Author: Dan Oshinsky

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Finding the Right Signals.

Blurred out faces on a Zoom call, with a green coffee mug in the foreground.

I’ve done a few AMAs on Zoom this year. These are private calls where teams can join and ask me, well, anything. They don’t tell me what they’re asking in advance. They show up, surprise me with questions, and give me the chance to share a few ideas back.

They’re a lot of fun to do — and I’m especially thrilled when I get asked a question and I have a link — or maybe even a few — from Inbox Collective that I can share to help answer it. 

A few years ago, when I started publishing original stories on the site, I told myself that I wanted to use Inbox Collective to answer the big newsletter questions that I hadn’t seen answered elsewhere. And I’m finding through these AMAs that I’ve done a pretty decent job of that!

I’m always looking for signals that I’m on the right track. Those could mean page views or email replies or client inquiries, but sometimes it’s the unexpected signals — like having plenty of links to share on Zoom calls — that are an indicator that I’m doing something right.

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That photo of a blurry Zoom call comes via David Montgomery and Unplash.

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Keep Betting on Yourself.

15 years ago, I quit my job at a TV station, moved to Biloxi, Mississippi, set up a basic website, and started publishing stories about the five-year anniversary of Hurricane Katrina. I was my own reporter, editor, photographer, publicist, IT team — I did it all. The end result was a fellowship, which led to more reporting in Springfield, Missouri, and then that led to my gig at BuzzFeed.

I bet on myself, and I certainly wouldn’t be where I am today if I don’t make that bet.

But not all bets are big. Inbox Collective was barely a few weeks old when I went to a journalism conference in New Orleans in September 2019. I told my wife that I wanted to host a happy hour for readers of my newsletter. I didn’t have any idea how many people would show up or even if any would show up — but my bet was that if I met some people, something good would come from it.

50 people RSVPed. A few no-showed, a few brought an extra friend. I ended up spending about $400 on drinks. (Thanks to everyone who bought happy hour beers and not full-priced cocktails!)

But most importantly: I landed five clients from that one happy hour.

Anytime I feel stuck, I try to remind myself: Keep betting on yourself. Place small bets, and place big ones. It’s worked before; it may work again.

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I took that photo in 2010 in Pass Christian, Mississippi. It’s of a bust of W. Dayton Robinson, whose $2 million donation helped City Hall expand after Katrina.

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You Can Do More Now.

We went on a hike this weekend. It was only four miles, but it took four hours — we started at about 8,000 feet, then went more than 1,000 feet up a mountain, all while I carried a two-year-old in a carrier on my back.

And as we went up, I kept thinking: There’s no way I could have done this last year.

Last year, we did some hikes around Utah, but rarely more than an hour at any one time. We just got too tired to do any more than that.

But the more we hiked, the stronger and more capable we’ve gotten. We can hike stuff now that would’ve been impossible not all that long ago.

All that work opened up new doors, new possibilities.

Keep going.

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That‘s the view near the top on our hike at Alta. Looking down, you can see another ski mountain, Brighton, in the distance.

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Make Time For It.

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!

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Embrace the Limitations.

I often wish the hours for our day care were a little better. Drop off is at 8:45 a.m., pick-up is at 3:45 p.m. There are days when I’m cramming five or six calls into that window, then driving right back to pick up Ben. (Lunch sometimes happens in the five minutes between calls. ) After that, I’m playing with Ben for a few hours, handling dinner and bedtime, and then going right back to my desk to work.

But this year, I finally got to a place where I realized:

1.) My son loves his day care teachers and his friends. He’s really happy there.

2.) We’re incredibly lucky to have such a good day care so close to our home.

3.) I have an excuse, five days a week, to cut my workday short and play with my son.

This schedule means I have to say “no” to certain projects — I don’t have time for everything. But it also means I can’t overload my days with calls or work. I have plenty of working hours during the normal business day, and I can always take care of writing or other stuff at night.

Is our schedule perfect? No. But it’s up to me to embrace the good that it brings into our lives.

Today, I got to spend an hour on the playground with my kid, and then eat dinner with him at home. We had a little conversation about the day. We laughed and played together.

Sure beats working.

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One favorite activity: Shopping at the supermarket together. Ben knows exactly where the good bread is, and he often sprints to the corner of the supermarket to grab a loaf.

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The Dream is Whatever You Want It to Be.

I was sitting on a hill yesterday in town, at a free concert in the park, with my son. He was eating a corndog — his very first. (He loved it.) The sky was blue, the air was cool. We’d biked up to the show together on the path behind our house.

And I was thinking about this line from Jon Batiste’s new album, “BIG MONEY”:

You can be living the life
But not living the dream

That means something different to everyone — certainly different to you than to me.

What I like about living up here is the pace. People aren’t in a rush, and if something doesn’t get done that day, it’s OK. There’s always tomorrow. The afternoons can be spent at the park, or on a bike, or at the golf course, or on the mountain. And I get to spend a lot of time with my family, and especially with my son.

I don’t know what “the dream” really means, but a summer afternoon splitting a corndog with my son in the park has to be pretty close to it.

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It Won’t Be This Way Forever.

Ben got sick last week and ended up in the hospital for two nights. Then we came home, and just as we thought things were getting better, he realized that he could climb out of the crib, which turned bedtime into a game of, ”Please, it’s time for sleep!” (We kept losing.)

And I had to remind Sally: Whatever we’re going through, it’s not forever. There are moments when you feel like you’re at your lowest; there are phases that don’t seem to end; there are weeks when you feel like you’ve absolutely been sucker punched by the universe.

And then there are stretches that feel perfect, that feel wonderful, that you wish would never end.

Nothing lasts, and I have to remind myself of that. The good, the bad, the in-between: It doesn’t last. It won’t be this way forever.

When you’re at a high, it can be tough to accept that things might not stay this way. But when you’re at a low? It’s nice to know that things can and will change.

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I took that photo of Ben at the airport a few weeks ago. He was so excited — he’s been reading a bunch of books about planes, trains, and automobiles, so he was just thrilled to see planes taking off in real life.

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I Don’t Always Have the Answer.

At least once a week, a reader asks me a question, and my reply is: “To be honest: This is one of those questions that’s so far outside my wheelhouse that I’m not sure my advice is worth listening to!”

People are sometimes surprised to hear me say that. I do run an entire business around giving advice for newsletter operators, and I’ve been working in this space for a dozen years.

But the most important thing I’ve learned through my consulting practice is that it’s OK to say, “I don’t know!” No need to pretend I have all the answers.

And if you’re the kind of person asking the question, you should also feel free to ignore my advice entirely! I am frequently wrong, even when I have strong convictions about my answers!

So much of building any newsletter or any business is knowing when to follow and when to find your own way. (And yes, the teams that tend to build the best stuff in the long run do a bit of the former but often more of the latter!)

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I couldn’t quite find the right art for this, so I had to draw something myself using the only art tool I’m qualified to use: MS Paint. (Or, in this case, a free online replica version of MS Paint.)

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Never Better Than Now.

I remember when my dad turned 40. They threw a big birthday party, and friends gifted him this giant inflatable cane. Everyone at the party signed it. It sat in his office for a long time, and I every time I visited dad at work, I remember reading the inscriptions and names on the cane. There were a lot of jokes about my dad officially reaching old age, and I couldn’t disagree.

To a kid, 40 felt like 100.

But I’m 38 now, and looking up at 40 feels strange. I certainly don’t feel 100; I feel a lot closer to the starting line than the finish.

I also know that I don’t know when the finish line arrives.

I’m trying to remind myself that there’s never a right time to do the big stuff. Sometimes I try to tell myself that the timing will be better just a few months down the road, even though I know that’s not true. If you want to do something, you should do it now. Next year, next month, next week — none of this is guaranteed.

There’s never been a better time than right now.

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I took that photo alongside the harbor in Copenhagen one morning a few weeks ago. I was sitting there, watching the sun rise on a beautiful morning, and thinking about the fact that I do something that lets me travel to such beautiful places and work with such interesting people. I know how lucky I am.

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It Never Stops Changing.

When my son was a few months old, he went through a stretch where his sleep started to change. He’d been pretty consistently up to that point, sleeping more and more through the night, but then suddenly, he was sleeping less and getting a lot more fussy than usual.

We mentioned it to a friend, who gave us great advice: “It’s just a phase. Give it a week or two, and he’ll get through it.” Sure enough, a few days later, he did.

And ever since, I’ve started to notice the phases more clearly. Now that he’s two, the phases move a lot faster. One day, he’s taking baby steps up the stairs, and the next, he’s sprinting up them. One day, he’s just starting to learn his numbers, and the next, he’s counting to ten on his own. The progress, as a parent, is astonishing.

And it’s a reminder for me that whatever phases we’re going through in our life are just phases. Ben changes faster than most of us, but we can, too. We grow, we change. We’re all capable of continuing to change.

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That’s a photo I took of Ben and I reading a book together the other day.

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