How I Almost Considered Myself A Failed Writer but Changed My Mindset

Miley Star
6 min readDec 19, 2019
Photo by Matt Artz on Unsplash

The Beginning of My Dream

Four and a half years ago I quit my job and bought a one-way ticket to Mexico. I had never been to Mexico before. But I had a plan.

I was going to be a freelance writer and live on the beach.

I wasn’t a freelance writer yet, but I had an English degree and I loved to write. With five thousand dollars in my savings, I figured I had three months to make it work and I had it all figured out. How hard could it be to find work on the internet?

It Was Really Hard

I tried and I tried. I signed up for websites. I applied with online companies. I failed grammar tests when everyone was telling me that grammar wasn’t important. I excelled at grammar tests with companies that paid $1.27 for three hundred words.

I was rejected left and right. My proposals were declined. My confidence was plummeting. Within the first four weeks of my arrival in Mexico, my dreams of becoming a freelance writer who lived on the beach were nowhere being actualized.

I was making about $15 a day for a writing mill where I received no credit for my work and I had zero prospects of finding a real writing job.

I Gave Up

I am embarrassed to admit this but I gave up. It was hard. Like too hard. I was defeated. I was two months into my plan and truth be told I was writing less and less every day. I fancied myself a starving artist but truth be told I was anything but a starving artist. I started drinking $3 lattes in the morning at a cafe with wifi, telling myself I was working. I started ordering $8 bagel breakfast sandwiches justifying the cost because at least I was making that a day. I began ordering my first beer at 2 pm instead of grinding all day and having one at 8.

The bars in the afternoon were full of young gringo freelancers. Facebook ads people, writers, freelancers who did who knows what. I never fully understood what they explained. But they seemed successful and I wanted to surround myself with them. Immerse myself with them. Have some of that success somehow reveal itself to me by being in their presence. Even though many of them guarded their secrets to success as though I were a potential enemy who might somehow steal it from them.

I felt defeated and so I was defeated. I nursed myself with the self-reassurance that I was networking, that one had to spend money to make money, that I still had time to “get it” and all the other falsities we nurse ourselves with when we know we aren’t doing what we really should be doing.

I Ran Out of Money

I had been in Mexico for over three months now. I had flown home twice. Once because my grandma, who lived far away had visited my parents and I hadn’t seen her in years so I flew home to see everyone. Another time I flew to Vegas to watch a friend fight in a Golden Gloves tournament. I spent too much money on lattes, breakfast bagels, beer, and other expenses I know I didn’t need. I had thrown in the towel and resigned myself to failing at my goal.

I had no business identifying with any starving artist. I was a fraud.

I Returned to North America and Got a Job

I’m proud to say that I didn’t return home-home. I was still determined to have an adventure type lifestyle one way or another. With the remaining money that I had, I visited Colorado for the first time and met the owner of a small wine tasting bar where locals could make their own wine. So cool. I asked about the help-wanted sign in the window. He needed someone to work a few hours a week — namely to write his monthly newsletter, follow up on emails, re-write the wine-making manuals, and to book the weekly entertainment at the bar.

I began dating someone who owned a chimney sweeping company and needed a website built. I taught myself how to build a simple website on a hosting site and I wrote all the copy for the website.

I got a second job working at a furniture store in sales, but the manager always needed me to edit her work. I began replying to emails, took over the Instagram and Facebook posts, and began writing the copy for our sales advertisements.

A lot of people in the freelance writing industry warn newbies not to mention their English degree because it works against us in this industry. I have found that in many instances there are still clients who value and trust an English degree or any degree for that matter. It might not be a necessary asset for many clients, but it’s not something I hold back when I tell people that I am a writer either.

Four Years Later and I am Still Writing

I am still in Colorado and I am a full-time high school English teacher. I write every day. I teach writers. I grade a hundred papers a month and write hundreds of comments a day. I write to persuade, I write to inspire, I write to share, and I write to teach. I am getting paid for my writing. It’s not exactly the kind of writing I envisioned myself doing but it is a start. I am still trying to break into this freelance writing world where I can work 100% online from anywhere in the world. Because I work full time at an extremely demanding job I find very little time to pursue my freelance writing career but I am determined this time to be successful. Slow and steady will win my race.

So I Wasn’t an Overnight Success

Four years ago I had this vision that I could fly into Mexico, set myself up with an ocean view apartment, and be making a couple of thousand dollars a month with my writing. With no experience other than my English degree. This didn’t happen. And I kind of gave up on my dream in exchange for a lot of fun.

I did find a little studio apartment a few blocks from the beach. I made a lot of really cool friends. I drank a lot of cervezas. I did do quite a bit of writing and surprisingly took up painting. I’ll never regret the experiences that I had while I was in Mexico, but I do wish that I had spent more time pursuing my goal of becoming a writer.

Just because I wasn’t an overnight success didn’t mean that I couldn’t be successful.

How I Changed My Mindset

It is difficult to admit but I almost gave up and considered myself a failure as a writer. Then suddenly I was in the right place at the right time and a writing gig practically fell into my lap. It wasn’t online, and it wasn’t freelance, but it was writing, and it was mine. This little bit of luck gave me the confidence to call myself a writer and continue to pursue writing opportunities while pursuing any opportunity that put food on my table at the same time.

I admitted to myself that I had been cocky.

I thought I could be something amazing without any experience, without any training, without clients, without any testimonials, without putting in the hard work.

I know now that I am going to have to put in the work. Not becoming an overnight success had been a blow to my ego, but not to my dream.

I look forward to the challenges ahead of me.

Now I Write Everyday With Fewer Expectations and More Effort

I am writing every day. And reading every day. I am reading Medium publications, subscribing to everyone and their dog’s newsletters, and am on Skillshare taking all kinds of content and copy and freelance courses. I am devouring everything I can get my hands on. On all kinds of topics.

I am reaching out on Upwork and People Per Hour for clients. I am even writing a few articles a week for a writing mill because the practice is good, the feedback is valuable, and $1.27 buys me half a latte. I am publishing on Medium and I am submitting to publications. So far I have had a few claps and a lot of rejections but I am okay with it. This is an uphill battle and I am learning to embrace the challenges. I am not defeated, and I will not give up as easily as I did last time. I am a work in progress.

And get this…tomorrow I have a phone interview with a potential client about writing content for her Yoga studio. My only expectations are those that I expect from myself: that I prepare well and do my best.

Still, though, wish me luck. I’ll take all the help I can get.

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