Travel While You Work While You Travel – 5 Tips

Travel while you work

When I started freelancing 10 years ago, I had goals. They involved working while travelling. Basically, I wanted to:

  • Make a living from writing (check)
  • Not work for a crazy boss (check, depending on how I feel about myself at the time)
  • Be able to do what I love from anywhere in the world (check)

These goals haven’t changed much, really. But, my implementation has. The beginning was rough but, as I type this looking out over the Knysna Lagoon, I realise how very much I love my work situation. So, for those that are still playing with the plan to travel while you work, I’d like to share a few tips (from my experience), and then some insights from a travelling insurance broker that takes this whole concept to new levels.

Tips for Travelling While Working While Travelling

Plan Before You Start to Travel While You Work

I’m not the queen or organisation. Sadly, this actually means that I have to plan things in advance so that I don’t get lost in the web that I attribute to creative people. So, instead of scanning social media for hours, use the time to write a list of things you need to accomplish and how you plan to get them done. I like to make these detailed. So, instead of saying something like, “Press release for Gerry’s book launch”, I create separate line items for 1. Email Gerry for time, date and venue of book launch; 2. Ask photographer for author’s picture; 3. Call venue to find out capacity; 4. Chat to caterer about the menu; 5. Contact graphic designer for a jpeg of book cover;…and so on. This breaks one assignment down into more manageable tasks.


Become familiar with your destination(s) and do research ahead of time to ensure that you know where you can access Wi-Fi or phone signal. Trying to find a coffee shop with internet on the day that you need to work is a waste of time, frustrating, and can cause massive delays.

Book Accommodation Wisely

When you have to book a place to stay, it’s important that the place has efficient Internet and a comfortable place to work. Make sure by reading reviews from past guests, looking up their amenities, or even calling them to ask. This is especially important when travelling overseas, as it might not be as easy to resolve issues (like no Wi-Fi) in a foreign land or language. Use websites like to book your accommodation, as they have thorough lists of what facilities each establishment has available.

Have a Back-Up

It doesn’t matter how much research you’ve done, you’ll run into hurdles. So, have a plan B. This may be a mobile 3G carrier (this is a must, you just never know), or screenshots of info you desperately need to keep safe. Whatever you need to do, do it to minimise the risks.

Stay Ahead

As mentioned, unexpected things are going to come up. There will be surprises you wish you’d missed. So, try to be ahead of your schedule so that these don’t throw a massive spanner in the works (as opposed to a little one, which is inevitable). This, again, takes preparation. But, if I can, you certainly can.

Meet Cindy…

Cindy and her husband recently packed their three (gorgeous) kids into a campervan called Optimus and have the goal of touring South Africa. While working. From a campervan. With three small(ish) kids. And I start hyperventilating when my laptop needs to reboot. I just can’t imagine this sojourn. So, I thought that she might need some time out to answer my interview questions. And, I was right! Because she agreed!

What is your money-spinning job?   Believe it or not, I’m an insurance broker.  Yup, those still exist and we’re not as bad as we’re made out to be.  I focus on short term insurance (car, household, guesthouse, AirBnB) and, every day, we manage to save people money, find them better cover and just provide them with a better, more personal service than uh, you know… the other ones.
Since this is usually an office-based job, how did you change over to doing it on the road?  It wasn’t easy.  But it was.  The thing is, I’m the co-owner of my business (Incompass Insurance Consultants – and so, after chatting it through with my partner, we agreed that it would be OK, as long as I kept up my work on the road.  Our business is quite big now, focusing on the guest house and AirBnB  industry so we have a team that works in the office every day.  They are there to support our existing clients by handling claims, renewals and queries.  My focus is on management of the business, our staff, and signing new clients.  Which means that, for the most part, I can do this on the road without issue.
What preparations did you make before the time, in terms of your work?  Not much.  My biggest issue is connectivity. Working on the road as we travel South Africa means that we can go for days in the “dark” with no signal.  But we bought the routers and data and hoped for the best.  I changed some responsibilities with my partner; like meeting with our staff, which I can’t do on the road.  But, my office is really a well oiled machine so clients are looked after when I’m not in the office, so this wasn’t too much of an issue.
Did it go as planned? Most of the time, yes.  It makes me wonder why everyone doesn’t do this.  It just makes so much sense being in control of your own time, space and work life.  I can work in the mornings before I spend time with my kids visiting something fun, or all afternoon while the kids do school, or even in the middle of the night if I need to catch up.  The work gets done.  Usually on time, but sometimes it takes me a smidge longer to do things than it would have in the office.  I think the key really has been making it top priority – if there’s something urgent, it doesn’t matter what we’re doing, my laptop is out and I’m dealing with it.
What are the advantages of working while travelling for you?  Aside from getting a salary while I get to see the whole of SA and more, it’s really great being master of my own time and only really answering to myself.  I like the discipline of meeting the deadlines despite the rest of our chaotic lives, it gives me some sensibility.
What are the drawbacks?  It’s stressful as heck.  Every place we get to, I have actual real life sweats when there is no internet.  I may not work every second of the day, but if I need to do something, I don’t want to have to travel two hours to be able to do it.  Also working in front of my kids, I’m sure they’ll tell you I work all the time.  But, really, they only see a small portion of it and MUCH less than I used to in the office.  But, it’s still there in their minds and that sucks.
What would you change / what advice would you give others that are planning to travel and work at the same time? Routine.  I still haven’t gotten it right because we move every couple of days and each place presents its own needs. But, having a routine helps so much.  Knowing that, from 7 – 9am you can work, then again from 11- 3pm, or whatever it is that works for you.  But, at the same time, it helps you know the limit.  It can be so easy to be caught up in the need that you never leave your laptop.  Just as an example, I worked from about 3pm today, I made supper while still answering emails and am still behind my laptop. Seth keeps checking me about working all the time.  It sucks you in.
See? I told you she takes working while travelling to the next level. Follow her adventure on her blog, Facebook, or Instagram feeds for more inspo on how to travel while you work.
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