A Year Into Being a Wandering Planner

Hitchhiking in Malaysia last year (hadn’t hitchhiked since I was about 16, it was a lot of fun!

It has been almost a year now since I’ve officially transitioned into being a digital nomad, working and traveling on the way. I remember a year ago I had just left from three fantastic weeks on the Perhentian Islands in Malaysia and got sick arriving in Kuala Lumpur with a mean tonsillitis. I was at the end of my travel budget and seriously needed to figure out what was next, being ill I couldn’t do much so I took it as a good opportunity to mull things over.

I had no particular desire to come back to London or anywhere in Europe where I’d be likely to get a full time job. I enjoyed the tropical weather and wanted more of it (still do). The other point is I felt I’d already experienced the agency life and maybe this is/was too cynical but I thought any other big city, office job would be more of the same thing, just a different flavour, and I wouldn’t be happy with it for long. The next thought was that it would then be the same question of going down a road I’ve already traveled whether I was in London, Paris, Shanghai, or Singapore.

The real exciting challenge was certainly doing my own thing and choosing to carve a path rather than walk one. I’ll admit I had the idea in the back of my mind, I was already set up as a sole trader in the UK given I’d done some extra freelance work the previous year and I’d made sure I had everything ready if I chose to go that way. Based on that I took the plunge, did a quick return trip to Hong Kong where I had started my trip and had left my laptop with one of my best mates James. I picked up my laptop, had some fun in HK for a few days and then went to back to the Perhentian Islands. I made good friends there, I wanted to keep scuba diving, and I thought if I was successful at working by the beach then I could definitely work anywhere. The first chapter of my travels was complete and a a new one had begun.

I could see three main options:

1. Come back to Europe and look for a new full time job (most likely as a planner in another agency)
2. Stay in Asia and look for a full time in one of the main business city platforms (Singapore, Shanghai, Hong Kong). Similarly Australia was another option in the same style
3. Go freelance full time, and while at it do it remotely and keep wandering.

A year into being a professional wandering planner I can tell you the experience so far has been mind-blowing and amazing.

A few things about my experience of becoming a digital nomad:

First, it’s damn tough.

You’ll need high doses of discipline and self-confidence with a side of stubbornness. Nobody is watching after you, you’re responsible for your own work, revenue, AND you may well be in a physical environment with many distractions, where everything is telling to just go and sit on the beach, forget about work. And I’m working online, so a LOT of distractions going on there too. If you don’t think you can focus and shut out the distractions, this lifestyle might not be for you. By the way, it’s not an innate thing, I believe everyone can do it with more or less training and practice.

For having a lot of freedom, I give up on a lot of certainty. I’ve been through several times of seriously worrying about where the next job was going to come from, not having any idea if or how much money I’d be earning next month or the following, not having enough work or finance visibility to plan my next traveling moves in advance, cutting down on treats, beers, or activities to save money, wondering if I’m doing the right thing or if I’m good enough for it, etc. Mind going berserk and I have to keep managing it, telling those thoughts to shut the fuck up and keep doing my new business contacts.

That’s important: quiet down the thoughts in your mind and look at real world actions, those determine your success – not your thoughts and feelings. In the beginning I had no idea if it would work at all, just going by the sheer conviction others have done it so I could too (and I have a good professional background, I know a few people, and I know what I’m doing job wise).

It does get easier though of course life also throws some curve balls, it’s all part of the ride. There are ways to alleviate some of the uncertainty and I’m working on that now. To start with, unlike me, you may want to start working and traveling with your savings, rather than spend it all and then start thinking about earning some more…

Second, it’s truly amazing. Words barely express how awesome it is.

Of course when I’m just casually talking about what I do, I don’t mention the above points. Yeah, I work on a tropical beach, it’s pretty damn fucking awesome. Throughout last summer when I started I was working in a resort lobby in my bathing suit. I didn’t wear any kind of footwear for about 3 months while on the island. If I’m not working on a project and I’m done with my new business contacts, I can close my laptop and stop working – I can go for a walk, I can go diving, I can go to the cinema, go shopping, have a nap, sleep in, write a blog post, whatever I fancy.

That said I’m rarely completely switched off work, gotta keep those new business contacts up and that pipeline full. If I don’t have any work on, I don’t need to stay at a desk pretending to work. If I have work on, I can manage the delivery schedule with the clients in order to give myself free time. Equally, I can work 16 hours or 12 days straight because the project is urgent and I can. I can take time to work on personal side projects. I get to visit brilliant new places around the world and meet excellent new people. I can set time aside to learn new things and have new experiences.

Some of you might be interested in what I’ve actually been doing behind my laptop. I’m mostly working directly with SMEs and startups these days:

• I spend a lot of time looking for work and keeping in contact with friends and professional acquaintances. ‘Out of sight, out of mind’ is pretty true so I make extra efforts to keep in touch (and I like keeping in touch anyways, I think it’s really important)
• I developed marketing, brand strategy and promotional tactics for a Kenya / US based Luxury African safari tour operator intending to develop a brand and service selling directly to people rather than competing on costs only with wholesale tour operators
• I worked on the launch strategy of a new Facebook social game of a small game development studio based in Hong Kong – really interesting stuff to get into
• I devised a brand and B2B strategy for a new mobile company in Nigeria who have secured one of the few mobile banking licenses recently granted by the government. Very interesting piece of work.
• I worked on two pitches (fairly large banking and energy clients) for an agency in Trinidad & Tobago. First pitch was won, still waiting on news for the second
• I developed marketing plans / strategies, brand or business advice for a bunch of startups, in the US, in Australia, in Europe, Singapore, and working on very different industries (film production, travel & tourism, education, etc).

I’ve also started on a bunch of personal projects and ideas though haven’t achieved much with any of them so far. That said there is one I’ll be talking about soon and is pretty exciting. Last year, I joined Heather’s team to help with crunching data for the Planner Survey.

This year, we are working on the idea of an online network for planners (widest sense of the term) to meet up in different countries while traveling, may it be for couchsurfing or having coffee. Heather had announced this as a Couchsurfing.org group but we’re looking on a new platform right now and we’ll be announcing it soon for a sort of soft launch until the Planner Survey later this year.