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When I was young, I dreamed of getting out of my small town, my dysfunctional family, and cold New England winters to places where palm trees rustled in the wind.
Once I entered the job market my dreams didn't fade a bit, but money was always a problem. The kinds of vacations I yearned for were far beyond my reach.
Not only would they cost many thousands of dollars, but the way I envisioned them, they would also take time. Not just the two weeks' vacation allowance my job gave me, but many weeks, even months. I intuited what I now know for fact. True travel takes time. You can see something of a new place by passing through, but only by hunkering down can you experience its essence.
Was I going to have to wait until retirement to travel? My grandparents-in-law did that, but one of them fell ill on one of their early trips and had to return for treatment. They never ventured out again. I was determined to go while I was young and see the world with the verve and vigor of youth.
Step one: Preparation—position yourself for flight
I quit my job in 1981—33 years ago—and except for a six-month relapse, have been self employed since. I've managed road and rail trips through Europe and England, sailing trips to Taihiti, Mexico, Hawaii, and Greece, dive trips throughout the Caribbean and South Pacific, Cruises to Central America, and am now on my sixth month in Iceland. I've managed to raise and launch a child and maintain my freelance business wherever I roam.
It's not necessary to quit your job if you're already in a company that pays you to travel or has jobs in other cities you can transfer to. But if you're tied to a desk in Peoria and you want to live your dream, it's time to plan your escape.
Mine meant transitioning from a well-paid job as a creative director of a small ad agency to a freelance creative director/copywriter. It took me two years to get my ducks in a row and find the right time to announce my departure.
During the "easing out" period, I made lists, started networking with potential new clients, joined professional clubs, went to industry events, confided in a few outside colleagues, worked on my portfolio (this was pre Internet), and saved money.
This is also the right time to accumulate the tools you'll need to operate on your own, like a high end, fully-stocked laptop and other equipment/software you'll need to function independently.
In addition, spend a few days friending every one of your professional contacts on as many social media sites as possible and commit to keeping in touch with them. Let everyone know you're involved and productive, wherever you may roam.
Step two: Practicalities—hone your skills
If you've saved or inherited enough money to take off now, go, and don't look back. But if you need to keep working, make the most of your time with your current employer. Ideally, you can convert them into your first freelance or consulting client, but that's never a sure thing.
In the meantime, keep networking with outside companies in your field. Even if your current employer takes you on as a consultant, you'll want to have several additional clients lined up. Sometimes there's a company hiatus on outside contractors, so don't take it personally if this happens, just be sure to have a backup plan.
Make a concerted effort to go many extra miles in executing your job while you still have it. Pitch in and be a team player, come in early, stay late, and be super productive. Look for ways to impress management and make your make your boss's life easier.
If you feel you lack organizational skills, take on some project management duties. If you need a stronger grasp on financial issues, befriend some people in the finance or business department. Consider volunteering for additional duties, taking classes to learn new job skills, and making yourself known to the mucky mucks. Even if your employer doesn't become a client, the people you've impressed will scatter far and wide, and will remember your diligence and professionalism for years to come.
Keep saving money. You'll need enough to keep your confidence up and your plan in motion.
If you're offered a promotion at this point, DO NOT ACCEPT IT. This is the best possible scenario. They love you. They want you. Just say, "Freelance." Offer to do the same job as a consultant.
Step three: Timing—leave when they can't afford to replace you
To maximize your chances of landing your current employer as a freelance client, choose your moment wisely. If you work for a small company, you'll have a feel for company economics. If you work for a large company, start reading the annual reports and keep an ear to the ground for news of mild to moderate financial unrest.
Once you've determined that the time is right, call your new industry contacts and let them know will soon be a free agent. Line up meetings, interviews, presentations, and make sure your portfolio and website are up to date.
How to know it's the right time:
- The company is struggling a bit, but layoffs aren't being considered
- There's no one nearly as good as you to promote from within
- Your boss couldn't possibly do your job and hers/his after you leave
Step four: Launch—make clients want you
First break the news to your existing company, if you want them as a client.
In your "I'm leaving, but still available" talk with your bosses and HR, have the financial aspects of your proposal in your back pocket, but focus on the added value you can bring, working from the outside, including fresh ideas, flexibility, and even greater productivity. Without the distractions of the office, you can be even more responsive and focused on projects (even—but don't say this—while lounging on a beach in southern France).
When presenting your services to any potential clients, tell them how they can actually save money by letting you work outside the system, and reassure them that you will be just as "present" as if you were just down the hall.
I'm in Iceland as I write this, working for clients in New York, San Francisco, and Kuala Lumpur. I make sure to be available whenever they want a meeting via phone or Skype and go out of my way to accommodate their needs.
Step five: Untether—out with the old. In with the new.
You can't adapt a traveling lifestyle unless you let go of your "rooted" one. You know, the one tied to mortgages, utilities, and Tuesday night dart games or choir practice. You've got to lighten your load in order to travel, that that will mean some trade-offs.
Whether you decide to sell your house, sublet, or become an occasional house sitter when you're in town, you'll want to reduce your overhead and then allocate that money towards living expenses abroad. There are many ways to live "lightly" in a new place.
With the advent of Airbnb and other online apartment rental services, you can negotiate a short or long term deal with individuals who rent furnished rooms, apartments, and houses anywhere in the world. If you're going to stay awhile, they're likely to be amenable to a reduced rate. After choosing your destination, browse the housing options, book a place to stay, a cheap flight or train ride, and just go. You'll figure out the rest when you get there.
Life is too short not to open your mind to different perspectives, immerse yourself in new cultures, and expand your horizons. You will never be the same, if you do.
Note: The same 5-step process will work whether you're single, a couple, or a family. You'll just need to agree on the details and budget carefully to make sure you can maintain your new traveling life for as long as you want.