What To Leave

I’ve been experimenting again with cutting out digital distractions.
I’ve been down this road before. It’s not easy to maintain.

And really, I think the deeper question underneath it all is this:

What do we leave?

What do we leave in?
What do we leave out?
What do we leave behind?

Take my long drive on Thursday as an example.

I drove a little over 750 miles. Left around 7:30 in the morning and arrived around 7:15 that evening. Overall, it was actually a beautiful drive. A couple mildly harrowing highway moments, but nothing too dramatic.

Since becoming FIRE — and especially after the pandemic — I’ve started taking several long road trips every year. One thing I’ve learned is that highway driving is not nearly as relaxing or safe as people pretend it is. But this trip was mostly smooth and reflective.

And it got me thinking about leaving.

First, I left my late fall-to-early spring residence.

I’m currently making my way back toward my permanent late spring-to-early fall home. And honestly? Leaving this place was harder emotionally than I expected.

This is the location where I’ve been experimenting with what I call my “Back on Campus Lifestyle.” And I’ve loved it.

It’s simple, fun, beautiful.
Not perfect, but deeply enjoyable.

And, I realized I was genuinely going to miss it.

Second, I left podcasts out of the drive.

Normally on long trips I use podcasts to “eat the time.” I’ll work through a backlog of episodes waiting in my feed and basically fill a lot of the empty moments with input.

But this time I decided not to.

No podcasts or endless information streams.
Just me and my thoughts.

What was that like?

Honestly, I loved it.

My mind raced all over the place. It whirred and spiraled and revisited things repeatedly without necessarily arriving at profound conclusions. I was trying to think through several major “next step” questions related to this whole Highway to YEAH journey.

But mostly? I just swirled.

Still, there was something good about letting my thoughts have room to breathe.

Third, I left an unhoused man with a large coffee.

Before leaving town, I got up early, posted my daily blog article, and went on one of my normal walks.

For the past week, I had noticed a man in a wheelchair wandering around the neighborhood. Sleeping in the park. Clearly struggling. Clearly with nowhere stable to go.

This city actually has far fewer unhoused people approaching strangers for help than many places I’ve lived or visited, but that morning he rolled toward me and asked if I had a couple dollars.

I told him sorry, no, I didn’t. I don’t carry cash on these walks. I use my phone if I buy something.

As I walked away, though, I realized something:
If someone asks me for money, I’d generally rather offer food or something practical instead.

As I was finishing the walk, I used my phone and ordered myself a coffee through the app. So when I walked out carrying my drink… who do I immediately run into again?

Him.

So I asked if he wanted something from the coffee shop.

He immediately said:
“Yes, I’ll have a coffee… and I need to use the restroom.”

The barista clearly recognized him. I got the sense this had happened before. They were being polite to me, but also not thrilled about the situation.

And I won’t lie. I didn’t like the experience, either.

Sure, part of me feels compassion in these situations.

But the larger part of me thought:
“Thank goodness I won’t be encountering this guy again every morning for the next few months since I’m leaving town.”

Awkward thought? Maybe, but true.

And I think these situations are more emotionally complicated than people admit. Compassion, boundaries, guilt, responsibility, discomfort — it all gets mixed together.

Fourth, I left the good ones in.

“The good ones” being songs from the 27-song set I’ve been rehearsing daily in preparation for open mics and possibly some booked performances this summer.

My “music coach” keeps encouraging to get a tight 15-song set, telling me:
“Just play the best songs.”

Which brings me to Keith Richards.

I’ve always loved hearing him talk about songwriting. He famously says he can’t pick favorites because all the songs are “his little babies.”

I totally get that.

But I recently watched an old interview where he described how he and/or The Rolling Stones decided what songs make it on an album. Instead of asking:
“What should we cut?”
they ask:
“What absolutely must stay?”

So, applying this idea during the drive, I listened to my scratch demos on shuffle, three songs at a time, asking:
“Which one of these absolutely has to stay?”

And the answers came easily.

I now know the core 9 songs that absolutely belong in the set.

The rest can rotate around them.

And that felt relieving. Much easier than trying to “eliminate” songs I still care about.

There are also a few other things I’ve been thinking about leaving behind lately, even on the trip, but I didn’t.

Some have to do with how I show up and experience the world.

Some have to do with the guardrails I want to create around my new One Hit Wonder goal of reaching and maintaining my target weight for the next year.

But those are discussions for another day.

Because the truth is we are all constantly leaving things.

Places, versions of ourselves, identities, rhythms, and distractions, to name a few.

Sometimes intentionally.
Sometimes accidentally.

So my question for you is:

What do you want to leave?

What to leave in?

What to leave out?

When to do the Hokey Pokey and shake it all about?

That’s right.

That may be a ridiculous ending to this article. But that is part of the point, too.

This blog is not meant to offer somber, overly earnest, stoic, crap advice you hear all the time…

The Highway to YEAH is not supposed to become another grim self-improvement project filled with stoicism, optimization, and joyless discipline.

It’s about building a life that actually feels alive.

Getting out onto the Highway to Yeah is about building a joyful, creative, authentic lifestyle.