The Pathless Path – or, why careers are overrated, and what to do instead

Several years ago I went on a blind date.

The girl was Venezuelan, and (stereotypically) quite late for the occasion.

I’d selected the venue: a Mexican restaurant off Calle Serrano in Madrid. I waited a while, annoyed, and sipping on a Modelo.

Finally, my date arrived. She was cute. A common acquaintance had put us in touch, saying the girl – let’s call her Sandy – worked at the Venezuelan embassy.

I was impressed by that. It sounded important. That’s why I’d picked this classy place for our first date.

We sat at a corner table, Sandy and I, sizing each other up over nachos and margaritas.

She started the conversation like this: “Most people have very normal jobs. But you don’t seem to have a job at all. What is it you do, exactly?“

I don’t remember what I said, but I think in those days my usual answer to the “what do you do” question was to give a long explanation of what SEO is and how I used it to funnel people into my email list, where they’d eventually buy one of my books or sign up for one of my online courses.

Now I just tell people I’m an author, but at that point I’d just retired from my day job, and wasn’t quite sure how to explain the whole thing.

In fact, I was having a bit of an identity crisis as well. I’d been a teacher for so long, it had basically become who I was.

Now all I did was sit on my sofa all day, writing blog posts and making videos. I was making good money, but secretly I felt like I might just be some unemployed couch potato who was enjoying a bit of temporary good luck.

I was, in other words, on the Pathless Path… and it felt a bit weird.

Questioning the Default Path

I recently read an article called The Great Contemplation by one Paul Millerd, a guy from Conneticut who quit his fancy corporate job to become a freelance consultant, travel the world, etc.

In the article, and also his book The Pathless Path, Millerd describes how the whole idea of Lifestyle Design popularized by Tim Ferriss’ Four-Hour Work Week has, over the years, become much more mainstream – not as a series of life hacks one could use to avoid work, but as a questioning of the Default Path of college, career and retirement itself.

And it’s true. Digital nomadry, remote work and lifestyle design are all becoming surprisingly popular, at least among the white-collar office-job crowd.

Personally, I’ve spent more than a decade designing my life so I can earn passive income and escape from pointless drudgery. And it worked. I quit my day job in 2015 – a few months before my blind date with the Venezuelan – and haven’t looked back.

But I came to all this from a different angle. I wasn’t working a cushy-but-unfullfilling six-figure consulting job when I started on my project of lifestyle design.

I was an illegal immigrant just trying to create a Plan B in case I got deported.

I’m not exaggerating at all.

Somewhere in my files, I have a page in a notebook outlining my plan to earn 800€ a month as a blogger so I could move to Latin America when I finally got kicked out of Spain.

I figured that if I had a Plan B that was just as exciting as my Plan A (working shitty jobs until I died poetically in my rented room in Madrid’s second-worst neighborhood) I’d probably feel less stressed about the possibility of my Plan A not working out… and I was right.

I also have, in my files, a letter from the Spanish government telling me my final work permit application had been denied, and that I had 15 days to leave the country, or else. In the end, I didn’t leave, and Spain didn’t get serious about deporting me. Eventually things worked out far better than I could have hoped… but it was hit or miss there for a while.

All this to say, I’m not the typical Ivy-League or Silicon-Valley lifestyle designer. I’m just a guy who decided I was never going to fit into “normal” society, so I should probably choose between entrepreneurship and a life of petty crime.

(And at first, to be perfectly honest, I figured I was better suited to a life of petty crime. I didn’t know many entrepreneurs when I was younger, but I knew plenty of criminals. So a life of crime seemed, sadly enough, like a more achievable goal.)

Suddenly, working on your sofa becomes mainstream

For a while, I felt more or less alone in this lifestyle.

Then covid hit. In the first weeks of the lockdowns in 2020, several people who had previously thought I was just a lazy, unemployed no-account got in touch, wanting to know how exactly I managed to make money online.

Suddenly, lots of people were working with their laptops on the sofa, and I felt like I was ahead of the game.

While the nine to five crowd frantically searched Amazon for new office furniture that would ensure their peak productivity at home, I just giggled, because I’d figured out years before that “peak productivity” isn’t a reclaimed wood desk or a lumbar-supporting chair: it’s a mindset, closely interwoven with desperation.

I’d written blog posts and books while sitting in bed, or in noisy cafés between classes, or at my greasy kitchen table while my emphysemic neighbor coughed her lungs up on the other side of a paper-thin wall.

My “standing desk” was the two-volume edition of Julia Child’s Mastering the Art of French Cooking sitting on my kitchen counter, with my laptop perched on top. I had a view, while I worked, of the rooftops outside, and also of the dirty dishes in my sink.

As the pandemic dragged on, we started to hear about the Great Resignation. Quiet Quitting. People questioning the basic assumption that work was supposed to be “at the center of life”.

Well duh, I thought. Didn’t we all figure that out when we were teenagers?

Apparently, we didn’t.

Trudging down the Default Path

My time on the default path, as Millerd calls it, wasn’t very long.

I remember the day I was sitting on the sofa (back on the ranch in Arizona, this was) around age 12, and I realized that I was trapped living out someone else’s life plan.

It went something like this: Get good grades in middle school so you can get good grades in high school so you can go to a good college and get good grades there, at which point you’ll be able to join the “world of work” and spend the next 40 years following a bunch of rules made by unfeeling corporate bureaucrats, until you finally retire and watch TV while waiting for death.

Twelve-year-old me was depressed as hell to realize he was being forced onto this path, but – living in the middle of the desert, with limited information – he didn’t know there were other possibilities.

So he went through the motions, got good grades, and spent several years hoping that at least he could use the default path as a way to escape from Arizona.

And eventually, he did.

See, he (or I) didn’t have a lot of exciting adult role models back on the ranch. We lived in the desert. There wasn’t much going on. And almost everyone around seemed to do one of three things: work in a cubicle, work at the school, or work at Safeway.

I wasn’t really even aware that better jobs existed… or at the very least, I assumed that all the cool jobs were all given to people who’d grown up in New York or LA.

And maybe it’s just a quirk of my upbringing, or maybe I’m weird, but I never had the same sorts of ambitions as other kids in my patch of desert.

Staying dry in the land of marine biologists

In school, when asked “What do you want to be when you grow up?”, I didn’t know what to say. But a surprising number of kids in my grade said they wanted to be marine biologists. Which brings up a few questions in my mind:

1. Where did they get the idea, out in the desert, miles from any naturally-occurring body of water, that they wanted to be marine biologists?
2. Did any of my class of 2001 actually end up becoming marine biologists? And…
3. What the fuck is, exactly, a marine biologist?

We had a career orientation day at one point, and I remember scanning through a long guide to different professions and their average salaries, thinking that adult life was going to absolutely suck if these were my options.

The aptitude test we took told me I should be a farmer. Is farmer a job you can just apply for? I wasn’t sure. There wasn’t a lot of agriculture in our area, so I don’t think I’d ever been on a farm at that point. Also, I hated my dad’s hobby of doing “yard work” already. How was I going to feel about farming for a living?

Finally, I finessed the default path into getting me out of the desert. At least I’d accomplished that.

My brief attempt at gettin’ educated

At university in Louisiana, I ended up meeting new kinds of people. I was impressed by the job of “college professor”, and briefly contemplated getting a PhD in English Lit so I could do that for a career. But it sounded like a lot of sitting in libraries, and mostly, I just wanted to have adventures.

Out there at my semi-decent deep-South university, in fact, I was even more impressed to finally meet a few people who had been to other countries.

Yes, it turned out that students at my university would occasionally engage in low-budget travel to locations like Europe or South America, and come back to the US having had a broad range of interesting life experiences. And the best part was that their parents weren’t necessarily millionaires. They – my classmates – were just kids who had saved some money from working summer jobs, bought a plane ticket, and spent a month or two backpacking around.

(Okay, probably some of those kids had millionaire parents, and they’d just downplay that part of the story in conversation. Either way, my mind was blown. Nobody in my dusty patch of desert had that sort of imagination.)

Could I just go places?

Yup.

After a few months I realized that liberal arts was a scam. I was going deeply into debt in order to have somebody give me a list of books to buy. And in the end, I was just going to end up working at a Starbucks anyway.

I figured I could quit now, with significantly less debt, and go straight to working at Starbucks.

So I dropped out.

Starbucks never called me back. But a small, local coffeeshop did. And with that, I was done with the default path forever.

Welcome to the Pathless Path

I went back to Arizona, and spent a few more years in the desert, working in coffeeshops, reading books and getting my heart broken.

Then I moved to Madrid, where I spent several years teaching English, reading books, and getting my heart (repeatedly) broken.

(When I say “moved to Madrid”, you should read that as shorthand for “overstayed my tourist visa for several years while working under-the-table as an English teacher”.)

Oh well. Scraping by at the edge of poverty in Spain was 100 times more exciting than the default path would have been.

Like I said earlier, eventually I started an online business so I’d have a Plan B, I got my work permit sorted out, and – several years later – quit my day job(s). The Pathless Path has been pretty good to me.

But it does bring a lot of uncertainty with it. And (as Millerd says) a lot of people might judge you for not having a “normal job like everyone else”.

Life as a status-seeking primate in the 21st Century

Do we have to define ourselves based on our jobs? Judge each other on our incomes?

It’s certainly popular to do so. I’ve never had a conversation with a stranger that started with “What are you truly passionate about?”

And, as highly sociable animals, I guess we have to size each other up somehow. Passion usually doesn’t pay the bills, or tell people what size bills you might be paying.

What does? Your job title. Your personal appearance. Your bearing.

We’re all just status-seeking monkeys, after all, with brains adapted for Dunbar’s-number-sized tribes out on the savannah. In a group of twelve dozen men, women and children, everybody except infants has to be useful in some way, and there are a limited number of paths to achieving social status.

Set a few billion primates loose in the modern urban and suburban landscape – and give them smartphones – and status becomes much more ambiguous. You can pick between thousands of career paths, found a startup, become a rock star, get famous by dancing on TikTok, show your butthole on OnlyFans… the options are practically infinite.

Turning the basic human urge to be useful to your tribe into a status game based on job title and salary – or number of followers on social media – is less than ideal, but I feel like it’s mostly inevitable in our current society.

So what do you tell people that you “do for a living” if it’s a hard-to-describe job you created yourself out of thin air?

What do I actually do for a living?

Seriously, folks. I’m still trying to figure it out.

On Quiet Quitting and the Great Resignation

I read Millerd’s book, The Pathless Path, and I didn’t hate it.

But I’m pretty sure I’m not the target audience for this sort of thing.

I feel like what the lifestyle designers are (often) missing is that they’re among the wealthiest people on the planet, and that leaving a six-figure job to become a freelancer is only a form of rebellion among the vanishingly small minority of people for whom six-figure jobs seem like the norm.

The fact that a majority of people on the planet live on 10 dollars a day or less – often much less – is easy to ignore if you’ve spent most of your life in Connecticut.

And if your job is to write clickbait for Business Insider, of course, the vague sense of dissatisfaction of the laptop class seems relevant to you.

But “Quiet Quitting” isn’t new.

We used to call it “sucking at your job”, and people have been doing it forever.

And “The Great Resignation” sounds like a cute adventure if you’re a corporate type, but the fact is, I’ve got alcoholics in my neighborhood who gave up on participating in the labor force long ago.

They decided work wasn’t going to be at the center of their lives, and now they live in sleeping bags and drink box wine. I’ve also got refugees on my street whose pathless path involves collecting scrap metal and pulling food out of the dumpsters, while living in abandoned warehouses on the outskirts of town.

You may worry that your upper-middle-class parents will love you less if you’re doing something you enjoy rather than something that’s considered high status… but what do the trash-pickers’ parents think of them?

Far from home, getting by on pocket change and canned tuna, rising at dawn to push around a shopping cart full of recyclable copper, steel and aluminum… Do they have moms back home who are still fuming because their sons didn’t make partner at the law firm?

For some reason, I doubt it.

Good news: you may already be on the Pathless Path

I don’t want to be that guy, but I guess I’m going to point this out anyway: lots of people aren’t cut out for the corporate world. And, just as important: lots of people never really had that option to begin with.

I try to keep an open mind when I read yet another story about “how I quit my unsatisfying six-figure corporate job to go hang gliding in Costa Rica”, but sometimes it really tests my patience.

If you think about it – or, say, take a walk in any urban area and look at what people are doing – you’ll find this “pathless path” is much more common than the laptop class tends to realize. Plenty of people don’t have careers, per se. They do odd jobs, they work part time, they have side hustles. They’re scraping together a living doing several different things at once, or with seasonal work, or whatever.

Is work “at the center of their lives”?

Maybe. Sorta. But certainly not in the same way it is for someone who works at McKinsey & Co.

So I’d like to propose that you don’t have to go to an elite university or work at a huge global company in order to quit a soul-sucking job and follow your bliss on the Pathless Path.

If you’re like me (or other the 99.9% of humanity) who never had a six-figure job to be unsatisfied by, don’t worry. You can still do big things, and create your own path. People do it all the time. They just don’t necessarily start a podcast about it.

Social class in America: it exists!

Millerd’s book uses the term “social class” a total of zero times in 200 pages, as far as I can tell. Which is probably natural. We Americans don’t like talking about class.

But I wish we would talk about it more.

If we were in the habit of talking openly about class, maybe we could discuss the fact that the media tends to wildly over-represent the concerns of people who go to a few elite universities on a postage-stamp-sized area in the northeast corner of our country.

And that as a result, a whole lot of other Americans end up feeling like we’ll never be educated or well-networked enough to do anything exciting with our lives, so we’d better just accept the life we have, out in our “flyover states”.

But don’t be discouraged, gentle reader. Just because you didn’t go to an elite business school – and, statistically speaking, it’s almost certain that you didn’t – that doesn’t mean you can’t have a lot of fun creating your own path.

You might just have to start small, like I did… working while sitting up in bed, for an hour every day, before going to my under-the-table teaching job.

I guess you could call it bootstrapping. And it’s a good American tradition.

But back to that blind date…

My date with Sandy the Venezuelan diplomat didn’t go well.

I should have started planning my escape when she interrogated me about why I didn’t have a “normal job”, but she had some interesting personal attributes – silicone, I’m pretty sure – and I figured it might be worth it to stick around for a while and see where this was heading.

We ordered a couple of main courses, and another round of margaritas. And it just went downhill from there.

First she started singing the praises of Bernie Sanders – remember ol’ Bernie? I hope he’s having a good day. Then it turned out she was an actual Venezuelan socialist… an elite one!

Yes, while her compatriots were starving in slums, or writhing in hospitals without medicine, electricity or clean water, she was at the yacht club, hobnobbing with the champagne socialists in the Bolibourgeoisie.

I’m not even exaggerating. I wish I was. But she literally went from Bernie bro-ing to reminiscing about her times at the yacht club in Caracas in the space of about two minutes. And that was the last straw.

I paid the bill with my dirty capitalist money – easier than trying to split it – and walked her to the metro. I never called her back, never saw those attributes.

I’d started out being enticed by the idea of dating someone with an actual career. But it wouldn’t have worked. The memory of that evening still gives me a fluttery sense of unease in the pit of my stomach.

I can’t stand elitists… socialist or otherwise.

This essay didn’t go where I was expecting it to. I wanted to write another “Yay, remote work!” article, about embracing non-standard career choices.

But then I started thinking about how few people I know are on the so-called “default path” at all. And about how, for most of us, that whole path sounds like something exclusive, far off, and expensive, where they’d take one look at us at the door and send us back to where we came from.

Yes, a lot of people are on the Pathless Path not because we made some grand philosophical conclusion – “Life is too short to waste your time earning a paltry $192,000 a year in Manhattan!” – but because the elite-university-and-six-figure-job path just wasn’t available to us. In my case, I barely even knew it existed, until the lifestyle designers started pointing it out to me.

Anyway, I apologize to Paul Millerd, who’s probably a great guy, and to Sandy, who… never mind. If you happen to have been born into some elite class of people somewhere, congratulations. If you’ve managed to work your way up, even better.

And if not, don’t worry. There are still plenty of opportunities out there.

See you on the path.

Yours,

Daniel (AKA Mr Chorizo).

P.S. I was feeling slightly bad about excoriating the upper-middle classes in this one, but then, in the middle of my research, I found out about a movie called Coastal Elites, made in 2020. You can watch it on HBO Max. It’s pretty awful. And guess what? Four minutes in, Bette Midler’s character starts ranting about how she hates “those other people”. Yes, the ones in Nebraska, and Ohio, and Alabama. She specifically mentions flying over “those people”. It’s obnoxious in every way imaginable. And now I feel less bad.

P.P.S. Questions? Got something to add? Hit me up with your stories from the path – default or pathless – right here int he comments section. Thanks!