An Accidental Crash Course in Starting a Business on the Road

In around August of last year, I decided to make the leap from freelance individual to limited company. This was initiated largely by the fact that I was getting hammered by tax and national insurance contributions as a solo entity, but early on I decided to make the most of the situation. ‘Here’s an opportunity to be creative’, I thought.

So Ink + Honey Design Co. was conceived, and little by little my germling of an idea has reached full term. The fact that whilst I was setting up my company I was simultaneously planning a months long backpacking trip, departing in January 2016 and culminating in a semi permanent move to New Zealand at the end of this year, was immaterial. ‘It’ll be perfect’ I told people chirpily, ‘I can work while I travel and make money on the road! It’ll be easy!’

Ha. HA.

It’s true, I can and have worked whilst travelling these past few months. I’ve even made some money. But it is definitely, DEFINITELY not easy.

Time for a little visual – picture, if you will, the following snapshot. Me, crouched in a dark corner of a dirty hotel balcony in Chichicastenango, Guatemala at 6pm, my head pretty much pressed up against the allegedly working Wifi box, trying desperately to Skype a client. Our Skype meeting was actually scheduled for 9am that day, but the power had been out across the entire city for close to 12 hours and this was the first internet I could access all day.

Or this one – getting up, bleary eyed, at 6am to upload design files, before anyone else in the hostel wakes up and jumps on to the fragile internet. Or pulling a 10 hour working day crosslegged on a floor mat at a low coffee table on a concrete roof because it’s the only quiet space with a flat surface available. Or the fact that my ‘day bag’ weighs almost as much as my backpack because I’m carting around a Macbook Pro, Canon SLR, digital drawing tablet and numerous sketchbooks, pens, paints and other drawing materials.

Working on the road, at least while backpacking in Central America as I’ve been doing for the last couple of months, is tricky. It takes determination and imagination, and what one of my University lecturers used to refer to as ‘creative problem solving’. It takes good time planning and organisation, both of which are skills that I need to work on (leaving my VAT return until the last minute and then realising the Wifi was down was particularly fun).

It’s also immensely rewarding when it works. The days when I get up early for yoga, have breakfast and then get five hours or so of good productive work done, leaving the rest of the afternoon free to spend at the beach or exploring a new city – those are really good days. I’m still figuring it all out, and it’s worth figuring out how to do this to create the kind of working freedom I crave. Even the most frustrating days, when everything goes wrong and there’s no power and files won’t send and I end up working until 11pm at night, still aren’t as depressing as I used to find the rainy commute into the office every single morning. So there’s that.

Things to Know When Starting Up Your Business From The Road

Prepare for the worst case scenario

There will be days when you can’t get online. There will be days when backpacking-related disasters happen that have nothing to do with your business, but that take you away from work for a day or two, or maybe more. You might get some horrible tropical disease, or have your passport stolen (yup, both happened to me!) Either way, try to minimise disruption for your clients. Communicate frequently and clearly, and always over estimate on deadlines by a day or two to offset internet problems – no-one ever got upset about their project being delivered early.

Understand that not everything is within your control

In a similar vein, accept the fact that the nature of travel means that not everything that happens will be within your control. If you’re chosing to run your business from the road, that means things might be a little more unpredictable than if you had a home office or worked from a Starbucks in London. Things will go wrong. Accept it. Move on and try again.

Travel slowly

This is a big one. I set off at a pace, thinking that I would be able to slot work in around my usual backpacking day of exploring, hanging out with new people, and wandering around eating all the food. This doesn’t work. You’re not going to get work done if you’ve only got three days in a place, and if you did you’d miss out on everything! I’ve found that planning a 2-4 week stop in one place that you want to travel to is a far less stressful way to do things – this way you can get a solid few hours of work in each day, be online to correspond with clients in whichever timezone they’re in, and still have time to explore. I’ve also always been able to negotiate cheaper accomodation when staying for longer than 2 weeks, so there’s that too.

Don’t try to be everything to everyone

It’s tempting in the beginning to take absolutely every offer of work that comes your way, even when the project isn’t really right for you or the client isn’t willing to pay what you want to charge. There are times when doing a project for a client for a reduced rate is beneficial, to build your portfolio in the beginning or to build relationships that can lead to more, bigger projects. Mostly though, if you know you’re not the best person for the job, pass on it. If you’re going to spend hours and hours on a project for $100, pass on it. You’re travelling, don’t waste time on stuff that’s not worth your while. Go out and hike a volcano or something, another project will come.


It’s supposed to be fun. This is exciting – you’re running a business and travelling the world! Enjoy it. If you’re stressed, adjust something. Stop somewhere that you love for a while and concentrate on work, or take a break from work, don’t take on any new clients and just travel for a couple of weeks. One of the pros of being your own boss is that you get to be your own priority, so do it how it works for you.  

Are you running a business from the road? Thinking about it? What are your top tips?

If you found this post helpful, please share it so others can benefit from my hard won wisdom!

To freedom chasing 🙂

Clare x

Clare x


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