Question from the comments:

I see you travel a hell of a lot, but you say you are a freelance writer. To afford all this globetrotting you do (aside from the trips paid for by magazines/conferences asking you to speak) is there some resource or site that you find cheap travel deals on? I'm about to go into hardcore globetrot mode myself and I need some money saving info.

How do I keep my costs down travelling? Complicated. And if I was doing a better job, I wouldn't have the credit card debt I have.

There's time and there's money. Generally, the more time you are willing to spend, the less money you'll need. The more successful I become in my work, the more time is precious to me. Increasingly, I pay money instead of time to travel.

If you have time, but not money, think creatively about routing your trips. Fly from unpopular airports. Fly on unpopular dates. Go to places in the off-season, when hotels and flights are cheaper. Travel part way by plane, part way by bus. Definitely stay with friends, family or even strangers. If the point is to go, to explore, and not necessarily to be somewhere for an event, your time flexibility is your greatest asset for saving money.

Sites like Orbitz are aware of this - they sell plane tickets and they can find you a cheap cheap fare if you are willing to a) travel from any airport nearby and b) travel within a wide date range.

I don't buy many tickets on Orbitz. I buy nearly all my plane tickets from United. There are a couple reasons there. One, San Francisco is a United hub, for international and domestic travel. So is Chicago, where my parents live. I can go straight from SFO to Tokyo and Seoul and London. It's convenient for me.

But also, I fly routinely with United because I realized that I could exchange my loyalty for comfort. Flying with them, I accumulate mileage credits. I have been a 1k ranked flyer, because I went back and forth to Japan on $500 and $600 tickets. Cheap coach tickets and I was able to occasionally upgrade them to business class. I'm like a United Airlines leech. But whenever I fly somewhere, I try to fly with them, because it might enable me to be more comfortable, and I know the system. I buy their cheapest tickets. But I always buy their tickets.

Worst case, I'm paying a bit more. I don't think I ever pay more than $100 premium to fly with United. Sometimes, I could save $80 if I flew America West ("Worst"), and I had another layover. It's not worth it to me anymore. I'd rather arrive somewhere earlier, or just feeling better. I don't do many redeye flights. I enjoy JetBlue - they're a nice mix of efficient and comfortable, verging on fun. And cheap. And convenient - working out of Oakland, my nearest airport.

Joining a frequent flyer program extends the value of your money. I belong to every frequent flyer program run by the major airlines, hotel chains, and rental car places. Each time I travel with them, I'm paying credit into a pool that might someday save me money, or make me a bit more comfortable. It's my impression that you are taken more seriously as a customer when they see you have a relationship (a marketing relationship) with the company. So even if you buy cut-rate tickets off cheap web sites, and you're flying with a different carrier each month, subscribe to their travel networks. Especially if you are flying overseas - holy smokes, one round trip between the US and Asia is enough to get you a free domestic US plane ticket on some airlines. You can browse the forums on FlyerTalk, where people figure out how to maximize money and mileage within Frequent Flyer programs.

A lot of cheap travel comes down to circumstances - so my specific vendors might not be useful for you. Ultimately, it's about flexibility. As you globetrot, you're likely to discover that whether you're waiting for an international flight departure during a blackout or a tree-hewn canoe, you're going to have to wait. More than you expected. Cheaper travel makes for more adventure. More interaction with the environment. More interaction with the locals. Fewer power outlets, fewer internet connections, and occasionally, a feeling of greater risk.

Travel is adventure. That can't, and shouldn't, be helped. I drove to Las Vegas recently for a conference, and I'm driving to San Diego tomorrow, for another conference. Process, not product - what you encounter on your way to death, that's what life is.