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How to Choose Your Adventure. 36 Questions to Hatch a Plan…


You’ve decided you want to do a big journey. You’ve begun saving. You’ve allocated time in your calendar to the trip. Your family and boss know that you’re doing the trip. Nothing is standing in your way. (You have permission to smile smugly at this point.)

What happens next? Well, next you need to work out what you are going to do, and where you will go. It’s time to make a plan.

For many of us, the yearning for adventure comes before having any idea of what it is you are going to do. Until you know something about travel and adventure it can be hard to work out what you want from your trip, and what ingredients are needed to cook up a decent journey.

This was certainly true for me when I started out. I knew nothing about the practicalities of making an adventure happen. I didn’t really know the ways in which my adventure would differ by heading to different parts of the world. I didn’t know very much at all!

I knew only that I wanted to head far away from everything that was familiar. I wanted to do something physically difficult. I had no specific skills I could draw on. Wild places appealed to me, rather than cities. And it needed to be cheap. I didn’t really care what I did: I just wanted to do something!

How then do you begin to narrow down your choices when the whole world is beckoning?

I said that back then I had no idea what I wanted to do, but in fact, if you look again, I actually had quite a few parameters in place already without realising. And though the world is huge, it’s pretty easy to narrow down your options:

  • I wanted to head far away from everything that was familiar: this ruled out exploring the UK or Europe.
  • I had no specific skills. No climbing technical mountains then.
  • I wanted to do something physically difficult. So no vehicles or hitch-hiking.
  • Wild places appealed to me, rather than cities.
  • It needed to be cheap. That eliminated ocean and polar journeys. It also makes made sense not to do the trip in pricey, developed countries.

I could therefore write down my thoughts more clearly than I realised:

  • I wanted to do something difficult, but non-technical, in Africa, Asia or South America.
  • It probably would be on foot or by bicycle.
  • I’md already been to Africa. Asia has better food than South America.
  • Cycling sounded preferable to walking.

And so, without much difficulty at all, I’md narrowed down my plan to cycling in a remote part of Asia.

It is important not to fret about all the adventures that get away. The previous paragraph, explaining the thought process that went into deciding on my bicycle ride along the Karakoram Highway, might sound glib and too-easily dismissive of a thousand other opportunities.

But looking from another angle, it was a series of decisions based upon both pragmatism and aspiration that led to one of the best rides I have ever done. Don’t worry about the ones that got away – that’s a mug’s game. I think often, and very fondly, of cycling over the 4600-metre Khunjerab pass border crossing between Pakistan and China. I could have done a hundred different rides instead of that one. Who cares?! What matters is that I did something that I will always remember.

To help narrow down the sort of adventure that might best suit you, try answering the questions below.

If you already know the person you will be doing your trip with, take them to the pub and discuss the questions over a couple of beers and some pork scratchings. Let’s call this occasion a Vital Expedition Meeting. It is really important to be clear about your plans and goals for a trip before you begin. Dissonance and disagreement brew on journeys when your goals are not aligned.

  1. What is the maximum amount of money you think you’ll be able to get hold of? (Most grand adventures can be done for £1000, but some trips cost considerably more: rowing an ocean, a guided ascent of Everest, a Last-Degree North Pole trip, or a trip into space…)
  2. How much money are you willing to live on each day? An honest assessment of the standard of living you are willing to endure is vital for working out how far you can go on the money you have available. Do you need a hotel and a pizza once a week? If so, you will probably be cleaner and plumper than someone willing to endure instant noodles in a ditch every night, but your trip will also be much shorter.
  3. Are you up for the gruelling, lengthy battle of seeking sponsorship to supplement your funds? If not, you’ll need to wave sayonara (for now) to oceans, Everest and Antarctica (unless you are considerably richer than most of the adventurers you’ll meet on your travels!).
  4. How much time do you have available for your trip?
  5. Do you wish to travel alone, with a friend, or in a group? Why?
  6. Do you want to travel quickly and go a long way, or would you prefer to have a more relaxed schedule with spare time factored in? Why?
  7. Do you want a motorised adventure (cars and motorbikes), a travelling experience (trains and hitchhiking), or something human-powered? Why?
  8. Do you want to have fun (don’t cycle through Siberia in the winter; do cycle through Sicily in the springtime), or do you want to punish yourself for some unknown sin in a former life and have a masochistic misery-fest in the speculative hope that at some point in an unknowable future this will make you happy? Are you searching for Type 1 Fun or Type 2 Fun? Why?
  9. Which appeals most: bicycles, walking, running, kayaking, rafting, climbing, or something else altogether? Why? Which of those appeals least? Why?
  10. Which parts of the world appeal to you most? Which appeal less? Why?
  11. Which environments and climates appeal to you most? Which appeal least? Why?
  12. What time of the year can you travel? This will add some direction to where you can go, depending on what weather you’re looking for. You can find summer or winter any day of the year, but only in certain places.
  13. Do you see this trip as a lifestyle choice (cancel your rent, quit your job, cycle into the sunset) or as a burst of madness away from the humdrum real world we spend most of our lives in (or should that be a burst of reality away from the mad world we spend most of our lives in?), in which case something more shorter and more dramatic is probably a good choice?
  14. Do you have any useful skills? Are you a climber, a mechanic, a linguist? Can you earn money along the way somehow? Does learning something new appeal to you as part of the plan?
  15. Are you looking for the heady excitement of a world-first journey? Why? If so, you’ll need primarily to think of something that appeals to the media and worry about the trip afterwards. Are you looking for something difficult and ground-breaking and meaningful only to you? If so you can come up with any idea, so long as it gets you so excited that you lie awake at night thinking about it. You’ll have to pay for it yourself, ‘“ nobody else will care about the trip but you, ‘“ but perhaps that is OK for you.
  16. Are you a novice or a veteran adventurer? Ask yourself this question only so that you can remind yourself it really doesn’t matter. Of course, if you want to climb a difficult mountain and not merely be hauled up it by a guide, then you’ve got a lot to learn. But whatever trip you do there will be lots to learn, so don’t let that put you off. Some trips require more expertise and experience than others, but that does not necessarily make them ‘˜better’. I have greater admiration for a young person who walks alone from Land’s End to John O’ Groats than one whose parents pay for them to do a last degree North Pole trip for a few days.
  17. Do you enjoy learning new things and putting together complex projects? If not, you might want to stick to something simple like walking or cycling out of your front door and seeing how far south you can get.
  18. Are you more interested in a journey (going from A to B) or a challenge (for example, climbing something, going from A to B in a difficult way, as fast as you can, or some other self-imposed criteria)?
  19. Which adventures that you have read about excite you the most? Why?
  20. What idea can you not get out of your head? Why?
  21. What will make your friends back home most jealous? Why?
  22. What, if anything, is still preventing you from doing all this? Why?

Hopefully this will help you start to get a better idea of what you might want to do. You know you want to go on a big adventure. You’re excited. You’re making plans. It’s actually going to happen!

This is a good time to pause and reflect on the reasons why you are going on the trip and what you hope to get out of the whole project. Many of the reasons for tackling big adventures are intangible, and I’mm certainly a fan of just saddling up and heading off out into the world with no fixed objective, time frame or destination. It’s a wonderful way of watching life unfold and shaping it to be more memorable, colourful and transformative than just staying at home.

But if you are travelling with somebody else, if your trip has sponsors (and therefore commitments to other people), if there is a specific destination or aim for your trip, if you’ll be doing research, trying to get your trip to reach an audience, or if your trip may be dangerous, then it would be sensible to reflect upon these questions. Better still, – discuss them out loud in another IEM (Important Expedition Meeting in the pub). Better still again, – write down your answers so that they are really clear and you can refer to them later. It’s so much easier to do this before you get out into the wild, where your answers will blur and shift and change according to your daily mood.

  1. Why are you doing the trip?
  2. What is the objective of the trip?
  3. What do you hope to get out of it?
  4. What will constitute ‘˜success’?
  5. What will constitute ‘˜failure’?
  6. Does your adventure benefit anyone else but you?
  7. How much do success or failure matter?
  8. Do you have enough time to do the trip justice?
  9. What are you willing to sacrifice for this trip? (cash, time, safety, friendship)
  10. Why are you going solo / with someone else? If you are going with someone else, Are you going with the right person?
  11. How will you deal with one person in the group being faster/slower, happier/sadder, richer/poorer, healthy/sick, etc.?
  12. If stuff goes wrong, can you cope?
  13. Do you have the skills, fitness, paperwork, contingency plans, and emergency procedures necessary?
  14. What will you do with the trip afterwards?

You might also find these posts useful

My new book, Grand Adventures, answers many questions such as this. It’s designed to help you dream big, plan quick, then go explore. There are also interviews and expertise from around 100 adventurers, plus masses of great photos to get you excited.

I would be extremely grateful if you bought a copy here today!

I would also be really thankful if you could share this link on social media with all your friends – It honestly would help me far more than you realise.

Thank you so much!

Grand Adventures Cover


Thank you to the many people who have kindly “bought me a coffee” for just £2.50 as encouragement to keep this blog going.

“Yes, I too would like to donate a couple of pounds to this site..!”


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