People are always sending me job applications. Between the job board notifications I’m subscribed to, several Facebook groups I’m part of, and well-meaning friends/family, I probably see at least a dozen new job descriptions a week.

Up until recently, I was happy to receive this information, as I was still contemplating getting a full-time job…someday

What I’ve realized lately, however, is that this mindset of “maybe someday I’ll take a full-time job” was holding me back. In today’s post, I’ll explore my journey from 9-5 job seeker to where I am today (hint: I’m no longer looking for a “job”).

Phase 1: The Traditional Job Mindset (childhood to early college)

Growing up, I didn’t have any personal models of entrepreneurship or self-employment. My mom was self-employed for most of my life. But she never described it that way, and I was too young to understand (or care). She still went to work in an office (even though she did much of her work at home during the evenings). And my dad had a fairly regular 9-5 (ish) job in law enforcement.

Sure, I had friends whose parents owned their own businesses. But even in that case, their lives still resembled those of traditional job holders. They went to work every day at a place that was not their home, and the nature of their work seemed sufficiently “business-y”.

Because of this background, for most of my life I figured I’d have a job that looked like this:

  • Go to work for 8-ish hours a day
  • Get the weekends off
  • Take a couple weeks of vacation per year

High school didn’t add much to my ideas of what a job looked like, except that I learned about things like salaries and paychecks and even vague images of insurance and retirement. All still pretty conventional stuff.

Even when (around my junior year of high school) I began to consider the possibility of a career in academia, I still figured I’d eventually:

  • Work in an office
  • Have set hours
  • Take paid vacations
  • Gossip around a water cooler

I never figured my life would be any more unconventional than that.

Until one fateful evening that would change everything.

Phase 2: Discovering Alternatives (early to mid-college)

For reasons that I won’t go into here, I found myself looking to get in shape at the beginning of January 2014. The details are lost to the browser history’s dark annals, but I imagine I googled something along the lines of “how to start working out for nerds” or “how to get in shape if you hate exercise”.

Whatever the case, I found myself on a site called Nerd Fitness. While it’s evolved a lot in the four years since I discovered it, Nerd Fitness remains at its core a site aimed at making fitness and healthy eating accessible (and fun) for everyone  (especially self-described nerds and non-athletes). The site’s message was life-changing in itself, but it also sowed the seeds for something I could never have anticipated.

While browsing the site one evening before I was set to leave on the College of Wooster Symphonic Band Spring Concert Tour 2014, I came across a guest post by Thomas Frank of College Info Geek. The post itself was helpful and relevant (how to eat healthy as a college student), but the site it linked back to–that was what would change my life in wholly unexpected ways.

College Info Geek was an eye-opening read. It was about lots of things I never learned in school: study tactics, personal development, and even self-employment. Here was a guy who had gone through most of college figuring he’d just get a corporate IT job, but then found his side hustle website making so much money that he not only paid off his student loans in record time–he turned the site into his full-time job.

WTF? I thought. You mean I can just type shit into a computer, people will read it, and the money will come?

Well of course that’s bullshit, but the whole premise of “making money online” was foreign to me up till that point. Sure, I knew it was possible to make money online, but my only images of that business were ecommerce giants like Amazon or large media sites like BuzzFeed. I never figured a regular guy like me could make any money on the internet.

Mind sufficiently blown, I wanted to learn more. I wanted to learn how I could get some of this online action. Which led to the next phase…

Phase 3: Faffing, Floundering, and Fucking Around (2015)

The chronology of this phase is fuzzy, so please bear with me as I attempt to parse it out. Much of it happened at the same time and it’s hard to say what led to what.

To start, I became a devoted fan of College Info Geek. I read through almost the entire backlog of content on the site, subscribed to the podcast (the first I ever subscribed to, in fact), and eagerly awaited email announcements of new posts. I also began to engage with Thomas via email (more on this in a bit).

At the same time, I created my first online project: this website. Way back in April or May of 2014, I registered the domain “”, followed Thomas’s website creation tutorial, and was online. Since then, this site has taken many forms but has remained (mostly) a place for me to showcase my professional writing and write about topics that don’t fit in my client work.

But I’m getting ahead of myself. How did I even get into “client work”? Well, at first, I didn’t. I built my website with the intention of sharing my thoughts and art, as well as having something more interesting than a business card to show prospective employers. But I didn’t make much of a (real) effort to make money online.

Oh, I read and listened to and watched a metric shit ton of content about “how to start an online business”. But I never took any tangible steps to start one.

This went on for the summer following my first year of college, which I spent cashiering at Wal-Mart (a story for another time). Throughout, I continued my correspondence with Thomas, engaging with his posts in the form of comments and social media shares. I did this out of genuine interest and curiosity–I wasn’t looking to promote myself or get any money out of it.

Eventually, Thomas asked me if I’d be interested in writing a guest post for College Info Geek. I was fucking floored. Me? Write? For a real website? With readers and subscribers and dropdown menus? I jumped at the opportunity and penned my first published article: 6 Writing Tips to Make Your Papers 300% Better.

Thomas was happy enough with it that he agreed to have me back for a second guest post, and after a couple of those he proposed that I write regular, paid articles.

Now if getting offered a guest post was flooring, this was flatteningPaid work? $$$ in exchange for my words (well, more like $, but I was a broke sophomore so any job that didn’t involve scanning groceries or lifting heavy objects seemed pretty damn good to me).

So what happened next? Well, I’d like to tell you that from there I hustled my ass off to leverage this first freelance gig into additional work, making enough to pay off my student loans before graduating and buying myself a round the world trip as a graduation present.

The reality, however, was less inspiring. I stagnated. I didn’t know to call it that at the time, but I was so new to running a business. Fuck, I didn’t even know what I was doing could be called business. I just saw freelance writing as another job, one that despite being infinitely more satisfying, netted far less per month than my hourly campus post office job.

I eventually picked up another gig writing for a plant nursery blog, as well as a couple random editing gigs. But overall, I was just spinning my wheels. And I was okay with that, because I still viewed freelancing as just side income, a way to build up a portfolio that I could use to get a full-time job at a marketing agency or media company.

That was, until I got a taste of another life.

Phase 4: The Year the World Opened Up (2016)

2016 was a year that would change my life more than any other before or since (though I have big plans for 2018). It was a year of many firsts: my first time ending a (bad) relationship, my first time going on a road trip with friends, and my first time drinking tequila.

Relevant to this story, however, it was the first time I lived abroad.

From February – June 2016, I studied abroad in Belfast, Northern Ireland, at Queen’s University. This experience taught me a lot about about the world, about life, but the most enduring lesson was this: I could live on my own, in another country, and survive. I could improvise when the shite hit the fan. I could make friends in a strange land.

More than any of that, though, I got a taste. I experienced whole new modes of living and realized that they were available to me. I, Ransom Patterson, could live a life of perpetual travel if I wanted. I could be work in a cafe in Vienna one morning and be sipping wine on a balcony in Barcelona that same evening. I had the skills, and how I saw the possibilities. I just needed to make one key piece work: the money.

Phase 5: Figuring My Shit Out (fall 2016 – summer 2017)

When I got back from Europe, I continued to travel. I went on a summer trip to DC with friends and took a weeklong solo trip to Portland, Maine, over my 2016 fall break. I continued to freelance for College Info Geek and did some editing work for Stephen Warley (who remains a mentor and friend).

My post-grad life remained uncertain, however. I was less anxious than many of my classmates, knowing that I always had freelance work if I couldn’t find another job. I half-assedly applied for some remote jobs, but my heart wasn’t in it (I should have taken that as a sign).

Out of the blue, a potential opportunity fell into my lap. I mentioned to one of my friends that I was a freelance writer, she said her dad hired freelance writers, we exchanged phone calls and emails, and a couple days later I was writing my first paid articles for one of his agency’s clients.

That work kept me busy enough, and it gave me a valuable glimpse into life at a marketing agency. They also more or less offered me a job. There was just one problem, you see. I couldn’t really accept a full-time position set to start in the summer because, well, I wasn’t going to be in the city.

Or the state.

Or the country.

Or the continent.

You see, before any of this had gotten under way, I had booked and planned a 3-month trip to Medellín, Colombia, because clearly my life wasn’t busy enough already.

Seriously, though, I had been learning Spanish for over a year at this point, and I was starting to get pretty good. I was on the verge of fluency, but I needed something to push me over the edge. I heard Medellín was a hotspot for digital nomads, had a low cost of living, and was a Spanish-speaking city (with the added bonus of few English speakers). I did some research, booked a flight, and found an Airbnb apartment. That done, I managed to convince my parents I’d be safe and began to count the days.

So when I got the job offer at the marketing firm, I found myself in a difficult position. Should I give up my trip to Colombia and instead take this job? That would have been the sensible thing to do. I had received an offer for the sort of job that many of my classmates were struggling to find. A job in my chosen field, with a tight-knit, hip office in downtown Nashville. To turn down such an offer seemed ungrateful, foolish, reckless even.

So I did what I always do in such I situations: I simulated the different outcomes in my head. I imagined myself taking that job and what that would be like. Some of it was sexy and exciting: a solid job straight out of college, benefits and paid vacation, the opportunity to travel, and an apartment within walking distance of the office. Not to mention, parents who would no longer worry about me.

But not everything I saw was so bright and beautiful. For along with the benefits, I also saw: creative stagnation, getting comfortable/complacent, and a tenuous pile of car payments, $$$ rent, and fat bar tabs all balanced atop this one job. My Spanish skills withered; my waistline expanded; I gave myself over to my 9-5 and the unlikely promise of retiring at 65 on my 401k.

I realized that I couldn’t take the job. As scary as it was to leap into the trip to Colombia with nothing more than a bit of savings and a couple freelance gigs, I knew I had to do it. If I didn’t, I would forever wonder What if? What might my life have been if I had taken that plunge?

Which brings us to the next section:

Phase 6: Otra Manera de Ser (September – November 2017)

If studying abroad showed me another way to live, then living in Medellín showed me another way to be. I saw and experienced countless things there that changed me, but the most relevant for this article come from the people I encountered. Specifically, the other online entrepreneurs.

More than anything, the expats I met in Medellín made me realize I had been playing small. Or at least, playing within a limited set of possibilities. I met people who made money doing things I hadn’t even heard of (or at least didn’t realize could be jobs). Professional online poker player? Check. Ranch owner? Why the fuck not. dish towel/dish towel hook seller? Yep, I met him. You can’t make this shit up.

While I didn’t aspire to do any of these things (or live the lifestyles of the people who did them), I did begin to question more seriously what I wanted to do with myself when I got back from Colombia. I realized that my time in Medellín had become, for better or for worse, a kind of sabbatical, a trip to figure some things out before taking the next steps.

In an effort to figure out what to do, I began looking at more of those online job boards. I had by this point decided that a brick and mortar office job would never be for me. But I was still open to a full-time remote position. I even applied to a couple. Partly this was out of genuine interest, but mostly it was out of the dreadful motivation of fear. I was beginning to think Oh shit, I’m making enough to survive here in Colombia but no way this will cut it back in the US, even in an affordable city like Knoxville, TN. 

So I decided the solution was just to get a salaried remote job.

Once more, however, my heart wasn’t in it. While the jobs did seem interesting and fulfilling, I was applying to them first and foremost for the money. I’m sure this came across in the applications, and I never heard back from the few companies to which I applied.

This was frustrating at the time, but in retrospect it was a blessing, because it helped me get to the final phase of this article.

Phase 7: Going All In (November 2017 – Present)

One fitful, insomniac night in my one bedroom apartment, I came to a realization that would change my career:

I’m half-assing two things; I should be whole-assing one. 

For those of you unfamiliar with Parks and Recreation, let me clarify: By holding out some glimmer of hope for a future full-time job, I was giving myself an excuse to half-ass my freelance business. Not the work itself, of course–the articles remained high quality. But the meta, business part of the business, that part was lacking:

  • Finding new clients
  • Optimizing my systems
  • Setting revenue goals
  • Building for the future

As long as I thought I’ll probably get a full-time job…someday, I would never be able to give my freelance business the fierce attention it needed to grow.

I cannot describe the burden that left me when I decided that, no, a full-time job with another company isn’t for me. No matter:

  • How sexy or remote or world-changing that company might be
  • How much it might suck sometimes to not know how much I’ll make next month or how I’ll pay off my student loans as quickly as I’d like
  • How much I’ll have to pay for my own health insurance

These are shitty, stressful concerns. But you know what? They’re worth it for the freedom, the total freedom of self-employment. They’re worth it because when working full-time for someone else’s company:

  • I still have someone who dictates when I work and when I don’t (no matter how “unlimited” that company’s vacation policy might be)
  • I still have someone who can fire me at the drop of a hat
  • I’m still beholden to someone else’s vision of success
  • I’m still helping someone else build their dreams

There’s nothing wrong with any of the above–you can have a fulfilling, joyful career as an employee and a soul-killing, dreadful existence as a self-employed freelancer/entrepreneur. One isn’t inherently “better” than the other, and it all depends where, how, and with whom you work.

It’s also (somewhat) a matter of preference.

But I know which one’s for me.

I’ve made my choice.

2018 is that year that I, Ransom Patterson, am going all in on self-employment.

I’m done half-assing my job search; I’m ready to whole-ass building a business and a career.

Featured image by Teddy Kelley via Unsplash

This post owes a great debt to Stephen Warley, for his continued mentorship, encouragement, and own inspiring career story. Many thanks also to Kristin Wong, who encouraged me when I wanted to give up on freelancing. And to my parents, for believing in me even when I wasn’t/am not the best at explaining myself.

One Comment

  1. Ransom this is one amazing and must read post! Thanks for the depth with which you shared your journey. I’ve bee so excited to be part of yours and thank you so much for the shout out! I really appreciate it! I know one day I’ll say, “I remember Ransom when . . .”! Keep working, experimenting and growing!!

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