Getting Started as a Digital Nomad

I recently joined an iOS Slack Chat and introduced myself as a Digital Nomad. A couple of people were really interested about the Digital Nomad part and asked if they could have a chat to talk about getting started and life in general. Rather than chat separately we arranged an Slack style online chat. The players were me, Jacky – an iOS developer with a couple of years experience based in Taipei – and Eugene (@EugeneBelinski) – a Computer Science Student from Minnesota. They’re both really cool guys. Hopefully this is as useful to you as it was for them.

I’ve applied some light editing to the chat and loosely dived it into the following topics:

Let’s get started!


Getting Started & Finding Work


Jacky
8:31 PM
Did you start off as a Digital Nomad?
Lewis
8:31 PM
No, I worked normal jobs for about 10 years before I became a Digital Nomad in 2012. My ‘normal’ jobs included working at a consultancy and contracting. But you don’t needneed 10 years experience to become a Digital Nomad.
Jacky
8:31 PM
How was the transition?
Lewis
8:32 PM
It was fine. Initially I set off purely to go backpacking for 9 months, but I always wanted to be a Digital Nomad and we kind of drifted into it. I laid some foundations before we left so that made it easier. I was lucky because I had a great relationship with my last employer and so when we first left they kept my job open for me, and then when I made the decision not to go back they gave me freelance work. I think if you can prove yourself in your job and stand out there is a possibility a company will either keep you on, or keep you in mind when they are busy. Finding good programmers is hard and taking on extra people is risky, so if a company who you know well get a big project in that they can’t do, it’s better for them to be able to call you than to have to employ someone new.
Eugene
8:32 PM
Keep you on in terms of working remotely?
Lewis
8:32 PM
Sort of. For me I did per hour/contracting work for the company I used to work for rather than staying on as an employee. I handled the support for some of the projects I’d worked on. You should look for things which are beneficial to them and really emphasise those when you are talking to them about it. You need to sell them on the idea, and you don’t talk about yourself at all during that stage, just why it’s better for them.
Eugene
8:32 PM
Ah, makes sense.
Lewis
8:33 PM
The other company I do a lot of work for, I always freelanced for them anyway, and they use me when they are too busy, or for projects I worked on before.
Jacky
8:33 PM
Ahhhh I see. I guess you just gotta be pretty good/make yourself irreplaceable where the company is willing to work with you remotely because they need your work.
Lewis
8:33 PM
Yeah, it is much easier to get work for people you’ve worked for in the past than to find new people to work for.
Lewis
8:34 PM
Is it your ambition to be freelancers? Or Indie devs? Or remote employees? Or?
Jacky
8:34 PM
It doesn’t really matter for me I guess, any type of remote work is good work for me.
Lewis
8:34 PM
I would pick the one you like the idea of the most and start working towards it now. I think freelancing is probably the easiest.
Eugene
8:34 PM
I’m personally not sure. The thing I’m thinking about most seriously is remote work. I don’t know if I could be an indie developer because I haven’t come up with any great ideas yet, haha, and I’ve heard of indie devs not really making much money.
Lewis
8:35 PM
Yeah it is very tough making money as an indie.
Eugene
8:35 PM
Freelancing could also be interesting.
Jacky
8:36 PM
But you handle multiple projects at once I assume? So you could theoretically do all of the above if you wanted to right? As long as you schedule your time efficiently, to bring in max income. From what it sounds like, freelancing is a good place to start.
Lewis
8:36 PM
Yes you can do freelancing and your own projects, but I would start focussing on freelancing as it is a more solid foundation. Or at least, if you work 1000 hours as a freelancer or 1000 hours on your project, you will be richer in the immediate term as a freelancer. For remote jobs there are a bunch of job boards, but as you are just starting out I would suggest trying to find a job with a company that you are a good fit with and then after you feel you have proven yourself you could bring up working remotely. You could start by saying you want to work one day a week at home or something like that.
Eugene
8:36 PM
Yeah, right now I’m working for a company that will likely hire me full time once I graduate, and they’re very open to people working from home often
Jacky
8:37 PM
Ahh I see, to slowly transition into remote work is good advice.
Lewis
8:37 PM
Yes, definitely transition slowly.You can look for jobs on the freelance boards and do them evenings or weekends. Or better still ask people who you know if they have any work they need doing (obviously don’t let your boss find out!). This is a really great article with advice on using freelance boards: http://www.lifehack.org/articles/money/hacking-elance-how-made-over–20000–4-weeks-doing-web-design.html
Eugene
8:38 PM
As you say, I don’t think I’d be ready to be a Digital Nomad doing iOS development right away, because I have a lot to learn.
Lewis
8:38 PM
It sounds like you are in an excellent position though Eugene! I would expect it to take at least a year after you have started full time, although I only know the culture in the UK. I guess as you have been there for a while already and they know you it might be sooner. You don’t need to rush though.
Eugene
8:38 PM
There is one downside with my company though: The only other iOS developer is at the same level as me, and I’m not sure if they’re going to hire a senior iOS dev soon. It would be nicer if there was a senior iOS developer to learn from, instead of learning on my own.
Lewis
8:39 PM
That’s definitely true. Although there are a lot of resources online these days. Even on the iOS dev slack there is a “code review” room and things that that.
Eugene
8:39 PM
I should start using that channel at some point 🙂
Lewis
8:39 PM
So you think there should be nothing in your way?
Eugene
8:40 PM
Well I don’t think they’d be comfortable with me working remotely right away.
Lewis
8:40 PM
The big things for an employers perspective are going to be:

  • Trust: If we’re not watching him is he still working?
  • Communication: Will we be able to get hold of him? Will it cause a problem if he’s not here with us

You address trust by doing a great job, especially at the basics, turning up on time, being well presented and generally being a model employee

Eugene
8:41 PM
Ok.
Lewis
8:41 PM
For communication, that’s much harder to argue these days. And you can prove it in your one day a week at home. Or even if you start with just occasional ad hoc days at home and build it up.
Eugene
8:41 PM
I’d say I’ve been doing a pretty good job at those things so far and we communicate through slack a lot.
Lewis
8:42 PM
It sounds like you have been doing a great job, just don’t be complacent 🙂
Eugene
8:42 PM
So you’re a PHP and iOS freelancer, how do you find your work?
Lewis
8:42 PM
So far it has all been either from people I knew before I set off or from people I met networking online.
Eugene
8:43 PM
Ok.
Lewis
8:44 PM
There seems to be real burst of remote job boards lately, but I haven’t really looked at them much yet. But I would focus first on people you know and trying to do work with/for them, it’s just so much easier when it’s people know you already.
Eugene
8:44 PM
Hmm, ok


Daily Life & Travel


Eugene
8:45 PM
What does a normal day look like for you?
Lewis
8:45 PM
In a lot of ways it’s not that different for most people:

  • Get up
  • Do a little meditation (Maybe that’s different? But not specific to being overseas)
  • Go to a co-working space and work
  • Go someplace nice for lunch
  • Do more work
  • Go for a jog or a walk (jogging is one of my favourite ways to see a new place)
  • Have dinner someplace nice
  • Drink some wine and watch some TV, or meet up with new friends
  • Go to bed

Going someplace nice is to eat easier when you are not at home, especially if you are in a cheaper country.

On weekends or days off we try and do a tour or go visit a museum, you know, the tourist stuff. You have an instant vacation then, it’s really nice.

Eugene
8:47 PM
That sounds like the ideal life!
Lewis
8:47 PM
I don’t want to make it sound perfect, but it certainly suits me well.
Eugene
8:48 PM
Where have you lived?
Lewis
8:48 PM
Going backwards from now: Mexico, Iceland, San Diego, New Zealand, Malaysia, Thailand, Australia, Jordan, Israel, Turkey, Vietnam, Cambodia, Laos.
Eugene
8:49 PM
Damn!
Lewis
8:49 PM
Next year I want to go to Spain. And I really want to go to South Korea, Japan and Taiwan too. And Berlin. So many places!!!
Eugene
8:50 PM
That sounds great, I’ve only been out of the country I think, 2 times.
Jacky
8:50 PM
If either of you guys come to Taiwan, I’d love to show you around if I’m still here.
Lewis
8:50 PM
Cool, thanks Jacky!


Productivity & Possessions


Jacky
8:51 PM
I want to ask a question more about management: How do you manage your materialistic things/finance/time as a Digital Nomad?
Lewis
8:51 PM
For materialistic things it is pretty easy: I have a bag and I put my stuff in it 😉 After a while the temptation to buy new things mostly wears off. I always used to buy a lot from Amazon, but that isn’t possible now, which is great, it saves me a lot of money.
Eugene
8:52 PM
Random materialistic question, what laptop do you use?
Jacky
8:52 PM
It’s gotta be a Macbook Air!
Lewis
8:52 PM
MacBook Air. But I’m going to get a Pro when they upgrade.
Lewis
8:53 PM
I like the air, and the newer ones are probably better, but I would like a bigger screen and I would like a bigger drive and I would like Xcode to build faster.
Eugene
8:53 PM
I have a 15” Pro but I’m planning on switching to a 13” as soon as I can. the screen real estate is nice, but I don’t want the extra weight personally.
Lewis
8:54 PM
In terms of managing finance, I use an app called Toshl to track my spending and then I have a google spreadsheet which I update every month which has the amount I have in all my accounts.
Lewis
8:54 PM
I don’t think managing finance as a DN is particularly different to managing them at home.
Jacky
8:55 PM
Makes sense.
Lewis
8:55 PM
I guess there are things to think about like finding a bank account which is cheap to draw cash from overseas, lower charges etc. In terms of managing time, how do you mean in particular?

Jacky
8:55 PM
Like how many hours do you make yourself work daily? Do you keep a rigid schedule? Or do you just work when you feel like it?
Lewis
8:56 PM
Yes and no. I normally do 8 hours a day and normally take weekends off. But sometimes I work less and sometimes more.

freedom == responsibility

which doesn’t mean no work, if anything it can mean more.

Lewis
8:56 PM
I think if you just work when you feel like it you would probably run out of work quite quickly.
Jacky
8:56 PM
I guess my question of time is how do you keep yourself efficient? At work, when the manager is behind you, of course it’s easy to focus on your work, you don’t really have a choice. But when you’re alone, isn’t it easy to fall for the temptations. Sleeping a bit more, a few extra drinks and what not.
Lewis
8:57 PM
That’s true! But getting paid by the hour is usually pretty motivating.
Jacky
8:57 PM
Ahhhhh I see, I see.
Lewis
8:58 PM
Yeah, you don’t get paid for hangovers or sleeping in. I think it would be possible to work less hours.
Jacky
8:58 PM
Are there any tools you use or things you tell yourself to keep yourself efficient and focused?
Lewis
8:58 PM
I guess I have one tool for focus: Self Control.
Eugene
8:58 PM
Hahaha, I know that app well!
Lewis
8:59 PM
I wrote a blog post about tools here: http://itinerantdev.com/my-kit/.
Eugene
8:59 PM
Oh awesome.
Lewis
8:59 PM
Productivity and focus are whole areas you can study in their own right. A few things to look at: The Pomodoro Technique and Getting Things Done (GTD) by David Allen. There’s also a chapter on it in “The Personal MBA” which is a really great book too.
Jacky
9:00 PM
I’ve read that! 🙂


Packing & Accommodation


Eugene
9:00 PM
So how much stuff do you take with you when you go somewhere else? And what kind of places do you live in?
Lewis
9:00 PM
Well. Packing is a whole field of its own. I don’t really travel very light. Here’s a decent read on packing. But they go very light and I don’t tend to bother. The more time you spend in one place the less you need to worry about bag weight. We mostly get a taxi to the bus station or airport so don’t have to carry it far, but I know lots of people pack light.
Eugene
9:01 PM
Oh that’s a good point, I guess you don’t have to travel super lightly.
Lewis
9:01 PM
Here’s another one on packing. In terms of places we stay, it depends on the country. in Thailand and SE Asia you can easily find short term apartments. In other places we often look on Airbnb to find places. Normally we get a “whole apartment” on Airbnb. Sometimes you can find things on craigslist too.
Eugene
9:01 PM
Ah ok.
Lewis
9:02 PM
Or local websites. You can also join forums and things for Nomads and ask for advice on there. Accommodation tends to be more per night than if you took a 6 month contract, but much much cheaper than a hotel.


Staying Social


Jacky
9:02 PM
What struggles and challenges have you been through, and is there anything you had to give up for the lifestyle?
Lewis
9:03 PM
The biggest struggles are a) keeping work coming in and b) that it can be quite lonely. I guess I had to give up my friends and family (to some extent), and my comfy couch and big tv and a general level of comfort. Travelling to new place often can very exciting, but it can be tiring because even simple things like getting a hair cut or going to the dentist can be really hard, especially if you don’t speak the language. You can worry about money sometimes if it’s been a while without work. And it can be lonely, it can be hard to make friends and then when you do make them they move on or you move on. Comfort isn’t as much of a problem, it’s just more tiring some times. But that’s all part of it. And of course you can Skype or FaceTime with your family and friends, you just have to remind yourself.
Jacky
9:04 PM
How do you deal with the loneliness of being a Digital Nomad?
Lewis
9:05 PM
There’s a few things, and it depends on the place, but meetup.com can be good and Couch Surfing meet ups. In fact I’d recommend looking for couch surfing meet ups while you’re at home. Another good one is co working spaces which is probably the best way to meet similar people. And then making sure to keep in touch with friends and family at home. I actually have reminders to text my brother… There’s also a nice site called Find a Nomad1 which helps with meeting people. There’s a few other sites like that too. There’s a Slack chat called #nomads which sometimes you can meet people on. The anywhereists.com networking group from makingitanywhere.com is great too,
Jacky
9:06 PM
Is there anyplace where you document your journey? Like photos of places you’ve been or things you’ve done?
Lewis
9:06 PM
My wife does some documenting: www.theadventuresmith.com​
Jacky
9:07 PM
I probably have to sign off soon but I would love to follow you on your journey and see all the good things you experience. Like Facebook?
Lewis
9:07 PM
I haven’t been on Facebook long, but you can find me here: http://facebook.com/itinerantdev/ and @itinerantDev on twitter and of course http://www.itinerantdev.com 🙂
Eugene
9:08 PM
Awesome.
Lewis
9:08 PM
Cool, I have to go too, it’s been really fun. Thanks guys!
Eugene
9:09 PM
Yeah, for sure!
Jacky
9:09 PM
Thank you! Super helpful advice!

So what did we miss?! If you have any other questions ask them in the comments 🙂

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  1. Full disclosure: I built this site ;) See other stuff I’ve worked on here