The Power of Staying

Everything changes when you’re allowed to change the expiration date

Once upon a time, I wanted to stay here forever.

For the last 2 years of my life, I’ve been living by the expiration date of whatever city I was in.

Maybe I was the one who set those expiration dates, but they were still there.

I had to be outta [insert city name here] by [insert date here]. And there wasn’t much I could do to change that. I was fresh outta college (AKA broke) and didn’t really understand what being location independent could mean for me. All I saw was an opportunity to work from different places, so I hopped on planes and stuck to whatever “plans” I had made for myself.


I spent a summer in New York City with a hard move out date in the early fall.

I crisscrossed my way from New York to D.C. to North Carolina for four weeks. And then scooched back again to catch a flight out of JFK.

I probably overstayed my welcome in a best friend’s bed in lovely Denver, Colorado for about a month.

From there, it was back to New York City to save face for two days before I hopped on a quick plane to Aruba for a freelance project, only to make sure I made it back to Los Angeles in time for Thanksgiving.

And that’s all before I started Remote Year.

Then the real fun started.


Changing what you call home every month isn’t easy. It’s exhausting, and exhilarating.

You’re not only changing what you call your physical home — a street, an apartment, a bed — you’re getting all that in a totally new country, plus a new language, a new set of a faces, a new culture.

With a one month time limit, you’re comforted and stressed about the amount of time you have to call this new place home. You strive to feel like a local, while still checking off some sort of bucket list you’ve crowd sourced from friends, family, and fellow Remotes.

The option to extend your time in each city was sort of there, but that’s not what the plan was. It was 12 cities over 12 months with 50–70 people. Plus, staying in a city required coordination, money, and thinking ahead of time, all of which Remotes don’t do much of.


And then Remote Year ends.

And you fall into one of three camps:

  1. Gotta Go Back Camp: Returning to your “home” before Remote Year and essentially resuming the life you were previously living.
  2. #DigitalNomad Camp: Continuing to do the darn thing! It’s month 13…and then 14…and soon you’re gonna lose count.
  3. Middle Camp: You have no idea what you want to do or where you want to go. You have some flexibility, so you find a safe base and don’t make plans more than a month out.

I’m in the Middle Camp.

I spent about 2 months traveling around Asia, Australia, and Hawaii after Remote Year. Then I posted up in my childhood bedroom in Palo Alto, California until something happened that forced me to initiate a change.

So I booked a flight to New York.

I came with the intention of staying for about three weeks to see friends and do some work stuff. Then, I’d head back home to California for about a month, spend a month in Colombia, half with friends, half solo, and that was as far as I had planned. I was making loose plans because I didn’t really know what else to do or what I wanted.

I was supposed to fly out of New York 3 days ago.

And then I changed my flight to fly out tomorrow.

And then I changed it so I’d leave 10 days from now.

And now I have a flight exactly one month from now.

Southwest Airlines must really love me right now. 🙃

At the beginning of the month, I was dead set on never living in New York City again. I was annoyed, overwhelmed, and felt out of place. But I did what I’d do on Remote Year: I sucked it up and tried to enjoy the city for all that it had to offer for the limited time I had there.

Then I had a change of heart (okay, maybe a couple) and felt the need to follow a place that was giving me more than I expected. It felt good to be in New York.

Needless to say, my intention changed.

I went from viewing New York City as something that felt like an obligatory three week trip to do the things, to seeing it as an experiment and an opportunity to follow whatever was making me happy. I started trusting my intuition, rather than just going and going until the expiration and accepting the end of something, whether I wanted it to end or not.

I was choosing to stay somewhere based on my intuition. That’s not something I’ve had to do a lot recently.

Remote Year takes you out of your comfort zones in a lot of ways. But what it doesn’t require you to do is make an active choice in where you want to spend your life. They do that work for you.

Then, Remote Year ends and you’re left with the reigns.

Depending on what “camp” you fall in, you get some control over where you’re going to go next. Who you’re going to surround yourself with. How often you’ll be there.

Based on me being in the “Middle Camp,” I now see being location independent (or being a #digitalnomad) more about trusting my intuition regarding where I should be, and less about seeing more countries, living cheaply in foreign countries, and taking my laptop to the pool.

I want to go where it feels good. Like I said in a recent post, “good” means a home that has:

people who are hard to say goodbye to, places that feel like home immediately, and experiences that soon become seared into my memory.

Finishing Remote Year with no real plan is scary AF. But then it’s empowering.

You realize that you can run in any direction you choose.

Sometimes you just need to choose what seems like the least attractive direction first and see how it feels.

Then, you go from there.

Trust your intuition. Follow your gut. Go where the good vibes are.

You stay, you leave, you do whatever you want. But you realize that there are no rules and you can follow what you choose to follow. It’s pretty damn freeing, actually.