Digital Nomad in Chiang Mai Rooftop

The key to Running A Business While Traveling The World

Loren Ross

Currently writing this from a rooftop bar in Chiang Mai, Thailand

There is live music in the background

A slight breeze in the air

Wispy clouds jetting out of the tree-covered mountains to my left

This is living

I’m wearing a tank top while it’s 9 degrees ‘back home’

A home I haven’t lived at in over 5 years

It’s Friday at 6:30, I don’t have any super pressing work to do

I’m fighting the urge to start drinking a couple cocktails and give into the moment

Give into the buzz of the atmosphere

I have a profitable business that I’ve been running for nearly 7 years now

I was asked earlier this week how I run a business while traveling the world, and I’m realizing on this rooftop how I do it

Because I’m able to discipline myself in the midst of boundless fun

For many people, travel is a time when you let go

  • You don’t worry about what you’re eating
  • How much you’re exercising
  • How much you’re spending
  • How much you’re meditating / praying / in introspection

Travel is a time to get a break from the chains of routine

If you want to run a business while traveling the world, you’ll need to let go of this

4 Tips for self-discipline – video taken in Franschhoek, just outside of Cape Town, South Africa

Burnout from overwork is well-documented

But there is another type of burnout

A burnout from overdrinking

From overpartying

From having the same shallow conversations with a new face every couple of days

From struggling to learn a new language, and struggling to connect

From feeling like no one really understands you

And the people who do are gone in a couple of days or weeks

Burnout from saying goodbye

From spending your day chasing the next sightseeing spot

The next beautiful beach

The next dopamine hit

That is gone way too fast

Leaving you eventually hopeless

But you were told that this was it

That traveling the world was the dream

That life in an office was a cage

That travel was your ability to fly free

Now you have no cage

You have no chains

You have nothing holding you back

And you’re miserable

There’s no one else to blame, and there’s no one else to look to to expect that they’ll pick up the slack.
This is your game….
The average person existing on the plane of average thinking
We can look to any number of things
‘ohh I would’ve done that, but you know I have this responsibility’
‘Man if it weren’t for ___’
…What happens when those things step out of the way?…
The spotlight is on you
‘You mean I can’t blame you for being in my way?’

Kai Greene – Bodybuilder
And a human who has overcome incredible odds

Kai Greene, pictured on the left

There is a price for freedom, and it’s instability

If you don’t have the discipline to deal with the increased instability, you will burn out

Sure, the burnout is more fun than burning out in an office

No one will feel sorry for you, because you’re living the dream

But it’s burnout nonetheless

How I Do It

I tell people all the time

I’m rarely fully on vacation and rarely fully in work mode

I have found a way to build a regime, to build discipline that I can manage year-round

While I still have periods of sprinting at work, it’s seldom

While I still have periods of completely checking out of work and lounging around, drinking cocktails on the beach, it’s seldom

I’ve found a life that I enjoy

A lifestyle that I don’t need a vacation from

A lifestyle that I can sustain well into my 60’s

Even with this, my business has increased in revenue pretty consistently every year since it started

For anyone trying to travel the world and run a business, finding this balance is the key

You won’t be able to scale businesses as quickly as your friends who are planted in one place

You also won’t be a carefree tourist in the city you live in, either

Video from my recent time in El Nido Palawan. Check out my guide here – might’ve went a bit too deep in the partying and vacation time here 🤣

I’m seldom travelling somewhere

I’m usually living somewhere

Building a routine that is quite similar to the routines I have in other places in the world

Thanks to my girlfriend Gisele, I am forced out of that routine though – which is important

I have absolutely created prisons of my own making in the past

So, ensuring I’m sticking to a routine while also being open to (or forced to) try new things really works for me

I can continue on about the individual tactics that I use

But if you can not figure out that balance for you, then you’ll never make it

In 2026 you don’t have to choose between”Follow your dreams, travel the world” or “grind to be a millionaire” you can do both

BUT you will never be “following your dreams” as much as the 20-something backpacker

And you may not be reaching millionaire status as quickly as your other friends

And maybe that’s the secret

Maybe that makes it something you can do for a lifetime, and not burn out on either lifestyle.

Additional resources

Gonna order another cocktail…