Lessons Learned in Two Years as Digital Nomads

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We are now into our third year as digital nomads and this journey has been exciting and challenging but not without its Lessons that arrived in their traditional disguises of psychological pain.

1) The Eighty-Four Hour Work Week…

You’re Neo and I’m the little bald buddhist kid.

Do not try to find the magic bullet—that’s impossible. Instead, only try to realise the truth: there is no magic bullet.

Running your own show is really, really hard. It requires constant reflection, high-level decision making, granular detail work, self-management, dedication, sacrifice, more coffee than a single person should safely imbibe and care.

2) …Is Totally Worth It

Stepping out in to the abyss was the single greatest thing that we have ever done.

Without getting too fluffy on you, somewhere out there in the world is your True Self (could be on the other side of the planet; could be just down the street) where the work you do no longer feels like work and Flow is not just a book by some guy with an unpronounceable surname.

If you like the idea of doing this whole Digital Nomad bit, or even if you just hate your job and wish you could do something else, please just do it. Yes, I know it’s scary. Yes, I know that you have a million reasons not to do it but (and not to put too fine a point on it) you will be dead much, much sooner than you’d like.

We are literally the world’s worst businesspeople (we have a certificate) and we are making this work. You could too.

3) Get Started

Reading about doing it is great and inspirational and motivational and all that but the truth is that every mistake you could potentially avoid by reading is just going to be replaced by a mistake that is 100% yours.

Never underestimate the human capacity for truly creative and innovative fuck ups.

But the quicker you get out there and start making your own special little errors (and, most importantly, learning from them), the quicker you’ll get to your goal.

There’s an irony here that I am well aware of, so let’s get to it:

  1. Stop reading this post
  2. Pick one of your goals
  3. Do the next action step

If you don’t have any goals, then your next action step is to come up with some goals (see below)

If you don’t have any action steps, then your next action step is figuring out all of the action steps you have to take to reach your goal.

Keys to Good Goals

  1. Make them measurable. ‘Write a novel’ is better than ‘get better at writing’; ‘write an 80,000 word novel’ is best of all.
  2. Give them a deadline. Bear in mind that human beings overestimate what they can do in a day and underestimate what they can do in a year.
  3. Don’t rely on luck or the whims of others. Replace ‘get on a reality TV show’ with ‘start my own reality TV show on YouTube’.
  4. Don’t worry about whether or not your goals are good goals. Anything is better than nothing and you can refine as you go.

Keys to Good Action Steps

  1. Make them actionable with clear and simple instructions. ‘Write a post’ isn’t as good as ‘Create a new draft post on the blog, put in a temporary title and write the first 200 words’.
  2. Put them somewhere you trust. Having a good system that you trust is super important. David Allen’s Getting Things Done is a great starting point for how to create such a system.

I know this is obvious and I know you’re too smart for spelling stuff out like this but when you’re looking at your to do list and you have a series of clear and simple steps that a child could follow, then you are so much more likely to actually start working through them.

Once you’ve done your first action step, come back and leave a comment telling us what you did.

We’ll wait.











One thing. 10 minutes.











You’re not missing anything. All the stuff below is just practical junk that doesn’t apply until you’ve started moving your projects forward.











Seriously, quit reading and go do it.











Did you manage it?

If you didn’t, don’t sweat it:

4) Defeat Self Doubt

One of the single biggest things that we have had to overcome is our own damn selves.

We fight this battle daily and you probably will too but you’re going to have to get good at making decisions and living with the consequences of those decisions.

Some of those decisions are going to involve large amounts of time or cash and some of those decisions are going to end up being wrong. Nothing creates regret like losing hundreds or even thousands of pounds on a bad decision but you have to accept it as a cost of taking charge of your destiny and move on.

Here are some things that we’ve found helps us to keep going—your mileage may vary:

  1. Don’t read the internet in the morning. The internet is full of Other People’s Noise which will drown out your faint and timid inner voice and make you question your actions. Move a project forward first, even if it’s just for 15 minutes, before you head online.
  2. Once your decisions are set, don’t question them. Decision made. Done. Move on. There will be consequences (either good or bad) and your only job is to deal with those consequences.
  3. Learn from your mistakes without beating yourself up. ‘We abandoned this project because we didn’t properly consider support needs’ is more constructive than ‘We are idiots for wasting so much time on this’.

5) Protect Yo’self

Most relationships between clients and providers fall apart for one simple reason: badly managed expectations.

The client thinks they’re getting one thing, you think you’re delivering another. Make sure that in whatever contract you make with people, however informal it is, things are spelled out clearly and concisely and with as much detail possible.

Other keys to managing expectations:

  1. Keep your clients/partners/colleagues in the loop. In the days of the Twitbook and FaceSquare there’s really no excuse.
  2. Be a straight shooter. Don’t hedge or fudge and certainly don’t lie. If you’re going to miss a deadline, apologise, set a more realistic one and redouble your efforts.
  3. Underpromise and overdeliver. If you’re an excitable little squirrel like me, this can be hard. Agree to the most basic version of whatever it is you’re selling and then wow them with the snazzy extras that you kind of had in mind anyway.

6) Triple Your Estimates

You don’t know what you don’t know.

If you do the kind of work where you quote a fixed price for work, then this response on Quora is all you need to read to understand why you should be charging more.

I think this idea applies to every new project where you are venturing out into uncharted territory.

Now the bad news: you will still go ahead and make this mistake. It’s pretty much a rite of passage for freelancers and entrepreneurs.

But don’t worry, you’ll get better at it.

7) Take More Risks

A housesit came up in Japan where things are really expensive but it was too good an opportunity to pass up, so we ponied up our last coppers, flew out there and had the most incredible time.

When we arrived Chiang Mai, we chose to stop doing client work to spend three months on a Premium WordPress Theme site that we later ditched.

Instead of trying to get some client work to cover the costs of those months, we decided that now would be a good idea for me to learn a whole new programming language and go and make iPhone apps.

Turns out I love making iPhone apps. Within 3 weeks, our first app was on its way to the app store.

Each one of those decisions was scary. Each one had an easy way out (usually a no) and yet each one has yielded a better understanding of who we are and where we really want to take our lives.

Here’s the most important lesson that we’ve learned as Digital Nomads: If there is something you really want to do, go do it. It’ll be the hard, but it’s worth it.

And if there’s ever anything we can help you with, please feel free to get in touch.


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