Are you trying to prove something?

In conversation with myself.

Do you think that a bike tour is the gateway to a more interesting life?

Do you think that the interesting things you can see from the seat of a bike make up for all the time you spent at your job, staring at screens, shut inside yourself? Staying up late because you felt unsatisfied at the end of another day spent working, saving up money so you can have an adventure?

Sure there is adventure, and good conversation. Stories to tell, fresh air, exercise, good food. Always a new thing rolling down from the horizon. There’s no denying that a bike tour could bring happiness. But why this particular choice? Any why persevere, through the hard parts — the inevitable rain and cold and hunger, the long empty patches of road where there is no one to talk to, nothing to chew on but your own curious thoughts — and the times when you’re deeply uncomfortable, when you wish for the chance to simply stop and put down roots somewhere, with an urgency that belies it as a human need like food and company… What compels you to spend your limited time on Earth doing this thing?

Is it ego? Are you trying to prove something to yourself?

Imagine you’ve already met your goal; made your journey, and you’re back home in your daily routine again. What have you proved except that you can exploit the available technology in a somewhat unconventional means, to go on what most everyone around you will see as a weird extended vacation? One that most people would not choose for themselves, and would not be able to relate to? Because really, people do not like riding their bikes as much as you do. They will not get it. You seem like a nut-job more than an adventurer, placing yourself in danger on the road, especially when everyone around you is “getting there” faster in a car.

People smile and say “that sounds cool,” and sincerely wish you luck. But make no mistake: They don’t relate. What you’re doing isn’t cool.

Likewise, you can’t be in it for the rebellion, for the “coolness points” of doing something different that sets you apart from others. There’s no happiness in competing for novelty — only a caustic version of pride. No matter how interesting your bike tour actually becomes, there are people all over the Earth who have spent their time doing far more interesting things, far more often, and being so dang humble about it that you don’t even know they exist unless you blunder into them and talk awhile. You will probably meet a bunch of them as you go.

No, if happiness does emerge from this journey, it comes from meeting your own personal expectations.

What do you expect?

What sets those expectations? You weren’t born with them, you learned them. Where did they come from? Consider your personal history.

You grew up playing adventure games, traveling far away in your imagination — and surrounded by the redwood forest, deep and quiet, blurring the line between your imagination and real places. You grew up riding a bicycle, and have come back to it in adulthood, integrating it with your daily life, working against the car-focused environment and economy surrounding you. Visions of far away lands have been brought to you by the internet, and a flood of practical information as well. This age of scientific wonders, and the accumulated toil of countless generations before it, has knit the world together with roads and airlines and shipping routes, and the gear to explore them is affordable. It’s all there, visible online.

You see a goal within reach, but not too close, like a mountaineer scheming to reach a summit “because it’s there.” Just how far could you ride? Just how far could your mind range? You calibrate your expectations and your happiness based on what’s available. You make it up as you go along, and perhaps you’re even conscious of how arbitrary that is.

It feels like these threads have been converging over years, over decades even. How much of your life, in retrospect, has been about this idea?

But then again, how much of this is just selective remembering — a story you’re making up about your distant past to justify your actions? A lot of it, probably. Why make up the story? Maybe it’s not your past but your present life that holds the answers.

Lately you’ve been spending way too much time immobilized behind a desk. That desk is the centerpiece of a routine you follow almost every day. It goes: Get up, ride to work, stare at screens, talk about programming and science with nice people, eat some food – hopefully something nourishing – spend a little time with loved ones, read a book or watch a film, run a few basic errands, and then go to bed for a night of unquiet dreams. Then start the routine again.

It’s not a bad routine. In fact, it’s a routine that most people on Earth would happily assemble and roll with for their entire lives. There are undeniably good things about it; things you cannot pack up and take with you on two wheels.

But it’s still a routine. And there’s no doubt you would break this routine if you started a long bicycle trip. If you picked yourself up out of your home, moved thousands of miles outside your comfort zone, dropped down in an unfamiliar land with some hardware and a map, and had to contend with the elements and interact with the locals to move yourself across the globe, your routine would be totally demolished. It’s impossible to stay in one place while riding a bike, so a desk is out of the question. (Same with computer screens. Only the tiniest of screens fits on a bike and if you stare at it for more than a few seconds you fly into a ditch.)

You would be forced to witness the world, rather than think about it abstractly like you have for too many years. And perhaps that’s exactly what you want. Maybe it isn’t happiness you’re seeking, or the execution of a grand plan; maybe it’s an intervention. Life in one place has gotten too easy, and you used to have expectations for how it would all arrange itself, but life outmaneuvered and outlasted your expectations, and now you’ve drifted into this weird place nobody warned you about, and been seized by this weird idea as a means of escape.

What do you want?

Is this a “midlife crisis?” What’s your crisis; being bored? If you did exactly what you’re doing now but you were 20 years old, even motivated by the same sense of boredom, would you doubt yourself? Would others?

“Go out there and explore!” they would say. “You’re young, you don’t need to think about anything permanent at your age.”

What about now? Instead they would say, “You’re old. You’re supposed to be settled into something and know what you want out of life.” And “settled in” means, among other things, staying in one place.

You’ve been settled before. More than once.

You’ve managed to work your way into plenty of situations that seemed ideal at the time – jobs, relationships, living spaces – and moved on from them eventually. Your only regret each time was not doing it before things got as bad or as boring as they did. Not everything requires escape of course; some things just require difficult adjustments, and then they continue in another way. But to pursue this particular crazy idea – a long-range bike trip – you are taking apart things in your life that are good as well as bad. That’s obsession. And probably stupidity as well.

People all over the world struggle mightily just to claim a fraction of the resources and connections you have acquired and kept during your life, let alone things that you have accidentally or deliberately wasted. If the extreme good fortune of your position is not apparent to you now, it will be apparent soon, because this journey will put you in close contact with many of those less fortunate. How will you feel then, about what you left behind? How stupid will you look to the people you meet, when you try to explain yourself?

But on the other hand…

What if you don’t have a choice?

Life is full of contradictions and it should not be surprising that something that seems like a really bad idea also seems like a really great one.

You’re well into your forties. By all accounts your life is more than half done. Way more, if you think of it in terms of the aging of your mind and memory. What kind of joke would the back half of your existence be if you spent years on the cusp of a journey that you could quite easily have taken, only to turn around and creep back into your house, close the door, and keep taking the paycheck and eating the fat meals?

Even if it’s a difficult journey to finish, it’s trivially easy to start. Just get on the bike and keep going. People have bicycled all around the world hundreds of years before you were born, and (you hope) thousands and thousands more will during your lifetime and long after. If they can do it, so can you. Do you really need a reason? Ego, identity, change, intervention, escape… Why are you so worried about it?

It doesn’t matter. Possible answers to the question of “why” erupt like weeds – fresh ones every day – and you pull them up, inspect them, and throw them in a pile. The only thing you are certain of is the obsession itself. Unprompted, irreducible, and stubbornly refusing to fade. You’ve spent so long thinking about it, outlining scenarios and testing hardware and saving money, that at this point if you didn’t do it, you might not have much of an identity to fall back on. You’d be some vague person with a job and a house and some good relationships who thought about something really hard for years to the point where it began to seriously interfere with and alter their life … and then dropped it.

Are you afraid of what you’ll learn?  Are you afraid in general?  For how much longer are you willing to put up with the cognitive dissonance of simultaneously preparing to go and planning to stay? The world is absolutely flooded with opportunities to miss. There is no shortage of them, only a shortage of time. Past a certain level of preparedness, the days you spend preparing turn into their own thing. Are you more comfortable with preparing than you are with actually doing? Are you comfortable in purgatory, and questioning your motives so you’ll stay?

Get on with it. Whatever happens – good or bad, or even just boring – it will be your choice. You’d better be okay with it.