Getting Comfortable Being Uncomfortable

Getting Comfortable Being Uncomfortable

For the second year in a row, I took a week off work with one goal: to get uncomfortable.

Last year that meant flying to Alaska to go king salmon fishing. This year it meant riding a BMW R 1300 GS along California’s Highway 1 and through Northern California.

If you know me very well, you’ll know both of those trips are way outside my comfort zone.

I’m not a fisherman. I don’t eat fish. I get seasick. Spending a week in remote Alaska without cell service didn’t sound like much of a vacation.

Motorcycles are still relatively new to me, and riding solo for five days through places I’d never been before was a little intimidating.

That’s exactly why I wanted to do it.

Over the last few months, (years) work has been incredibly busy. As my responsibilities increased, I could feel myself getting more and more burned out. When I’m tired, I become short. I lose what little patience I have, and I slowly turn into someone I’m not proud of.

I needed a reset.

The problem was, I didn’t have a plan.

So I did what any self-respecting guy without a vacation plan would do…

I asked ChatGPT.

My prompt was simple:

Plan a 5-day motorcycle adventure leaving from San Francisco through Northern California focused on the best riding roads, great scenery, places for awesome photography, and unique overnight stays. Prioritize Highway 1 and a return to San Francisco. Keep daily mileage reasonable, avoid unnecessary interstate riding, and leave plenty of time for photos, coffee, and exploring. I will be riding a BMW R 1300 GS, so keep fuel range in mind. I am not very experienced, so nothing too crazy.

What it gave me was honestly incredible.

It mapped out a five-day route through the Northern California coast, the redwoods, the Lost Coast, and wine country. It suggested scenic overlooks, coffee stops, restaurants, fuel stops, and unique places to stay each night.

I rented a BMW R 1300 GS from EagleRider in San Francisco and used Airbnb to find everything from an old barn in Elk to a vintage Airstream overlooking the coast. I didn’t own the bike. I had never ridden these roads. I didn’t spend months planning the trip. Yet somehow, everything came together.

The motorcycle was everything I hoped it would be. It handled long highway stretches, tight mountain roads, and rough backroads with ease. As someone who’s still pretty new to riding, the technology gave me confidence without making me complacent. More than once I rounded a corner to find wet pavement that unexpectedly turned to gravel, and I have no doubt the rider aids earned their keep. There were a few moments the bike was probably smarter than I was, and thankfully it didn’t let me find out the hard way.

Technology made planning the trip easier than ever. Ironically, the best part of the trip was getting away from it.

Then the trip started.

Five days of winding roads.

Towering redwoods.

Miles of rugged coastline.

Black sand beaches.

Small towns.

Coffee shops.

More cows than I expected.

Thousands of photos.

And almost no notifications.

Somewhere between the Pacific Coast Highway and the redwoods, my brain finally slowed down.

For a while, work disappeared.

There weren’t any emails to answer or meetings to think about. Riding demanded all of my attention. I was looking through corners, watching for wildlife, keeping an eye on the weather, and figuring out where the next gas station was. The only thing that mattered was where I was at that exact moment.

That alone made the trip worth it.

Unplugging clears the noise.

I didn’t realize how mentally exhausted I had become until I got away. It took a couple hundred miles, but eventually the constant noise disappeared. My mind finally had room to breathe again.

Being uncomfortable forces you to be present.

Almost everything about this trip stretched me. Solo travel. Long days on the bike. Roads I’d never ridden. Places I’d never been.

There wasn’t room to think about work because the ride demanded my full attention. I can’t remember the last time I was that present.

Inspiration comes from changing your surroundings.

It’s easy to get stuck in the same routines, seeing the same things every day.

Every day of this trip was different.

One morning I was riding beneath some of the tallest trees on earth. That afternoon I was following the Pacific Ocean with nothing but cliffs and waves beside me. Another night I stayed in a vintage Airstream overlooking the coast.

But my favorite stop wasn’t the Airstream.

It was the old barn in Elk.

After one of the best nights of sleep I’d had in months, I stepped out the front door with a cup of coffee in my hand. Standing just a few feet away was a family of deer, completely unfazed that I was there. No crowds. No schedule. No notifications. Just a quiet moment I’ll probably remember longer than any famous viewpoint or scenic overlook.

You can’t plan moments like that.

You just have to put yourself in a position to experience them.

This trip reminded me that adventure doesn’t have to mean climbing Mount Everest or flying halfway around the world.

Sometimes it just means saying yes to something that makes you a little uncomfortable.

I’m going to make this an annual tradition.

Not because I enjoy being uncomfortable, but because that’s usually where the best experiences seem to happen. Every year, I want to find an adventure that gets me out of my routine, takes me somewhere inspiring, and reminds me to slow down.

Working in a creative role, I’ve realized inspiration doesn’t come from sitting in the same meetings or looking at the same four walls every day. It comes from seeing new places, meeting new people, and giving yourself permission to slow down once in a while.

I have no idea where next year’s adventure will take me.

But I know my Leica will be coming with me.

I hope you enjoyed following along as much as I enjoyed living it.