Better Questions For Those About To Leap

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.

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    1. Enjoyed your questions to reframe what it takes to move into the unknown. Favorite question: “Am I a good judge of character?” Honing this skill will help you so much in life.

      If you desire to travel the world, but have yet to leave the country, plan a short 10 or 2 week trip to a foreign country with a buddy or two. Just get your feet wet and you’ll learn quickly what you’ll need to know when you set out, and what can be left for when you’re on the road.

      • Right on, Mitch. My little hitchhiking adventure through Spain and France last August did wonders for my travel confidence. I saw it as a kind of test run for this big trip to see how much uncertainty I could handle.

    2. This is so true (I think I say that everytime I comment on your posts… but it’s because it IS true, you writing resonate so much.)

      When we left our academic careers and up and left to Edinburgh, everyone else were full of questions. Questions like ‘what will you do for money?’ ‘What will you do for jobs up there?’, ‘what will you DO?’.

      my answer was ‘if we work at it, things will sort themselves out’, and it has. Yes money is a little tight at the moment, but we’re learning to adjust our spending (which we would’ve never learnt otherwise) and we are both so much happier. Happier because a)we did what we wanted and b) we know we’re getting better at adapting to uncertainty.

      my next project is to travel for something like 6-weeks. Hope I may get to rendezvous with you somewhere along the line.

    3. I was full of the same questions last year. I was so desperate to leave my job, but still had debt and credit cards to pay off- and with the wage I was on, it would have taken way over a year to pay this off. A year with no breaks. No holiday. Nothing

      It was only when I realized that this debt is only a shackle if I consider it so, so threw in the towel at my job, and set up my wee little online venture, and left the country with much, much less than a penny to my name.

      Most people let me know how idiotic I was being, but you know what? Right now, 6 months on, I’m earning more than 3 times what I was in that last job, and paying off that debt faster than ever before, while STILL managing to travel as much as I like…

      So, in a nutshell, you’re spot on. These questions are just excuses waiting to happen. Push them to one side, and there’s no reason to put things on hold any longer.

    4. Great post. I am currently battling ‘planning demons’ as I have a trip coming up where I want to deliberately let go of needing to plan so that I can feel the risk, take it, and learn, instead of always being shielded. Tough lesson, and you’re right, only practice will make it easier!

    5. When I went to Barcelona last year, apart from deciding to go only 2 weeks before I did, I didn’t buy a map and just knew I’d work things out myself when I got there, including figuring out how to handle the language barrier.

      I got on fine without any incidents and learnt that I should be willing to let go a little more if I wanted to enjoy myself fully.

      I also remember reading a LOT online about the whole pick pocket problem in Barcelona, even my parents were paranoid about it! However, I knew it was mostly exaggerated and provided I had common sense and kept my wits about me, I wasn’t going to be pick pocketed ( that and anyone wearing pocket pouches may as well as had a huge neon flashing sign attached to them saying ‘ I’m a tourist – ROB ME! ‘ 😛 )

      As for my big trip to Oz, apart from things like how much I’d want to have, insurance where I am going to stay for the first week or so, I’m leaving everything else open. Sure, I have a rough idea what I’d like to do but I know things will change once I am actually there so I’m generally gonna leave things open.

      I’m generally not worried, I know I’ll make things work. I’ve found a way to make things work out for me in the past, there is nothing that can prevent me doing it again.

      • I’ve had the same experience with pickpockets here in India, Adrian. That is to say, nobody’s tried to rob me. And there’s no hiding the fact that I’m a tourist here!

        But yeah, most of those worries turn out to be overblown. Bad shit can and will happen, but like you say, if you keep your wits about you and trust yourself to stay cool in a crisis, things will generally turn out okay.

    6. Great post.. great advice especially for traveling. Nothing beats “wingin in”. No amount of planning can prepare you for the real thing, and half the time it’s more fun to get yourself out of a tricky situation than anything else.
      But planning doesn’t need to be 6 months down the road, planning can be preparing a shopping list for groceries or planning the order of stops on an errand list.
      And with that I’ll leave you with one of my personal mantra’s in life.. The 6 P’s.. Proper Planning Prevents Piss Poor Performance.

    7. My planning is driving me nuts. I have to budget/plan for the equivalent of four adults (my kids are older and cost as much for everything from food to flights). It’s hard enough planning normal days here (even the daily, ‘what will we have for supper’) I wonder how it will be in foreign countries(food/school/sleep/travel/
      clothes/teen angst, you name it). Sometimes I wish I could just take off and do it solo. Sigh. Sorry for the rant, just going crazy here.

    8. In most of my trips I like to have two things planned. The plane flight, when I’m leaving and when I’m returning, and my first nights accommodations. Usually the long flights make it difficult to make good decisions, so at least one pre planned hotel to rest up in before moving on to an adventure.

    9. Your last few posts have been wonderfully inspiring. I love reading about how your growing and changing throughout your travels!

      I’m spending my first time alone in a foreign country(Thailand) and finding the different perspective here to be a real listening experience for myself.

    10. This. Post.

      I’m gonna start my own journey in June 2014, and I know all the planning in the world won’t prepare me for what’s gonna happen on the road. Who knows what will happen anyway?

      It helps that I love spontaneity and surprises. LOVE IT. WITH A PASSION. I love that there are so many “unknowns” in the world for me to discover, to find out about. Cheers to Chaos and Randomness!