To kick back on a Caribbean beach with a margarita in one hand, a book in another; to curl up around the dying embers of a winter fire in a log cabin nestled in the Alps; to get lost in the crowds around the banks of the Ganges in India – and find yourself in the process…

That’s the dream.

This is reality: 8 hours of grueling work every day, 14 days of vacation time a year, and endless weeks of worry about bills, debts and watching the best years of your life waste away behind a computer screen.

Since you are reading this, you obviously care about traveling and hold a full-time job that keeps you from traveling.

In this post, I’ll talk about how you can travel while still maintaining a full-time job – and not lose your sanity.

1. Quit your job

Err…what?

I’m not being facetious: the easiest way to travel with a full-time job is to not have a full-time job at all.

When you free yourself from the yoke of a job, you realize you can travel anywhere, anytime.

“But Jay”, you say, “how do you make the money for traveling?”

Good question. For this you have three options:

• Make tons of money, invest it in safe but high-yield assets, then live off the interest.
• Get a job where you can work from anywhere.
• Start a business you can run from anywhere.

Unless you have a rich uncle with the last name “Deeds” who left you a fortune, option #1 is out of the question.

This leaves us with option #2 and #3.

Option #2 is amazing…if you can get a job like that. Fortunately, letting people work remotely is an idea that’s taking root among companies big and small. Not a few startups are even running entirely distributed teams (including WordPress, the blog this, and virtually every popular blog runs on).

If you’d prefer option #2, I highly encourage you to check out this blog post by one of Buffer’s employees (a startup with a completely distributed team).

As for option #3, this is what this blog is all about. Unfortunately, this is a topic too vast and too deep to delve into here. Watch this space for details.

 

2. Make complete use of vacation time

If you’re like me (back when I had a job, that is), you get around 15-20 vacation days a year.

I know that that’s around 350 fewer days than you’d like, but 15-20 days is what you have to work with.

If you plan smart, you can easily stretch these 15 days into 25-30 by utilizing long weekends and scheduling trips around vacations.

For example, let’s say you have a long weekend coming up and four days of vacation time left in the year.

Utilize four days of the long weekend (starting Friday evening), plus four days from the next week, and you’ve suddenly earned yourself a grand ten days of vacation time (well, 9.5 to be exact) – Four day long weekend + four day vacation + two day weekend.

That’s good enough for a trip to France, Italy and back!

 

3. Turn business trips into vacations

The secret of successful travelers is that they don’t wait for vacation time to start traveling.

Take business trips, for instance. You pack your bags, hop onto a flight, check into a hotel and find yourself in a new city. After you’re done with the business part of the business trip, what’s stopping you from exploring the city and doing some touristy things?

This is why I like to schedule my business trips just before weekends. This way, I can get done with the boring bits and head out to the city and be back in the office by Monday morning.

Sure, it gets hectic, but it also gives you tons of additional travel days every year.

(Plus, you can get your company to pay for your hotel over the weekend as well. Some managers might frown upon it, but most large businesses won’t care at all).

 

4. Master the art of travel-negotiation

If you’re a traveler (and not just a tourist), you travel to understand the world, and to understand yourself.

I have never met a single person who wasn’t changed by extensive travel. It makes you calmer, stronger, and overall, a better human being.

This is how I would pitch my travels to my manager when I was trying to negotiate additional paid leaves. “Dave”, I would say, “it would make me a better person – and a better employee”.

7 times out of 10, my manager agreed. Smart bosses know the impact a vacation has on employee performance. If you work with bosses who care about long-term results, you can usually wiggle out extra vacation time by pitching your travels as personal development.

If they’re still not convinced, show them this article about the benefits of travel.

(And if you have bosses who care only about short-term results, it’s time to find a new job).

 

5. Explore everything nearby on weekends

I know the typical urge is to wind-down and relax on weekends, but for the incontrovertible (I learned that word around 8 minutes back!) traveler, weekends present an opportunity to explore everything around you.

If you live in a densely populated region such as New York, it’s all the better: you likely have hundreds of unexplored destinations within half a day’s distance.

The key to successful weekend travel is energy management. Your time is limited, your energy even more so. You want to reach your destination and still have the energy to explore.

This is why I recommend the following tactics to make the most of your weekends:

• Fly, instead of driving. Sure, it will be more expensive, but you will arrive at your destination without depleting all your energy points.
• Bike, instead of walking. Nearly every major city has some sort of bike sharing program these days (especially if you are in Europe). Most travelers like to walk around. This is great when you have time, but if you just have a weekend, I recommend picking up a bike instead. You’ll save tons of energy and see more of the city.
• Plan ahead. This is true for most things travel, but even more important for weekend travel. I like to book flights weeks, even months ahead (don’t fret about work – you always get stuff taken care of in time when you know you have a trip planned ahead). You can get some very steep discounts this way. For example, I’m in Asia right now and Air Asia is offering flight tickets for as low as $15. The only catch is that all flights are six months from now.
• Explore aggressively. Get a map of your local area, a start marking every place you want to see within the next 3 months. I use a real map and a red marker for dramatic purposes. You can use Google Maps instead. Once you have a list of destinations, sort these by distances. Then start attacking the furthest away the earliest.
• Leave some plans for last. I hate searching for hotel rooms. It’s the biggest bane of my travel life. So some time back, I decided to say “screw it”, and book hotel rooms at the spur of the moment. I use apps like Hotel Tonight to find deals in my city. I usually don’t get the kind of rooms I’d really want, but the time, effort and money saved is well worth the reward.

 

6. Take a fakecation

This ties in to option #2, but if you work a job where you can work remotely without anyone really missing you, go ahead and head out on a vacation while still doing your work.

Diana from Just Wanderlust calls it a ‘fakecation’.

I call it being smart.

If you can do your job remotely, it shouldn’t matter to your boss whether you are working from your home or a hotel in Chiang Mai, Thailand. Talk to your boss about the possibility of working away from home. Use the “personal development” strategy I outlined above. Allay their fears and reassure the boss that your work will see no drop in quality (in fact, it might actually improve in quality – as this study by Harvard Business Review points out).

It also helps if you already have a stellar working record. Bosses are much more amenable to hearing outrageous ideas from top performers than people scraping the bottom of the barrel.

 

7. Take more drastic measures

If all above fails to scratch your travel itch, you might have to take matters into your own hands and quit your job.

If you decide to do that, keep tabs on this space.

I’ll teach you everything I know about building a life and a business working anywhere in the world.

Including firing your boss and living a life of travel.

 

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