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How to Travel Whenever You Want

A few days ago while browsing Instagram, I came across a disturbing video. In it, a coven of drugged-up barely-20 somethings danced in circles around a terrified-looking harpist, inside what appeared to be a mid-sized convention center, the lobsters atop the banquet table equal in number to the chandeliers above it.

Curious as to how such imagery had made its way into my feed—there was no “Sponsored” tag—I tapped through to the poster’s profile: Miami, Vegas and Krug, oh my! I’d followed a trust-fund kid and I didn’t know why.

A glimpse at my direct messages revealed the answer. Seems we live similar lifestyles, the young man had written without explanation, but with a series of flirty emojis. Follow me back?

Knowing my work has attracted such people—further analysis of my social networks has revealed this person is not a fluke—conflicts me. On one hand, it’s as shitty to judge someone for being born rich as it is to judge them for being poor. However, my overarching social mission is to inspire people of modest upbringings (like me) to create extraordinary lives for themselves, so it disappoints me to think I come across as someone who didn’t create his.

Thankfully, today is the seven-year anniversary of the last time I worked a “real job,” which is the perfect opportunity to explain how I went from broke to balling in almost no time. And how you, with hard work, the right strategy—and yes, a bit of pent-up animus toward the 1%—can do the same.

My Story: From Poor and Late on Rent, to the “Pearl of the Orient”

I got a better hand in life than most, having been born white, male and middle-class in the United States. But I drew several bad cards, too—the “gay” one; the “parents who hate each other” one; and the “destined for a liberal arts degree” one—which left me emotionally and financially barren by the time I reached my early 20s, when the “ideal” American is just revving his or her life’s engine.

Aware that I had limited options, I chose the one that seemed to have the greatest chance of success: Moving to the Far East to teach English, as several of my classmates had done. But unlike most of them, I boarded the plane to Shanghai aware that teaching would merely be a means to an end. I spent my days (and nights) off writing for others, first on an unpaid basis, then on a (poorly) paid one.

The rate people were willing to pay me quickly went up—eight months after I arrived in China, I was making enough freelancing to quit my job and set off into the world. While it would take me another 18 months to sell my first ad, and a couple years after that to get my Travel Coaching business going, my perseverance paid off: I haven’t been formally employed since June 6, 2010—seven years ago today.

Robert’s Four Steps to Freedom

1. Diagnose the Problem

I wanted to travel more, but I also lacked career prospects—I needed to address my professional atrophy more than my wanderlust. For most of you, this step will be much simpler, whether you need to increase your disposable income, manage your time better, exit a controlling relationship or some combination thereof.

2. Devise Several Solutions

My “Plan A” worked out, but I had a few back-ups in case it didn’t, most notably the idea that I would teach English in a different country every year until I got sick of it. Indeed, while getting a roommate or trading your car for a bus pass will help you spend less money, you also need to come up with ways to make more, whether you ask for a raise at your current job, or seek out a new one entirely.

3. Turn Ideas Into Action

The job waiting for me across the Pacific presented a perfect storm of opportunity, but none of it would’ve mattered had I not gotten on the plane and worked seven days a week for the better part of a year. If you decide the best way to free up a two weeks for travel is to save your vacation time instead of taking a day or two off every month, you must follow through 100% if you want your idea to become reality.

4. Up the Ante

I continue hustling, even as I earn more from my blog than I ever did at any “real” job; the moment I tick one destination off my travel bucket list, I add another. If dumping your possessive boyfriend or girlfriend allows you to take your first big trip, don’t be afraid to consider that different sorts of co-dependency might be what stand in the way of your next one.

The Bottom Line

It would be ignorant for me to say that “anyone” can live the life I do, but if you have a good passport, a college degree and a firm grasp of the English language, there’s no reason you can’t. Once you identify the issues keeping you from travel, devise solutions and take action to remedy them. Continue raising the bar, both in terms of your travel goals and your life ones, to continue increasing the quantity of the former and the quality of the latter.


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