How to Be a Digital Nomad? I Stopped Waiting for the Perfect Plan
On mistaking preparation for courage, the plan that became procrastination, and learning to trust yourself by accident.
Sunday, 8:47 PM.
Closed my laptop. Opened it again to check Slack.
Nothing urgent.
Closed it again.
Monday's meetings already loaded. Friday's deadline circled.
I wasn't unhappy. Just... somewhere I couldn't name yet.
That's when I started doing something I couldn't explain.
The Thing I Did Instead of Leaving
Every few weeks after work, I'd take the Q70 bus to LaGuardia.
Not to fly. Just to watch the departures board.
Mexico City 8:45 PM
Buenos Aires 10:20 PM
Lisbon 11:55 PM
I'd sit there for an hour. Then take the bus back home in traffic.
My roommate finally asked: "Why don't you just book a vacation?"
"I don't want two weeks," I said. "I want to leave."
Leave what?
I couldn't explain. I just knew: sitting in that airport felt more real than sitting at my desk.
I Thought Planning Would Make Me Brave
I spent six months researching.
Visa requirements. Cost of living spreadsheets. "Best cities for digital nomads" listicles.
Seventeen browser tabs open. A Notion board titled "The Plan."
I was reading "how to be a digital nomad" guides like they were instruction manuals. Treating other people's experiences like formulas I could copy.
But no departure date.
I told myself: I'm being responsible. Thorough.
What I was actually doing: building a plan perfect enough that I wouldn't have to feel afraid.
The goalposts kept moving.
First: "I need three months of savings."
Then: "What if I need a year?"
First: "I'll go to Mexico City."
Then: "Maybe I should research five backup cities first."
I thought I was preparing to leave.
I was building a more sophisticated way to stay.
The Plan Became the Problem
Month four of research, I caught myself reading a 47-page guide on "How to Choose the Perfect First Destination."
I wasn't looking for information.
I was looking for permission to not be afraid. To be certain.
But that permission didn't exist.
No amount of research was going to make leaving feel safe.
I Left Anyway
I wrote my resignation on a Sunday night.
Sent it Monday at 9 AM before I could think about it.
My boss called me into his office that afternoon.
"You don't have another job lined up."
"No."
Long pause.
"Good," he said. "If you did, you'd just be trading one desk for another."
Two weeks later, my last day, he gave me his old backpack. Worn. Faded. A patch from Torres del Paine.
"This was supposed to go to Chile twelve years ago."
Inside, a note:
"Don't come back when it gets hard. That's when everyone comes back."
I didn't feel ready.
I didn't feel brave.
I just felt: I can't do six more months of research.
My Body Didn't Get the Memo
First morning after I quit, I woke up at 6 AM.
Old habit.
Then remembered: I don't have to be anywhere.
I cried. Not sad. Relief.
Week three, Oaxaca.
Woke up at 7 AM, heart racing—late for standup.
Except there was no standup. Hadn't been one for weeks.
My body didn't know that yet. Monday morning panic with nowhere to go.
I checked my phone. No notifications. No "can we sync?"
Just silence.
The decompression took longer than I expected.
My brain kept reaching for the old metrics.
"Am I productive enough?"
"Am I on track?"
But those were questions from a life I wasn't living anymore.
I Didn't Figure It Out—I Stumbled Into It
Week two, I tried three coworking spaces. Two felt wrong. One felt right. Couldn't explain why.
Week six, I needed to move my body. Closest option: a climbing gym.
I didn't go to "build community." I went because I needed to not be sitting.
Met two people. Became Tuesday regulars.
Week eight, I stopped booking Airbnbs with "good natural light for photos."
Started booking for "desk that doesn't wreck my back."
None of this was planned.
I was just... responding. Adjusting. Trying again.
And slowly realizing: I was handling it.
Month Nine: Still Not Sure
Medellín. 2 AM. Hostel bathroom floor.
"What if I'm just running away?"
I called my friend Sarah.
"I don't know what I'm doing."
Silence.
"Do you want to come back?"
I thought about it.
"Back to what? Your desk?"
"So you're not running away. You're just lost."
"Yeah."
"We're in the same quarterly planning meeting you left," she said. "Same meeting. Nine months later."
The next morning, I didn't book a flight home.
I just kept going.
The Thing That Broke
Month eight, weekend hike outside Medellín.
Friday afternoon, packing for an overnight trail.
The backpack my boss gave me—main zipper gave out. Completely.
Standing there, I realized:
I'd been using borrowed gear the same way I'd been using borrowed confidence.
"Good enough to start" got me out the door.
But eight months in, I finally knew what I actually needed.
Not from a blog post. From eight months of using and breaking and adjusting.
Laptop wrapped in a hoodie → learning that doesn't work when you're moving cities every few weeks.
Week-to-week repacking → needing something that works Tuesday and Saturday without switching bags.
I wasn't looking for the smallest pack or the most features.
I needed something that wouldn't make me choose.
City or forest. Work or weekend.
Something that tolerated the in-between.
That's what became the 7706.
26 liters. Waterproof. Durable enough for both.
Most days, half empty. On purpose.
The extra space isn't for filling. It's for not having to decide in advance what kind of day I'm allowed to have.
What I Didn't Expect
The confidence didn't come from planning.
It came from the moments I had no plan and handled it anyway.
Wifi cutting out mid-call → found another cafe.
Airbnb falling through → found another place same day.
Getting lost → figured it out.
Not dramatic moments. Small ones.
Each time: "Oh. I can handle this."
What Planning Actually Did
Planning didn't make me ready.
It gave me something to do while I waited for courage that was never coming.
The courage didn't arrive.
I just ran out of reasons to wait.
And then—in the actual stumbling, the actual "I have no idea but I'll try this"—
That's when I started trusting myself.
Not because I proved I was prepared.
Because I kept moving even when I wasn't.
If You're Still Reading Digital Nomad Guides
This isn't a digital nomad guide. It's what happened when I stopped following them.
I'm not saying don't plan.
I'm saying: if you've been planning for months and still haven't moved—
Maybe the plan isn't the issue.
I thought if I researched enough, I could eliminate the uncertainty.
But you can't plan your way to certain.
You can only move your way to capable.
Two Years Later
People ask: "How did you know you were ready?"
I didn't.
I just knew I was done waiting to feel ready.
The plan I was building—it wasn't ever going to be enough.
Not because I didn't plan well enough.
Because I was treating preparation like it could replace action.
It can't.
For people who start before they're ready: The 7706 Lightweight Backpack
Part of the Escape Life Template series:
The Backpack My Boss Gave Me When I Quit | I Still Dream About My Old Job | When Borrowed Capability Becomes Your Own
