How I failed as a Digital Nomad

Beware the lure of Hong Thong. She’s an evil mistress.

A normal day

It’s 10am on a Wednesday in Chiang Mai, and I’ve just opened my eyes after a long night drinking Hong Thong.
It’s crystal clear I won’t be spending much time out of bed today.
I nudge my partner, who usually wakes up better after a big night. She spends a few mins adjusting to the morning light and takes a drink of water. I make the suggestion that she should get some breakfast from Baan Bakery.
Back to bed I go for another hour…

That’s not how it was supposed to be..

I learned about the digital nomad lifestyle in early 2014 after stumbling on this reddit post. I spent the year consuming everything I could on the subject: Podcasts, books, videos, and forum posts.

In December I pulled the trigger. I had a large amount of savings and was ready to begin my life as a digital nomad.

My days were going to be spent banging out quality work, while I enjoyed low living costs.

Next stop: Chiang Mai, Thailand — the nomad capital.

The Reality

I spent my time in Thailand drinking cheap beer, visiting beautiful temples, and eating amazing food. That’s out of character for me. Back in the 9–5 life I was motivated and productive.

Faced with unlimited time and freedom, I achieved nothing productive.

This went on for 3 months before I packed up and returned to “real life”. Instead of creating something long-term, I vacationed.

What happened?

The key reasons my goal failed:


Andddddd productivity's gone.

I stayed in a popular digital nomad location: The Smith Residence. This place has quality internet, a gym/pool, and friendly staff on the front desk.

It’s an awesome atmosphere, if you’re a traveller looking to meet interesting people. But it’s terrible for productivity.

Not socializing was impossible. After a week in The Smith, you’ll know everyone. Unless you have willpower of steel, you’ll be spending every minute doing something exciting — even if you’re antisocial.

Lesson learned: Stay in a ‘real’ house or apartment instead of a long-term hotel. It’s cheaper and less distracting.

2. Planning and research

I did a lot of planning and research before leaving. I even developed a daily budget, which was surprisingly accurate and effective (my daily limit was $30AUD per day).

My workflow goals were less successful. The initial target was to work 8 hours a day on various projects (50/50 split between my own and clients). Following the colloquial wisdom of digital nomad forums, I attempted to work from cafes.

I had some success after finding a quiet place (if you’re in Chiang Mai check out librarista), but I didn’t have the initial infrastructure. I needed privacy to hold Skype meetings and room to spread out.

It got easier after a while. I can comfortably work for 2–3 hours in a cafe environment now. But the initial difficulty was a key barrier to my success.

This hurdle isn’t rare. It’s a common complaint online that working remotely is difficult at first. I didn’t pay enough attention to the possible issues; instead, I was busy looking at the positives.

Lesson learned: Take note of the common issues when researching and keep your assumptions in check.

3. Commitment

“If you’re serious about becoming a digital nomad, you have to go all in. Don’t think for a second that it’s possible to ‘try it’ — it’s all or nothing.”

I wish I had this advice (and actually listened to it).

I gave myself three months to trial the digital nomad lifestyle. This was my biggest mistake.

That three month trial made the experience feel temporary. My goal was to stay long-term, but the theoretical end date distorted my thinking. It gave me a sense of safety and decreased my drive for success.

Lesson Learned: Get serious and commit 100% of your time and energy to the long-term goal. No trial periods — dive in.

Was It A Waste?

No, it wasn’t a waste. Although the journey didn’t end where I had hoped, it was a valuable experience. I now have a much better chance of success in round two.

Best of luck in your digital nomad journey. I hope you can learn for my mistakes and succeed on the first attempt!