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Freelancer? 5 Secrets to Travelling and Working

As a freelancer, you’re able to capitalise on some huge benefits — remote working and flexible schedules, incredible control over your income, and work that isn’t just for money’s sake, but interesting, fulfilling, and fun on its own.

If you’re aiming to escape a self-imposed office hell, don’t jump the gun.

Thousands of freelancers leap into remote work every year, and a large number end up walking away with bad experiences and negative perception.

It’s a preparation game, and without the right amount of time invested in structure, motivation, and organisation, it’s very easy for a working vacation to turn into a nightmare.

Freelancer travel tactics

These five tips, tactics, and strategies can help you work effectively while travelling or living abroad.

Whether you’re aiming to earn 24/7 — enjoying the income from freelance contracts wherever you may be — or simply in the mood to continue generating income while enjoying a change of scenery, apply these five strategies and you’ll find yourself which a greater chance of success.

1. Create a schedule, test it, and stick to it

Every freelancer has experienced a self-engineered lack of motivation.

You wake up at midday, sink in behind your work desk, and end up wandering off to bed several hours past midnight.

It’s a product of our profession, and it’s one that can become highly unproductive, especially when paired with a lifestyle that allows you to travel on demand.

Creating a schedule is vital for success as a travelling freelancer.

We’ve all experienced downtime and weeks of poor output.

Our earnings slump and the amount of power we seem to have over our businesses appears to diminish instantly.

Without a clear structure to keep us grounded, focused, and alert, it’s quite simple to fall out of sync with our work and lose long-term focus.

So create a strict, simple, and productive schedule.

Spend weeks following it, observing your output and determining how effective the schedule is for you.

Experiment with other work arrangements until you find one that fits, one that you’re not tempted to stray from.

The temptation to ‘adapt’ your schedule to your lifestyle will grow tenfold once you step out of the office — eliminate it by creating a work arrangement that you’re comfortable and productive with.

2. Be honest with your clients and customers

Dishonesty will cost you far more than a single upfront mistake.

There are some classic telecommuting stories out there — anecdotes about cross-continent work arrangements and major discrepancies between what a client thinks is going on, and what’s really going on behind the scenes.

The problem with these deceptive ‘I’m in the office’ stories is that they’re not crisis-proof.

As a freelancer, you have the power to slip away from their city, country, or continent without needing to alert their major clients, but doing so isn’t a great strategy.

When a major setback occurs, you’ll be left without any way of explaining yourself, any method of rearranging your work, or any possibility of honest contact with your clients.

So be upfront and honest, and accept that an unusual work arrangement could cause you to miss out on contracts, appointments, and opportunities.

There are thousands of potential clients out there with no interest in having their contracts managed remotely — fighting for their approval and bidding for their business is nothing but a waste of time; focus on business that works for you and you’ll end up with a more effective remote working arrangement.

3. Test, analyse and change before you commit

In 2008, some of the world’s largest companies dramatically reduced their advertising budgets, pushing thousands of designers, artists, and creative people out of their positions and into unemployment.

Most people stagnated, searching for the same positions straight away with little progress, though a small percentage of those thrown out of work adapted to their new situation and found their own opportunities.

It’s a rough transition, and it’s one that almost every freelance worker has experienced before.

The temptation to fall into old patterns of behaviour is difficult to fight, and it’s a particularly alluring option when we find ourselves in new situations.

Rather than testing and building a strategy before committing, we walk into new fields and opportunities with plans of adapting along the way.

Before you move to an exotic island, sail the world, or drive across a continent, it’s worth testing whether your work arrangement will be effective.

Take small doses at first — week-long vacations with a project to keep you company — and see which parts of your work arrangement work and which don’t.

Then adapt.

Cut out what’s ineffective, focus on your new work situation, and modify your schedule, strategy, and long-term planning to make things less stressful.

4. Have a backup plan ready

"Anything that can go wrong, will go wrong."

Edward A. Murphy

It’s 8PM on a Thursday night.

Your flight from London to Singapore has been delayed for twelve hours, leaving you stranded in a departure lounge and unable to access an internet connection.

In twenty-four hours a major Shopify project is due — one that could lead to future long-term contracts and valuable business.

You have no assistants, no contacts, and no way of submitting anything on time.

What do you do?

Rigidity is important.

It helps us stick to schedules, get work done, and remain disciplined.

It’s also a curse when it encounters surprises and unanticipated events.

Delayed flights, nulled connections, and missed appointments can and will happen when you operate outside the standard work arrangement and creating a flexible backup plan is essential for ensuring that they don’t interfere with your work.

Some experts suggest hiring a reliable assistant, someone that’s able to work without your guidance and stay calm under pressure.

Others recommend keeping in touch with your peers, offering them last-minute opportunities and chances to take care of your urgent appointments.

Whichever strategy you choose, ensure that your work arrangement is both rigid enough to keep you disciplined and flexible enough to allow you to effectively, quickly, and easily work through setbacks and inconveniences.

"The simple willingness to improvise is more vital, in the long run, than research."

Rolf Potts, Vagabonding: An Uncommon Guide to the Art of Long-Term World Travel

5. Invest in reliable equipment

Few things test someone’s patience, focus, and skills like being forced to work remotely, this is amplified significantly when you’re forced to work on outdated and unreliable equipment.

Power cuts change patience from something that’s celebrated into something that’s expected, while unreliable connections can force even the most reference-heavy designer to adapt and work in relative isolation.

However, it’s significantly more common for outdated equipment and unreliable work settings to reveal the weakest points of your working arrangement — the things which have been waiting to go wrong but haven’t found the right setting.

Eliminate the potential for gear to falter by investing in equipment that isn’t just flashy and useful, but highly rugged and reliable.

For permanent travellers, Tynan’s packing list is a good point of reference.

freelancer accustomed to two screens and graphics tablets may find themselves in an unusual position; do you pack it all at the expense of comfort, or force yourself to adapt once out of the office?

While your gear will doubtlessly look different to someone else’s, the main purpose should be the same: maximising reliability and ensuring that you can get things done (so that you can get out and enjoy travelling).

Finally, if you are looking for a travel companion… I highly recommend Rolf Potts’ — Vagabonding: An Uncommon Guide to the Art of Long-Term World Travel as recommended by Tim Ferriss.