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.