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Leaving a regular paycheck to struggle as a professional writer

Remote friendly. Check. 35 hours per week. Check. Foosball table and free beer. Double check. "We'd like to offer you the job."





I showed my wife that e-mail in borderline disbelief. For the past 14 months, I had been banned from working in Canada while waiting for my residency papers to come through. Well, let me rephrase that, I had been banned from *legally* working in Canada. I was able to get a few odd jobs teaching English for $50 gift cards to Shell (yes, the gas station) and doing yard work during the summer. But when I became a legal resident in October 2018, I could finally throw my hat into the professional ring. By November, I acquired what many would describe as a dream job with Snipcart, an e-commerce solution that fits into any tech stack. Snipcart is a bootstrapped start-up that relies solely (or at least nearly solely) on organic traffic to attract customers. The working conditions were unreal for a red-blooded American like myself (3 weeks vacation + sick days + 2 weeks off at Christmas??? like... for real???), and the schedule allowed me to work from home whenever needed with little to no reason required. As a father of a 2-year-old and a newborn, that was pretty incredible. And I won't lie, I had an amazing—and productive—time working with Snipcart. But just one short year later, I made a decision that most people would assume is crazy: go back to the struggle of freelancing and leave a solid paycheck behind me. In this small post, I'm going to explain 3 lessons I've learned from working as a content marketer for a startup that has now led me to head out onto terra not-so firma.


1) I love writing.





And I'm good at it. I know, I know... what a douchey thing to say about myself. So let me try and rephrase this in a way that makes me sound like less of an arrogant tool:


I'm not great at everything. In fact, I'm not great at a lot of things. But I am great at writing.


One of my tasks with Snipcart was to write, co-write or ghostwrite articles on very technical concepts on subjects about which I had little prior experience. HTML, JavaScript, Headless CMSs, front/backend development, APIs... the list goes on. However, I could always fall back on my passion for one thing: the writing. When I was tasked with creating an engaging article on these topics, the concepts themselves became fun because the writing was fun. With many technical articles under my belt, I am now confident that I can write about anything. Hence one of the reasons it was time to move on. See, upon entering Snipcart, I agreed to stop writing for other companies—not just direct competitors—because I would be learning to master SEO strategies and the fear (I believe) was that I would be trained on Snipcart's dime only to make myself more valuable to other organizations. For the record, this was (and is) a totally fair agreement. However...


I enjoy writing too much to honestly fulfill my end of that bargain. As I said, I am confident that I can write about anything so there's a part of me that wants to be open to writing about everything. I am now able to pursue writing on other topics that I am passionate about including travel, fitness, learning French, or any other subject that tickles my quill (writer's note-to-self: never use that expression again...).


The point is that I love writing, I'm good at it (or delusionally think I am), and don't want to limit myself to only one avenue.


2) If you want it, you've got to earn it.



Before diving too deep into this next point, let me make something clear: I hate the term "freelancer" for two reasons: first, it gives the impression of "amateur hour" at the open-mic comedy night. Something about that word "freelance" tends to make people think you're not cut out for producing the high-quality writing expected from a "real job" so you've decided to take on cheap contracts. This brings me to my second point... ...that term has the word "free" in it which, I think, gives some potential clients a false impression about your pricing. Nonetheless, my chosen term of "professional writer" is nearly identical in meaning to "freelancer" and comes with all the hardships attached. Namely, I'm on my own to find clients which can only be described as bittersweet. The bitter part is that finding something other than $10 contracts is tough and time-consuming; it is, however, incredibly rewarding (that's the sweet part). Here's why:

Most people don't actually work nearly as hard as they think they do. This isn't conjecture and it's not just my opinion. This is an evidence-based, documented, and well-accepted fact. Melanie Curtin, writing for Inc.com, says the following:

"Research suggests that in an eight-hour day, the average worker is only productive for two hours and 53 minutes. That's right--you're probably only productive for around three hours a day." (That entire article is worth a read).


Now, I'm positive that I was working more than that, but when I was sitting behind a desk, distractions came easy. Twitter was a part of my daily tasks, so maybe I spent 5-10 more minutes on the platform than I should have in the mornings; I had to answer Quora questions as part of the marketing strategy, but then questions like "Who would win in a fight, Conor McGregor or Bruce Lee" caught my eye; or maybe I was just having an "off" day and needed a few more trips to the coffee machine than usual. The point is that in most jobs, people can slack off and still get paid the same amount of money. As a professional writer (ok...freelancer), the extent to which I earn is directly correlated with how much quality output I can produce for my clients. And I love that. By 9:00 am, when most people are starting their workday, I've written two articles, gotten both my kids ready for daycare, and hit the gym. I'm writing and editing between 3,000-5,000 words per day. And, most importantly, I'm not wasting any time because I can't afford to. There's a great scene in the new Netflix series Living With Yourself where the "old Miles" (played by Paul Rudd) is speaking with his sister (played by Alia Shawkat). In a moment of frustration, old Miles yells, "Why can't I just be happy for once."


His sister calmly replies, "Because you didn't earn it."


Even though it can be difficult at times, venturing out as a professional writer has sharpened my skills, made me more disciplined, and forced me to get better with time management. But the biggest benefit is that all the hard work has been rewarding as hell.

3) Family projects outside of work matter, too



My wife and I love to travel. It's what bonded us as a couple and now, with kids, as a family. And this is really where the rubber meets the road: Our goal is to live life as a digitally nomadic family. In fact, we likely won't be happy until we learn how to accomplish that goal. My family lives in California, her family in Québec. That means that if we keep working the kinds of jobs we've traditionally held, we would have to sacrifice all our vacation time going back to one or the other's hometown (so our parents could see the grandkids). The problem is that there's so much left of this world that we want to explore. Fortunately, in 2019, there's loads of remote work so this becomes a non-issue. "But Nathan," you may be asking, "you started this article by saying you had a job that was 'remote-friendly.'" Yes, but not to the extent we are looking for. With my former job, I was able to work from home or even for stretches of time in California—though the time difference complicated things even then. I am sure after a few years and with more seniority, I would be able to work/travel to a larger extent, but it simply wouldn't meet the company's culture to have that as an ongoing situation. Again, that's 100% fair and place in their position, I can't say I would honestly feel differently.


I just know from experience that there are opportunities that allow the type of life my family and I are trying to build. Personally, I feel obligated to at least try. After all, if other people have done it, that means it can be done. If it can be done, that means I can do it, too. Am I a spoiled millennial? Check.


Am I crazy? Check.


Am I delusional in thinking I can have it all and likely to end up with nothing? Double-check. But no matter what you call it, I'm excited to be a part of the professional writing world, to be creating new relationships, and to be stumbling upon opportunities I never would have found had I not taken this step. The only downside? The empty chairs in my home office are a lot less entertaining than my former colleagues. I miss you guys. Thanks so much for your support!

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©2019 by Nathan Thompson.