Writer on the Side #1: My Story

This is an excerpt from my new book Writer on the Side: How to Write Your Book Around Your 9 to 5 Job.The book is meant to help anybody who has been struggling to fit their writing despite having a sometimes brain-crippling full-time job. This particular section is about my story and how I overcame a lack of motivation to become the writer I am today.

The book is available now, check out the right column links for Writer on the Side. 

The Post-College Blues

I was afraid. I had just graduated from college and I was absolutely terrified of becoming a part of the real world. Throughout most of school, I had actually been somewhat focused, producing and directing some theatre, writing stories for my creative writing classes, and getting the full college experience with parties, girlfriends and activities. During my junior year, after a few dating relationships went sour, I had thrown myself into my work and considered myself a full-time actor and writer, writing my first full play in my dorm’s laundry room with a second play that I had co-written going up that summer.

By my senior year, however, I had a full blown case of senior-itis. I had stopped working as hard and moved my work and my development far down my list of priorities. While many people were securing jobs for the following year, I was putting off the inevitable. I even decided to stick around Chapel Hill for the whole summer, working for the University to fix up dorm rooms for the following year. It was obvious that I was grabbing hold of college and that someone or something was going to have to drag me kicking and screaming away from it. After a summer filled with drama in my personal life, I finally ended up in the suburbs of Chicago. I decided that I was an improvisational comedian, partly because it was a lot of fun, but I think a little bit because it was an artistic career choice with little to no commitment necessary.

I took on 9 to 5 temp jobs, because they similarly offered little commitment. On days that I had comedy classes or rehearsal, I would commute into the city, have some laughs with friends and colleagues and then make the long commute home. While this put me on trains over two hours a day, I hardly took a second to think about anything productive. I spent my time focusing on past dating relationships, regret at not doing as much as I wanted to creatively and plenty of sad sack wallowing. On days without comedy class, the amount of wallowing time doubled.

I remember looking at myself in the mirror one day thinking, “You have all this time, why aren’t you doing anything with it?”

I was stuck in neutral (or maybe even reverse). I couldn’t start anything, or at least, I wouldn’t start anything. Partly it was fear of failure. Also, it was partly fear of success, believing at least in part that I wasn’t worth it. Over the course of my first three years in Chicago (which eventually took me into the city itself) I feel like I packed in over a decade of worrying and negativity. 

A Turning Point

I bounced from temp job to temp job, eventually settling on a job at a coffee shop, which gave me a bit more time per week to find acting gigs and work on any shows I could get up the will to produce. The coffee shop gig was a bit less money per week, and I was already hurting financially, so this caused me to get into a mess with my credit cards. In a drastic effort to turn things around, I attempted to produce a Web series, borrowing tons of money from my relatives, friends, and various loan websites. Instead of taking the slow and steady approach, I thought I could do it all in one fell swoop.

It failed. Now, I had hit the bottom.

Here’s the great thing about the bottom though. You can either look at the ground the rest of your life, or you can take the opportunity to look up at all the other directions that you can go. Thankfully, I chose this second path and I started looking for a way to dig myself out of this hole.

On a random Internet search, I came upon the subject of “Personal Development.” I didn’t really know what this was, and I certainly felt “underdeveloped personally” so I figured I’d give it a shot. The subject was a lot more multi-faceted than it appeared at first glance. It dealt with subjects like optimism (which I was certainly lacking), creating goals and a plan for yourself (ditto) and attracting positive situations and people into your life (which I needed desperately).

I threw myself into the personal development game. I would listen to podcasts I found online, I made a popular personal development site into my home page and I started talking about it to everybody I knew. I noticed that some of the extremely negative people in my life, started to fade out and that my financial situation somewhat stabilized while I concentrated on the positivity of this new subject matter.

I wanted to do something with the energy and motivation I gained from all my research and excitement. I had read in Stephen Covey’s 7 Habits of Highly Effective People that you learn 90% of what you teach, so I created a website dedicated to teaching people how to push past their blocks and start writing immediately. The site was called Build Creative Writing Ideas. It was the jumping off point for over a hundred articles and the several books that I’ve written. Even in just the first few months, I received some amazing comments from people who read my work and gained some sort of hope from it all. While this didn’t correct my course completely, I felt like I was finally starting to head in the right direction. 

Barista to Freelancer to Author

Despite gaining some ground on feeling more purposeful, I was still a barista at a coffee shop and I was still paying off some pretty hefty bills. During a free trip to Israel through the Taglit Birthright program, I had a moment of clarity. This moment caused me to put in my two week notice upon my return. The problem was, I still didn’t have a plan, but I figured I’d leave it to chance and try to find something more in my wheelhouse than coffee and pastries.

While I took on various gigs like promotional work and acting, the one I settled on as the direction I was supposed to go in was freelance writing. Most of my work was in the form of articles for various websites and it paid by the article. While it wasn’t a 9 to 5 job, to ensure that I was moving upward financially, I usually worked over 40 hours a week. It was very cool to be writing for most if not all of my income from week to week, but I was getting drained. Plus, I hardly ever had time to work on my Build Creative Writing Ideas website. And when I did have time, I felt creatively stifled from writing all the dang time!

The solution I found was to find something I could write quickly and easily on the side for BCWI while I still made my living through writing articles. I started writing pages on my site dedicated toward writing prompts (also known as story starters). I would come up with a particular topic and generate 10 ideas per page that people could use to get their thoughts out of their heads and onto the page. I had previously done a few in the early days of the site and they ended up being the most popular by far.

Within a year, I had over 75 pages of prompts (a bit over 750 prompts in total) and I was almost completely burned out from my 40 hours a week of article writing. I took on a few less taxing freelance jobs and some extra promotional work, but I was still having trouble making ends meet.

Another random online search took me to a page about an eBook writer who was having major success without getting something published the old fashioned way. An idea dawned on me.

“750 prompts are pretty close to 1,000. 1,000 prompts would be an awesome book...” 

Read the rest by purchasing Writer on the Side today! 


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