Tiny Talk with Scott Dawson

Tiny Talk with Scott Dawson

Time for a closer to home talk with my buddy Scott! He’s a positive guy with a great perspective. He’s also very talented, which you’ll get a glimpse of through these questions. Luckily we get to hang out once a month at a local design meetup, but I’d be thrilled to make that twice a month. Heck, maybe thrice!

You just ran a fast half marathon and won your age group (congrats!). How does being a runner help you in life?

My wife and I started with an “annual challenge” concept — biking around Cayuga Lake, finishing a triathlon, running a half marathon. Pretty quickly, “annual” became perpetual, and we’ve been pushing each other through physical challenges ever since, with running front and center.

Running keeps me feeling young, but the deeper gift comes from racing. When you toe a start line, you’re making a deal with your body — and for the next however-many miles, your mind has to keep winning the argument. You have to ask for a little more, push against the urge to quit, and resist being too hard on yourself when things go sideways. Those are skills that transfer directly to life. There’s a quote I keep coming back to: “Hard choices, easy life. Easy choices, hard life.” Racing has a way of making that concept feel palpable.

Grinding it out at the annual Skunk Cabbage half marathon

Tell me about the reasoning — and maybe the result — of moving your entire website from your personal domain/setup to Substack.

My personal site has always been in flux. In the 2000s, it was a handcrafted HTML affair — family photos, favorite links, odds and ends. It gradually took on more of a storytelling shape in WordPress, with a lot of running content and in-depth how-to guides from my work as a web designer and developer. Then the pandemic hit, and I got tired of babysitting a self-hosted WordPress install, so I rebuilt everything as a static site using Eleventy.

Over the same period, I’d been drifting away from social media — almost fully gone in the last five years. Substack appealed to me as a way to connect with people who actually wanted to read what I had to say. For a while I ran both: weekly dispatches on Substack and longer writing on Eleventy. Then I hit a wall and went quiet on both, partly worn down by the friction of it all.

What finally tipped me to Substack was simple: I love writing there. The editor is a pleasure, and I don’t have to think about any of the other noise that comes with putting something on the open web. So I migrated everything over and haven’t looked back. It lets me focus on the writing — which was the point all along.

A comic from Scott’s wonderful Cartoons! He also completed a 365 project!

What’s the best piece of advice you’ve given your kid(s) that they actually followed?

The biggest one: always advocate for yourself. People will take advantage of you if you let them, and when you’re clear about what you need, things go so much better. I’ve seen both of my kids put that into practice as adults, and it still makes me proud.

I also asked them what they thought of this question — and what came back was a reflection of the work ethic and love of running I’d hoped to pass along (wonder where that came from?). In their words:

  • Work hard even when you don’t want to
  • An object in motion stays in motion
  • Live below your means and practice good money management
  • Follow your passions (both of my kids went into music-related industries)

Hard to argue with any of that.

At the NYSE during a visit to the mothership.

You’ve been working remotely since way before the pandemic. Even wrote a book about it. What are three things that a remote worker (like me!) can do to make their life better?

Despite all the “return to office” noise, there are still a lot of people living and working this way — and I love to keep meeting them. Here are the three things that have made the biggest difference for me:

1. Design your environment intentionally. My home office has always had qualities that keep me productive and sane: natural light, good ergonomics, things on the walls and shelves that make it feel like mine. But the most important feature? A door. Being able to close off the workspace when you’re done is essential to balance.

2. Protect your lunch hour. I block it on my calendar so it doesn’t get scheduled over. That’s not laziness — it’s what keeps the second half of my day productive. In the summer, when my wife Amy isn’t teaching, we walk around the neighborhood after lunch together. That hour is something I genuinely treasure.

3. Take loneliness seriously. It’s something a lot of remote workers quietly deal with and never talk about — I devoted a whole chapter to it in the book. The antidote is a mix of physical outlets (exercise, hiking, acupuncture) and emotional ones (writing, therapy, and getting yourself around other people in your field). Don’t wait until it’s loud to address it.

Finding the wild places like Mount Hood in Oregon

We only live one town apart but Trumansburg and Ithaca feel very different (intentionally). What is something that neither town has, but desperately needs?

A Nordic spa. We’ve driven to Montreal, Ottawa, and Mont-Tremblant to indulge in this tradition, and every time I come home I find myself daydreaming about building one on a remote hillside overlooking Cayuga Lake. It would be an absolute “if you build it, they will come” situation — but would require a consortium of capital to get it off the ground. In the meantime we have a sauna and cold plunge in our backyard, two of our most cherished improvements.

Scott’s Nordic spa-leaning backyard with sauna and cold plunge

The other thing I think about is access. Getting out of this region — and getting into it — is genuinely hard. No high-speed rail, limited flight options. In a way, that inaccessibility is part of what makes it special to live here. But the world is a big place, and it’d be nice to be able to reach more of it without such effort.


Where he lives

Trumansburg, New York

Passion

I’m passionate about music and the arts, especially where they intersect with technology

Cold/hot drink

Medium decaf latte

Third space

Out where the wild things are, right in the middle of nature