Bali or bust: What it takes to quit your job and embrace a digital nomad lifestyle?

There are two types of people. The ones who daydream about jacking in the day job and heading to Bali with a laptop. And the ones who, you know, have actually done it.

While the daydreamers are still in the majority, the have-actually-done-its are catching up fast. According to the data 16.9m people in the US now class themselves as ‘digital nomads’. There may be as many as 35m worldwide - a number that’s up 135% in the last four years.

Digital nomads. Remember them? They’re the young attractive people who’ve coughed up 4.1m Instagram hashtags. As a job description it’s a little hazy, but if you go by their posts, it mostly involves a dream lifestyle of gazing into the middle distance from a beach or bar, possibly a yurt, balancing a laptop in one hand and a cocktail in the other.

Thirty-five million is a big number. But when you look at those pictures you can’t help but think ‘Really? That’s it?’ Because who wouldn’t want to trade in the daily commute for a taste of those caramel sunsets?

Except, it’s not that simple. Behind the promise that anybody with a laptop can go anywhere and do anything is the cold, hard reality that the freedom to work on your own terms comes at a price.

Nobody understands the hustle behind the hashtag better than Ali Gallop (although, let the record show, he hates the term ‘digital nomad’). Ali used to have a steady job at a tech company (it has a social media app and some other stuff - you’d know it) but he walked away to start a creative content agency called There’s This Place. In Bali, of course. But that’s where the clichés ended.

Check out Ali’s video essay below then read on for a little more background about how it all happened and what he’s figured out along the way.

Meta for Work Explores: Tell us about There’s This Place.

Ali Gallop: Right at the beginning it was about making videos for hotels because I wanted to make videos and I wanted to travel. But as it’s evolved over the last seven years it’s gone from hotels to travel brands, tourist boards, airlines and then into pretty much any brand. So, at this point I guess you’d call us a creative content agency.

MFWE: Why did you quit your steady job to do your own thing? What gave you the confidence to make that decision?

AG: It’s very hard for me to understand where my head was at then. I remember thinking, ‘What am I doing?’ To work at a big tech company was my dream. I didn’t go to university. This was mad for me. But genuinely, these life decisions are based on the premise that I’m going to die. These are the years of my life. If I don’t do it now, then there will come a time when I can’t do it. So, I just had to maximize my life in my thirties.

MFWE: What did you imagine it would be like as you set off for Bali, and what was the reality?

AG: All I’d seen of Bali was Instagram. I thought I was going to be walking up the beach, sipping on a coconut, getting a tan, walking into these hotels and getting work because I knew about mobile video.

This was January 2016, and if you go to Bali in January it rains all day, every day for about three months. I remember getting to Ubud, I went to a co-working space and sat there on my laptop and it just wasn’t anything like I thought it was going to be. No one wanted to give me a chance. They would speak to me about occupancy rates, about hotel stuff. And I’m like, ‘I don’t know what that is.’

I thought I was just going to get opportunities given to me because of what I’d been doing. The reality is that it doesn’t matter what I did before. I had to start understanding their business if I wanted to try and sell them a solution. I must have spoken to 50 hotels and all of them were saying the same thing: ‘No, not right now.’ I didn’t earn any money for six months. Not one penny. That was the reality.

MFWE: What sustained you?

AG: This is the crazy thing: That first six months was the best six months of my life. It was the least money I’ve ever had but it was just so interesting. And I wanted to prove myself. I had this idea when I was leaving and I wanted to prove that right.

MFWE: Have you felt free?

AG: Yes in the sense that I’m free not to worry about 20 days of holiday a year, not to worry about any restrictions in terms of where I have to be and things like that. It’s given me incredible opportunities to feel free in that way. But the worry about having money, the next month or the next year, that doesn’t feel freeing at all. It feels restricting. But that is changing. Now I get a bit of both. I feel free both logistically and financially.