal isn’t around revenue.
It isn’t about growth.
It isn’t about launching new products.
My goal? I want to be able to ski or play golf 50 times in 2025.
To me, success isn’t about building the biggest, most profitable business. It’s about making something that brings in the revenue I need, has the impact I want, and gives me the time to do the things I love.
If I can run a business that does all three, then I must be doing something right.
Here’s to a lot more days on the mountain in 2025 — and on the links this summer.
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That’s me on the mountain at Deer Valley a few weeks ago. If you see a tall guy in a loud jacket skiing around Park City, it might be me!
One little thing that’s worked for me when it comes to New Year’s Resolutions: Starting just a little bit early.
I used to do the thing that everyone does: I picked a resolution or two at the end of the year, started in January, and completely quit on it by the end of the month.
But what I discovered works a little better for me is if I start now — not in January.
Let’s say the resolution is to work out more in the new year. (In this case, this is something I genuinely want to do next year!) I know that if I try to go from 0 to 60 in January, it probably won’t stick. I need a little time to warm up to the new habit.
So instead, I’ll start now — in December. I’ll put a few workout classes on my calendar. I’ll make sure to make time during the month to use that stationary bike. And by January, I’ll already have started to slowly build that habit.
Once you’ve gotten the ball rolling, it’s so much easier to keep it moving when January comes around.
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That is 100% not me on an exercise bike, but it is a lovely black-and-white photo of someone biking from Josh Nuttall for Unsplash.
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.
