Freelancing, Year One

Here’s stuff I learned.

Today marks my one-year anniversary of leaving my full-time job and becoming a fully freelance journalist. It’s been a weird road, and I figured I’d do a little bit of an update post with what I’ve learned, and how I’ve grown as a person.

Originally, I was working at a software company job that didn’t really satisfy me. I was working at multiple outlets on the side, making side money to supplement my entry-level salary, and after doing some math, I realized that I would be able to make enough income to get by, while giving me free time to try new things.

At the time, I was working for the Toronto Star doing game reviews on a bi-weekly basis. I was also producing content for Android Police, a blog which focused on reviewing apps for mobile platforms; between these two gigs, I was making enough to cover rent, Internet, my cell phone and student loans. My plan was to keep doing these things while pitching new publications for one-off articles which would pay more, expand my portfolio and hopefully raise my status in the communities that I was working in; this would, in turn, produce more work.

However, once I handed my two weeks’ notice in and got down to the brass tacks of working from home, things became a lot more difficult. I had always had a problem with self-discipline, and the best laid plans of waking up at hours similar to my old 9-5 quickly fell apart. I was embracing working from home in the same way that a recent high school grad takes to the university life: my sleep schedule, diet, social life and workload suffered.

I suppose that’s the first bit of advice that I can give to people: if you have a plan, you need to be roughly twice as disciplined as you think you are in order to pull it off. You need to be able to send pitch after pitch after pitch, and recognize that you will likely get little money for the work you are putting in; even respected publications in your niche may not have a budget for you in the beginning. You need to show your value, and spiral outwards from there.

When I started freelancing, my main goal was to keep making enough money to pay rent and stay in Toronto. While this doesn’t seem out of the ordinary, my methodology ultimately made it toxic to my mental well-being, as well as my career path.

I had a certain pride about having 100% of my income come from freelancing, because it meant that I was a valuable and productive person. Being able to say that I used my degree in order to make rent and bills was pretty cool, because journalism as a career is often devalued to the point of people thinking pursuing an education in it is a mistake.

Therefore, when money issues arose, I fought very hard against the urge to take “the easy way out” and get a part-time job, or working in a more lucrative niche. In my head, this meant that I’d be sacrificing the freedom of waking up whenever I wanted and writing about things I cared about, or being able to pull a long night of writing just because the mood felt right then.

What I didn’t realize was that I was already making a sacrifice: in order to have the freedom of schedule, I was forgoing a lot of the stable income. That was the trade-off. I was under this… illusion that being free was going to give me more time to work, but in reality I was goofing off the same amount I always was, if not more.

I also felt that by going to work at a newspaper, or by writing ad copy, I’d eventually come to hate writing; this scared the crap out of me, because I tend to turn all my hobbies into things I write about. Writing is tied to so much of who I am and so much of my self-worth that hating it was scary.

Getting a part-time job also meant admitting that I was a failure, because if I worked hard enough, I wouldn’t have to make the compromise. This kind of thinking started a vicious cycle that kind of compounded in on itself; I would believe that I wasn’t working hard enough, but then I would get depressed, which would keep me from working and then start the doubt anew. It was silly. I’m still working on it.

I tried multiple times to reign myself in by using strategies like RescueTime,Pomodoro or just plain editing my hosts file in order to block sites that I was visiting. However, the stuff that I ended up abusing the most was the stuff I tricked myself into thinking that I “needed for work”, like Reddit, Tumblr or Twitter.

Ultimately, while I would like to say that I’ve lasted a year, I feel like a bit of a fraud by saying so; I’ve relied on a lot of help to maintain my bills and finances, along with just plain luck. The first couple months were close to Christmas money, and with my leftover vacation pay, I was able to keep rent and bills at bay. However, once those ran out, some months I needed to ask for assistance from my parents, which again, compounded the doubt that I wasn’t working hard enough.

That was the weirdest thing about this whole experience so far. Despite being abnormally hard on myself with the standard that I needed to live up to, I found myself making the same mistakes in mindset and work habits that allowed it to perpetuate. While freelancers are assumed to be constantly pitching and working on features, or at least constantly working, I wasn’t doing that.

I wasn’t seeking out new publications to work for, or networking with new people in my field. I wasn’t expanding my work base. I was trying new projects here and there, and working on “big” things that were well-received. However, I think my main mistake was putting so much weight on these new projects that they became must-win scenarios for both my confidence and bank account. When they didn’t, it became really easy to wallow in the situation, wondering if I was good enough in the first place.

This changed in early 2013, when I seemingly had a couple projects lined up that I could consider “my big break”. Life-changing things. Things that would’ve eventually lead to dream careers. In January, I got a press pass to go to South Korea to watch and report on the OLYMPUS OGN Champions Winter League of Legends event, which would be my first live watching of the game.

This came as a result of pitching a story previously, so I had two features to do for a publication I really respected. I also looked at it as a really big career move: the social media exposure I would get from publishing these pieces would be great for giving me credibility and showing my expertise.

I also entered into a hiring process with Riot Games to potentially be an on-site journalist for League of Legends. This was also a huge deal, as if successful, I would move to sunny California, start with a “blank slate” in terms of being able to fix bad habits (socially and otherwise) and just meet a lot of new people. The cult of Riot kind of took hold in me hard, and it was something I wanted — orneeded — to work out.

However, both of these projects didn’t, to say the least.

Both of my features were initially not received well by my editor, and it hurt my confidence considerably; my self-doubt really took hold, and got worse when both stories were killed before publication. Riot also had some issues with paying me on time for the first bit of my contract, which lead to some rough times financially; I had borrowed so much from my family at this point that asking for more felt like a point of weakness.

Eventually, Riot told us that they would be moving away from full-time writers to freelancers, which means I would be doing more work for less money if I wanted to keep working for them. This also meant moving to California and full-time employment was off the table, as was the benefits that came along with it. Ultimately, it was really disappointing; both of these projects ended in the same week, and it made me think I was unsuited for anything involving journalism.

What made it worse was that both of these projects were backups for each other; when I experienced difficulty or problems with one, I was able to tell myself “at least I have X that will work out for me.” When both of them didn’t deliver, it was really hard to deal with. It felt like a lot of wasted time, or at least wasted confidence; getting to those points made me think I was good at what I did, so failing hurt.

I still wonder what could have happened if I had just compromised more in one direction or another; I haven’t quite “gotten over it”, even after some months. I had applied for a job previously with Riot that I declined when I found out it wasn’t involved with reporting, and the guy who eventually did get the job is doing work close to what I wanted, ironically.

Since then, I’ve made a lot of realizations about my craft, and what I want out of this whole freelancing thing. I wrote a longer piece about my eSports-specific journey here, but I feel this applies to everything I do, not just that one niche.

After the Season 3 World Championships, my main revelation was that I needed to do more work: while this doesn’t seem too out-of-the-ordinary, it was at the time. To a lot of people outside looking in, it looked like I was working myself to death; however, they were only seeing one side of things, which hid my slacking.

My mindset was to focus on what I was good at, which was longer features, and things that ultimately took time to develop. The problem with this is that my momentum would shift back to zero every time I published something; I was doing “big” things, but needed smaller pieces of content to keep my name circulating and my expertise growing. Even with a semi-large following I found it hard to draw eyeballs to my content; it wasn’t so much “oh hey, it’s a Matt Demers article”, but a “oh, it’s an article by someone who I happen to follow.”

And in all honesty, I need to change that. I have to motivate myself to constantly work on pieces that are going to expand my reach and influence while simultaneously hustling to get bigger money projects done that will secure myself financially. I need to constantly be pitching and not worrying about working for new publications. I need to be able to push aside the fear of failure and learn from the failures that do happen. I need to stop being jealous of peers, because that stuff is deadly. I need to find people to work with that I respect. I need to find hobbies that I don’t automatically turn into work.

Unfortunately, I think this this comes a bit too late.

As it stands, I returned from the Season 3 World Championship without a stable source of income, and since I hadn’t put a lot of time into being consistent, I wasn’t in a place to be a “hot free agent”. What was once a “never happening” scenario is now going to be my future: I’m leaving Toronto, and going back to my hometown to live with my parents.

On one hand, I feel really defeated going back; this is my admission that my first year of freelancing should have been undertaken better, and all I can do from this point on is move forward, learn from my mistakes and try to be better.

Since I will no longer have rent to worry about, this means that I’ll be able to try new things without that constant need to make them “pay off”. I’ll be able to invest the time needed into these new ventures that is required before giving up. I will be able to build confidence, and stop beating myself up so damned much.

This is the plan, and hopefully it will lead to something good.

So wish me luck, and hopefully I’ll be back here for year two, a little bit wiser.

This is Matt Demers, over and out.