Learning the Right Path by Trying the Wrong Path.

A reflection on a mini-career.

This post is deeply personal and I feel I’m making myself quite vulnerable in writing it, I hope you enjoy and consider subscribing to help support me on this new endeavour. Also, this is going to be long, but I think you could learn a lot if you read it.

As I finished up my university degree in Computer Science I had a (in retrospect) solid job lined up at a bank, writing software and working on other technical matters. I had done an internship there the year before, it was a smashing success, and this seemed like a great career path.

And then everything changed.

The Background (or the “Wrong” path)

(You can skip to “The Lessons” if you don’t care about the background)

First, I remember doing my usual evening walks on the treadmill in our apartment building and seeing more and more news every night about the “virus” that was emerging in China. COVID-19 really changed the direction of my life. And second, my wife got a job offer in a substantially better paying and more prestigious role at an actual software company. Being what I think is a good partner, I said sayonara to my “good” but not particularly exciting job and moved across the country so that my wife could be where she needed to be for hers (ironically, had we waited until the pandemic became a little worse, we could have probably stayed where we were living Toronto, or I could have done my job remotely from Vancouver — but that’s just not how things shook out and it was pretty hard to predict that would happen when we made the decision to move).

In about March we moved (things were actually locking down by this point) and I remember the feeling being pretty weird. My wife’s job didn’t start until early summer and we were done university, so there was a lot of hanging out, playing video games, and building computers — in retrospect, it was fun and very relaxed because we were just waiting out the pandemic in somebody else’s house in a nice neighbourhood. Eventually though, we got an apartment; the views were stunning, but like many new apartments in Vancouver it didn’t have air conditioning, so while I have very fond memories I think they would be less fond if I remembered the process of “pre-cooling” my spot on the bed with a crappy fan from Staples before bed every night. Anyways, when living in this apartment (for such a short period of time it’s almost embarrassing) I kind of went back and forth about my “direction” a few times, but with my YouTube channel making as much as... $240 a month, I figured it was worth shooting my shot and seeing if the project I had already been working on for a few years could be a career.

Mountains! Cool modern high rise towers! Trains!

It was around this time that I started talking about cities around the world in my videos as opposed to just cities in Canada. I was actually pretty familiar with other cities (I’d often visited them, and obsessed over them online to a level of detail I wouldn’t for Canadian cities because obviously I knew them well). A few videos blew up and my income also went up (very slightly), and so over the summer I explored that direction, but I also applied simultaneously for a Masters Degree in Urban Studies in Vancouver since Masters Degrees feel like what people do when they don’t have another clear path forward. By late summer, I had discovered I had a problem of oscillating between different paths (I stopped making videos for a period — probably because the money while increasing was still a joke compared to my partner’s) and I found myself flipping between imagined future lives as an urban planner, or a software engineer, or a YouTuber. I got into the degree, and we moved to a different apartment (no air conditioning will melt your brain in a hot smoky Vancouver summer). But, eventually (it wasn’t even all that much longer) a sort of dream position came up working for a major Engineering Consultancy in Toronto (which I had been missing — oddly, now that I reflect on it) as a transportation planner. It paid pretty poorly (better than YouTube at least, but much worse than a basic software job), and it seemed like they might want me to use software skills that should probably have commanded a higher salary, but it was the dream and so I basically made plans with my wife to move back to Toronto the day it got offered to me (by this time her job was fully remote anyways).

Once I was back in Toronto (driving across Canada in three and a half days was a very cool experience, if a little harrowing at times), I started the job, and while it was fun at times, there were a few things working against it. In retrospect, I think too much of what was working for it was my need to prove to a tiny portion of people commenting on my Youtube videos that I was actually qualified to give my opinion on various things — even though I never really advertised the fact that I took this job (I didn’t work on projects I talked about so there wasn’t a way for it to come up without me feeling like I was just weirdly boasting).

For one, Ontario did a long and hard Covid lockdown: I think it was close to eight months after I moved back before I went to a restaurant with a friend. Literally 95% of every week was spent in a small apartment, with short days and crappy cold weather outside. I never met most of my coworkers, and probably between the terrible weather and the lockdown I ended up with the most unbelievably bad sleep habits imaginable which was extremely mentally draining because I’d feel tired all the time and be sleeping and random times. The work, while generally interesting, included one project which was software-based, and while I was happy to be involved, the reality was I quickly realized that Engineering Consultancies are not set up to develop software (no shit if you’ve worked in tech and ever dealt with a “non-tech” company), and despite the project being finished with far fewer resources than anyone seemed to expect and with just two people instead of a much larger team that people seemed to think we’d need, it ended up being pretty exhausting. I think that they hired me probably in significant part to work on this is a good signal of the power of a degree in Computer Science — assuming you aren’t looking for a Google level salary. (It also didn’t help that when the project won an award after I had left the company as a full-time employee they left my name off and didn’t give me credit I felt I deserved). Between the crazy environment, my rapidly declining mental health, and frustrations at work, I left the company after less than a year (they liked me enough to hire me back as a sub-consultant, so it was at least amicable!), and pivoted once again back to YouTube, and by this time (after working on YouTube for almost five years) it finally was paying enough to make a basic income (not much to pay for when you’re stuck in your apartment!).

Eventually I got to a point, which was more or less where I was until recently, where I was uploading videos regularly, and ended up making close friends out of a number of people that worked in the transit industry. Video-making and YouTube in general was exhausting, but there was no shortage of stuff to talk about (I think people underrate the extent to which having clear things to work on makes work easier), but the transit side was complex.

On one hand, most transit agencies, even when my channel got really big, would barely respond to an email from me (for reasons I will discuss in “Lessons” below), and the friends I had working in the industry, while positive about all the stuff going on (like I was) were always raising red flags about the political influence that existed on projects (obviously), but probably more importantly just bureaucratic and organizational problems, as well as various weird cognitive biases that kept us from making smart decisions in so many situations — some of these were related to politics, but many were not!

To give an example, Toronto has trams, which are slow and unreliable in large part because they use old-fashioned infrastructure different than most places in the world. Despite this, the transit agency in charge doesn’t really seem to be interested in changing the infrastructure, and I remember someone asking someone responsible at a conference once and saying that the new style of infrastructure was not a good idea “because we tried it once and it didn’t work” (the rest of the world using them to great success didn’t seem to register). So many of the problems of public transit in Canada have nothing to do with politics (there is broad political support for public transport in Canada), and instead are rooted in organization dysfunction (but this seems less fun for people to rail on). I think part of what makes this hard is that the idea of a transit organization being very small ‘c’ conservative is hard for a member of the general public to imagine (I don’t think it was always this way), even if most people working in the space know it’s a often huge problem.

It is frustrations like this that made me ponder the Not Just Bikes-approach of just moving somewhere with more functional and less hostile and conservative transit organizations that were more open to things like online media. Unfortunately, despite entertaining moving — including quite seriously to Australia, I didn’t really have a very attractive path to do so. I think if I lived in Japan or Switzerland I might still be doing transit YouTube, but I do not, and if I did it might be because I grew up there, which would mean giving up a lot of my actual identity.

I was able to detach from some of the transit problems that existed over time because as YouTube grew larger I could lean more into being a YouTuber, and less into being a transit YouTuber. But, especially after 2023, I started musing more regularly about stopping, not because I didn’t think what I was doing was valuable — I think I made a lot of very useful stuff over the years that still holds up — but because talking about the right way to do things so much and highlighting how often Toronto was doing things the wrong way was very draining. It’s sort of like being into startup culture, but having no way to move to Silicon Valley and instead being stuck in some small village in a forest in Indonesia (hyperbolic I know). Once I knew I was having a kid, the idea of stopping making regular videos was attractive, and the emergence of more and more YouTube channels who were doing similar things made making a lot of the videos I used to make seem less interesting. A few major problems that emerged in 2024 and early 2025 sort of sealed the deal that I was sick of the lack of organizational progress, and political leadership of transit in Ontario, and to an extent Canada more broadly, and so I decided to basically call it on this “mini” YouTube public transportation career.

Now, many people (who I think enjoyed my videos) have told me they would like me to keep making videos. But, I think what was one of the most interesting things — and validating things — was having a close friend tell me they were happy I was stopping. Their message was basically that clearly I was flying a little too close to the sun, overworking myself, and just had too many irons in the fire, and being able to step back was actually a respectable thing (and I think this person — who is quietly brilliant about so many things — was right). As I already said, maybe if I was Swiss I’d still be making videos, but I’m not Swiss, and I don’t want to be... I like Canada! The reality of my situation is that I just live in a place that (while better than the US at this stuff) is kind of dysfunctional on transit these days; that may well change — I hope it does! — but I don’t need to feel responsible for moving the needle. I have a lot of passions, and a lot of the pressure I feel to keep pursuing just one of them was external (though I will say since I have spent so much time on the topic, writing something about it is easy — I can put down thousands of words like nothing, and being asked to go on the news is cool, so stopping isn’t so simple and I wasn’t only continuing because of peer pressure).

Instead. I view this as a natural time to prune this branch in the tree of life that I am exploring. I think I can do this confidently because there’s not a clear path forward along the branch. I could keep doing YouTube, but I’d be exhausted, and it’s eventually not fun to talk about how great something is elsewhere, while you have to put up with the second class version. I could try and work in politics or a transit agency, but I’ve seen how exhausting and undervalued that work so often is (from industry friends, who despite being really smart and capable were so often sidelined by others, and prevented from asking good questions or implementing positive changes), and I just don’t think I’d enjoy that (the dream was always a small town where there was broad political support for amazing, common sense transit policy, but I don’t think it exists right now in Canada). I am not wedded to public transit, I have other interests, and it would feel a little silly when things get so rough on this part of the tree not to explore elsewhere.

That brings me to the wrong path, in the sense that I’m at the end of the branch and I think I need to return back to the branch point and go elsewhere. When I say wrong path I’m not saying there was nothing to learn, but that there is probably more to learn, and more to be found elsewhere.

What happens next? I’m not so sure, I will talk about it here though, as I talk about slowly moving my life forward across so many different dimensions, career is bound to come up, but for now, let me share some of the lessons.

Lessons

I think a big motivating factor for this blog post is simply the task of trying enumerate my learnings from my YouTube and Public Transportation careers firstly because it allows for some closure, but also because it forces me to think about the larger lessons, and what I can take forward, and how those lessons have changed me and made me a better (if sometimes more cynical) person. Each of these is a learning, but some of them are incredibly deep and really consist of many other learnings, while others are smaller and more self contained.

Media

I think one of the biggest things I learned the most about doing YouTube is why traditional media has been struggling, but also why I think it often doesn’t do a good job covering various topics (if it covers them at all).

One thing that’s clear is that the current funding model for legacy media is pretty bad. In all of my time doing YouTube I’ve happened across new articles from all over the world (and I think someone with a world spanning interest would do this anyways) and the “subscribe for only $2 dollars a month!” in addition to “we’ll make it hell for you to cancel!” is a terrible business model. Maybe this brings people in, but I know from doing “media” myself that the stuff that everyone can actually read for free (or at least more widely) is where you want to put your best work, because why work hard for something that only a subset of interested parties will see, and that people won’t really be able to share? I get that it’s financially hard for news organizations (though as I’m going to say thats probably their fault in part), but this model just sucks as a reader and seems deeply suboptimal.

I also really learned that media just doesn’t cover so much. When I say this, I’m not talking about how tragic incidents in foreign countries don’t get attention (this is a problem), but how even huge occurrences in the focus area of a news organization might not get covered. Toronto since the late 2010s has seen tens of billions of dollars of funding funnelled towards public transportation, the total sum is getting so large that taken together it’s getting into single digit percentage points of Canada’s national GDP! The number is astronomical, I do not think any other jurisdiction on this continent is spending as much on public transport, or infrastructure of any kind — it’s probably bigger than most budget items for governments in Canada! And yet, there is very little coverage. Sure, the projects get covered (the ones going badly, or which are simple enough that a non-interested person can understand and talk about them), but there is more or less zero coverage of the whole ~$80-100B package together. When there is coverage, it’s often regurgitated press releases or statements from the transit agency or contractors (which rarely tell the whole story, or well, even the story), and the narratives are also overly simplistic, missing key details, and not really grounded in global, or even national context. Part of the problem is a lack of dedicated reporters for transportation (and even when they exist reporters are unlikely to get too invested or learn too much because they get cycled around), but it’s also because news organizations seem suspicious of anyone proposing they talk about a narrative that isn’t the one they mostly report, even if that narrative lacks any real substance at all. I don’t particularly blame any one person for this: it’s a collective and organizational problem, but what it does show is that legacy media (who people often rush to defend) doesn’t even really seriously try to talk about lots of topics, and if that’s the topic you’re interested in, why would you subscribe? To some extent, subscribing is sending a signal that you think the news org is doing a good job mapping its coverage to the things you are interested in, or that you think society should know about — and I don’t think thats the case in Toronto (obviously with some exceptions as always).

What’s scary is that eventually you realize that most people do not look at YouTube channels from subject matter experts, and so a lot of peoples views on various issues are just what the media tells them, I know this starts to sound a little fringe and conspiratorial, but it really is the case that most people, especially in Canada trust the media, and if the media isn’t mapping the territory well, then people get led astray. Of course, this is rarely something that happens purposefully, but it is a real deficiency. One of the biggest things I’ve learned about in my career are all manner of cognitive biases and effects that can be helpful tools in explaining a problem you are dealing with, or something of the sort, and while this one doesn’t necessarily apply perfectly to everything I am talking about, I think a lot about the Gell-Mann amnesia effect (definitely a real thing, and relevant to media coverage!) and will probably mention others as well.

“You Moved to Toronto for a Transit Project”

This one is a learning from literally yesterday — or well, it’s not, and an extension of the last point. Sometimes you learn something, but it just floats around in the back of your head until you feel something inspiring you to voice that learning.

The motivator here was me saying on social media that I moved to Toronto for university in part because of the large number of transit projects happening here (as I described above). Some random on the internet who doesn’t know me, or seemingly follow me closely at all, tried to dunk on me by saying “You Moved to Toronto for a Transit Project” with the clear subtext that Toronto sucks at transit projects and that I am an idiot.

The problem here is partly context collapse, and it’s partly the fact that speaking more than you listen, defaulting to Occam’s razor and without any real understanding of the situation is the default on certain websites. (This person was also clearly acting like a jerk, but fortunately I have Hanlon’s razor for that) But, I think the bigger problem is 1) people can’t imagine other people having motivations or interests that are wildly different from their own, 2) people just default to the most common media narrative and then add an additional layer of simplification and generalization to it (Toronto is bad at building — mostly one — transit project, and so clearly is bad at transit), and 3) many people want to think of other people not as thinking beings, but as mindless drones.

I think the ultimate thing that upsets me about this is that due to some combination of the above, and that the internet often discourages nuance, you find a lot of people who don’t understand the ground truth for all kinds of subjects. Which, in this case, is…

Toronto is fairly good at running a unique transit system which is better than almost anywhere else on this continent, and even globally competitive in some ways. Toronto often gets stuck in its ways because of its conservative institutions and attitude of continuing to do things the same way outside of an actual crisis. Toronto is building more public transport than most cities in the world, but many of the projects are not particularly good, and most of them are being executed in a suboptimal way for world beating prices.

Not only is holding that in your head a lot harder than “Toronto SUCKS at transit”, it’s also just not much fun to be nuanced: it requires effort, and does not make for great internet zingers.

Most People are Hopeless Slaves to Their Local Context

One final extension from the last point is that most people cannot for the life of them understand how their local context fits in the world. This is especially baffling as a Canadian, because so many Canadians were not born in Canada, and spend a lot of time travelling (I assume this would be worse in, the United States).

When someone says “Toronto SUCKS at transit” it’s not always clear to me what they think they are saying. Is the experience of public transit objectively great? No. Is it objectively terrible? Also generally No. Whats helpful is to compare transit in Toronto to other places, and if you compare the city to almost anywhere else in North America you will find it cleaner, more frequent, and more comprehensive. When people say things like “X SUCKS” they are often just saying they have had some bad experiences, and ignoring that something might actually be pretty competitive.

And this isn’t some Toronto thing: some degree of exceptionalism (in this case negative exceptionalism) is common basically everywhere. Germany runs literally thousands of times more trains every day than Canada, and far more than most countries in the world. There are convenient train services all over that country, and they are often on lovely trains and infrastructure. And yet, probably mostly because (like many train systems) DB has a decent number of delays, I still get comments from people telling me how Germany has the worst trains in the world, or that Canada has nothing to learn from Germany. Which I have compared to saying that the average cyclist cannot learn anything from the world’s 10th best cyclist. Deeply odd!

Confidence Matters

I remember being terrified of public speaking for most of my life. In university I was a bit better, I even gave a mini-speech once (from the audience) where I said a professors plan to have the class’s students work for free was unacceptable (there was applause naturally). But, that professor had me one-upped because there was no way I’d go in front of a lecture hall and talk.

I think that’s largely because I lacked confidence to talk about most subjects. YouTube and years studying public transport changed that for me. To be fair, a lot of it was the process of “public speaking” to a camera sitting in front on me hundreds of times (there is a whole YouTube side to this effect). But, I think it was also learning enough about a topic to be extremely confident in my knowledge about it. Public speaking gets a lot less scary when you know the thing you are talking about very well.

Eventually I could speak in front of pretty large crowds and to people in positions of authority quite confidently. And I think the thing that provides extra confidence is that people could ask me almost any question — not just a technical question like “What is X?”, but also second-order questions that you don’t find in a textbook or info doc, such as “Ok, but what about Y?”. I also think that once you know the feeling of confidence and comfort in speaking in front of large groups of people, or small groups of intimidating people, you can transfer some of that to other topics, and this can be dangerous — it’s probably a big part of why people who are experts in some subject areas get themselves into trouble talking about other topics where they truly don’t have the same insight (though it’s also dangerous to assume people don’t know more than you think, or can’t see a useful parallel issue worthy of discussion, so generally it’s good to be slow to pass judgement).

Anything is Legitimate with Sufficient Scale

Ok, this learning’s title is certainly “meme-able”, but I like the title because it reflects how I used to feel about... my YouTube enterprise?

When I was making ~$250 a month from YouTube (even though it was already my “full-time” job at this point) there was no way in hell I was going to say what I did for work to people. I’d probably say “I’m figuring it out” or that “I had a job lined up before I moved”. There’s a real insecurity in taking a risk in the early stages, at least for me.

Over time I’ve got pretty comfortable with being a YouTuber, it’s funny because the work I did didn’t materially change, but the validation of a larger audience and financial success did. I think it would be helpful if society was less judgy towards people taking risks and buildings things, but I think people tend to feel a lot more confident about the legitimacy of the stuff they are doing once it scales up in various ways.

People are Ruthless with Creators

Something which I certainly experienced lots of when doing YouTube is people who were trying to take advantage of my knowledge without fairly compensating me. Now, I personally think the idea that the only legitimate compensation is monetary is silly, because in life most things are a negotiation — but, I certainly had the experience of some unknown person reaching out, and asking for me to provide them a ton of information (which takes time and effort) with no clear benefit to me.

Now, I did entertain this a lot over the years, and much more than I should have. You eventually realize that people (often reporters) find it much easier to ask someone who knows a lot about a topic than to learn something, especially about a topic they are not interested in. The issue is that what actually gets broadcast onwards is not within your control, leading to the same narrative issues I mentioned above.

But, this also gets extended to a more transactional (but, really exploitative) negotiation you deal with, where someone wants you to write something, but they will take the credit or the benefit for it. Or when somebody would basically ask me to make a video about their thing, or even about them. This would betray a sense that they didn’t understand what I did, or even do their homework (I don’t make videos about people), but it also taught me that many people only see other people as a tool or asset to be used to further their own goals, and don’t understand that everything is a negotiation, and if I ask someone I don’t know or have history with to do something big for me, they aren’t going to just do it.

Probably the funniest experience is having someone reach out to you asking you to do something for them (often basically consulting), and then adds that they have no way to compensate you for this. In this case the person knows what they are doing, and is doing it anyway.

Of course, I’ve mentioned that these engagements are negotiations because there are always grey areas, and these are often ill-defined. I might do something for “nothing” happily for someone who I don’t know but respect, and I might not take money to do something for someone who I think is doing a bad thing. But, the interesting thing is just how exposed to people engaging in these negotiations one is as a creator (or a small business owner I guess).

Everyones Isn’t On the Same Channel

One of the funny things I learned doing YouTube (though this could also apply to anything where a person is saying something in a public forum) is how often people just aren’t on the same channel.

A big part of my YouTube channel was centred on the nuance: a subway project might be good, but, a light rail project might be bad, but. And yet a lot of people over the years seemed to think I was a “ban cars”, sit along the rail line for hours waiting for a specific locomotive type of guy. There would also be situations — like one that happened recently, when a person who hadn’t did there homework came up to me at an event and said something that they thought I’d agree with (and as most people would I nodded along), but which I’ve actually spent a lot of time railing against.

These moments when you realize you aren’t on the same channel as someone are pretty varied. Sometimes it’s a person telling you they like videos/blog posts/articles like yours and (person you disagree with), because they “believe” in the same things (didn’t know I was starting a religion here!). Sometimes it’s a person who (like I referenced above) cannot imagine that you’d be talking about a certain topic for non-stereotypical reasons (it would really grinds my gears when even friends would say “Reece is into trains” or ask me question about public transit like I have a romantic relationship with it), all because clearly nobody could talk about trains without having a giant model layout in their basement and a wooden train whistle they blow before they enter or leave a room. And then there’s the people who just assume you’re “on the team”, that you have some view that is widely-professed, or which has been historically popular among a certain group, instead of… just asking, or not making an assumption.

It’s Not [Politics]

So often people default to a simple, highly-available answer. I mention politics in the heading, but that’s just the most commonly-cited answer to questions about transit and cities; there are surely other answers that commonly come up to other questions.

The issue is these answers are often wrong, or at least not completely right. It doesn’t help that a lot of people talking about something like public transit default to “politics!” “car brain!”, sometimes because other people beat this into the public’s head constantly. Like a lot of incorrect answers, the problem with it is that it’s not entirely false, let me give you an example.

Toronto is exploring some new bus lanes on some urban streets right now, and people are opposed for reasons that can broadly be summarized as “car brain”. All good so far. But, funnily enough, Toronto has a number of places that already have dedicated transit lanes, which… don’t work all that well. The issue here is two fold: on one hand, people think that if we just had some visible intervention our problems would be solved, and it’s the car people getting in the way (they are maybe 20-50% right); the issue is that often times the problems we have are orthogonal to politics and car-brainism. You might wonder why this is a problem: if there is a well-known problem in any subject area, even if people are being overly blunt with the solution, at least progress is heading in the right direction! But, again, so often progress is orthogonal to the solutions and boogeymen that the public grabs hold of, often it’s more complex and nuanced. Dedicated transit lanes are great, until all the political capital you have is spent on them, and the transit is still slow, because dedicated lanes are just one component of what would create a functional solution.

One of my great frustrations is that even though I’ve talked about why dedicated lanes aren’t a panacea (and that’s definitionally not the same as me saying they aren’t a good idea), when people are asked what needs to happen phrases like “ban cars” are still among the most popular. This would be sort of like if someone repeatedly preached the solution to getting in shape as diet and exercise, but casual participants couldn’t help but always bringing it back to “burning down the local McDonalds”, which is neither necessary nor sufficient (but possibly helpful).

I think in any field it can be frustrating to hear someone respond to a common problem with an equally common, and widely known “solution”; sometimes there really is just a single silver bullet solution, but usually it’s not the case, and it often signals a lack of deep thinking about an issue, and falling back to the herd mentality.

Many Skills are Transferrable, Learning Failure Modes has Value

Clearly, even when you take a path that ends up not leading you somewhere you wanted there is a lot to learn. The simplest form of this is the form of skills. I think it’s pretty obvious that learning to make a video is useful not only for a career in YouTube for example. But, something which is less well-appreciated and goes beyond just learning is that there are a lot of second-order effects that have wide reaching unintended consequences for almost anything. Learning how to make a video might teach you how to structure a book, or it might teach you how to get in shape, or any manner of other things — perhaps directly (the universe has a way of relying on fundamental truths), or perhaps indirectly.

Much of what I think I learned covering the transit industry was common failure modes or cognitive biases and common fallacies, problems which come up again and again, in groups or individuals, and which when you put a name to them can be easier to “call out” and move beyond. Examples include bikeshedding, sealioning, dunning kruger, and palace intrigue. Learning these and various other mental models is a useful way to identify poor thinking and dysfunction, and ideally head it off there and then.

Starting a Business Teaches You A Lot

A YouTube channel is basically just a small business (unless it’s a really big YouTube channel), and you learn a lot running a small business. You realize that the world of business is really more oriented towards large ones, and that there’s a lot of hard stuff you need to deal with, from taxes, to potentially hiring people, managing an enormous volume of email, scheduling things, to managing all other kinds of logistics.

Caring is a Double-Edged Sword

People will tell you that when you love what you do you won’t work a day in your life, but what they won’t tell you is that you might feel like you’ve lost a loved one if a project gets cancelled, or potentially worse: changed from a good project into a bad project. Passion is good, but it’s a two-way street.

It’s Hard to Understand People from their Actions Alone

I’ve already talked about it in a few of these points, but people are complex! Mixing people with assumptions about motivations and actions is a recipe for missing the point, and not understanding someone — potentially leading to conflict. If you want to understand someone, or something they are doing, you really need a more holistic understanding, and the best way to get that is probably just asking!

Tip of the Iceberg is Real in the Truest Sense

So often people see something is happening and imagine some potentially plausible rationale. This rationale is shaped by human bias and so will often be too simple, and sometimes too coloured by preconceived notions. If you want to understand something, or why something is happening, there really is no replacement for going under the surface and “seeing how the sausage is made”.

Big Things Make Disappointment More Likely

Transit projects, like many big things, are potentially hugely impactful, but individual people don’t generally get to experience the vast majority of that impact — a subway might move a million people per day, and you as an individual will never capture the full benefit being provided to more than a handful of them. Big things can still have a big impact on individuals, but by its very nature — bigness — means a lot of people probably being involved, which means a lack of individual control and agency in outcomes, and a much higher risk of disappointment. The delta between the satisfaction you could get making something with your hands in a workshop and building a megaproject is probably smaller than you imagine.

A Lot of People Just Want a Job

Something you will come across when you work out in the world is that some people do their jobs because they love the job or subject matter, and some people just do a job because they need to pay the bills. This makes sense, and we shouldn’t hold anything against people who are working to survive. Unfortunately though, people doing something just for a job can have a broader impact. They might be ok with substandard work, and they might not want to take a risk that potentially means additional work, even if there is a lot of upside. I think it’s important that some jobs are done by people who are passionate about them, and that organizations make sure that people who are “working to live” don’t accidentally get in the way of people who want to go the extra mile.

Some Industries Reject the Passionate

Though I never made a video about it, a recurring thing that annoyed me was people (who I do not really identify with) telling me how some transit agency didn’t want them taking photos of something, or doing something else benign out of passion. One of the worst things about the “North American” transit industry (and the industry in many countries to some extent) is its utter hostility to passionate amateurs or enthusiasts. Not all industries are blessed with people who are fuelling things, and sometimes even doing work for free, and with a smile on their face, and fewer still manage to be jerks to these people in the way that the transit industry so often does (Japan, which is excellent at transit perhaps unsurprisingly embraces “densha otaku” to an extend unimaginable for North Amercian railroaders in their relationship with “railfans”).

By Vantey - Own work, Public Domain, https://commons.wikimedia.org/w/index.php?curid=19148465

What’s crazy is that many enthusiasts get into the industry and then start being jerks, it’s sometimes sort of like a weird exclusive club of mediocrity, in the cases where I met someone who is clearly enthusiastic, and within an organization, they often seemed marginalized — changing this seems like a very important thing.

I can’t help but compare this to tech. Where passionate individual hackers start companies, companies hire people without any formal credentials besides passion and skill (when they can), and those who care are frequently brought into the fold.

Competition Matters

I don’t want to be misinterpreted here. People sometimes suggest the solution to better public transportation is private sector competition, which, if it’s true, is only true in a very technical and esoteric sense (things like bus concessions in Europe, with public planning and private competition to operate the network), and thats not what I’m saying.

What I am saying is that competition has some useful features which are hard to emulate. For example, Toronto’s transit agency frequently compares itself to its contemporaries, generally in the US (a reflection of Toronto’s lack of openness towards the rest of Canada or the world perhaps), and generally determines that it is the best of the bunch.

In a competitive environment, you don’t decide you’ve won because some subset of competitors you’ve chose are worse than you. You’re probably facing off against a local rival, who is better than you on some metrics (and so have something to teach you), or you’re looking to and learning from the best of the best (who are the biggest threat to you).

Time and again I see people and organizations fudge the numbers, or the space, to make it seem like they are doing better than they are to stakeholders (this feels related, but different from MAUP). This is something that you can’t do (at least not forever) if reality will be forced to set in when your company is put out of business by a competitor. Organizations which aren’t forced to reckon with reality need to tread carefully.

Learning Matters

More than once people brought up with me when I was working on YouTube that my opinions changed, or that I seemed to be way more interested in one thing or another from week to week. All of this is downstream from learning. Your opinions should change (even if only at the margins) when you learn more and more, and as you discover more of the colour in the world you will almost certainly see things differently.

If I can imagine one universal truth that’s become clearer to me in all my time working on YouTube in my last career, it’s that one can always benefit from learning more. This is true across so many dimensions. Sometimes you will know a lot, but you should always be open to the idea that there’s something important that you don’t know, or hadn’t considered, and that you might find this thing in a very unexpected place.

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These are just some of the things I learned, taking the “wrong” path. I hope that this can highlight that sometimes even a dead end has some value exploring.