lessons learned | danoshinsky.com

05/09/202405/09/2024

Shift, Pivot, or Sunset?

The sun sets behind clouds as trees glow in the foreground.

We sometimes need to make a change with the work we do. The question is: How big a change do you need to make?

Sometimes, you just need to make a shift. The change is small — you’re refocusing on something new, but it’s within the normal scope of what you’d do already.

Sometimes, you need to pivot. You’re making a big change — taking your skills and applying them to something outside your current orbit. The skills and the work might look similar, but you’re doing it in a different space.

And sometimes, you need to sunset things. You’ve done the work, you’ve learned the skills, but you’re ready for something brand new. You’re ready to shut down what you’re doing and move into a brand new field.

For my work, for instance, a shift would be changing my focus from working with newsrooms to working exclusively with non-profits. A pivot would be moving from newsletter consulting to building an agency to help newsletters grow. And to sunset would mean shutting down Inbox Collective to focus on something new.

None of these match where I’m at right now, but maybe they will be in the future. When it comes time to make a change, the big question remains: Shift, pivot, or sunset?

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That’s a photo of a sunset, taken by Dawid Zawiła for Unsplash.

04/08/202404/08/2024

Give Yourself a Constraint.

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.

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That video comes via Fried Egg Golf.

03/25/202404/03/2024

Try It. Then Figure Out What You Want to Keep.

A few years ago, I saw Adam Sandler perform live. He was recording what would become his first comedy special in decades, and honestly, I wasn’t sure what I was in for.

What I was in for, it turned out, was something both funny and unpolished.

Sandler’s set, which he’d trim down to about 70 minutes for TV, ran nearly two hours. He performed original songs and some stand-up material. Some bits worked; others didn’t. The cameras rolled the whole time.

What I discovered later was that this was Sandler’s creative process. He does the same thing with movies: He records lots of takes, lots of different ways, and then figures out which is the funniest once he gets to the editing bay. The goal when he’s recording is to capture all sorts of options — he’ll figure out what works later on.

That’s not a bad way to approach your work. Some things become hits, and others flop. You don’t really know which is which when you’re making it. You can’t always see around corners.

So instead of hoping that your first idea will be the right one, try doing a bit more than you expect. Leave yourself some alternatives. If something doesn’t work, that’s OK. You’ll have a Plan B already waiting for you.

03/19/202403/19/2024

Be Something to Someone.

The Pitchfork homepage in late February 2009.

The team at Slate put together a great oral history of Pitchfork, the music site that ran from 1996 until 2024, and there was a line in there from Chris Kaskie, Pitchfork’s former president and co-owner, that really stuck with me.

“We are not trying to be everything to everybody,” he said. “We’re trying to be something to someone.”

It’s something a lot more of us could take to heart. Whatever it is you do, your work doesn’t have to matter to everyone — just to someone.

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At top, a screenshot of the Pitchfork homepage on a random February in 2009.

03/13/202403/13/2024

Should You Work on That Idea?

Using Domainr, I can see if a domain name is available

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!

02/27/2024

Every New Experience Can Be a Learning Experience.

I’m lucky to have a job where I learn new things every day.

Every new client brings me questions I haven’t had to answer before. Every new project introduces challenges I’ve never dealt with before. Every new year brings opportunities I’ve never had before.

And that’s just what happens at work. When I come home, being a new dad means I learn all sorts of new stuff every day — sometimes, a few new things a day. (Sometimes, that new stuff involves learning ways to not get peed on.)

You try, you do, you screw up, you learn. I’m not going to say I get smarter every day — I’m still working on that part! — but every new experience is a learning experience. You just have to be willing to see it that way.

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That photo of a bookshelf comes via Jason Leung and Unsplash.

12/05/2023

Good Advice Can Come From Anywhere.

A few weeks after Ben was born, we hired a photographer to take photos of our newly-expanded family. Midway through the photo shoot, Ben got hungry and started to fuss. I grabbed a bottle to feed him, and the photographer followed along to take a few shots of us together.

When it came time to burp Ben, I put him into the position I’d been shown at the hospital: His chest on my shoulder, with me gently patting his back. But I couldn’t get a burp out.

“Would you like me to show you how I do it with my kids?” the photographer asked. It turned out she had four young kids, so she’d had plenty of practice.

I immediately handed over Ben, and watched as she propped him up on her knee, tilted him gently forward, and placed her hand on his chest.

Before she could even pat his back, Ben let out a massive belch. Naturally, that position became my go-to any time I needed to burp my son.

It was a reminder that day: Good advice and ideas can come from anywhere. You just have to be willing to make space and listen.

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That photo of lightbulbs comes via Unsplash and photographer Daniele Franchi.

11/01/202311/01/2023

What More Do I Really Need?

There are days when I look at what I’m doing and wonder: Shouldn’t I be doing more?

Sure, I’ve grown my email list from 0 to 10,000 subscribers — but couldn’t I have more subscribers?

Sure, I’ve built a successful consulting business — but couldn’t I bringing in more revenue?

Sure, I’ve created a profitable website — but couldn’t it get more readers?

Couldn’t I sell courses? Couldn’t I write a book? Couldn’t I give more talks? Couldn’t I charge more for each speaking engagement?

And then I have to take a few steps back to acknowledge what I’ve actually done.

I’ve built an audience, I’ve built a business. I’ve created, from nothing, the best paying and most flexible job I’ve ever had. I’ll take more time off this year than I’ve taken since college. I’m in a position where I get to pick and choose what projects I take on and who I work with.

I’m proud of the success I’ve had. Success should be enough — do I need to be excessively successful? Do I really need to do more?

I know the answer to those questions, but it’s hard to quiet the voice that wants to do more. I have to remind myself: I don’t need to do everything. This is more than enough.

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That’s from a talk I gave in Denver in September. It went well — but yes, I still do wonder if I could’ve done better for those who attended.

09/09/202309/09/2023

People Remember The Little Things.

On a Delta flight today, the flight attendant stopped by my row. “Mr. Oshinsky,” she said. “We wanted to thank you for your loyalty.” And then she handed me the note above.

“Aww, that’s nice,” I thought.

A few minutes later, the flight attendant stopped at the row in front of me and handed another passenger a similar handwritten note.

“Aww, that’s so kind,” she said.

And then I saw the flight attendant do the same for someone else a few rows ahead of me, and then for the passenger sitting beside me. All gave a big smile after reading it.

The notes were a tiny gesture — but the fact that someone took the time to hand write a few words of thanks felt meaningful. Had I gotten that exact same message in a marketing email from Delta, it probably would’ve felt far less powerful. The medium — a hand-written note — changed everything.

Those little things get remembered. Those little gestures often feel extra meaningful.

Sometimes, it’s a small act of kindness. Sometimes, it’s someone taking the time to make sure you feel seen and heard.

Whatever you do, do the big things well. But don’t forget about the little moments, too.

09/03/2023

Only the Prepared Can Be Spontaneous.

Daddy walking his baby in a stroller in front of one of Stockholm's emblematic creamy façades in Södermalm.

One funny lesson from parenthood: In order to be spontaneous with the baby, we’ve learned we first have to be prepared.

Whenever we get home from being out with the baby, the first thing we do is prep the stroller to go out again. We’ll restock the diaper bag with new diapers and wipes. We’ll make sure all the stuff we need to feed the baby is clean and ready to go. We’ll add a fresh outfit to his bag if he wore the last one we’d packed.

Why? Because we want to be able to be spontaneous. We want to be able to meet friends out for a last-minute drink. We want to be able to go for a long walk in the park. We want to be able to stay out a little longer than we expected with the baby.

But that starts by being prepared. Imagine being out and about and wanting to do something spur-of-the-moment — but realizing that you’ve left a few key things at home? You’re probably not staying out — you’re heading home right away, and probably not heading back out.

I always want to be a more spontaneous person. But having a baby’s reminded me: The only way to be truly spontaneous is to be prepared for anything.

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That photo of a stroller — which, I’ll note, doesn’t seem to have anything packed underneath — comes via José Jóvena and Unsplash.