I Still Dream About My Old Job: Digital Nomad Lifestyle Reality
On decompression, phantom belonging, and why escaping takes longer than leaving.
I'm back in the office.
Three days before I quit. Again.
Sitting across from my manager, trying to find the words. Again.
"There's something I need to tell you—"
My throat tightens. The words stick.
I wake up gasping. 4AM. Mexico City.
I quit that job 18 months ago.
But my brain is still trying to leave.
This isn't the first time. And it won't be the last.
I've been having this dream—or versions of it—for over a year now.
Not every night. Just when things get uncertain.
New city. New apartment. New neighborhood to figure out.
The first few days are exciting. New cafes, new streets, new faces.
Then day four hits. The novelty wears off. The uncertainty sets in.
That night, I dream about work.
My body is in Mexico City. My brain is back in that conference room.
Still trying to leave. Or trying to stay. I can't tell anymore.
I wrote about the day I actually quit. The backpack my boss gave me. The note he left. How that moment looked from the outside.
But that story is about the decision.
This one is about what comes after.
The digital nomad lifestyle reality nobody posts about.
The decompression. The loneliness. The phantom belonging.
The part where freedom feels less like liberation and more like freefall.
The Ghost Employee
Leaving looked clean:
- Packed up my desk (two boxes)
- Returned my badge
- Left 14 Slack channels
- Deleted work email from my phone
- Bought a one-way ticket
Done. Right?
Wrong.
Week three in Oaxaca.
I woke up Monday at 7AM in a panic. Late for standup.
Except... there was no standup. I hadn't had a meeting in weeks.
But my body didn't know that. Heart racing. Adrenaline pumping. Monday morning anxiety with nowhere to go.
I checked my phone. No notifications. No urgent emails. No "can we sync?"
Just... silence.
For ten years, Mondays meant something. Now they were just another day.
And somehow, that felt worse.
In the dreams where I'm about to quit again, the conversation is never smooth.
In the dream, I panic. Fumble. Can't explain why I'm leaving.
In reality? My manager actually got it.
"You don't have another job lined up."
"No."
"Good. If you did, you'd just be trading one desk for another."
He gave me his old backpack that day. I wrote about the full story here.
The conversation was calm. Professional. Even supportive.
But my brain, 18 months later, is still rehearsing it as a disaster.
Because maybe I'm not afraid of what actually happened.
Maybe I'm afraid it was too easy.
That leaving should have been harder. That if it was this easy to walk away from ten years, what does that say about those ten years?
For ten years, when someone asked "what do you do?" I had an answer.
Now?
"I'm living the digital nomad lifestyle." (Which means what, exactly?)
"I'm traveling." (So... unemployed?)
"I'm working remotely." (On what? For who?)
The digital nomad lifestyle sounds aspirational until you realize: It's just another way of saying "I don't fit into the old boxes anymore."
In the dreams, maybe I'm not mourning the job.
Maybe I'm mourning the certainty of knowing who I was.
The Loneliness Nobody Talks About
I left 14 Slack channels on my last day.
Two email lists. The "Happy Hour Crew" thread that hadn't been active in months anyway.
Click. Click. Click.
The next morning: silence.
No "good morning team!"
No Sarah's memes.
No "quick sync?"
No complaints about the VP.
I'd spent two years complaining about the noise.
Now I woke up to nothing.
Month four. I visited home for a week.
"Coffee Thursday?" I texted Emma, my college friend.
She replied two days later: "In a meeting until 6, can we do 6:30?"
6:30PM. Rush hour cafe. Loud. Crowded. Everyone exhausted from work.
We talked for 40 minutes. She checked her phone twice.
"I have to get home to put the kids down. But this was great!"
Was it though?
The irony wasn't lost on me:
When I worked: "We should hang out more!"
Reality: Too tired after work. Weekends booked with errands.
Now: I have entire afternoons free.
Reality: That's exactly when they're at work.
I started avoiding peak hours. Lunch rush. Dinner crowds. Weekend brunches.
The noise. The lines. The stressed-out energy of people squeezing life into lunch breaks.
Which means I'm avoiding exactly when normal people socialize.
We're on opposite schedules now. And neither of us can adjust.
In my dreams where we're all still working together? At least we had lunch breaks at the same time.
I tried explaining this to my mom on a video call.
"You have so much freedom now! Isn't it amazing?"
I wanted to say: Freedom just means nothing is decided for you. And you have to decide everything.
Your rhythm. Your routine. Your purpose. Your community.
From scratch.
In a language you barely speak.
In a city where nobody knows your name.
Instead I said: "Yeah, it's great."
This is the digital nomad loneliness nobody warns you about.
Not the "I'm alone in a hostel" kind.
The "I'm surrounded by people but don't belong anywhere" kind.
Work wasn't just income. It was:
- Built-in social structure
- Daily rhythm
- Sense of belonging
- Answer to "what's your purpose?"
The digital nomad lifestyle trades all of that for "freedom."
But freedom without belonging just feels like floating.
I didn't escape "just a job."
I escaped an entire life operating system.
And nobody warned me that rebuilding takes years, not months.
The Pattern
Month six, Oaxaca. Moved to a new apartment. The dreams came back.
Month eight, Medellín. The backpack my boss gave me finally gave out. Zipper broke while packing for a weekend hike. I wrote about what happened next—how I eventually built the gear I needed for this life.
But before I could build anything, I had to survive this.
The dreams. The uncertainty. The decompression.
Month nine, Medellín. New neighborhood. Dreams intensified.
Month twelve, Mexico City. Changed coworking spaces. Dreams came back.
I started seeing the pattern.
It wasn't about missing work.
It was about uncertainty.
When I worked:
- Every Monday looked the same
- Same desk, same people, same rhythm
- My life was boring, but predictable
Now:
- Every few months, new city
- New apartment, new routine, new faces
- My life is exciting, but uncertain
The dreams? They're my brain reaching for the old certainty.
Even if that certainty was killing me slowly.
The new apartment in Medellín had huge windows. Mountain views. Perfect light for working.
The first three days, I loved it. Explored the neighborhood. Found a good coffee shop. Felt that familiar rush of possibility.
Day four: the novelty wore off.
I finished work at 2PM. Sat on my couch. Opened Netflix. Closed it.
Opened Instagram. Saw friends at a baby shower back home.
That's when the thought came: What if I'm just running away from real life?
2AM. Hostel bathroom floor.
I'd moved from the nice apartment to a hostel to save money. Met nobody yet. Had ten hours before bed and no idea what to do with them.
I called my friend Sarah. 11AM her time, her lunch break.
"Hey! How's Colombia?"
I couldn't do the "everything's amazing" script this time.
"I don't know who I am anymore."
Silence.
"What do you mean?"
"For ten years, I had an answer to 'what do you do?' I was on a team. I had a purpose, even if I hated it.
Now I'm... what? A tourist? A dropout? I have freedom, and I don't know what to do with it."
"Do you want to come back?"
I thought about it. Really thought about it.
"Back to what? The same desk you're still sitting at? The same meetings?"
"So you're not running away from something. You're just... lost."
"Yeah."
Silence.
"You know what?" she said. "We're in the same quarterly planning meeting you left. Same. Exact. Meeting. We've been having it for nine months."
I laughed. Then I cried.
"The dreams where you're about to quit again," she continued, "Maybe you're not afraid of leaving. Maybe you're afraid that leaving didn't fix anything."
That hit hard.
What Nobody Tells You
After that night, I started therapy via Zoom.
Digital nomad mental health is something people don't talk about enough.
We post the sunset photos. We don't post the 2AM bathroom floors.
Yes, even nomads need therapists. Maybe especially nomads.
Because when you're constantly moving, you can't outrun yourself.
The first session, my therapist asked: "Are you running away from something, or toward something?"
I said: "Both."
She said: "That's honest. Let's start there."
Here's what they don't tell you about escaping the template:
The template was boring. Suffocating. But it gave you:
✗ Daily structure
✗ Rhythm
✗ Social connections
✗ Purpose
✗ Certainty
When you leave, you lose all of that.
And you have to rebuild it from scratch.
Nobody warns you about this part.
They show you laptop-on-beach photos.
They don't show you the 2AM bathroom floor moments.
I thought I could quit Friday and be "free" by Monday.
Turns out, decompression takes time.
Like a deep-sea diver can't just shoot to the surface—you can't go from high-pressure life to zero-pressure overnight without consequences.
Your psyche needs time to adjust.
The dreams? That's my brain decompressing. Slowly letting go of the old operating system.
Eighteen months in, I still dream about that office.
But the dreams are changing.
At first: Panic (late for meeting, unprepared, failing)
Now: Observation (I'm just... there. Watching.)
Like visiting a place I used to live.
Month ten, Mexico City.
I joined a coworking space. Not for the wifi—for the familiar faces.
Started going to the same desk. Same time. Building micro-routines in macro-chaos.
Met other people in transition. Some staying a month, others a year. We didn't become best friends.
But we became Tuesday afternoon regulars. That counts for something.
I started small rituals:
- Same cafe Monday mornings
- Same desk at coworking
- Same climbing gym Thursdays
- Video call with my family Sundays
Not because I craved routine. Because I needed anchors. Something to hold onto while everything else shifted.
The template provided structure. I thought I was escaping the structure.
Turns out, I just needed to build my own.
Both Can Be True
Six months ago, I still dreamed about that office every week.
Now? Maybe once a month.
The dreams are still changing.
At first: panic (late, unprepared, failing)
Now: observation (I'm just... there. Watching.)
Like visiting a house you used to live in. You remember the rooms. But you don't live there anymore.
Month eighteen, I moved to a new city again.
The first night: the dream came back.
But this time, when I woke up, I knew what it meant.
Not that I made a mistake.
But that I'm adjusting to something new. Again.
And my brain needs time to catch up. Again.
I don't know if I'll ever fully "leave."
Maybe part of me will always be in that conference room.
But maybe that's not failure. Maybe that's just... memory.
You don't erase ten years. You integrate them.
The difference now:
When I wake up from those dreams, I'm not relieved to be away from that life.
I'm grateful I had it.
And grateful I left it.
Both can be true.
People ask: "Is the digital nomad lifestyle worth it?"
I used to try to answer that.
Now I just say: It's not about worth it.
It's about whether you can handle the trade-offs.
The loneliness for location freedom.
The uncertainty for autonomy.
The belonging for independence.
Some days, the trade feels worth it.
Other days, I wake up from that dream and wonder.
But I keep choosing it. One uncertain day at a time.
These days, I pack the 7706 when I move cities.
26 liters. Light enough for the next beginning. Durable enough for the next uncertainty.
It won't stop the dreams.
But between certainties, between cities, it carries what matters.
If you're thinking about leaving:
The digital nomad life won't fix you. It won't make you less anxious, more confident, or suddenly clear about your purpose.
What it will do: Remove the noise long enough for you to hear yourself.
Sometimes what you hear is scary.
I almost went back that night in Medellín.
But back to what? The same desk? The same meetings? The same Sunday scaries?
I chose forward. Even when forward meant sitting on a hostel bathroom floor at 2AM.
Two years later, I still have hard days.
Days when I wake up from the work dream and feel that familiar disorientation.
Days when the freedom feels less like liberation and more like vertigo.
Days when I scroll through photos of friends' babies and promotions and mortgages and wonder if I'm missing something.
But those days are fewer now.
And they're mine.
I'm learning: Uncertainty isn't something to fix.
It's something to carry.
One dream, one city, one day at a time.
The template promised security. My old life took that deal.
I chose the questions instead of the answers.
Some mornings, I still wake up at 4AM, heart racing from a dream about a meeting that doesn't exist anymore.
And I remind myself:
I'm not late. I'm not unprepared. I'm just adjusting.
And that's okay.
Read Part 1: The Backpack My Boss Gave Me When I Quit to Travel
For people living between certainty and freedom: The 7706 Backpack
