Internal Auditor to Digital Nomad in 18 months – Dylan Wolff

Dylan Wolff was an internal auditor in Melbourne, Australia before deciding to make the switch to a location independent career in Web Development. Within just over a year, Dylan had taught himself enough to land his first job as a junior developer and 3 months later, he began working remotely while travelling the world.

After meeting with Dylan in both Kuala Lumpur and Chiang Mai, I asked him if he’d like to share his experience as the first interviewee in this new ‘Inspiring Nomads’ Series. Here are his answers:

What made you decide that you wanted to be location independent and how did you make it happen?

In late 2015 I came to the realisation that I wasn’t happy with the direction in which my life was heading; it felt like I was living life on “easy” mode and I’m sure that the best way to stimulate personal growth is to place yourself into unfamiliar and potentially challenging situations and expose yourself to new environments and cultures.

After reading a few blog posts that I found incredibly inspiring (like this one by Tomas Laurinavicius and this one by Pieter Levels) I resolved to make a major change to the way I lived my life. I started researching the ways I could make a living while working remotely and examined where these intersected with the things I’m interested in. For me, web development ticked all the boxes so I set about learning to code.

After around nine months of self-directed learning I landed my first job as a junior developer with a studio based in Melbourne. During the interview process I was upfront about my desire to pack up and work from the road, and the only stipulation by my employer was that I stuck around and worked in the office for my first three months which was completely reasonable, and actually a useful exercise in getting to know the rest of the team and learning how they worked.

What are the challenges of being a junior web developer, working remotely?

The biggest challenge for me so far has been communication. Fortunately our team uses some great tools to stay in touch (like slack (https://slack.com/) and Basecamp (http://basecamp.com/) and to date I’ve only travelled within Southeast Asia so the time difference hasn’t been too much of an issue, but I find that as a junior it can be difficult to find the right balance between putting your hand up and asking questions and figuring things out for yourself. I think if I was working in an office environment with other developers I’d be more inclined to ask for help at the first sign of trouble, but perhaps that not being so easy has been a good thing as it’s forced me to learn more about how to debug and solve problems on my own.

I’ve been really fortunate to find a company with such a strong culture around remote work. We’ve had members of the team work from Thailand, Phillipines, Laos, and the US (among others) and even within Australia a few of the team work remotely from home.

Which destinations have you worked remotely from so far and what would you say are some of the drawbacks of living and working in places like these?

It’s still early days for me working remotely but to date I’ve worked from Singapore, Kuala Lumpur and Chiang Mai. I can’t say I’ve experienced any drawbacks so far as these are all pretty safe choices (with plentiful high-speed internet and loads of cafes and co-working spaces to work from) but I certainly found it more difficult to make connections in Singapore and Kuala Lumpur given the relatively low number of people living this lifestyle (compared to Chiang Mai anyway).

Which are your favourites?

Without a doubt, Chiang Mai. It’s obviously the safe and easy option when first becoming location independent, but given how well the city is setup for working in this way it’s hard to look past it. After being in Chiang Mai for a few weeks and then heading to Kuala Lumpur for a month, I was blown away by how much returning to Chiang Mai felt like I was “coming home”. I made some great friends in my first stint here and continue to do so with each passing week; there is always someone up for grabbing dinner or a drink, you just need to put yourself out there a little and I think nine times out of ten the people you meet will respond positively to this.

What’s an average day in your life look like?

A typical weekday for me looks something like this:
6:00 – Get up and hit the gym
6:45 – Shower and make the first of several coffees for the day
7:00 – Jump online and browse slack to catch up on any discussion that’s taken place in the 2-3 hours that my teammates back in Australia have been online, then get stuck into whatever it is I’m working on
10:00 – Relocate to a cafe (Rustic & Blue and SS1254372 Cafe are two of my favourites) to continue working and eat & drink something delicious
14:00 – Head back home for the last couple of hours of my workday
16:00 – Finish work and run any errands (e.g. shopping, catching up on personal emails)
19:00 – Meet up with friends for dinner and drinks (Bar Basic and Knockout Cafe are two low-key favourites)
22:00 – Call it a night, write up a plan for the following day and then head to bed

What advice would you have for others who are looking to live and work anywhere?

I would say just do it. Set yourself a goal and make it happen. In December 2015 I set the goal of becoming location independent within twelve months and for the first time in my life I told myself that not meeting this goal would be unacceptable (it ended up taking me thirteen months). There are people living this lifestyle working in such a broad range of fields that I think almost everyone could find that same intersection between skills you can use to earn a living from the road and the things you’re interested in as I did.

Are you happy with your current lifestyle and would recommend it to others?

I absolutely am and would; the last three months that I’ve been on the road have been the happiest and most rewarding of my life. Having said that, it’s clearly not for everyone. Being away from family and friends for an extended period can be difficult for some, but I haven’t found that aspect particularly challenging given I’ve met so many great people along the way.

What are your goals now that you have achieved location independence?

I’m not thinking too far ahead, but in the immediate future the plan is to continue travelling and exploring, and connecting with as many like-minded and inspirational people as possible. I can see myself living this lifestyle for the foreseeable future so I don’t feel pressure to travel at any great pace but so far my travel plans for the rest of the year include South Korea, the US, Germany and hopefully Morocco at some stage.

You can discover more about Dylan at his website here

Have you been inspired by Dylan’s story?
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About the Author

Hi, I'm Chris. I'm a self-taught web developer, YouTuber, Blogger and Digital Nomad.

To find out more about me, check out the 'About page', the 'Hire Me' section of this website or connect on social media

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To read my full story on how I left my corporate career in Accounting to pursue Location Independence, check out my book 'How I Learned to Code'


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