On the Joy of Just Winging It

A world constructed from the familiar is a world in which there’s nothing to learn … (since there is) invisible autopropaganda, indoctrinating us with our own ideas.

— Eli Pariser

Back in college, I did the study-abroad thing in Europe. I was living in Barcelona, and I used my Eurail pass to go to Genoa, Italy. I went to Genoa because it seemed like it might be less touristy than other parts of Italy. The first trip every kid with a Eurail pass did was Rome and Florence, so I wanted to try something different. Genoa was on the water, near Cinqueterra, not too far from Barcelona, and judging from the pictures I had seen online, looked like whatever the 20-year-old version of me imagined to be authentically Italian.

I brought with me my Let’s Go Europe guidebook. I ripped the pages out of the section on Genoa and stuffed them in my pocket, so as to not stand out too much as a tourist. I was self-conscious about not wearing clothes that stood out as too American-y, so when I arrived, I tried to blend in to the bustling if not somewhat grimey city that was Genoa.

Of everything I read on Genoa in Let’s Go, what I was most excited about was this small, super friendly, cheap, hole-in-the-wall family-run pasta place, with Mom serving the pasta, and with Dad and Grandma making it in the back. Pasta was my favorite food growing up, so going to a real Italian pasta place sounded like the coolest thing on earth to me. I had to check it out.

The restaurant was nowhere near the hostel I was staying, and so I had to navigate three buses to get there, getting lost multiple times on the way. It was early May, but unseasonably warm and humid. The buses were crowded. I was sweating on those around me and they were sweating on me.

The restaurant was at the top of a steep hill and then down an alley. It was as close to a literal hole in the wall as any restaurant I had ever been. I opened the door, tried to mumble a few words of half-Italian, half-Spanish, and a surly-looking woman pointed me to a table. I peered around the room, and of the ten tables in the restaurant, probably eight of them had a Let’s Go book.

In my quest for an authentic Italian dining experience, I had trudged across Europe, to a remote part of a dingy Mediterranean town, taking three buses, only to find myself in what must have been the only restaurant in the city whose patrons were mostly American college kids.


In the last five years I’ve probably read a dozen books that mention the famous split-brain experiments on confabulation. A few examples include Sam Harris’s Waking Up and Kevin Simler and Robin Hanson’s new book The Elephant in the Brain.[1]

The split-brain confabulation studies are fascinating and fun. But that’s not what I’m questioning. What I’m questioning is how, in my efforts to learn new and different things, I keep converging on books that talk about stuff I have already read.


A little more than month ago, I had never heard of Jordan Peterson. And then I heard about him in this article by Conor Friedsdorf of the Atlantic. And within days, I saw a few people posting about their own 12 Rules for Life, riffing off the title of his new book. And then I figured I’d write my own version. And then I noticed a friend writing about him on his blog, and how he was reading about Jordan Peterson everywhere, too.

In a matter of days, Jordan Peterson went from someone I had never heard of, to someone who was everywhere I looked online.

Kudos to his publicist.


If you come here often, you may have noticed that I occasionally post links to other sites.

I take articles from my favorite sites and blogs, including Kottke.org, the Browser, 3 Quarks Daily, the Legal Theory Blog, Semi-Rad, Crooked Timber, Marginal Revolution, Slate Star Codex, Shtetl-Optimized, and Calculated Risk. I’ll copy and paste whatever I find into Evernote and then write about them here.

And then I kept noticing that the links I was saving were appearing on my other favorite sites. Somehow, in my quest to find new and interesting links to share with people online, I had converged upon the same articles everyone else thought were interesting and worth sharing.


I live in a town near lots of running, biking, and hiking trails. In the last few years, an increasing number of apps provide descriptions of the trails, and users rate the trails based on their experiences. With so many trails, only a few get the best reviews. One of those here is the Monarch Crest Trail, which is considered among the best biking trails in the country. But it’s also more crowded than parts of Central Park in NYC every weekend from late June through October.

But then, there are also lots of other trails that are only slightly less beautiful than the Monarch Crest Trail where you can spend a holiday weekend and often not see another soul.


I’ve always prided myself on trying to be different in what I do. When I travel, I like to seek out experiences that aren’t super touristy. When I read, I like to learn stuff that’s different from what everyone around me already knows. When I go outside to play, I’d rather it not be at the Grand Canyon on a holiday weekend.

But clearly, try as I might to be different, I still kind of suck at it.


The problem is, I don’t want experiences that are just different: I also want to find some cool stuff. I want to find some places that are nearly as spectacular as the crowded spots, but nowhere near as crowded.

I’m looking for the hidden gem, the spot that’s beautiful, pristine, and I have all to myself.

But places that are crowded tend to be crowded for a reason. The Grand Canyon is so damned crowded is because it’s one of the most awe-inspiring places on earth. So even though it’s usually super crowded, it’s still absolutely worth going there (you just have to be picky about when and how you do it).

The reason the Italian restaurant in Genoa was full of Americans is because another American college kid published a snippet about it that inspired everyone else to follow her there.

We converge on things that come highly reviewed. I get it.

The question is whether there’s a way to find the hidden gems while avoiding both places that are unpleasantly overcrowded and places that are, well, not worth visiting for a reason.


Eli Pariser coined the term “filter bubble” in 2010. According to Pariser, the filter bubble is caused by algorithms that lead us to have our own opinions and biases confirmed in our interactions with the internet. The sites we visit collect data on what we like, and then gives us back more of what we like every time we use it. The algorithms at Netflix, Amazon, Google, Facebook, Twitter, predict what we will like in the future based on what we have consumed in the past.

It’s good to get more of what we like. But getting future experiences based on our past experiences means we’re stuck in a feedback loop. According to Pariser, these algorithms “close us off to new ideas, subjects, and important information.”

There is growing data that these recommender systems are leading to convergence in the way we learn and what we like, not just ideologically, but for simple tastes and preferences as well.

If you enjoy one book that talks about split-brain patients in the context of Buddhism and spirituality, it would stand to reason that you might like another that talks about split-brain patients in the context of mixed motivations. But the same algorithm that correctly predicts that you’ll like “X” because you liked “Y” starts to feed you more and more of the same crap. And then everything starts to feel, taste, and sound the same. If you use Netflix, Amazon, Google, Facebook, or Twitter (do you know anyone who doesn’t use any of these?), then, unless you alter the default settings, your life will reflect this convergence.

Twitter doesn’t suggest that you follow someone whom only a few people think is interesting, but most people think is a weirdo. Netflix doesn’t suggest that you watch shows that a few people think are great, but most people think are bad. You’re being directed to the same media that appeals to everyone else (with your same age, gender, socio-economic status, and ideology cohorts).


I suspect another part of the explanation for this convergence is a sort of winner-take-all effect of popularity. The top .01% of 1% of influencers are all connected to each other through mutual contacts and by sheer force of mutual influence. They leverage each other’s platforms to expand their influence and promote their work. If I were influential, I’d do the same. But there is a limited circle of people with a big enough following to create this effect, and so they start to converge on each other. People who like Tim Ferriss’s podcast pick up on Jocko Willink’s podcast and Sam Harris’s podcast (and James Altucher’s and Debbie Millman’s) and then the same guests appear on each other’s podcasts and then everyone has podcasts where, after a few episodes, you can easily predict what’s going to happen next. And then those people talk about the same few books, topics, and habits, and then all of those things converge on each other. And since those people collectively influence so many people, all of those people converge on each other, too.


I think there’s something to be said for reading the blogs of weirdos and outcasts. For checking out podcasts that don’t already have millions of downloads. For going to the library and picking up a book by an author you’ve never heard of.

People who are successful are usually successful for a reason. But there are a lot more people who are talented than there are people who are famous. It’s worth spending some time on your own searching for them.


Maybe it doesn’t matter much if we’re all reading and thinking about the same things. But to me it feels off—like we’re losing forms of intellectual and cultural diversity. Count me in the group that believes that diversity is a critical precursor to growth. And so I think it’s worth the effort to take extraordinary efforts to try to do different things.


The thing about critically acclaimed, highly-reviewed hidden gems is that they don’t tend to stay hidden gems for long. Once the word gets out, you’ve probably already missed your window.

Markets in experiences, books, places, and restaurants all tend to self-correct. If everyone wants to find a delicious, cheap, not-too-crowded, authentic Italian restaurant, and publishers, writers, and food critics are highly motivated to find those restaurants and to share them, then the critically acclaimed, highly-reviewed delicious, cheap, not-too-crowded authentic Italian restaurant is going to be about as easy to find as a $20 bill on the ground. We might stumble upon $20 bills on the ground a few times in our lives, but maybe not even that often.


Don’t get me wrong: I still think there are hidden gems. I just don’t think you’re likely to find out about them on Tripadvisor or on All Trails.

I think you just have to go and figure that shit out on your own.

The expression, “you have to kiss a few frogs to find your prince charming” is sexist and stupid, but I think there’s some value to thinking that way with life experiences—specifically, acknowledging that you have to have shitty experiences if you also want to have rich, novel experiences.

Without the prior filter, we’re wandering into the unknown. With the filter bubble, we’re picking a known quantity. But so is everyone else.


If you base all of your choices on other people’s previously cultivated experiences, (and on your own prior cultivated experiences), your life just won’t be that interesting. It’s just becomes a copy or a copy of a copy.

If I had wandered around Genoa back then and eaten at any restaurant that seemed popular with the locals, I’m sure my experience would have been better than the one I had. Genoa didn’t have that many tourists in 1998. So nearly anywhere I could have eaten would have been a novel experience for a 20-year-old kid. Instead I chose the safe route to eat where the most popular guide book for college kids suggested I eat. By trying to rely on someone else’s advice for what was authentic, I got the opposite.


A few years back, I met a guy on the island of Ometepe in Nicaragua, and this was how he traveled: He got off the plane, and he talked to people. And he asked them what they were doing. If what they were doing sounded like fun, he asked if he could join them. If what they were doing sounded boring, he went and talked to someone else.

My wife and I only had two days on the island of Ometepe, and so on the last day we were there, we were going to hire a taxi driver to take us around the island. He struck up a conversation with us at a crowded hostel bar, and that’s where we told him about our plan. He said that sounded like fun and asked if he could join us. We said sure.

He was a fun and interesting guy. And though he traveled less frequently and on a tighter budget than my wife and I did, it sounded like he had better stories to tell.


If you make all of your decisions the same ways everyone else does, your life will end up exactly like everyone else’s.

I’m not saying we all need be exactly like the guy I met in Ometepe, but I think most of us would benefit from more of that tendency.

With globalization and the emergence of a handful of companies (Facebook, Google, Amazon, Apple, Netflix) that influence nearly all aspects of how we collect and process information, pre-filtered life is growing increasingly homogenous. That might be more true today than ever before.

Better to get offline and get analog with experiences. It’s ok to let algorithms, critical consensus, influencers, and public opinion shape your decisions some of the time, but probably best not to let them do it all of the time.

Sometimes it’s better to just wing it, even though sometimes this will suck. You might get food poisoning. You might find out too late you’ve gone camping next to a swamp with an infestation of mosquitoes. Sometimes you will meet unpleasant and uninteresting people.

I do not have it all figured out. But I’ve come to believe that even crappy experiences like that are worth something if it feels like you came up with the crap on your own.

Better to live my own life badly than spend my whole life living someone else’s seemingly well.