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How Leaving The Army And Dropping Out Of College Helped Me Build My Own Dream Job

It took some trial and error for this full-time freelance writer to nail down “that whole ‘purpose’ thing,” then monetize it.

How Leaving The Army And Dropping Out Of College Helped Me Build My Own Dream Job
[Photo: U.S. Air Force photo by Senior Airman Micky M. Bazaldua ]

“Private Dowling, why are you here?”

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Finally, it’s happened. My company commander has at last acknowledged the pink elephant that’s been following me around since I first enlisted in the Army in 2007: I just don’t belong here.

“Uhhh . . .” I stammered. “To serve my country, sir.”

“Bullshit!” the captain fires back. “You don’t want to be here, and we both know it. So shit or get off the pot!” (This, of course, was said with many more expletives than just these two.)

To make a long story short, I got off the pot. But I spent the next several years floating around aimlessly before settling on something I actually enjoy, which also happens to pay the bills. Now I’m a full-time freelance writer and I couldn’t be happier. After a few false starts, I’ve found a field where I do want to be and built a career where I do belong. There are no elephants, of any hue, following me around anymore. Here’s how I did it.

Discharged, Enrolled, Dropped Out

I’m fully discharged by 2009. At 19 years old, I’m a freshly minted Army reject, and as far as I’m concerned, I’ve got a failure streak that dates back to my parents’ divorce when I was 12. With no higher hopes to aim for than a low-wage job and maybe a girlfriend, I spend the next couple years cycling through variations of both without substantially revising my goals. After each failed professional dalliance, I’m safely deposited back onto my mom’s couch.

Suddenly I’m 21 and my peers are graduating from college. Some are even taking out mortgages. Meanwhile I’m arguing with my little sisters over who cleans up after the dog this weekend. I decide this has to end, so I start applying to colleges. I’m accepted, and when I finally start my first semester, I breathe a sigh of relief: Maybe I’m beginning a little late, but I’m finally on the right track.

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Cut to age 23. I’m enrolled in college and steadily racking up credits. But I’m also racking up tens of thousands of dollars in student-loan debt. I made the Dean’s list in my freshman year, but now I’m feeling some nascent pangs of that whole “purpose” thing, and I’m starting to wonder whether I’m ever going to find it on campus.

As I watch my debt climb past the $20,000 mark, I have an epiphany: The only reason I’m going to school is to write. If I’m being honest with myself, my only real motivation week-to-week is to debate other students in class and argue with my professors about their grading practices. This isn’t what I came here for. Why keep racking up debt when I can try to make money?

So I drop out. It’s 2015, and I’m back at Mom’s. Ugh.

My First Days As A Writer

Still, I call myself a writer because I’ve read Peter Bowerman’s The Well Fed Writer and have earned my first $1,000 with just my keyboard. That feels great, but aside from the few flashes of inspiration I sometimes get at 3:00 a.m., I’m only writing when I’ve got work. And I rarely have work.

In my inexperience, I thought a freelance career would be automatic. But the only automatic part is rejection: “Thanks, but you suck. Try again never.” “Don’t ever pitch us again.” “We appreciate the effort, but we can’t imagine anyone paying you to write.”

No one put it quite that way, but it’s how the results of 98% of my queries from 2015 sounded in my own head. Meanwhile I’m working on and off on a book about relationships, which I self-publish in May. By August, I’ve racked up all of 10 sales–mostly by coercing family members. In certain moods, I consider putting my writing career out of its misery. In other moods, I think, “What in the ever-loving hell is wrong with people? Why aren’t these mental pygmies gushing over my genius!?”

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Then I realize something: Every single best-selling author is working to woo the same audience as I am–the English-reading public–yet they’re selling bushels of books, while I can’t even sell an article.

It’s not the audience. It’s me.


Related: How I Finally Learned To Compete With Much More Experienced Freelancers


New Goal: Get Better Fast

Armed with my newfound humility, I devise a new plan to relaunch my sputtering freelance career: Get better fast.

I devote the month of August to incremental improvements, which involve studying my craft for two hours a day and implementing the lessons I learned into daily articles. I stick with the program. And by September, I’ve landed my first full-time freelance writing gig with a time-management and lifestyle site called The Cheat Sheet. The job application required a bachelor’s degree, but I leveraged my freelance portfolio, which included articles I’d published on some large websites, and it worked!

Now I’m writing four articles a day, making what I consider to be “real” money–around $1,000 a week at least. It’s December, and I’ve racked up several grand in the bank. Now I’m searching for my own place.

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Then I’m fired.

I’m not given a reason why I was let go, but looking back, I have to admit to myself that my quality slipped in the last few months. Nearing burnout, I was producing hacky articles that were bad enough to be embarrassing (see for yourself). Plus, writing lots of articles a day wasn’t leaving me enough time to keep polishing my writing skills or have fun doing it.

It’s probably a blessing in disguise, but it doesn’t feel too great. In retrospect, I might’ve been able to prevent it had I learned to make the “love-to-do lists” that I stick with these days.

But the firing teaches me not to put all my eggs in one basket and to dust myself off quickly. Losing a contract or a client is just part of the freelance experience. It happens–sometimes it’s your fault, and sometimes it isn’t. So after quickly grieving my loss, I begin pitching my ass off. If I write for three hours a day and spend four pitching new clients.

From Fired To Hired (By Fitbit)

Now it’s March. I’ve got my own place, but my savings are shrinking–almost at the same rate as my confidence. But the law of averages works in my favor: Of the hundred or so carefully crafted pitches I’ve submitted over the last three months, I hit a home-run: my first dollar-per-word gig. I’m writing and editing for a corporate wellness company called Nuvita. Just in time, too. Had the offer come a week later, I wouldn’t have been able to pay my rent. I’m discovering that the freelance game is equal parts faith and persistence.

It’s now August of 2016, and Nuvita has just dissolved. Poof–gone. But by now I’m disciplined enough in my pitching to have other prospective clients on deck. I’m still scared, though. I’m waking up most days with high anxiety. And money is crazy tight–so much so that I’m not buying food as much as I probably should be. Then another gig comes rolling my way, except this time it’s a giant: I’ve just landed Fitbit.

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Apparently Fitbit liked the health and wellness articles I’d written for places like Entrepreneur and mindbodygreen. And since I’ve stuck with my pitching regimen, I cold-clocked them with an awesome query letter. I’m the only non-credentialed journalist on Fitbit’s roster.

Writing at an average of $400-800 an article, I’m beginning to feel security for the first time since I’d left my parent’s house half a year ago. It’s September. I’m finally independent. And I’m doing what I love.

Flash-forward to today, April 2017. I’ve pitched and pitched (and pitched) my way into top-tier publishers with great audiences. (As an aside, I sent seven submissions to Fast Company before my first one was accepted; lots of writers cut their losses and quit after the first couple of rejections, but I was persistent!) These days, I rarely have to pitch for work because companies come to me. I spend one or two hours a day drafting unpaid articles and guest blogs, in order to get my name out there and build my reputation, and the rest writing on a paid basis. I’ve created a virtuous circle this way; business owners who read my articles often contact me directly to see how I can write content that helps them make money.

In fact, my story ends here, because I have to get to work on a $2,400 article that just plopped onto my desk.

I effing love my job.


Daniel Dowling is the founder of MillennialSuccess.io, where he shares action steps and inspiration for millennials and their employers. You can find more of his work on Entrepreneur, mindbodygreen, and Fitbit.com.

About the author

Daniel Dowling is the founder of MillennialSuccess.io, where he shares action steps and inspiration for millennials and their employers. You can find more of his work on Entrepreneur, mindbodygreen, and Fitbit.com.

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