20 Lessons From Two Months of Travel as a Digital Nomad

Digital nomad VAs

Not too long ago, my husband and I made a decision which led us down a super awesome path.

It all started with the choice to head back down under after a two-year stint in Vancouver B.C., and then the subsequent desire to be able to:

  • swing by Brunei to visit family on the way back
  • tick Tokyo and Kyoto off our bucket list
  • eat our way through Singapore
  • do all of this without breaking the bank + while keeping the business running too.

Thinking back – we went from “should we?” to “what will it take?” very quickly. As soon as the decision was made, we just ran with it and I think a lot of that had to do with the fact that the business would “travel well.” All I needed was the internet and my trusty sidekick – a MacBook Pro.

But back to the point of this post.

Two months 

Six cities.

Four time zones.

Twenty thousand kilometers.

Two kids.

Several bucket lists.

One big a$$ dream.

And all of that needed to happen while I continued to support my clients and run my business.

So, what exactly did I learn about doing remote work & setting yourself up for location independent success?


Get All Your Tech Sorted

01. Make sure your laptop is a happy camper. I used a program called CleanMyMac to get rid of all the junk that was bogging my laptop down. I went through all my old files and cleaned those out. I made sure the operating system and all my usual apps + programs were up to date.

02. Backup all your important stuff across several devices. At the very least, you’ll want to travel with a hard drive and your laptop.

03. Check if your mobile service provider works where you’re at (mine didn’t!) and make the necessary plans to deal.

04. Be prepared to invest in data.

05. Make sure your connectivity matches the work you’re doing. I was doing a lot of work on WordPress, Squarespace, YouTube, LeadPages, and MailChimp – so I knew up front that I needed a pretty decent connection.


Stay on the Safe Side

06. Think worse case scenarios – I had my work synced across my laptop, tablet, and phone. And when I packed my devices, they went into different bags. (I’m not kidding!)

07. Protect your client’s data like your own – I installed two-step verification on everything. I also used a secure VPN connection when working off public Wi-Fi etc.

08. LastPass every password you can – I don’t know what it is about holiday brain, but there was no way I was going to be able to remember all of my own passwords and then all of my clients’ too. LastPass is the perfect password manager, encrypting and storing not just my own passwords but the ones my clients had shared with me.


Client and Expectation Management

09. Get super clear about your scope and availability for the time you’re away. I had conversations with my clients a good six months before the trip to give them time to think about what would work / wouldn’t work vis a vis their specific plans for that time of year. I also set the tone for how we’d stay in touch. Make sure your clients know if there are days when you’ll be incommunicado (cos you’re stuck in a plane somewhere).  

10. Front load what you can to take the pressure off yourself. Granted, some tasks are time-sensitive but there are heaps of things that tend to be planned months in advance (e.g. blog posts, podcast releases, email blasts, Facebook ads creation etc.) If your clients are happy to, and you have the capacity to do so, it helps to get these kinda things out of the way even before you leave.

11. Only work with your ideal client. One of the things I really, really appreciated was the fact that every single one of my clients was happy to stay with me in my relocation to Australia despite the time zone differences that would be introduced to the mix. Over the course of the trip, I even managed to land another two project management gigs (#blessed). I also appreciated that every client was happy to work with me so that I could go on this trip, and still deliver on what they needed for their businesses to keep chugging along. I think this is really about making the right choices up front, and only working with clients who you really connect with and clients who value what you value.


Productivity Related Lessons

12. Find your go zone. For me, this was 4 am to 7 am so when I had tasks that required 100% of my brain power, I’d save it for my go zone.

13. Chunking really works and by this, I mean grouping like tasks and tackling them in batches. Working holidays are very different to those days when your routine ticks along predictably. You almost have to grab your moments when they present themselves, and you have no rev up/wind down time – you have to get in the zone super quick.

14. Learn to spot “dead times” in your travel plans (e.g. 3-hour bullet train ride from Tokyo to Kyoto!) and make them productive.

15. Find a way to track the different time zones cos doing the math in your head each time can give you a headache (client A is 13 hours behind and so this piece of work is due then, client B is 1 hour ahead and so his piece of work is due then, client C is…*yikes*)


Keep Well

16. Oh, the jet lag! Not sure why, but the Tokyo from Vancouver leg was a serious struggle. I found myself falling asleep at 4 pm and getting up at 2 am every.single.day. I really didn’t factor that into my plans. Only thing I can say is “Be kind to yourself. And if you need to, just pick one small thing to work on, and then the next small thing, and the snowball effect will help you move jobs forward.”

17. Stay safe, stay hydrated, eat well, rest, have your usual culprits in terms of meds and vitamins handy. If you’re not 100%, work isn’t gonna happen and even if it did, it might end up being shoddy work. Not good for business.


Get in the Right Headspace

18. Be realistic with your expectations. It’s great to be able to do the digital nomad thing, but it’s not all fun and games. There will be days when you’re dog tired from all the sightseeing you just did but you have a deadline looming. That’s when you dig deep and keep going.

19. Compartmentalize! When you’re out experiencing your new surroundings, don’t bring work with you.

20. A change of scenery can be an amazing blast for your creativity. Always have a notebook handy for when an idea strikes you.