Classic lessons from Che Guevara on how to truly have an Adventure (and perhaps discover a life purpose fired by compassion along the way)

Mark Jacobson
Grey Beard Adventures
8 min readMay 30, 2021

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When he was 23 and not yet a revolutionary, Che Guevara set out on an epic 8000 km (5000 mile) nine-month journey — by motorcycle, ship, horse, raft, and foot — across the Americas. He kept a journal which later became a book about his travels, published posthumously as The Motorcycle Diaries: Notes on a Latin American Journey.

It has since become a classic, widely regarded as one of the most cited and inspiring — as well as informative — tracts on adventure and what I think of as transformative travel. (If you saw the movie and/or the documentary, those are Hollywood renderings that stripped the account of most of its wisdom. Read the book!)

Fortunately, I read it just prior to a small adventure of my own — a solo motorcycle journey up the spine of Central America and back. The book blew me away. I didn’t follow all the lessons described below, and none certainly to the extent that Che did. But his extremes and ideals inspired me to take more chances and embrace the unknown, ditch a lot of the meticulous prep, and just ride, winging it as I went along.

These lessons though aren’t meant to be so much a prescription for how to have an adventure. They will be too extreme for most people (including myself.) Rather, I think they’re valuable as inspiration for what we can accomplish when we resolve to infuse our own journey with more risk-taking and authenticity.

ON ADVENTURE
(all page references are from the Kindle version of the book, The Motorcycle Diaries: Notes on a Latin American Journey)

Some of the best adventures are decided on the spot.

In this excerpt, Che relates how he and Alberto Granado Jimenez, his traveling partner, decided on their trip:

“Why don’t we go to North America?
North America? But how?
On La Poderosa [the motorcycle], man.

The trip was decided just like that, and it never erred from the basic principle laid down in that moment: improvisation.” (Page 33)

Set your departure and destination points, and forget the rest.

Don’t plan (beyond what’s absolutely necessary) the intervening steps. Go from day to day. In fact, if you overthink it you might shrink from it.

The first commandment for every good explorer is that an expedition has two points: the point of departure and the point of arrival. If your intention is to make the second theoretical point coincide with the actual point of arrival, don’t think about the means — because the journey is a virtual space that finishes when it finishes, and there are as many means as there are different ways of “finishing.” That is to say, the means are endless. (Page 37)

The enormity of our endeavor escaped us in those moments; all we could see was the dust on the road ahead and ourselves on the bike, devouring kilometers in our flight northward. (Page 33)

Don’t overprepare, don’t overthink it, don’t turn it into a textbook.

Skip the reading of all that admittedly expert advice in guidebooks and travel forums on countless websites. Don’t sweat the gear too much, looking for the absolute best. Don’t pack for every eventuality. Instead, accept that you’ve got just enough covered and that you’ll make up the rest with your wits and resources (and helpful people) along the way. Yes, you will probably confront unexpected challenges — challenges that more planning might have prevented. But then you might also have avoided the exciting process of soul stretching and strengthening that comes from meeting and overcoming them. Those unknowns turn a trip into a real, invigorating adventure.

Don’t pay attention to the urgent appeals from friends and family.

They will for sure tell you to be sensible, be safe, scale back. “For God’s sake, if you want ‘adventure’, take the zipline in Cozumel! Why does it have to be the Congo?!”

Appreciate and live with the fear.

[Fear is] one of the few experiences which makes you value life. (Page 163)

With their motorcycle dead, they took to other forms of transport, like this raft they built themselves.

Expect things to go wrong, or different from planned, on a daily basis and just ride with it.

(In fact, if this isn’t happening at all — and assuming you are seeking adventure — it might be a sign to push out more, take more risks.)

Almost every page of the book details some mishap, unexpected obstacle or setback. But instead of a ‘poor us, see the woe we went through’ that you often find in travelogues, Che gave the events a unique spin — it was precisely these setbacks that made their adventure, an Adventure! I could pick from hundreds of examples, but here’s just one about the number of crashes they had on their motorcycle — in one day!

A fine sand covered part of a bend and — boom: the worst crash of the whole trip. Alberto emerged unscathed but my foot was trapped and scorched by the cylinder, leaving a disagreeable memento which lasted a long time because the wound wouldn’t heal. A heavy downpour forced us to seek shelter at a ranch, but to reach it we had to get 300 meters up a muddy track and we went flying twice more. Their welcome was magnificent but the sum total of our first experience on unsealed roads was alarming: nine crashes in a single day. (Page 39)

The tighter the budget, the steeper the risk and challenge — but also, most likely, the greater the rewards.

Che and his partner had little money. They occasionally even went hungry. They relied a lot on the donations of food and lodging of people along the way, as well as a bit of income from part-time work. However, they didn’t let this distract or overwhelm them from the travel itself, or from the wonders and people they met along the road. Instead, this lack gave them the sweet reward of camaraderie with the poor, and a revelation about a world lived by so many, but unknown to them.

We were at the end of one of the most important stages of our journey, without a cent or much chance in the short term of making any money, but we were happy. (Page 143)

We’re not terribly poor, but explorers with our history and stature would rather die than pay for the bourgeois comfort of a hostel. (Page 156)

Any house we come across that has a garden, we seek food, lodging and whatever else is on offer. (Page 50)

From the hardships — the challenges met and faced — a delicious hardiness and confidence will come.

[We] felt incapable of making any decision but clung to the thought that no matter how bad things became, there was no reason to suppose we couldn’t handle it. (Page 153)

ON THE TANTALIZING POSSIBILITY THAT TRUE ADVENTURE WILL LEAD TO A LIFE OF PASSION AND PURPOSE — ONE FUELED BY THE FIRE OF COMPASSION

What makes this book a classic isn’t the travel or even the adventures Che experienced. Others have done the same, often with much more arduous and perilous travel. Instead, its greatness lies in portraying how this experience helped transform Che into the revolutionary he became.

As he journeyed across the Americas, he met, interacted, and even lived with many people who were living in desperate circumstances — poor, oppressed, voiceless, beaten. He also experienced some hunger and deprivation of his own. Both were new experiences for this young medical student from a prosperous Argentine family, and were crucial to his transformation.

Some of the most eloquent passages in the book are Che’s discovery and growing empathy for people living in poverty, living in dire conditions imposed on them by history, by prejudice, by the greed and cruelty of others, by an economy rigged in favor of the few over the many.

In the way I traveled… I came into close contact with poverty, with hunger, with disease, with the inability to cure a child because of a lack of resources, with the numbness that hunger and continued punishment cause until a point is reached where a parent losing a child is an unimportant incident, as often happens among the hard-hit classes of our Latin American homeland. (Page 167)

In general they didn’t try to communicate with us, as is typical of the subjugated Araucanian race who maintain a deep suspicion of the white man who in the past has brought them so much misfortune and now continues to exploit them. They answered our questions about the land and their work by shrugging their shoulders and saying “don’t know” or “maybe,” quickly ending the conversation. (Page 43)

[The campesinos’ appreciation sprang from the fact that we never wore overalls or gloves, that we shook their hands as we would shake anybody’s, that we sat with them, talking about all sorts of things, that we played football with them. It may all seem like pointless bravado, but the psychological lift it gives to these poor people — treating them as normal human beings instead of animals, as they are used to — is incalculable and the risk to us extremely low. (Page 145)

It is there, in the final moments, for people whose farthest horizon has always been tomorrow, that one comprehends the profound tragedy circumscribing the life of the proletariat the world over. In those dying eyes there is a submissive appeal for forgiveness and also, often, a desperate plea for consolation which is lost to the void, just as their body will soon be lost in the magnitude of the mystery surrounding. (Page 7)

It is at times like this, when [one] is conscious of his complete powerlessness, that he longs for change: a change to prevent the injustice of a system in which [the poor suffer needlessly]. (Page 70)

I knew that when the great guiding spirit cleaves humanity into two antagonistic halves, I would be with the people [the poor, the campesinos, the oppressed.]…I steel my body, ready to do battle, and prepare myself to be a sacred space within which the bestial howl of the triumphant proletariat can resound with new energy and new hope. (Page 164)

The potential lesson here — for those of us craving more purpose and meaning in our lives — is adventure that includes intimate contact with the misery and suffering of others can in turn ignite a compassion, kindle a burning desire to dedicate your life to a cause far greater than yourself. And from what I’ve seen, that psychological transformation is a most fortunate and blessed miracle.

Whether you agree with the political solution that Che believed and fought for — communism (I don’t) — you can still admire the deep empathy he developed for the poor, and his choice to get in harm’s way and battle (and ultimately die young) for their sake.

From what started out as a bold adventure by (some would say) a foolhardy young man, sprang a life that defined the word “passion,” fueled by genuine, selfless compassion. Who could ask for more than that?

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Mark Jacobson
Grey Beard Adventures

Adventure-Seeker. World-Explorer. Curator of Practical Wisdom. Entrepreneur, Strategizer, Writer. Joyfully circling the planet on my little Honda 250. :)