Over a year ago, I got rid of all of my worldly possessions except for two suitcases (one big and one small) and a backpack and set off to live my dream life as a digital nomad. Since then, I’ve traveled to over 20 cities & 16 countries including:

  • Seattle, WA, USA
  • Keflavík, Iceland
  • Amsterdam, The Netherlands
  • Auckland & Rotorua, New Zealand
  • Tokyo, Japan
  • Honolulu, Hawaii, USA
  • Chicago, IL, USA
  • Seoul, South Korea
  • Warsaw, Poland
  • Budapest, Hungary
  • Sofia, Bulgaria
  • Oslo, Norway
  • Zurich, Switzerland
  • Frankfurt, Germany
  • Port Townsend, WA, USA
  • San Francisco, CA, USA
  • New York City, NY, USA
  • Genoa, Volterra, Florence, Elba, Venice & more, Italy
  • Singapore, Singapore
  • Bangalore & Chennai, India
  • Buenos Aires, Argentina

Some people have asked me if I’ll continue doing this. The answer is absolutely! This lifestyle fits me perfectly. Of course, it has challenges, but now that I have a taste of it, I don’t think it’s possible for me to live this type of life in at least some form (for example, I can see myself settling down in a country for 5 years or so, but still going to the Southern Hemisphere for the winter months, or to see cherry blossoms in Japan in the spring, etc). You can’t untaste true freedom.

The truth is, there is no right time to become a digital nomad. It’s something I’ve always wanted to do, and when the opportunity came out of nowhere in the form of a remote dream job, I just did it right then without thinking much about it. I’ve always lived in a way where I can give everything up and do this, so it was a no-brainer - I didn’t have many possessions anyway (all my spare money was already going to travel vs things) and I was single with no mortgage or anything else adults are supposed to have.

About a month into my adventure, I realized that it was all too much. I was unprepared for my journey. I just moved, changed my lifestyle, started a new job, and was working on the most ambitious side project I could have ever thought of. Any one of those things would be too much, but I somehow thought I could tackle all of them at the same time (don’t try this at home 🙈).

Needless to say, I was overwhelmed, and I had to give up something. Well, there is never a right time to run your own business either, so I went crazy and gave up my very nice job.

I was in New Zealand, the furthest I could imagine being from anything I knew, and now I really had nothing. No home, no friends, no job. It was terrifying. It continued to be terrifying for the next six months or so as I was living in survival mode just trying to learn and do what seemed like the impossible on the fly. But eventually the chaos started to be normal. And of course, I’ve been able to learn and adjust for what I needed to thrive vs just merely survive.

Here is what I learned over my journey last year:

Finances

One of the biggest mental blocks to traveling the world is finances. It seems very expensive. However, keep in mind that if you only travel for 2 weeks out of a year on a nice vacation and stay in a hotel, yeah, that’ll be expensive.

Longer term travel is cheaper. How cheap? Well, I immediately learned that it was much cheaper to travel the world than my rent for a 277 square foot studio in San Francisco. While living in San Francisco, I haven’t dreamed of quitting my job and doing my business full time, because my business just didn’t make that much money. It was unfathomable to consider!

However, as soon as I gave up the rent and started traveling, I realized that while my business doesn’t make that much money, it was enough for me to survive on without my full-time job. I knew that if I quit and did my business full time, I would be able to get by on the money - and since I’d now be working on it full time, I’d have the potential to make a lot more money. That made it easier to quit my job when I needed to.

So think of all the monthly expenses you pay now - maybe rent, maybe a mortgage, maybe a car, electrical bills, internet bills, cable bills, etc. Add that up! Now imagine not having any of those bills and traveling the world instead.

The thing is, when you have stable rent / monthly expenses, they’re fixed and you’re stuck. But when you travel the world, you have the option to fluctuate how much you spend per month. For example, living in Warsaw, Poland is much cheaper than living in New York. I tend to alternate between cheaper and more expensive places. But I know that if I’m stuck financially, I can just go live in a cheaper place for a bit and save up again.

Another part of it is being smart about taking advantage of points and rewards. This is not something I’m an expert in, so I just followed the basic advice of @nomadicmatt from his amazing book How to Travel the World on $50 a Day. Just read it.

While I’m not going to disclose my personal finances in details, traveling the world and running my own business has to my big surprise left me in much better financial state than when I was working at a nice job and living in San Francisco.

Relationships

The biggest thing that hit me as a surprise when I started my journey was the extreme loneliness. I always thought of myself as independent and I’ve been even happy to be alone. But it was different before.

In San Francisco, I had the best co-workers that I interacted with on a daily basis. So being alone on the weekend was great and even desired a lot of the time. After all, I’ve had so much social interaction during the week that I didn’t even think about.

But there I was in Amsterdam, my first long nomad stop, with no friendly faces around. Soon I learned to prioritize making new friends, but while that helps a lot, it is not the same as being with a really really good friend you’ve known for a while who you connect with absolutely no effort. I then learned that catching up with friends on Skype pretty regularly was key!

I also go to see a lot of the same friends as I traveled to several industry conferences. And I even traveled with a few friends. But I also learned that sometimes traveling with a friend who has a different travel style than you is sometimes worse than traveling alone.

And then, an even bigger shift happened… As I was working with a group of good friends at an event I organized mostly solo, I realized that doing everything alone, including traveling alone is a choice. I actually had enough good friends to travel with.

Since then, I rented a big house in Volterra, Italy and had two friends join me to travel around Italy with. For one friend, it was a vacation, and it was awesome. If any of my friends want to travel with me during their vacation, I’m always up for it!

I also planned my trip to India during the time that my other friend would be there for her vacation. It was a blast! And now I’m in Buenos Aires (instead of Melbourne) because another nomad friend said she’d be there for the winter.

As I go to Japan next, I will have a bit of much-needed solo time before I have another friend come join me for an epic adventure.

Some friends are new ones that I’ve connected with very fast, some are good friends I’ve known for a while. Some friends I learn are not that great to travel with (for me at least). But some are amazing. My goal is to create a network of friends to travel with - it might be for a week, it might be for a month, maybe even longer, and it is some work, but if you’re flexible and set on making it happened, it’s more than doable!

Basically being a nomad does not doom you to a life of loneliness. Another surprise to me.

Work

I remember my first job in high school. I worked in a movie theatre. There were fast times when all the movies started and very slow times in between. During the slow times, there wasn’t anything to do, but if the manager walked by, you had to pretend to clean or something. To just look busy.

Since college, I’ve worked the typical hours in the office. The key was you had to show up. Even if you weren’t productive some days, you still had to show up and pretend to work, just like in that movie theatre. I’ve taken this for granted, but it’s a big waste of human energy.

Now that I work for myself, I’m much better with my time. If I’m not productive, I can take the day off, refresh, and move fast the next day. I love working on weekends when there are too many people out and about, and going out on either Friday or Monday or sometimes in the middle of the week to touristy places that have a lot less tourists during those days. I love taking long lunches and going on a small adventure. Or meet with a friend when and where it’s convenient for them.

The best part is that it’s all guilt free! I always have more work to do and I’ll get it done. But if I’m not being productive anyway, the best thing I can do is take the time to reset. Unfortunately, employers in the US often make you feel guilty for taking any vacation! I once got sick and when I told my manager, he told me he was sick too and was on drugs working, making me feel bad for taking the necessary days off to recover better. Now that I work for myself and not feeling well, I fix it the most effective way I know how without anyone judging me.

One big thing I learned is that creativity doesn’t happen on a schedule. I could be on my day off sitting in a beautiful Japanese Garden in Buenos Aires and that’s when ideas start to flow, making it the most productive day!

Working without constraints is definitely different and something that takes time to get used to, but overall I think it helps me focus on the actual work that needs to get done. Oh, and nothing is as big of an incentive to stop needlessly browsing Facebook like the prospect of having time for a small adventure if the work gets done!

Health

One of the hardest things to maintain as a digital nomad is health, both mental and physical. Being in a new beautiful place can be extremely overwhelming emotionally. I seriously have been to places so breathtaking (looking at you Elba), I wanted to cry at their heavenly existence. Other places need a lot more mental energy - such as Japan for example, because of the language and culture barrier.

So I try to have as much stability as I can at a given time. For example, staying in one place for 3 months makes it easier to establish a healthy food and work out routine and to spread out sensory overloading adventures to longer in-between timeframes.

Unfortunately, last year, I didn’t do as good of a job staying in each place for as long as I should have. I’ve alternated between hopping around a lot and then hiding out somewhere remote to reset.

In September and October, I’ve traveled all throughout Italy and ate all the amazing food, which was absolutely heavenly (seriously, no regrets there), but it was definitely not healthy. Now that I’m in Buenos Aires for the next three months, I’m obsessed with going to the gym and cooking the healthiest fresh foods there are, staying mostly gluten free and vegetarian.

A few people have asked me recently why I’ve only stayed in the same neighborhood in Buenos Aires - the only place I’ve really explored is the Japanese and Rose gardens, which are next to each other. I’ve also gone mostly to the same two places to eat out. Even the ice cream I get once a week is from the same place and the same exact flavors (chocolate + raspberry!). My friend who visited said something like “but you’re a nomad, you have to try new things!”. He was shocked I wouldn’t try a new ice cream place. Well, I just need consistency right now. Places I know I will like and will not fail me.

After all, trying new things is a risk. A fun one I’m willing to do a lot of the time, but not right now as I’m focused on stability. Think of how often you try something knew in your daily life? Most people who live in the same place probably don’t do it more than once a month. Trying too many new things is mentally challenging, and it’s something I need a break from once in a while.

Just like Buenos Aires right now, New Zealand and Port Townsend were also such places where I focused mainly on my health.

My goal for 2017 is to focus on longer stays in each place so that I can maintain my health better vs switching between unhealthy extreme adventure and extreme health.

Health is the most important thing we have, so it’s something I really care about. I need to make sure my nomad lifestyle is sustainable long term.

Summary

The last year has definitely been the most challenging one I’ve had in a while. I learned a lot about my limits (I can go way past what I imagine!), my strengths, my weaknesses, what breaks me down, what builds me up, beauty, the world, cultures, business, friendships, relationships, everything! And there is a whole world of things I have yet to learn!

This lifestyle has always been my dream, and now that I’m living it, it’s better than I could have imagined. This has truly been the best year of my life, and I can’t wait to see what adventure the next year of digital nomading brings 🚀