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How I Plan my Next Adventure


Turning an empty calendar and a lack of direction into an exciting, rewarding, challenging, money-generating expedition is both easy and difficult.

Here is how I go about making stuff happen.

  • Block off the biggest chunk of time possible. Guard this jealously. Time is so precious and demands on it so numerous. I can always earn more money. I can never reclaim lost time.
  • Sit and daydream. Think of all the places I have not been. Think of all the journey styles I have not done. Pore over an atlas as I pour the coffee. Browse my bookshelves for inspiration. Drool over Google Images and Flickr and Sidetracked.
  • Try to think of a trip that is, for me at least, fresh, novel, difficult and different.
  • Draw up a shortlist of the few plans that currently excite me most.
  • Narrow this list down against criteria such as cost, season, timeframe and potential partners available.
  • More or less settle on one preferred option.
  • Faff around for a while.
  • Send out an email / meet up with somebody / do something that tips me over from day-dreaming about how fun this would all be to actually getting off my arse and making it happen. The tipping point is often small but significant: walking across India was solidified merely by having dinner with a friend’s parents, for example.
  • Buy a plane ticket or whatever is the single most expensive, painful, committing action to take. This is without doubt the most significant and difficult stage of the entire process (hint: it’s far harder than the scary expedition you are worrying about). This single act of commitment is what differentiates dreamers from do-ers. It’s not hard, but it is bold.
  • Run around like an idiot, realising that I have grossly underestimated the time and expense involved in making the trip happen. (NB: I have never looked back at a trip and regretted how much it cost. I have often looked back and regretted not taking a trip. If you want to do something and it feels important, find a way to pay for it. Make it happen. Or do it cheap and embrace the ensuing hassle and suffering). Because I am committed to the trip, I know that it will happen. It might not be 100% perfectly planned for, but that doesn’t matter too much: I have momentum.

These are additional questions I ask myself now that ‘adventure’ = ‘work’ for me:

  • – Will this trip generate good writing opportunities (book or magazine)?
  • – Will this trip generate good photography / filming opportunities?
  • – Will this trip provide interesting new material for my talks?
  • – Will this trip enhance my Expedition CV?
  • – Will this trip build my skills towards a future epic?
  • – Does the trip have a nice, succinct ‘story’?
  • Will this trip impress girls?

And here are questions I do not ask myself, rightly or wrongly:

  • Will this be a ‘first’?
  • Will I get a ‘world record’?
  • Does this fit into a carefully-choreographed plan towards world domination and retirement?
  • Will this trip impress anyone?
  • Do I have the required CV to go do this trip?

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


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Do you have any thoughts on this article? What have I forgotten or got wrong? Please have your say in the comments below…

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  1. Nice piece Alistair! It seems to work like that for us too, searching for ideas, purpose, narrative, an edge, taking little steps that make it more real, then somehow personally or publicly committing past a mythical point of no return.

  2. Yes! Really interesting to get an insight into your planning, especially your questions – I don’t ask enough of them. And I’m glad you put “Faff around for a while.” into the list. People underestimate the importance of faffing in getting things done. If you don’t come back to the idea after faffing, was it ever worth doing and were you ever the person to get it done?

    I definitely run around like an idiot a lot as well. That’s the sort of “planning” that saw me cycling through Northern France in winter, in a t-shirt, shorts and sandals. Brilliant!

  3. Enjoyed that one 🙂 It’s amazing what inspiration you can get when hovering over a map. I personally like to look at the pictures posted on google maps. You realize that there is somethng to see almost everywhere! Where you thought you would travel in a straight line, this function will make you d-tour 🙂

    Also history books do well for me…they are often a lot better than travel guides!

  4. Lena! You know you want to. Some vicarious living for the rest of us!

    It is almost your duty…

  5. Ash Bhardwaj Posted

    Great article Al,

    I especially liked the point about buying the most expensive element – it creates a level of mental investment that forces you to undertake the rest of the admin.

  6. Kyle Jerichow Posted

    Do you earn enough money?

    Right now, I actually earn nothing I am living purely off of my savings. My last job I earned six figures and wasn’t happy at all, and had no time at all.

    I made a decision a long time ago that experience is a lot more important than things, and I have very much tried to live my life like that.

    So in short, no I don’t even have enough to pay my bills, but I can yes that I need far far far less that what I thought I needed a few months ago.

    Do you enjoy your job?

    No I hated my last job. I quit. with no back up plan, just knowing that I didn’t want to to what I was doing.

    Right now I don’t have a job, so I am using my time to think and to take care of things around the house.

    This though is driving me bat shit crazy. I need to get out. I need to explore, and I need an adventure. It is so hard to go from 100 miles per hour with my hair on fire to nothing.

    Do you prefer Saturday or Monday?

    I always loved Saturdays, again why I quit my last job. No I see Mondays as the start of my week. I send out resumes, check up on applications, and am able to have some time myself to think.

    What would you like to be doing one year from now?

    To be honest, I just want to be happy. For now that means doing something bigger than myself and trying to help others as much as I can. That is where I get my biggest drive from.

    My current goal is to walk the coast of the England and Scotland to raise money for various military charities that I believe in. I don’t know how I am going to do it, but my start date right now is scheduled for 1 March.

    Can you make that happen?

    I require little money to do it, I just need some good shoes, a pack and something to make the rain not fall on me while I sleep, I have all of that.

    I have no job or anything like that so I have no excuse not to.

    What would you like to be doing five years from now?

    I want to be in South Africa working as a Safari Guide. Working on my second book.

    Will you make that happen?

    I have already begun selling my possessions in order to raise my savings enough to make this happen.

    What would you do with your life if you were a billionaire?

    I would climb more, travel more, see and experience as much as I could.

    Is it possible to live a modified version of that life anyway?

    It is, and I strive to do it everyday. This comes with varying levels of success, but so does everything in life.

    How much could you cut your outgoings by?

    Right now, I live no frills minus pints at the pub. My hobbies don’t take much money. The only thing I spend a lot of money on is food. Good, sustainably grown food. I could cut down and get rid of it all together, but it is something that I believe in, which is why I spend money on it.

    How much time at work does that equate to?

    To be honest, to much. I spent a lot of years of my life working for something I didn’t believe in for people I hated and for almost no personal time. They canceled my adventures because I was too “crucial,” but then would they just discard me. Any time spent in a job that I don’t enjoy is too much for too little.

    Do you have enough spare time to do the things you really enjoy?

    Right now, no. I am too focused on trying to find work so I can continue my travel, which is what I really enjoy.

    f not, why not?

    Money and responsibility is a bit crushing. I know that I need to make time for what makes me happy. I am working on moving in that direction. The first major step was leaving my last job.

    What takes up a lot of your time but is neither unavoidable, rewarding nor enjoyable?


    Why don’t you cut that/them out immediately, or pay somebody to do it for you?

    I need the to feel connected. I only moved to the UK five weeks ago, so it is hard making friends right now, I am leaning very heavily on my friends back home.

    What mildly pleasant, but pretty pointless things do you fritter too much time doing?

    Worrying about the future. Now I know that it says mildly pleasant, stress to me is pleasant. It makes me think, it pushes me to make the most of what I have, but I waste to much time on it. It makes me stay awake at night, and at points ruins the good times that I am having.

    How many times a day do you check your email/Twitter/Facebook?

    At least 40 to 50.

    How much TV do you watch?

    None, gave that up three months ago.

    What would you like to do more of?

    I want to read, climb, trek, make a difference in people’s lives.

    What motivates you to do something well?

    Having a purpose, knowing that what I am doing makes others lives better, or brings them some kind of fulfillment.

    Who do you envy, and why?

    I can think of several people. They make adventure their job. While they do have desk time, they have so much time doing things that other people dream of doing but are to scared to do.

    They do for a job what I try to do for fun. I want that.

    If you were 100 and looking back on your life, would you be happy with a life well-lived?

    If I died right now yes I would think that I have lived eel. At only 27 I’ve graduated from one of the best institutions in my country, been on five continents (lived on three), been to 46 or so countries, been to war, served a higher purpose than my self and married the women of my dreams.

    What makes you proud, satisfied, and content?

    A hard day’s work and being able to look at myself in the mirror at the end of the day and know that I did everything I could.

    What makes you frustrated, bored, and unfulfilled?

    Serving as a means to other people’s end. Working long hours on something for someone who doesn’t care. Being treated like shit, but relied on for everything important. In essence the job that I quit.

    What would you do if you had more talent?

    I would take more pictures, I would play an instrument, I would leave this world better than I found it.

    What would you do if you had more guts?

    I would climb Everest.

    What would you do with your life if nobody was watching, judging or commenting?

    I would like to think that I have lived my the way I wanted. Though I have made some wrong turns, I have corrected my route and am still driving on.

    What are you going to do about all this?

    Step 1 was quitting my job. Step 2 was moving to the UK. Step 3 is unknown. Step 4 is sustainable happiness.

    Now if I could just figure out what Step 3 is, I would be set. I hope that my adventure helps me see clearer.



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