You'll never "find time" to rest.

My wife and I just got back from two weeks in Tokyo.

It’s the third time we've been, but the city is so massive that you could go a hundred times and still find completely new neighborhoods. On this trip, we spent most of our time exploring the small stuff. Little alleyways in Shinjuku. Tiny ramen shops with six seats. Random buildings in Shimo-Kitazawa, where we'd just walk up the stairs and see what was on each floor.

Tokyo has this thing where the best places are almost always hidden. And you’ll never find them unless you're willing to just wander, explore, and get lost.

That's kind of how this whole trip went. We had no real plan at all. We just walked around, tried things, and let ourselves end up wherever the night took us.

And somewhere in the middle of it, I realized I wasn’t thinking about work (or my business) at all.

Why I almost didn't go

I almost canceled this trip three times.

Not because anything was actually wrong. But because I kept telling myself I didn't have time. Too much work. Too many things that needed my attention. Maybe I’d go in a few months when things slowed down.

But things never slow down. There's always another project, another launch, and another thing that feels urgent.

I'd been doing this for months. Telling myself I'd take real time off after I finished this thing or hit that milestone. But the milestone kept moving. And new milestones made their way onto my calendar before time off did.

Finally, Jennifer just booked the flights, put it on the calendar, and made the trip real.

If she hadn't done that, I'd still be telling myself I'd go "soon."

What I was afraid would happen

Before we left, I automated everything that I could. I set up my newsletters in advance, put up an auto-responder, and scheduled all my social media content.

But I was still anxious.

We were at dinner on the second night at this little izakaya in Shibuya, and I'm reaching for my phone when Jennifer notices.

"You're doing it again," she says.

I put the phone away, but the urge doesn't go anywhere.

This went on for the first three or four days of our trip. Part of my brain was running through everything that could be going wrong back home.

When something shifted

By the end of the first week, we found ourselves in Shimo-Kitazawa, exploring a random building.

We'd been walking around for a couple of hours, just going into shops, when Jennifer spotted an interesting building that we decided to explore. We start going up the stairs, floor by floor. Vintage clothing store on one floor. A cafe on another.

On the fourth floor, we open a door, and there's just this Coca-Cola machine and nothing else. I notice a little handle on it, so I reach out, turn it, and find a jazz bar inside. It’s small, maybe eight people inside, with a band playing.

We sit down and just stay there, listening to the music for two or three hours. Not talking much. Just being there.

As we sat there, I realized something. I hadn't thought about work since we left the hotel that morning. My anxiety had loosened up, and I was no longer fighting the urge to look at my phone.

For the first time in months, I was just there.

My friend Amanda Goetz writes about this in her new book called "Toxic Grit." I got a chance to read it before it’s out (October 21st), and she talks about our different characters — the CEO, the Explorer, the Partner, etc. — and how we get so stuck playing one character that we almost forget the others exist.

Right before we left for Tokyo, Amanda taught a workshop in my community to explain this concept, so the idea was fresh in my mind.

I realized that this was exactly what I'd been doing before this Tokyo trip. My CEO character had been running the show for months. Maybe years. And sitting in that jazz bar, I realized I'd forgotten I have an Explorer in me who likes wandering through random buildings, a Partner in me who can be fully present with my wife, and a Creative in me who can sit somewhere for hours and just listen to music.

And something really interesting happened: When those other characters finally got some space, my brain started working better. Ideas started showing up, and I don’t mean the forced ideas where you sit down and try to think of something to write about. Just thoughts that pop up naturally.

I'd been struggling with this for two months prior to the trip. Every time I sat down to write, it felt like searching for something to say and coming up empty.

But in Tokyo, ideas started showing up. My brain finally had space to think, 6,736 miles from my desk in New York.

What actually happened while I was gone

When we got back from Japan, I opened up my dashboard to see how the business was doing after two weeks of relatively low effort.

Revenue was up seven percent. Every newsletter went out on time without any emergencies. My social posts all performed fine. And some emails needed responses, but nothing super urgent.

All that anxiety about what would happen if I stepped away? It turns out that none of it was real.

And here's what really got me. When I sat down to write on my first day back to work, the ideas flowed effortlessly. I wrote three newsletters in four days without forcing anything.

The two weeks I spent not working probably did more for my business than the two months before that, when I was constantly in CEO mode, never letting my other characters come out to play.

The lesson I should have learned years ago

You'll never "find the time" to rest.

I've been telling myself for years that I'll take a real break when things slow down, or I finish some project, or hit some arbitrary revenue number.

But things don't slow down, projects keep stacking, and the numbers get bigger.

So now I’m trying to schedule rest the same way I schedule work. I’m putting it on my calendar weeks and months in advance, and I’m going to treat the breaks as non-negotiable. Meetings that can’t be moved.

Next month, I'm taking another week off. It's already on the calendar. I know things won’t be “settled down” by then. But I scheduled a trip with Jennifer, and we’re heading to Austin to see some good people and enjoy some Hill Country barbecue.

And I know that if I’d waited to find the right time, I never would have found it.

The bottom line

I'm writing this from my desk in New York, but part of me is still back in that jazz bar in Shimo-Kitazawa.

Our trip to Tokyo reminded me that I'm not just my CEO character. I'm also the Explorer who wanders through foreign countries. The Partner who can be present with my wife. The Creative who can sit and listen to music for hours without thinking about what's next.

If you're waiting for the perfect time to take a break, you may be waiting forever, because the work is never done. You’ll never “find time” to rest. So you have to make it.

So here's my question for you this week: When are you going to take your next real break?

Put it on the calendar this week. Treat it like a meeting you can't miss. Plan around it. And for heaven’s sake, get some extra stuff done ahead of time so you can actually enjoy it. Because, as Jennifer likes to remind me, spending time looking at your laptop from a foreign country doesn’t count.

Reply and tell me about your choice. Where will you go, and what will you do to give your other characters a chance to come out and play?

While I can’t reply to everyone, I do read every response.

That's all for this week.

See you next Saturday.

P.S. I was introduced to the concept of having different characters within us from my friend Amanda Goetz. Her new book explores how we forget some of our characters exist when one character takes over, and how to make space for our whole cast of characters. If you want to dive into this topic for yourself (or if you need some inspiration deciding what a proper break should look like for you), Toxic Grit comes out October 21st, and you can pre-order it here.