TL;DR: I started this site five years ago this month. This is my story, and a reflection of what’s happened since, with some musings for those wondering “what career is right for me”.

“Washington is not a place to live in. The rents are high, the food is bad, the dust is disgusting and the morals are deplorable. Go West, young man, go West and grow up with the country.”  – Horace Greeley

In 2011, I bought a one way plane ticket to Brazil. I was running. Whether I was running towards an unknown frontier or away from a known civilization, I’m still not sure. What I am sure if is that I am glad that I ran West.¹ It has made all the difference.

A year earlier, I had been getting ready to apply to law school for lack of better things to do with my life.

I was living with my parents and freelancing as a medical interpreter in Memphis, Tennessee. I had the sense that I should be doing something else, that I was capable of something more. I wasn’t sure what though and so I ran.

Through a Craigslist ad, I found someone who had a friend that ran an English school in Sao Paulo, Brazil. He offered me a job. I took it. It was warm. The people were friendly. I started teaching English, early in the morning before students had school or work and late in the night after they finished.

I thought the school’s methodology was ineffective. Two months in, I rewrote the whole curriculum. The school wasn’t terribly happy about that.

By December of 2011, I realized teaching English wasn’t the answer to “What career is right for me?” I started looking for other things to do. This was probably just a bit past the peak of the blogospere and being the perenially-late-to-the-party type, I registered an ill-advised domain name: FrontierLivin.com

Of course the domain FrontierLiving.com was taken so I dropped the g and figured it was ok because I’m from the South where we don’t pronounce the g sound in -ing it anyway. I migrated everything on that site to TaylorPearson.me in 2013.

It was inspired by a quote from the transcendentalist, Henry David Thoreau:

“It would be some advantage to live a primitive and frontier life, though in the midst of an outward civilization, if only to learn what are the gross necessaries of life and what methods have been taken to obtain them.”

The idea of a frontier life struck resonated with me. A frontier is a realm of yet unclaimed space, rife with potential where the settler may build something new, something truly his own. It is a place which demands self-reliance but in so doing allows for self-determination.

And so, having declared to the vast masses of the internet coming to my site (read: my mom) that I was in search of the frontier, I set out.

I started listening to podcasts, including one called The Tropical MBA. The name belied an elegant idea: What if, in place of spending a few years and tens of thousands of dollars for a MBA, you instead invested a few hundred dollars on books and did your learning and publishing in public, on the internet.² And, importantly, what if you took it just as seriously?

What if the frontier of education was not in another degree but in an apprenticeship: reading and self-study on nights and weekends and putting those ideas to work for a small, entrepreneurial company during the days?

I applied for a job to be a content manager. I thought I didn’t have much of a chance, but I applied anyway. It would give me something to write about, some proof of Westward movement.

I was surprised when I found out I got through to the final round of three people. I got on a call with one of the founders, Dan, and we talked for about an hour.

It started badly. I was late to the call because I forgot. I am the most forgetful person I know. I still don’t know anyone in my family’s birthday. Thank God for my iPhone calendar and to-do list.  I thought it went alright at the end and I walked out the office where I had taken the call late at night with a buzz.

The next day I got an email saying they had hired someone else. Their response was, in sum, “you seem reasonably smart and a decent enough human being but you have no specific skills to being a content manager.”

It stung, mostly because it was true. I was looking for the right opportunity, but when the opportunity came, I didn’t have the skills to take advantage of it.

Marx meets the Internet: Self-determination ensues

The rejection forced me to realized that my problems weren’t because some unjust system were weighted against me, they were a result of my own failure to take responsibility. Why I had believe that my problems were the result of some external source requires a (very brief) flashback.

During my sophmore year in college, I had read two books which have come to underpin my world view: Karl Marx’s The Communist Manifesto and Jared Diamond’s Guns, Germs and Steel.

Marx’s thesis was that the wealthy people control access to the means of production and poor people don’t and that really sucks. In Marx’s time you either owned the factory or you worked in it. If you were in the latter group, you had very little self-determination over your life. Therefore, you should band together with other people who work in the factory and overthrow the guy running the factory. Marx’s philosophy was historical determinism: that what happens in your life is constrained, if not predetermined, by historical forces.

Diamond’s thesis was that the reason some people are wealthy and other people were poor is environmental. Eurasia, particularly Europe, had access to the best natural resources in terms of crops, livestock, minerals, and germ resistance. Diamond’s philosophy was environmental determinism — that the environment you are born in is the primary factor on your life.

Combined, the two suggested that people who happened to have been born at the right place and at the right time were screwing everyone else.

I left school for a month to travel to Southern Mexico and Guatemala. My observations of the poverty there confirmed my initial conclusion: that history was determined and not particularly just. I started reading and looking up to leftist Latin American leaders like Fidel Castro, Hugo Chavez and Evo Morales.

I moved to Cordoba, Argentina and studied at the Social Justice Department. I marched for the rights of Bolivian workers and studied existing social movements to better understand how the goals Marx outlined might be realized.

These were questions I was still exploring when I was rejected for that job.

What I came to see as I studied more about technology and entrepreneurship is that much had changed since Marx’s era.

Marx lived at the dawn of the industrial economy when the tools of production and distribution were expensive and closed to most.

If you wanted to start a media company in the industrial economy, it meant buying an office, a delivery fleet, and a warehouse. It meant hiring a team of reporters. The tools of production and distribution: the printing press and deliver truck were expensive.

Looking down at my internet-connected, $800 laptop, I saw those were no longer a factor. I could write a blog post that could be read by millions. The tools of production and distribution were now cheap.

We are living through the dusk of the Industrial economy and the dawn of the Entrepreneurial Era.

I still think Marx was right about the problem: not having self-determination, that is not being able to exercise agency and control over your life, sucks. It turns out he was wrong about the solution.

It is the power of technology, not a political movement like communism, that is giving individuals the opportunity to chart their own path, to seek out their own frontier.

You used to need a few million dollars in printing equipment to publish your thoughts but I was publishing mine using free, open-source software.

The printing press disintermediated the Pope and the Catholic Church at large, because suddenly people could read the Bible themselves. There weren’t enough books prior to the printing press for people to even learn to read.

Luther and the early members of the Protestant Church asked for the Catholic Church to change. It didn’t. The extent it did change was due to competitive pressure created by other Christian sects.

The Enlightenment and its accompanying technologies, including democracy and capitalism, distributed power from kings to bankers, CEOs, and industrialists.

Today, that trend has continued. The New York Times and Wall St. Journal are lined up next to bloggers on the newshelf of the internet.

And so, business, entrepreneurship and technology, which once seemed to me time banal if not evil, became a new frontier.

What career is right for me? What do you find easy and fun that others find hard?”

The first (and perhaps still my proudest) accomplishment that stemmed from a new sense of self-determination was that I got in shape. I had been overweight since I was 10 years old, reaching 335 pounds (150 kilos) by 18 and staying there.

I downloaded every podcast and read every blog I could find on health and fitness. Within two years I had lost 120 pounds (50 kilos).

I played football in college (left) and also got to play American football for a team in Brazil. We won the Brazilian equivalent of the Super Bowl (that’s the trop on the right) which then-president Lula da Silva attended and was broadcast on ESPN. I played in different weight classes in each.

I moved back to Memphis and cold emailed twenty online marketing agencies. One agency replied and we set up a meeting.

At the meeting, I suddenly had something to show. I had built a few websites and gotten them to rank in Google. They gave me minimum wage and 20 hours a week.

Within a month I had gone from part time to a full time SEO. Within two months I was a project manager.

Six months after I had been at the agency, Dan and Ian from The Tropical MBA put up another job posting. This time for a marketing manager for an ecommerce brand they ran.

I applied again. In the year since we had originally spoken I’d built a profitable side business and was project manager at a digital marketing agency.

“You told me I didn’t have any skills. You were right. Now I have skills.”

I got the job. I discovered that if someone gives you advice and you follow it, they are likely to give you more advice and, sometimes, opportunities.

I moved to Asia a month later to build out a web marketing team for their ecommerce brand. Our three biggest product lines were cat furniture, valet parking equipment and portable bars. (If you can sell parking equipment and cat furniture, you can sell anything.)

I was living in Ho Chi Minh City, The wifi was fast and the cafe density world-class. It was loud. It was gritty. It was full of energy. It felt like the frontier, what I imagined California felt like in the late 19th century.

Ho Chi Minh City, Vietnam (Saigon to locals) has perhaps the most amazing cafe culture outside of France. If you’re in town, I highly recommend L’Usine and The Workshop.

I continued writing this site on the weekends. The first time it got any meaningful amount of attention was when I posted my notes from Nassim Taleb’s Antifragile. The concepts in the book were fascinating but there wasn’t much in the way of applications. I went back through the book to try and understand how I could apply the concepts and posted them in my notes.

Others who had read the book found this helpful.

When people ask me some version of “What career is right for me?” my favorite response is to ask is “What do you find easy and fun that others find hard?”

The answer for me is deconstructing complex systems and explaining them in eas(ier) to understand and implement ways. I love being thrown into complexity and messiness and trying to figure out what is going on. My notes on Antifragile helped me start to see that.

Businesses are, of course, also complex systems which benefit from being broken down and rebuilt more efficiently. And so, I started to see inefficiencies in the business. I began building out a set of Standard Operating Procedures for the company to make it easier to hire, train, and scale their brands.

I spent a year in Saigon and San Diego building a system to hire, manage and scale a 25 person remote team which let the founders spend less time working in the business and increased the company’s valuation.

When the company went up for sale, I moved to Austin, Texas.

Over 18 months, the product lines I had been managing had grown by 527%. I wrote a case study about how we had done it.

The two founders whose company I had just left had me back on their podcast to talk about it. (Thanks for that!). Others asked if I could do the same for them. I had clients.

Turning Pro: A New Frontier

In October of 2014, I went back to Bangkok, Thailand for a conference. Sitting around the breakfast buffet, talking with a group of internet entrepreneurs, we remarked that there was no one who had fully explained what was going on in the world of work right now (or at least our corner of it).

“How do you explain what is happening in the labor market right now to a college student or a middle manager?”

Many had tried to explain to their family and friends the logic of what they were doing but were met with either vague regurgitations of tired arguments about risk or simply blank stares.

When people ask “What career is right for me?” they think of known possibilities. Everyone knows what the lawyer, doctor and accountant life script looks like. It is pretty well laid out how to become a doctor or a lawyer: which classes you need to pass and what scores to get.

What’s the internet entrepreneur equivalent? How can someone break smart, leverage technology to take control of their life?

It’s a complex question, one I had spent the past five years trying to figure out for myself. I had travelled to half a dozen countries, reads dozens of books and met with hundred of entrepreneurs trying to understand why it was possible and how to do it.

So I started writing about it.

In June of 2015, I published the conclusions of my research in a book, The End of Jobs.

The book, much to my surprise, became a #1 Amazon Business Best Seller. Inc Magazine rated The End of Jobs one of the Top Three ‘Start Your Own Business’ Books of 2015 and a Top 25 Business Book of 2015. It has since solds tens of thousands of copies and been translated into Chinese (simple and complex), Japanese, Korean, and Thai with more foreign editions on the way.

I had, up until that point, been writing my site for a couple hundred readers, mostly personal friends. Those few people, with their tremendous support, changed that for me. I crossed into a new frontier. I turned pro with my writing.

Currently,

• I read,  write and speak about complexity, business strategies and mental models then explain how you can apply them to your life and business.
• I  work with a small group of personal clients on deconstructing and optimizing business and personal systems for achieving peak for performance.
• I’m a contributor to a small handful media outlets including Business Insider, Entrepreneur, The Huffington Post and The New York Observer.
• I run a community for entrepreneurs looking to grow their business and increase their personal effectiveness. You can click here if you’d like to hear about when it re-opens for enrollment.
• I like long walks, books, fishing (particularly bass) and powerlifting. Peanut butter with ice cream is my kryptonite.

Across the street from where I used to live in Saigon, there was an older woman who sold snails and beer lady from a rolling cart late at night. Late at night she would roll out her cart and set-up little red, plastic stools around small fold-out tables. She would steam snails and other seafood from the Mekong Delta and serve them on big plates with cold Saigon Red beer.

Once a week or so I used to go sit and eat snails late at night with friends.

To me, it felt like those little plastic stools were sat on the edge of a just-discovered coastline. The motorbike traffic zooming up and down Nguyen Thi Minh Khai ducking in and out of the hems were currents flowing from rivers and streams, stretching into the great blank space of the map.

I am speaking, of course, metaphorically. The geographic maps have long since been filled in, but the frontier is not gone, only moved. I feel the same when I sit down at the keyboard or over a cup of coffee with a friend.

The search for that frontier is no longer one conducted by nation states across continents, but by individuals across their own lives.

Man is, for better or worse, a creature made for the frontier. To dance on the edge between the known and unknown, between civilization and the blank spaces of the map, is to feel truly alive.

To the many, many people who have helped me along the way, thank you. I have, in more moments than I can count, been held afloat, if not aloft, by your generosity, kindness and support. To journey with you is its own reward.

Here’s to many more journeys together across new frontiers.

The frontier is yours to define. The great promise of our time is that we are not simply filling in a map given to us, but defining which territory we want to explore.

Yet, the imperative remains: Go west.

Last Updated on July 30, 2019 by Taylor Pearson

1. Or, well, South if you want to get technical, but whatever, it’s a metaphor. You get it.
2. And if you were going to be doing it online, why not do it from somewhere warm, cheap and exotic?