How I Got Into Touring

This was not my first bike.  I don’t remember anything about my first bike, except that I rode it around the vast weedy parking lot of an abandoned amusement park.  My father would haul us kids out there every now and then to give us riding lessons in a place safe from cars.  He would pull each bike from the back of the truck, hold it steady while one of us clamored aboard, and then give us a gentle push so we could pedal up to balancing speed without falling over.

I don’t remember how many times he did this, but I do remember one of the last times, when I clamored over my bike, put my foot on the pedal, and pressed down.  I thought my Dad had his hands on the back of the bike and was steadying me, but he was actually turned around and hauling out another bike.  He saw me take off and let out a whoop of happy encouragement. “Look at you, you started all by yourself!”  Astonished, I turned my head and smiled, wobbled slightly, and then kept riding.

I don’t remember what happened to that bike but a while later it was replaced with that beast you see above.  A single-speed BMX with kid-friendly upright handlebars.  To brake, you pushed the pedals in reverse.  I was delighted to have my own bike, but what really lit up my eyes was how shiny it was, like a gleaming metal space robot, big enough for me to ride around and pretend I was a rocket.

I remember that it seemed to weigh a ton.  I remember not caring.  I remember crashing it dozens of times, mostly while trying to do jumps.  Plenty of holes in my pants and skinned knees.  I remember riding it up and down the patchy gravel road near my house endlessly, standing up in the pedals to grind slowly up the biggest hill.  It gave me a sense of personal freedom and mobility that encouraged my already developing habit of quiet, semi-random exploration, inside and out.  It was easy to get around on a bike, and easy for me to think about things while riding.

8 years old and ready to roll!

I rode it for years.  I don’t remember what happened to it, but it was probably stolen one day after I rode it to elementary school and didn’t bother to lock it up, one too many times.  After that I got a larger bike with gears and handbrakes, but it was awkward and I didn’t know how to maintain or adjust it properly.  It got covered in rust and it too was eventually stolen.  For a while – years perhaps – I didn’t have a bicycle at all.

Then in my last year of high school, one of my sister’s boyfriends sold me his old bike.  He’d assembled it from mail-order parts, using a Bridgestone mountain bike frame as the foundation.  The components were all excellent, and his price was extremely low.

With that bike, I finally started paying attention to basic maintenance.  I learned how to change a tire, how to adjust brakes, and so on.  I rode it sporadically for about ten years, but for big chunks of time it just sat in the weeds of the back yard, leaning against the side of the house.

Then things got serious.  I began to spend a lot of time working behind a desk, which starved me for exercise, and the thought of sweating on weight machines in a gym felt depressing.  I hauled out the bike and started commuting to work, once or twice a week.  It was ten miles through dense urban sprawl.  I stayed late at work so the return trip could happen at night, when the air didn’t stink so much.

That got me familiar with long rides, in a way I’d never been before.  And then, one day at my workplace, a man walked on stage and unveiled a device that would rearrange the world:  The iPhone.  I got one for free.  In just few months I found a way to attach it to my bike.

Now I had a way to stay connected and socialize, while pedaling far afield.  On the weekends I took trips way up into the San Jose hills, and sometimes over them and down into Santa Cruz.  I stuck bags on the bike to hold sandwiches and extra clothing.  I installed different pedals and gears.  I got a generator so I could go for hours in the dark.  It was exercise and adventure, with music and audiobooks and texting and phone calls.  It was glorious.

Somewhere in there it moved from a hobby to an obsession.  The idea of a multi-day tour, with a tent and sleeping bag, snuck into my mind and began quietly rearranging the furniture.

Just before I was set to embark on my first tour, I got a recumbent.  It was a total impulse buy.  A co-worker was selling his, and gave me a test ride, and in two minutes I was hooked.  It was the bike for me.  In a few weeks of frantic adjustment, the recumbent was kitted out for my first major tour, and off I went, starting at Crater Lake and zig-zagging into the middle of Idaho.

As I write this in 2023, I have ridden that recumbent and its successors at least fifteen thousand miles.

Same coffee shop from two years ago!

An 8-bit touring checklist

Got ambitions to go bicycling all around the world? Got fond memories of playing the Carmen Sandiego games on your old Apple II computer with the fuzzy color monitor? Well I sure do, on both counts!

I put these slide shows together from the original games, just following my sense of nostalgia for an afternoon, and when I was done I realized they could serve as hyper-ambitious checklists for bicycle touring.

“Where In The World Is Carmen Sandiego” from 1985:

Currently I can only claim London, New York, and Reykjavik, and I feel pretty accomplished already.

“Where In Europe Is Carmen Sandiego” from 1988:

I built this slide show to run a little slower, so you stand a chance of reading the scattershot descriptions on the right. On this list I can claim Reykjavik (again), Amsterdam, Brussels, and Copenhagen.

Don’t forget to be there

There’s a wilderness of land and people out there. More than anyone could know. And then there’s this other wilderness, almost entirely decoupled from the first one, that exists in people’s heads. It’s made of shorthand summaries and untested assumptions about the first wilderness, and it’s cramped and twisted like a funhouse ride and teeming with deranged fictional characters.

People who have done some traveling across the first wilderness – especially if it’s for fun – just love to creep into conversations and point out features of the second wilderness, all the time believing they are saying something meaningful, accurate, and wise about the first. They sorely want it to be true. Sometimes, sounding knowledgeable in the power play of the conversation at hand is what matters. We all love to play the wise mentor role.

This is how you get twenty-something know-it-alls at parties who say stuff like:

  • “Seattle is just a worse version of San Francisco.”
  • “People from Missouri are bigots.”
  • “New York is gross.”
  • “Everyone in Paris is so rude!”
  • “There’s more to do in Los Angeles than anywhere else.”
  • “All these new people moving to Austin are ruining the place.”
  • “People in Italy really know how to live.”
  • “Watsonville is full of Mexican illegals and if you go there you’ll get stabbed.”

(That last example may seem especially upsetting, but unfortunately, the inner wilderness is a place that can foster opinions that are not just pointless, but vicious as well.)

I know about this because I’ve caught myself doing it a few times. It’s very tempting to point out some very personal, very subjective chunk of my own second wilderness and declare that everyone else will see exactly the same thing if they just go where I did. I keep trying to rein myself in, and talk about statistics instead, or give purely logistical advice.

But, paving the world around us with generalities and wishful thinking is a very human behavior. We do it to stave off madness in the face of an ultimately unknowable universe, because we are all far less capable of dealing with uncertainty than we want to admit. And sometimes our confidence needs the boost we can get by talking out loud, and we say something at a party like, “Oh I would never enjoy living in Canada.” … Conveniently forgetting the fact that 37 million people live there, and if they have a pretty good time of it, we probably could too. It would be no less honest – but far less flattering – to rephrase that confident statement as, “I’m mostly ignorant of how to enjoy life in a place like Canada and I want to remain that way, because I need to narrow down my choices for the sake of sanity.” I mean, let’s admit it: Learning is work, and sometimes we have to prioritize.

I have to be okay with this, and so does everyone else, because we’re all only human. I really only bring it up because sometimes it’s very useful to recognize that we’re wandering around in the second wilderness – in the funhouse of our own assumptions – and if we just wake up a little and look around in more detail, we can find really useful connections, and gain new confidence. Every new place I go I’m astonished at how poorly I actually see things, and how much I lean on previous knowledge and trust that things will be predictable. I have to stop and go back, sometimes more than once, and ask “What did I just see? What did I just ignore?” and most important of all, “What’s being hidden from me because I’m a stranger?”

If you’re traveling, take a page of advice from a slow-ass bicycle tourist, and slow way down for a bit. Ask yourself a couple of those questions and give yourself time to seek an answer. Chances are, it will lead you somewhere way more interesting than the next picturesque monument on the madcap package bus tour you were offered by the tourist bureau. It was hard enough getting to that new place — so don’t forget to be there when you get there.

Iceland Round 2 Gear And Bike Setup

For my own reference, here is the overwhelming amount of gear I packed for my second Iceland tour, and how I arranged it.

This is what everything looks like packed on the bike. It’s basically the same as my 2019 trip:

Here are the bags without the bicycle:

In the back: Two Ortlieb sport packer plus bags, each with an add-on net pocket and an add-on large roll-top pocket.

In the middle: Two ortlieb recumbent bags. The one on the left has three net bags attached to its underside in a row. The one on the right has a net bag, and then two small roll-top bags attached below, since it hangs over the drivetrain of the bike.

In the foreground: A Kelty Redwing backpack. On the loaded bike, this is placed sideways on top of the recumbent bags, where it fits nicely behind the seat, and is held down with two bungee cords.

All the gear I'm taking with me. Can you believe this all fits on a bike?

This is everything that’s packed onto the bike, including the bags shown above. As with the 2019 trip, the majority of the weight and space is claimed by the sleeping bag and the tent, shown on the far left.

In The Large Bags

These items went into the recumbent-style bags on the rear rack, or into the attached pockets:

In The Small Bags

These items went directly into the sport packer bags below the seat, or into the attached pockets:

The following mesh bags and their contents went into the sport packer bags as well:

The white bag: Assorted USB cables and adapters.

The green bag: Media cards and drives, and the cables for reading them.

The biggest change here is, I left out any kind of multi-port USBC hub doodad. I have wasted money on so many of them, and they all have problems. Some get very hot. Some of them have misshapen connectors. Most of them can’t read from an SD card and a Micro SD card at the same time. And almost all of them have annoying power problems and fail to reliably charge or stay connected to more than one USB device at once.

A pox on the lot of them!

The pink bag: Lens and laptop cleaning supplies.

  • Generic lens-cleaning wipes (For cleaning laptop and camera.)
  • Microfiber cloth (For cleaning/drying lenses.)
  • Extra microfiber cloth (In case the big one is soiled.)

A lightweight power brick with 3 USB-A and 1 45-watt USB-C.

This charger has one fewer USB ports than the one I took in 2019, but it’s a good amount lighter. Like the old one it allows me to charge the laptop and my other doodads at the same time, from one outlet — which in turn means I need only one international plug adapter when I’m traveling.

My Frankensteined portable speakers, and an iPod Nano to drive them.

I use the iPod Nano to play bedtime music. An iPod shuffle is not suitable for this purpose since it has no ability to stop playing! It will always repeat the current playlist forever or until it runs out of power! How silly.

Not that it matters, since all iPods have been discontinued and will soon die out, and we will all be locked into digital subscription services and completely abandon the whole idea of controlling what we listen to without it being mediated from one minute to the next by a jealous corporate overlord in the sky. (I’m not bitter.)

A good wind-resistant microphone for conference calls.

The above items attach to my headphones. The resulting setup works with the laptop and the iPhone lightning adapter, there’s no flaky Bluetooth involved, and it sounds far better than anything else I’ve tried. The strangest place I’ve used this so far is by the side of the road next to a geothermal power plant in the middle of Iceland.

The sport packer bags also hold two SenReal Mesh Makeup Organizer Pouches that contain camera-related gadgets:

In The Backpack

These items went into the Kelty Redwing backpack:

The toiletries bag. Basic stuff for a mixture of hotels and camping.

In Other Bags Or Directly Attached

The following items were attached directly to the bike:

These items went into the Allnice 1L PVC Bicycle Pouch just behind the seat:

These items went into the FastBack NorBack Frame Pack between the seat and the front wheel:

Also in the NorBack pack, my toolkit:

Replaced or Removed

These are items I brought in 2019 but have replaced with newer items for this trip:

These are items I brought in 2019 but decided to leave out entirely for this trip, with no replacements for them. They were just not useful enough.

Iceland Redux: Is Bicycle Touring Romantic Doom?

I have a lifelong habit of continuing in uncomfortable situations that are predictable and safe, rather than changing the situation in some uncomfortable way to pursue a greater happiness that is not guaranteed. I’m sure we all suffer from this habit to a degree, but I feel like it’s really messed with my life. It’s too easy to reinforce, because playing it safe today is more likely to get you to tomorrow.

At many points in my life I have also used the possible inconvenience of other people as an excuse to delay my actions, without consulting the people involved. This is the worst kind of selfishness, based on the conceited idea that you know better than other people what they would choose if they had all the facts.

In the depths of this kind of self-imposed purgatory, I’ve often asked myself the question, “If I keep doing it, what am I doing it for?” After all, if I didn’t derive some strong benefit from this pathology I would have ditched it long ago. Over time I’ve realized that the reason is subtle, but powerful: I keep trying to play a role, of someone who is as stable and committed and undemanding as the masculine role models I aspired to early in life. And while there definitely is a part of me that is remarkably stable – you need to have nerves of steel to deal with many aspects of long range bike touring, complex software development, and living in Oakland – there is also a part of me that is intense, difficult, boundary-pushing, and swings between craving solitude and craving disruptive, creative mayhem.

Without hard-won wisdom to temper it, this disposition has the following outward appearance: I find something that works really well and do it happily for long stretches of time, running it into the ground, and then with little external warning or apparent reason, I abandon it and make a lateral leap into something else. Sometimes I leap a few times very quickly. Then I find the next thing that works really well and burrow into it, for another long stable run.

The tempering wisdom is this: Being entirely stable is not the goal to aspire to, despite what the role models – of cowboys, and suburban husbands, and workaday dads – were insisting to me when I was young. The goal is to safely integrate change and adventure with the rest of your life, and the people in it. And that includes advocating for what you need in relationships, with a mixture of insistence and empathy, instead of being quietly discontent. And knowing the difference between what you really need, and what just sounds good because it would make you feel better. (Or eventually, feel anything.)

In the recent past I have not been particularly good at applying this wisdom, so I feel like I need to nail it down in words right now, and re-read it a few times to myself for good measure.

Now it’s time to take a left turn into a major part of my life: Bicycle touring.

DCF 1.0

For a long time I believed that my desire to go on long-range tours was pathological. I believed I was either obsessed with the idea of touring because it was a convenient distraction from other problems in my life and a good excuse to avoid “settling down”, or I believed it was a kind of curse because if I went on long-range tours I would be logistically unsuitable as a partner for a committed romantic relationship. And for almost all my adult life, I’ve always either been in, or been eagerly pursuing, a committed romantic relationship. So it’s either a case of: I’m avoiding my problems, or I’m screwing myself out of what I want.

Over the last ten years, without really understanding what I was doing, I tried multiple times to make a specific compromise to this: Having my romantic partner go with me on these journeys. One time I outright pitched the idea, and helped her shop for a bike, but she was physically unsuited to such long rides and found it miserable. Other times the idea arose organically, but got derailed by my own lack of experience guiding people comfortably into it. The most recent time I approached it with a healthy skepticism: My partner was already interested in touring before I met her, and as we got to know each other she casually set about buying a touring bike and gathering gear and discussing potential trips, and I soft-pedaled the pursuit because I needed to be sure she wasn’t doing it because she thought it was necessary for getting closer to me. Meanwhile, whether these relationships were going well or going poorly, the desire to go on bike tours remained.

In fact I began to be plagued increasingly by a grand vision of going on a bike tour around the entire world, which would charge into the front of my mind and thoroughly distract me, then vanish for a while. It got the most intense a few years ago, when I found myself newly single, and with the financial and logistical means for the first time to actually attempt such a thing. I traveled for three months and then deliberately set it aside to attend to other matters in life, involving my family and career, and though I was not entirely at peace with the decision, it felt like the right one. I realized I could pick up the epic journey where I left off, and do it in segments. I planned the next segment with my nephew, and folded it into a foreign vacation with a big chunk of my family. We did practice rides and I made an itinerary and bought plane tickets. It was going to be awesome! Then COVID blasted those plans apart.

I shrugged my shoulders and planned some smaller trips. I was exploring a long-term relationship during COVID times anyway, and put most of my attention into that and my job. At the end of last year I went on a pretty epic trip with my nephew, then jumped through a series of exhausting COVID-related logistical hoops to get myself to the East Coast to visit my significant other, but when I arrived I was exhausted and uncomfortable and she was distracted, and then some absurd drama piled on top of that. I suddenly found myself entirely alone on the wrong side of the country with a bike and a pile of gear, three days from my birthday, with a massive storm approaching. It was another logistical nightmare getting out of that, with repercussions that took months to sort out.

The foul taste of that experience informed my most recent span of dating: I became convinced that any attempts to combine my bike touring plans with my romantic life would turn into a disaster, and the only sane option was to put one on hold in favor of the other. That worked for a good while, then the “grand tour” idea ran rampant in my mind again and I decided the only way to be rid of it was to clear everything else from my life – developing romance included – and just do it. I put a plan together, and then it was immediately derailed by a family emergency that made me reassess what I was doing. Instead, once things were under control again back home, I assembled a much smaller and easier trip, a return to a known quantity I wanted more time to explore: Iceland.

Detail of the Carta marina created by Swedish ecclesiastic Olaus Magnus and initially published in 1539

In this era of my life, after so much experience, I can confidently say that I am not pursuing bike tours in order to avoid problems at home. I go on bike tours, and I have problems, but the two don’t correlate any more than other parts of my life. Still, they are great fun to think about, and I am guilty of obsessively planning the next one when my attention would be more useful elsewhere. It’s taken a lot of effort to move away from that habit. It helps that I’ve accumulated a big list of potential trip plans I can just dip randomly into when there’s time for a journey. Many of those are suitable for casual bike tourists, and perhaps I’ll start a relationship with someone with that level of interest, and we’ll explore those together. But I don’t need that to feel fulfilled.

Now I’m happily single, and embarking on another bike tour, and the other potential pathology comes to the foreground: Am I no good for a long-term relationship with all this traveling? Does a hobby like this really factor me out as a desirable romantic partner?

I don’t believe that any more. I found a pretty good compromise in my last long-term relationship, with frequent enthusiastic sharing and check-ins and the engineering of visits along the way, and in retrospect that relationship died on its own terms, for its own reasons. That said, I do know I’m not in a position to start or nurture a long-term relationship while touring — without some pretty specific coloring outside the lines of courtship. And I’m okay with that. What matters to me right now is the adventure I’m having, the work I’m doing, the stories I get to share with my family and the plans I can make to involve them, and so on. The bike touring is not the lateral leap; it’s not the unstable question mark, it’s not the vision quest or the segue into something else. It’s a part of who I am long-term, and it can fit into other things without crowding them out. It provides a measure of both the solitude and the creative mayhem that I need in my life to complement the stability I desire, and that is extremely useful. I don’t sleep around, I’m not emotionally distant, I don’t escalate conflict, I don’t get drunk and carouse, I don’t blow through my money, I don’t have ridiculous expectations … but I do this. It’s a pretty good package.

I look forward to the next romance, and aspire to make it long term. I’m looking forward to all the sharing, and jokes, and dancing in the kitchen, and the adventures. But dang if I’m not also happy riding around, building software and hanging out with cats.