Author: Dan Oshinsky

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Don’t Overthink This.

a brown chair, a white table, a simple fern, up against a white wall.

90% of my advice to clients is boils down to three words:

“Don’t overthink this.”

People get into their heads when it comes to tweaking their strategy or tactics. They get caught up thinking that there are a series of three-dimensional chess moves that will fix what’s wrong.

But usually, the fixes are simpler than that: Your positioning is unclear. You’re not targeting the right audience. You’re doing too many things at once.

My job is often to tell teams: You’re overthinking things! Let’s simplify and get back to the core of what you do well.

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That’s not the fanciest desk set up in the world, but it’d work just fine? Why? It’s so darn simple. Thanks to Unsplash for the photo.

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Stay Right Here.

As silver DeLorean, like the one seen in “Back to the Future,” as photographed from behind.

I keep thinking about this line from poet Andrea Gibson in their book, “You Better Be Lightning”:

Regret is a time machine to the past
Worry is a time machine to the future

I’m as guilty as any of having my head somewhere else. Sometimes that means thinking about mistakes I’ve made or things I could have done better. Sometimes that means spending too much time thinking about all the stuff I have to do in the weeks and months ahead.

Gibson’s lines are a reminder: Wherever your feet are, keep your head there. There’s work to do right here, right now. That’s where your mind needs to be, too.

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Feels like the only appropriate photo for a post like this is of a DeLorean. That photo comes via Unsplash.

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Enjoy Where You Are.

Lots of white snow — and mountainous peaks behind — at Alta Ski Resort.

We went skiing at Alta today. Alta is a special place. You’re up in the mountains, a 20-minute drive away from anywhere. From the top, you won’t see homes or hotels or any sort of city — just snow and trees and mountains — and the skiing is fantastic.

We rode up one chair with someone from Pittsburgh, and we asked him if he did a lot of skiing back east. “Oh, tons,” he said, before listing off the mountains he’ll ski within a few hours of his home. Some of the mountains he mentioned are tiny, one-chairlift kind of mountains. But he said he loved skiing them just as much as he enjoyed skiing out west.

“Any day I have my ski boots on is a good day,” he said.

It’s such a wonderful sentiment, and it really stuck with me throughout the day. I grew up skiing tiny mountains in Maryland and Pennsylvania, and now I’m lucky to live just minutes from world-class ski resorts. I’m not going to try to convince anyone that the quality of skiing is as good at Whitetail as it is at Deer Valley — it isn’t.

But that doesn’t mean you can’t enjoy those mountains. I’ve had amazing days skiing at tiny resorts. 

The conversation on the chairlift today was a reminder that no matter what you’re doing, you can make the most of the experience. It’s up to you to stay in the moment and to find the little things that make that experience special.

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I took that photo while riding up the Sugarloaf chair at Alta today. Tough to complain about blue skies and plenty of snow — in April!

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It’s OK to Ask the Question.

A white question mark painted on a faded brick wall.

Something I tell at least one client every week: There are no dumb questions.

I’ve been helping clients since 2019, and working in my field since 2012. It feels like I’ve heard it all — and yet, every week, someone on a Zoom call starts off with “I know this is a dumb question…” and then asks something really interesting or something that I’ve never been asked before.

You don’t need to be an expert in everything. You don’t need to have all the answers.

But don’t underestimate your instincts. Give yourself a little credit — you know more than you think.

Just ask the question.

I promise — it’s a lot smarter than you realize.

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That photo of a question mark against a brick wall — taken along Smith Street in an English village called Cheadle — comes via photographer Matt Walsh and Unsplash.

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Start Writing. Keep Writing.

I launched my consulting business in 2019, and in the years since, I’ve never sent out a cold email request to a potential client. My website mentions my consulting practice, but honestly, it’s a little bit hidden. Yes, I’ve got a newsletter and a welcome series, but I barely promote my consulting work at all. (I’ve had clients tell me they were on my list for months before realizing that they could hire me.)

And yet, I’m fully booked for the next six months.

So what’s the secret?

I just keep writing.

For the first few years, I shared what I was learning in Not a Newsletter, a public Google Doc I published. Later, I moved everything over to WordPress and started publishing every week.

But just through the act of publishing — at this point, hundreds of thousands of words about newsletters — I keep proving to my audience that I know what I’m talking about. (At least a little bit. I’m still learning new stuff about this space every month!)

If you’re in the services business and you’re not sharing what you learn — on your blog, in your newsletter, regularly via channels like LinkedIn — forget about those cold email strategies that promise to bring in new clients.

Just start writing.

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Speaking of longtime writing projects: I’ve been writing here on danoshinsky.com since 2008. That’s a screenshot of my website back in summer 2010 — I think dropping the tagline about my mom was probably a good move!

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Anything Can Happen.

This first week of March Madness is always one of my favorite weeks of the year. I haven’t watched a minute of most of the teams in tournament — truthfully, I had to Google where High Point University was before picking them to upset Purdue in the first round — but I’m excited to watch the games anyway.

Why? Because this is a week when anything can happen.

I’ve seen tiny schools beat brand name universities. I’ve seen buzzer beaters, improbable comebacks, and heartbreaking collapses. I’ve seen ordinary kids suddenly become legends. (Finding out that Ali Farokhmanesh was an assistant coach on 12-seed Colorado State immediately sent me to YouTube to watch a shot he hit 15 years ago.)

I have no idea what will happen this week, but I know that anything can happen, and there aren’t many days on the calendar when it feels like that’s true.

I’ll be tuned in, ready for whatever, and I can’t wait.

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That photo of two basketballs on a rack comes via Unsplash and Todd Greene.

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You Ain’t Hamlet.

This interview with Jason Alexander, of “Seinfeld” fame, popped up in my feed the other day, and I think it’s worth watching in full. In it, he says:

I went to Boston University as a theater major, and because William Shatner was my muse, I wanted a dramatic career. I really thought I was going to play some of the great classical roles and be a dramatic actor. Sure, I hadn’t done much comedy. I’d done some musicals, so there was that, but I hadn’t done much comedy. And the summer second semester of my sophomore year, I had a professor named James Spruill at Boston. He was the only black member of the faculty. He was a guy who had come up in the ‘60s with street theater — theater is to change the minds of the masses, affect change. He brought me into his office for my my semester consultation, and he had this great basso kind of James Earl Jones voice, and he sat back, and he just kind of nodded his head and looked at me for a minute. He went, “I know that your heart and soul is Hamlet, and you would be a profound Hamlet. You will never play Hamlet, so you best get good at Falstaff.”

And he basically said, look, look in the mirror. You are 5’6’’. You are 20 to 25 pounds overweight, and you are losing your hair. You have a large performing persona. If you want a a commercially successful career, you’re going to be a comedian, and you’re not embracing it, you’re not looking at it, you’re not doing it.

Had he not said to me, “You ain’t Hamlet, man,” I would have finished that school and gone into the professional world thinking, ”Here’s Jason Alexander and the Iceman cometh. It’s what everybody is waiting for.”

And I would have been wrong.

It’s such a wonderful reminder: We all need someone in our lives who’ll be truly honest with us. Sometimes, we need that person to lift us up. Sometimes, we need them to keep on the right path. But all we need those voices we can trust, and if you find someone who can do that, you owe it to yourself to listen to them. They’ve got something worth hearing, even if it’s not what you want to hear at that moment.

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It’s OK to Do Nothing.

2025’s been a lot. There’s been travel (Denmark, New York, Florida), multiple visitors staying with us, and a lot of new projects. I’ve been saying no to just about every new opportunity that comes across my desk — but that’s because I’m already fully booked.

And this past weekend, I hit the point where I just couldn’t tackle another thing. I usually do a little work on weekends: Reply to emails, maybe do some writing, definitely some prep for the week.

I didn’t do any of that.

Instead, I barely opened my laptop.

We went skiing on Saturday. We had friends over on Saturday night and Sunday. I cooked a few meals. We spent a lot of time on the playground with our son. I even went for a bike ride — it was warm enough to actually bike outside in shorts here! (It snowed 24 hours later.)

Look, 48 hours of nothing isn’t some magic cure. I’ve still got plenty to do this week, and I need to continue to work on saying yes to the stuff I’m most excited about.

But everyone needs breaks. Everyone needs to step away for a few days.

It can be weirdly hard to take time off. I need to get better at it — in the long run, I can only do my best work if I’m making space for the stuff outside it.

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Sally and I went skiing at Park City on Saturday. We stopped for a while to eat lunch outside, and that’s when I took that photo. It was a gorgeous day that felt like spring skiing — blue skies and temperatures in the 50s!

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Be Excellent, Not Perfect.

My Missouri Tigers had a huge win this past week in men’s basketball, and I went back to watch the highlight package that the basketball team put together. Mizzou’s coach, Dennis Gates, has a bunch of different sayings he uses. (For instance, his eight core values for success: “Friendship, love, accountability, trust, discipline, unselfishness, enthusiasm, and toughness.”)

But watching the movie, I heard one line I’d never heard before.

Gates: Communication has to be excellent, OK? It has to be excellent. It don’t have to be perfect, it has to be what?

Team: Excellent!

I’ve written a lot — like, so many different things — about perfection. But I love the idea of reframing the concept. For most of us, the goal shouldn’t be around perfection. The goal should be to put in the work, to enjoy doing the work, and to try to do something great.

Aim for perfection and you’ll usually fall short. Aim for excellence and you have a chance to do excellent work along the way.

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It Might Not Happen Today.

A funny thing about being a parent, especially a parent of a young child in daycare, is that your entire schedule can change in a moment.

One phone call from daycare — “Hey, your son has a runny nose and a weird cough, so I think you need to pick him up” — and suddenly, there goes your week. Calls get canceled, work gets postponed. That big project you wanted to do today? It’s definitely not happening today anymore! (And maybe not next week, either.)

All of this has made me weirdly grateful for the days when things go right. There are days when things actually work out, where the work gets done and your child comes home completely healthy. Those are great days, even if this winter, it feels like there are far fewer of them than before.

Still: The mindset shift is important. I used to get mad when the work didn’t get done. Now I know it’s part of being a parent — and it’s my job to adjust how I work, adjust what I work on, and adjust my mindset. I’m a dad and a business owner. This is just how things work now, and that’s part of what I signed up for.

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That’s a photo of my son carrying a reusable bag upstairs. Why? Who knows, but parenting means a lot of unexpected moments — like my son deciding that a bag is far more fun to play with than the toys we got him.

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