• When did you know that this is what you currently want to devote your life to? – Sirena
• When you go off on an adventure, macro/micro, do you feel that you are running towards something or away from something or a bit of both? – Rob
• Being an adventurer do you not miss out on the ‘it all’ to escape from? – Ben
• What do you miss when you look at your peers who took a more ‘normal’ route in life? – Abs
• Did you have to shut down one identity in order to step into this one fully?
• Do you ever feel like you have an obligation to keep adventuring? Do you get tired of this? Ever want to go back to “normal”?
• Will you keep doing what you’re doing? – Alan

I’ve received quite a few questions on a similar theme. They all link quite nicely together into one coherent answer, I hope. Let’s dive in… 👇

Upon returning from cycling round the world in 2005 I was thrust immediately into a semblance of what I do these days –writing a book, hustling for paid magazine articles and talks– through the financial urgency of paying rent. But even then I did not consider this a permanent way of life. I was also busy applying for ‘real jobs’: the Army, the fire brigade, a travel agency, a charity, schools.

[Pause for my favourite interview recollection…

Interviewer: “So, why do you want this job?”
Me: “Well, I’m not sure if I do want it, to be honest. I’d also really like to be a fireman etc.”
Interviewer: “I think we’ll just end the interview now.”
And then he kindly gave me about 15 minutes of interview technique advice! 

Next Interview:

Interviewer: “So, why do you want this job?”
Me: “I’ve always wanted this job because…” 😂]

Fast forward through various bits and bobs and I became a full-time teacher at a school in London. I was also busily writing a book and hustling for paid magazine articles and talks around the margins of my days and in my spare time.

At some point in that year (2007) I realised that I was 30 years old. It was perfectly plausible for me to remain teaching in that school for as long as the entire span of life I had already had! I realised that I could be a great teacher aged 40 or 50 or 60.

But if I still wanted to pursue hard expeditions (I did) then I’d be smart to get on with that while I still had gas in the tank and very few constraints on my life.

I told the school that I was leaving.
“Oh! Where are you going?”
“South Pole.”
“St. Paul’s? Lovely school!”

Cue the exciting terror of waking up on Monday morning with nowhere to go, nobody to answer to, and no money coming your way!

I was firm with myself that if I was going to reconcile this reckless decision with my conventional, sensible inner work ethic, I must earn as much each year as I had as a newly qualified teacher.

I was never under any illusion that I was plumping for an option that was less work.

Yet, equally, I have never since been under any illusion at how lucky I am to have found something this fun, free, mentally and physically stretching, carefree, vaguely useful and sufficiently remunerative. I am a lucky man.

[Quick pause for a VITAL, but usually-neglected observation before people give the “Quit your job and follow your dreams!” speech…

Heed this sentence from the previous paragraph, back when I was a teacher with a pension and a Union rep:

• “I was also busily writing a book and hustling for paid magazine articles and talks around the margins of my days and in my spare time.”

In other words, when I woke up on that first Monday morning to live as a self-employed, self-proclaimed ‘Adventurer™’ I was not beginning from a standing start. I had talks booked in the diary. I had 46,000 miles of stories, words and photographs under my belt. I had self-published a book and done a night-school photography course. I was already in motion.

All that I needed to do now was slam my foot to the floor and pour everything I had into making this work.]

But I also hope that these Working Adventurer newsletters will dissuade you of the notion that this is all that the adventurer’s life contains. I want to show the realities lurking beneath the dazzling turquoise tip of the Instagrammable iceberg tip.

Because there is loads of boring stuff in my life that I love running away from out into the great wide yonder.
The tedium of dealing with hacked websites and the IT problems in setting up these newsletters.
The endless grunt work of writing books before you get to the fun, satisfying parts, the light final edit where I can post a humblebrag photograph of ‘working’ at the cricket or up a tree.
Pointless conference calls.
Faaaar too many emails.
Tax questions I don’t understand that stress me.

Additionally, being a ‘working adventurer’ means that however much I love it, this is only a job. It only occupies part of my weeks’ ration of 168 hours. So I also have all the humdrum aspects of normal life which are appealing to escape from: middle age, folding laundry, traffic jams, pylons, shopping culture, wittering gossip, Covid, Trump, Brexit, climate change et al.

In short, no: I do not miss out on the ‘it all’ to escape from!

I hate the discordance between that need and the practical necessities of my real life which dictate that what I really need to be is a reliable, present dad. At the school gates by 2.55pm, tea on the table, put a wash on, get to gymnastics on time, brush your teeth, get off that screen and read a book…

The friction between these two does not feel like a yin and yang, more like two magnets pushing each other apart and making both sides even more of a struggle. (See My Midsummer Morning for an amusing vignette of me throwing a bicycle over a hedge in a rage!)

I hate that a large chunk of my identity is linked to online approval. And I hate that my income is very much linked to those approval levels. I’m not a President hoping for re-election; I’m a free spirit who wants to cycle to the cafe and have enough money in my pocket to treat my friend to breakfast.

What else do I miss?

• Someone else taking care of my taxes and pension stuff.
• The tacit acknowledgement that they have a ‘proper job’ which doesn’t need justifying.
• A clear demarcation between ‘work time’ and ‘not work time’.
• Being able to go on a bike ride without feeling compelled to turn the experience into a pithy blog post.
• The excuse to meet mates after work for a ‘quick drink’ now and again.
• A less lonely working environment.

But funnily enough, on my very first morning of cycling round the world, I ditched that notion. Crying to myself and feeling thoroughly overwhelmed by what I had got myself into, I decided that I wasn’t going to hide that aspect of the adventure. I would write the truth of my experience. And if people were disappointed by lack of stiff-upper-lip like Ranulph Fiennes, then too bad.

Reflecting back, I’m interested that I was so matter-of-fact about this given that for my entire life I’d always been desperate to fit in, to belong, and above all not to stand out!

So, no. I didn’t shut down one identity. But I do very much separate the strands of my identity. Way back in about 2009 I began only sharing adventure stuff on my blog rather than any old tidbits that interested me. Continuing until the present day I tell the world only about certain aspects of my life – not what I had for lunch (re-heated mushroom risotto, since you ask), what I’m wearing (Hiut jeans and novelty Xmas elf slippers), who I vote for (Green), my house, my family, or anything else that is not relevant to the Working Adventurer side of my life.

Becoming a professional Adventurer felt, at times, like becoming a teenager. There was a lot to figure out, and plenty of awkwardness, mis-steps, brashness and ill-advised hairstyles.

At first I felt far too embarrassed by the notion of self-promotion. (Without that, you can’t be a working adventurer, so you have to either suck it up or get a proper job!) Occasionally I became far too thrusting, earning a well-deserved smackdown or two from gnarled old climbers:

“A lot of folk find this type of self promotion over the top. Might sit alright with folk who don’t know much but there are thousands of folk doing real adventures and just getting on with it. You are obviously highly motivated and talented to your causes but take a tip from me: such statements only throw egg on your face. Sorry to be brutally honest but better you get feedback than think such things are cool. You don’t need to do this; you have an impressive CV. Just enjoy it for yourself.”

Which reminded the weird curators inside my brain about this advice from Andy Kirkpatrick:

“I don’t think most people make a career out of adventure (although there seems to be a raft of career adventures at the moment). All you do is cover your costs and make a little extra, and it takes decades of graft and self promotion to get anywhere near having an income close to that of your pears, and when you stop, get old or injured, then what do you do? My advice would be to get a trade or a career that you can pick up and drop, fill your pot and go away. It’s not healthy to try and make yourself a golden goose.”

But I got myself to a position, fairly quickly, where I think the tone of my output reached an acceptable balance between being interesting, honest, and also loud enough to be noticed. (Correct me if I’m wrong!)

From about the age of 30 then, I found a working identity that was successful in my speaking work and online content. The mistake I made was that I did not allow that ‘adventurer’ identity to evolve as I myself changed over time. By the time I hit 40 the disconnect was jarring.

The growing-up metaphor works well here because, in my work as in my life, I eventually settled into an acceptance of who I was and who I was not, what I was good at and what was best left alone, that I’m not the best but that I’m doing fine etc. In other words, I’ve slowly stepped fully into the identity of being me: both in my working adventurer life, and in the strands of my life that are not lived on the internet. It has been a relief to no longer feel that I had to play some sort of scripted reality-show version of myself online. 

Aside from the sheer madness of feeling that you somehow have to fake your adventurous identity, there’s the win-win bonus that if you really want to tell compelling stories and build a viable audience as a working adventurer, then you are much better off to just be authentic and honest. There’s no need -thankfully- to put on an act to impress people or shut off your identity.

I hate that.

I have felt this as a heavy pressure on my life since I climbed off my bicycle having just cycled 46,000 miles over four years and the first person asked me, “what’s next?”

I feel it still.

I interviewed Ed Stafford for my book Grand Adventures:

“When I got back from the Amazon, everyone was saying “what is your next big expedition? What are you going to do next?” I still find it extraordinary that you can do something that no human has ever done before, and people just consume that bit of information and then move on to what you’re going to do next.

It’s like, who said I’m going to do anything next? I might just go home and have a cup of tea. I personally think that, in terms of massive expeditions, If I haven’t proved what I wanted to prove to myself by walking two and a half years through the Amazon then I’m probably going to be forever chasing it if I don’t look for a slightly different option. I think to try and do a bigger expedition, then a bigger expedition, and then a more dangerous expedition isn’t the way to prove that to yourself. I think everyone needs to not allow chapters of their lives to define them.”

There are certainly times when I would love to end the performative dancing monkey part of being a working adventurer: the knowledge that if I’m to stay ‘relevant’ and keep earning a living from adventure, then I need to keep coming up with clever ideas and shouting loudly about them.

If I won the lottery I would keep going on adventures. I’d keep writing. I’d keep the podcasts. I’d keep doing a few talks (the ones that feel genuinely helpful for an audience), but I would disappear from the worlds of social media and self-promotion for ever. 

Sometimes I do want to ‘go back to normal’. But in this regard I feel like many a middle-aged person with a mortgage and kids to feed and a fear that changing career right now would be folly. I’m certain I am no longer employable for an office environment. My enthusiasm to work in schools has waned. I don’t have many skills beyond the world I already work in. In other words, I don’t know if it would be really possible for me to change path if I ever reach tipping point. So I fear (hope / expect) that I’m destined to be a working adventurer for ever.

One of the most wearing aspects of what I do is telling the same old stories time after time.

Some days I have to take a deep breath at the start of an interview or a keynote talk, strap a smile to my face, and remind myself that of course I need to talk about cycling around the world: without that I’m vastly diminished as an ‘adventurer’. I sometimes feel like Chesney Hawkes. I must have told that tale more than a thousand times by now!

So I am very aware that I am my own golden goose: for as long as I remain interesting and whilst I keep dancing in the spotlight then everything should be fine: I’ll keep earning enough to pay the bills. But what happens when the music stops? What happens when my knees are creaky? What happens when I cannot bear to tell the story of cycling around the world again? I don’t know, yet.

Recently I had reason to listen back to one of my very first podcast interviews, all the way back in August 2008. To my horror I could predict –verbatim!– many of my answers a dozen years later. Because those are STILL.THE.WORD.FOR.WORD.ANSWERS.I.GIVE.TODAY! 

I am much better than many of my adventuring friends (who shall remain nameless) at shaking things up. Every year I sit down, tear apart the slides that I’ve used for my presentations, and begin again with newer stories and fresh insights. But inevitably the best stories and the best photos remain. This means that the best days of my life get distilled down to a handful of snaps and polished anecdotes.

Many of my most wonderful experiences, in contrast, get shelved as they don’t make for such slick schtick. These tend to get muscled out of my memory by the noisier soundbites. So I feel that trips get diluted for me either by telling too much or not enough!

Spare a thought then for astronaut Michael Collins who suffered this fate far worse than me after returning from the moon! Here are a few quotes from his marvellous book:

1. I am going to spend the rest of my days catching fish, and raising dogs and children, and sitting around on a patio drinking gin and talking to my wife.
2. I share with him [Buzz] a mild melancholy about future possibilities, for it seems to me that the list of exciting things to do here on Earth has diminished greatly in the wake of the lunar landings. I just can’t get excited about things the way I could before Apollo 11.
3. If one more fat cigar smoker blows smoke in my face and yells at me, “What was it really like up there?” I think I may bury my fist in his flabby gut; I have had it with the same question over and over again.
4. There is money hanging around, but it is tainted PR money, trading great piles of greenbacks for tiny bits of soul, in an undetermined but unsatisfactory ratio.

For example, the adventures I aspired to arced through gigantic bike rides to epic, elite polar expeditions to sleeping on suburban hills to redefining ‘adventure’ in my life to include playing the violin.

The story-telling moved from emailing a kind volunteer to manually update my blog once a month (a big FTP palaver), to my first Tweet, my first couple of Instagram posts, my first YouTube video, my first podcast episode.

And my income has changed from talks at primary schools to corporate talks (and then disappeared with Coronavirus), from self-published books and mappazines to a traditional big publisher and now to an emphasis on self-publishing to grow a drip of passive income. From whooping at receiving free gear as sponsorship to getting paid a lot for occasionally tenuous brand campaigns, to becoming an ambassador of big outdoor brands (and then quitting as I no longer feel I deserve that).

Writing those last three paragraphs has cheered me up enormously: it shows me that I haven’t just been doing the same thing for 20 years, and therefore there’s no reason for me to feel duty-bound to keep the next 20 years the same. In other words, it frees me to write what I wanted to be the final sentiments of this loooooooooong article.

The times they are (always) a-changing. But 2020 has truly changed so many things. Throughout lockdown I was convinced that if this period did not see you starting that oft-dreamed of hobby, making a leap in direction with your career, or reading that weighty tome by your bedside, then you ought to accept it would never happen! 

I began going on photography walks and asking myself questions about my direction. I began challenging all my assumptions that I held about being a working adventurer and consciously asking myself whether I wanted to hold on to each of them or ditch them (see postscript below).

My conclusion from these musing was that I do not intend to keep being an ‘adventurer’ in the way I’ve interpreted that word for so long (Big trip → Big story – book, talk film → Money → Big Trip).

I’m less interested in macho adventure for the thrill of it.

I am more interested in the natural world, nature, creativity, and encouraging positive change. 

Yet whatever direction this leads me in the years to come, I certainly hope that I will keep living adventurously and pursuing paths that are both thought-provoking and interesting.

Assumptions

I began by scribbling long lists about all the assumptions I hold about my life as a ‘working adventurer’. Then I sorted these into assumptions which were still relevant in my life and helpful, and those which were obsolete, unhelpful or hindering.

I narrowed these down into a few simple bullet points which I could pin above my desk to help me make fresh decisions about the direction I want to go next.

Assumptions to Abandon

❌ I am an ‘Adventurer’
❌ My adventures must define my work
❌ All the work I do has to have an adventure/outdoor element to it
❌ Social media is only for my ‘work’
❌ Regular social media presence is key
❌ 9 to 3, 5 days a week
❌ I have to write one book a year
❌ I ought to have an element of education for kids
❌ I need brand partnership roles

Assumptions to Keep and Nurture

✅ Regular online content is key
✅ This content should scale up into passive income / books
✅ I need a good answer to ‘What’s next?’ [I’m surprised this made it into this column, given my personal dislike of it!]
✅ Living adventurously is my core message / guiding light
✅ Books, ultimately, are the most worthwhile use of my working time