Milles/Shutterstock

Milles/Shutterstock

You can’t be too prepared.

I understood that in the abstract sense — who doesn’t? — but it wasn’t until one day exactly 20 years ago that I learned what it really meant. That’s the drizzly, bitter cold Northern California day I discovered I was broke.

I lived in a rat-infested tool shed that had been turned into a spare bedroom in a run-down part of East Berkeley. Down to my last $20, I trudged up to Telegraph Ave., to visit my bank. There, an ATM delivered the bad news dispassionately: I didn’t have enough money in my account to cover next month’s rent.

Come March, I’d be homeless.

I’d taken an enormous risk, leaving my job in New York to become a freelance writer. But fortunately, I’d also taken with me the best advice I’d ever gotten: Not just to be prepared, like a Boy Scout; but that it’s impossible to be too prepared.

Only a few months earlier, when I told my friend Charlie Leocha about my plans to go independent, he shared with me the 90/10 rule of freelance writing. Many try, but few succeed.

“Within six months, 90 percent of the people who go freelance return to their 9-to-5 jobs,” said Leocha, a veteran writer himself who at the time owned a publishing company.

“How do I not become another statistic?” I asked.

On paper, I had a good job as a section editor for a travel magazine. But in practice, the workplace was unbearably toxic. I couldn’t imagine coming back — ever.

“You need to have at least six months of work lined up,” he said, adding, “you can’t be too prepared.”

Before I tendered my resignation, I asked everyone I knew if they’d let me write for them after I left on Jan. 1 — a date I’d carefully chosen because I figured no one gets fired on New Years Day, so it would look as if the decision to leave was mine alone. By the time I landed in San Francisco, I had assignments lined up through June.

Don’t just prepare — overprepare

I didn’t know it in 1994, but over the next few years I would specialize in a particular kind of journalism: consumer advocacy — specifically, helping travelers. You don’t have to be an expert to know that calling your hotel to confirm your booking or verifying that your flight leaves on time is a sound practice.

The value of being too prepared can’t be overestimated in my line of work. Over the years, I’ve dealt with literally thousands of cases that wouldn’t have happened if a traveler had just picked up the phone or logged on to a website to verify a few details.

In my new book, How To Be The World’s Smartest Traveler the value of preparation is a common theme. But it wasn’t until I worked on my bonus chapter — interviews with the 24 smartest travelers in the world — that I understood the value of being truly prepared.

One by one, serial travelers from Pauline Frommer to Rolf Potts underscored the importance of careful planning. And they don’t just plan; smart travelers overplan.

For example, many travelers will buy a guidebook before they go on a trip, but smart travelers purchase several guidebooks (you’re welcome, Pauline) and find online reviews and consult a trusted travel advisor and they ask friends for advice and they talk to a local. Put it all together, and you have all the makings of an incredibly smart trip.

A happy ending?

If you read my stories about consumer advocacy, you probably know that my favorite endings are the happy ones. The traveler gets an apology and a refund from a hotel or cruise line then rides off into the sunset.

But in travel, as in life, you don’t always get a happy ending.

Even with all the preparation in the world, things can still go wrong. That’s what the rest of How To Be The World’s Smartest Traveler is about: dealing with the inevitable bumps on the road.

They don’t have to ruin your trip, by the way. In fact, they can make the journey more interesting and rewarding, because overcoming adversity, as my dad used to say, can be a character-building experience.

My story does have a happy ending. All those assignments I’d asked for before leaving my job paid off. After a week of teetering on bankruptcy, I received one check that covered the rent, for a story I’d written in early January. A week later, another check arrived. I could afford groceries!

I was in the 10 percent. Thanks, Charlie.

Fast forward to today. The support of readers and editors who share my passion for advocacy have propelled me to a nationally-syndicated column and a job as the reader advocate for National Geographic Traveler. A network of trusted friends helps me mediate tens of thousands of cases every year.

Next month, Leocha, who went on to become one of the most influential policy advocates for travelers in Washington, is joining me to create a new membership organization called Travelers United.

I’m prepared for anything.