You have the most information when you’re doing something, not before you’ve done it. Yet when do you write a plan? Usually it’s before you’ve even begun. That’s the worst time to make a big decision…

Give up the guesswork. Decide what you’re going to do this week, not this year. Figure out the next most important thing and do that. Make decisions right before you do something, not far in advance.


I asked a couple of weeks back via a survey how I might be able to help out you foxy Disrupting the Rabblement readers. It seems quite a few of you would like to know more about planning, particularly as regards work and travel.

  • How do I make money on the road?
  • Is it difficult to organize boats/trains/buses?
  • What about visas?
  • Should I have a big savings cushion before setting out?

I had all those questions and more before leaving home last September. And I’m glad I didn’t wait around for the answers, because I’d probably still be waiting. I’ve found that most solutions present themselves when needed, not months in advance when the problems exist only as hypotheticals.

Yes, it’s smart to consider what might go wrong and to take precautions. Buy insurance. Avoid dark alleys. Let someone know where you’re going.

But at the same time, know that all the planning in the world won’t prepare you for real life. Actually living it is the only way to learn.

Self Trust

Instead of the questions above, a better one to ask is this: How much do I trust myself?

More specifically:

  • How well do I handle uncertainty?
  • Can I be frugal when I need to be?
  • Am I a good judge of character?
  • Can I make friends easily?
  • Do I stand up for myself when I need to?
  • Can I stay cool in a crisis?
  • Am I willing to make mistakes and learn from them?

These questions hint at the preparations you most need to be making.

Instead of spending an entire afternoon trying to figure out which bus will take you from Bucharest to Istanbul three months from now, mosey on down to your local station and hop on the next bus out of town. Strike up a conversation with whoever sits near you, get off after an hour, then find your way home.

Instead of working another hour of overtime to save an extra thirty bucks, call up your credit card company and convince them to waive that late fee. Then cancel your cable and go dance sober at your buddy’s birthday bash.

Those are just examples of course. Anything that pushes you out of your comfort zone is good. Whatever helps you embrace uncertainty, build social skills, grow more assertive, know yourself better… go do it.

What you’ll gain will be infinitely more valuable than any well-researched itinerary or carefully considered business plan.