Dan Oshinsky | danoshinsky.com

11/05/202311/05/2023

Just Keep Running.

There are a lot of great places to watch the New York City Marathon, but for my money, nothing beats the corner of 59th and 1st.

Runners are coming off the quiet of the bridge and on to 1st Avenue, where crowds gather four or five deep to cheer family, friends, and total strangers on.

It’s also mile 16 of the race. Runners still have 10 miles to go.

And every year, I go to that corner and watch thousands of runners hit mile 16, with so many more miles to go — and they keep going.

And every year I think: It’s amazing what truly determined humans can do.

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I took that photo at 59th and 1st today during the 52nd running of the Marathon.

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.

10/23/2023

Maximize What You Have.

I’ll often talk with newsletter operators who tell me they want to launch another new thing: Another course, another ebook, another product.

But the question I always have to ask is: Have you gotten everything you can out of the stuff that’s already out there?

I’ll see newsletters with great engagement that are missing obvious monetization opportunities, like running ads or affiliate content.

I’ll see operators with a paid membership who aren’t promoting it nearly as much as they could — even though with every new member they get, they’re getting more value out of a thing they’re already working on.

Forget about launching new stuff for a second. Look at what you’re already doing — is there an opportunity there to get more out of the work you’re already doing?

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That’s a random snippet of emails in my inbox at the moment. (I’m not trying to pick on any of these particular newsletter operators!)

10/17/202310/17/2023

Don’t Assume. Prove It.

a no. 2 pencil works through math homework on a white sheet of paper

There are things you know. These are things you’re certain of — you’ve got data, you’ve got proof. These are things that are absolutely true.

And then there are things you think you know.

Assumptions are dangerous. They start out as ideas that your team kicks around, maybe based on something you heard at a conference or something you read online. They’re based on casual conversations or hearsay. With time, those assumptions can easily turn into things you believe. And if you don’t take the time to prove them out, they will quickly turn into universal truths.

These assumptions might be right or wrong — you don’t know yet — but you can’t let them guide your thinking. You can’t let these untruths or half-truths or maybe-truths influence your long-term decision-making process. You can’t confuse them with things that are actually, provably true.

One bad assumption can lead to a whole slew of bad decisions.

So be willing to challenge your assumptions. Prove them out. See what’s actually true and what’s not. Then you can make the best decisions for you, moving forward, with the proof you need.

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That photo of math homework comes via Unsplash and photographer Chris Liverani.

10/07/202310/07/2023

10,000 Tiny Puzzle Pieces.

a stack of hundreds of colorful puzzle pieces

I had a call with a client last week about their newsletter strategy. “I feel like we don’t have a complete picture of what our audience wants,” they told me. “What are we missing?”

I’ll tell you what I told them: Building a strategy is like putting together a 10,000-piece puzzle. Every time you do something — like sending an email, running a survey, or talking to readers — you collect a few more puzzle pieces. But you’ve got to be patient — it takes time to collect enough pieces so you can start to see the full picture.

Your goal is to do something every day that helps you discover a few key pieces of your puzzle.

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That photo of a puzzle comes via Unsplash and Hans-Peter Gauster.

10/04/202310/04/2023

I Figured One Thing Out Today.

I had a moment last night with my newsletter. I wasn’t sure what to do about the intro section — I knew there should be an intro, but I wasn’t sure what I should say. And I felt stupid for not knowing: People pay me every week to help them figure out stuff like this! Why couldn’t I figure it out on my own?

And then I thought about a conversation I’d had with a client earlier in the week. They were feeling a little down, so I gave them a pep talk. It seemed to help.

And I thought: Could that be the intro?

So I wrote it up last night, but didn’t schedule the email. I wanted to read it again this morning.

This morning, it still made sense. It gave the newsletter something it didn’t have before — a bit of life, a bit of personality. It made it sound more like me.

I think I figured this one piece of the puzzle out today. And I know there’s a lot more to figure out.

But just figuring that one thing out made me feel a little lighter — the weight of this one task, however small, has been lifted.

For today, that might be enough.

10/01/202310/01/2023

Apologize, and Move On.

Shit happens when you’re doing the work.

Work doesn’t get done, or doesn’t get done as well as you expect. Mistakes get made.

Don’t dwell on those errors. Own up to your mistake, apologize directly to those that were affected — and then be willing to move on past it.

It happened, and you admitted your error. Don’t let one mistake lead to another.

You’re onto the next.

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Those neon arrows come via Unsplash and photographer Charlota Blunarova.

09/17/202309/17/2023

Be Brave Enough to Ask For Help.

a bright sky over the Sixth & I synagogue in Washington, D.C.

There’s a great story in the New York Times this week about Michele Lowe, a former advertising executive, who now coaches rabbis on their public speaking skills and helps them improve their sermons.

I’ll quote this section directly:

Some of Ms. Lowe’s clients are confidential, concerned to be seen as needing a crutch. At first, Dara Frimmer, a rabbi at Temple Isaiah on Los Angeles’s Westside, was reluctant to share that she had sought help on a sermon.

“There is a fear that rabbis have to be wholly original and brilliant and poised and always have the right words,” Rabbi Frimmer said. But she came to realize that turning to community in a time of need was a profoundly Jewish ideal. “With great pride I wrote at the bottom: ‘Thank you to Michele Lowe.’”

Everyone needs a little help sometimes — even people like rabbis, who spend their careers speaking publicly. Rabbis lead public services and private services. They stand before their congregations at bar and bat mitzvahs and at weddings. They spend time with their congregants during moments of joy and sorrow.

And yet: They still need help! It takes courage to be willing to ask — and to truly listen to the advice being given.

No one has all the answers. Everyone — even the pros — has questions.

Always be willing to ask.

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That’s the outside of Sixth & I, a synagogue in Washington, D.C. The photo was taken by Ted Eytan and is used here thanks to a Creative Commons license.

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.