How Steven White Went From Sleeping in His Car to Travelling the World as a Freelance Writer

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I can’t believe I got to write that clickbaity title, but it’s true

Steve (Shcteve) from is a freelance writer currently living in Bangkok. While Thailand might be the current place he calls home, Steve has the flexibility to do what he wants, wherever he wants to live, and he can do it whenever he wants to. Some people might be forgiven for calling him lucky, but I know for a fact that his circumstances are the deliberate result of planning, determination, grit and working his ass off. 


When you’re at a party and you get the inevitable question: “What do you do?” How do you answer that? When someone is interested in learning more about what I do, which is quite often, I try my best to answer with something more exact than “I’m a freelance writer”. When I was living in California, my roommate at the time would usually just tell people that I “wrote the text on the back of shampoo bottles”, so there was a time where I would just use that as my answer. Now I’ve progressed to, “You know those top ten lists and stuff you see on Facebook—that’s me writing those.”… or something along those lines.


Now that you have such an unusual answer to the above question, do you notice how often people ask that question and define themselves by what they do? I have been thinking about that ever since I dropped out of college and people continued asking me “What’s your major bro?”.


Would you say you define yourself less or more by what you do now, compared to when you had a “normal” job? Now I hold more pride in what I do, and therefore it has become a greater part of how I define myself.


Why have you left the US to “set up shop” in another country? I left the U.S. because I felt lost in such familiar surroundings. It felt like no matter where I went, I was having very similar experiences to what I could have had living with my parents. Frankly it was driving me crazy.


Out of any country in the world that you could have gone to, why Thailand in particular? I feel I was definitely drawn in by the social media buzz going on about living in Thailand as a Digital Nomad. Still, as an expat living in Thailand, I certainly do experience significantly more freedom and live at a higher standard than would be possible for me in the U.S. with minimal sacrifices.


Seeing as you have still been establishing your identity as a freelance writer, while being overseas on your new adventure, have you found any benefit to being outside of your comfort zone and away from the socially reinforced baggage that you grew up with in Chicago? I know that for me personally, it’s hard to notice what limiting beliefs the society I grew up in has until I moved away from it. When I left Chicago to live in Las Vegas, and later California, I noticed the exit from my comfort zone massively expanding my worldview. Now that I’m living abroad in another nation halfway across the planet, I’m always pleasantly surprised when my negative expectations of the world fall short of reality. Once you leave the United States, black people love fried chicken and watermelon becomes more of a general observation than a racial stereotype.


What was the moment when the penny dropped and you realised you could have a future as a freelancer? The moment it really dawned on me that I could make it as a freelancer was actually rather spectacular. I had my first conversation with a full-time traveler while staying in a hostel in Las Vegas. She was a freelance English teacher who did her lessons online via Skype. After 7 years of constant travel, she’d ended up in Las Vegas and we spent 2 days discussing her lifestyle. After that, I made the effort to discover how I could emulate that same lifestyle—and the obvious answer was freelancing.


Were there any key moments leading up to it? I’d run off to Las Vegas in September 2016 to try and develop a professional organization business that I’d started in Chicago. Unfortunately I was quite broken financially at the time, and was essentially homeless, living from my car, several seedy hostels, and the home of a family friend. Yet still, this difficult experience was the catalyst for my growth as an entrepreneur and freelancer. After discovering that freelancing was an option, I gradually moved away from the business venture that I’d come to build upon, and focused my attention on finding the freelance route that fit me best. Before coming to Las Vegas, I secured work as a door-to-door canvasser for the Democratic party, soliciting voter registration. During my work I met a man who happened to be interested in launching a podcast and blog focused on entrepreneurship. As he explained his project to me, I learned more and more about the inherent value of written “content”. This lead to me doing some unpaid “for exposure” type work for him to get my feet wet, but I quickly cut that tie and began researching how I could effectively capitalize on my affinity for writing by becoming a professional freelance content writer.


Could you break down, into a simple format, what the steps you took to achieve life as a freelancer were? The path to achieving life as a freelancer started with developing my understanding of selling and entrepreneurship. During my journey, I took direct steps to become more mindful of what it would take to defeat the fear that was inevitable in the life of a freelancer/entrepreneur. I poured an incredible amount of my energy into personal development, identifying and repairing the ills and mental pitfalls that had held me back in the past. After the arduous path to achieving these three things, it became rather simple, though still very difficult. I found a mentor and took myself out of the environment that was holding me back. I dedicated myself to studying the freelance writing world and developing my craft as a writer. I used Facebook as a means of finding my voice in front of an audience and I further progressed my ability to write by launching a blog that I used to test out new writing styles and translate my deeper thoughts into content. Finally, a bit of isolation and persistence allowed me to sharpen my writing ability, allowing me to gradually secure a steady line of clients.


Were there any moments when you wanted to give up and quit? There were too many moments to count. While living from my car, I was still in the process of developing my writing, therefore I was not receiving any income from it whatsoever. The stress reached a peak and the walls seemed to be caving in, so I desperately craved an opportunity to back out and find myself a “normal job”. And for a short time I moved back from Las Vegas to my parents house and worked in a local call center for $12.25/hour. That bit of respite lasted a short three weeks before the freelance bug bit me again, and I packed up to go back to being a semi-homeless writer in California. Story here: How-to Exchange Comfort For Your Freedom


Can you describe the amount of hard work that went into it, writing work and non-writing work inclusive, before you made a single dollar? Was it difficult? Leading up to that first dollar, I’d spent countless hours (hundreds) researching freelance writers and what they had done to become successful. Prior to that, I had the experience of developing real sales and business skills by running my own professional organization company out of my apartment. I also operated a residential exterior house painting franchise a short time before that. It was difficult to hold so much direct responsibility over my life at first, but as I grew addicted to being in business, not being engaged in business as a freelancer/entrepreneur became more difficult. The first paid project I got was from Upwork, it involved writing 3 1500 word articles for $15. I did it, and after those first dollars online, I refused to ever work for so little ever again. Aside from content mills, my first private clients were sourced from job boards on Reddit.


Can you tell the audience, from your perspective and motivations, what you and I are doing for our freelance/apprentice/padiwan project? From what I understand, Toby and I will be engaging in a freelance development project that will help him secure a sustainable income through writing. From what we discussed, our hope is that he will be able to travel to his heart’s content while producing content for clients and gaining a following on his own blog. I’ve been helping him get practice through content mills and done some oversight/editing on his work. Right now I’m proud to see him steadily writing and honing his craft through his own blog, though I can’t take credit for that. My only real motivation for getting entwined in this project is my desire to watch others grow, as I feel that the teacher is likely to benefit just as much as the student.

Schteve and Toby
Looking back, I’m quite upset with how Chubby I was back then, with that whole double chin thing going on but I’ve explained how that happened here: How I Lost 18kg in Two Days and Barely Avoided Death

What has been your strategy for creating visibility to yourself and your blog? So far, my strategy has been limited to just writing content, creating a strong social media presence, and sharing my posts regularly (maybe semi-regularly when I’m distracted). I could definitely perform better in this area, my blog does not receive nearly as much of my attention as it should.


When people ask you questions about freelance writing and blogging, and you think they might have potential, what’s the question that most people forget to ask? When I see someone with the potential to write, many of the questions seem to be focused on dollar amounts, finding clients, and how many hours I must work. I think people often forget to ask about the aspect of freelance writing that if poorly managed, is likely to impact their health and happiness significantly: the mental strain of writing for long hours to hit deadlines and keeping up personal writing projects on the side.


Can you tell me about your desire to bring soul food to the streets of Bangkok? Shcteve’s Soul Shack – Opening in 2020. As far as my favorite activities go, cooking for others is on equal terms with writing. These streets are definitely lacking in collard greens and cornbread, so I think it’s about time someone made a move.

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6 Responses

  1. Great story, and I can relate to the extreme circumstances we often face in the beginning that refine us, make us stronger people and force us to own our craft. It’s a distillation of sorts.

    Great story, Shcteve –and Toby, blog is looking epic. Happy to know you both.

    Will be in Thailand this Fall, hope to run into you gents.

    1. Hey hey, glad you liked it.
      We need to get together for a pow-wow of sorts, I’ll certainly be out here for some time.

      If I had the option to remove those extreme circumstances, I certainly never would.

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