“I’m my own boss, and I’d probably fire myself.”

Originally posted onto TealMagazine.com 2/4/17.


Who wouldn’t want to quit their job and become their own boss? You get to work at a pace that works for you, in a location that is selected by you, in clothes that are seen by only you (pajamas anyone?), and even at hours that work conveniently for guess who? –You!

It sounds almost too good to be true, working for yourself. According to Forbes (that magazine that your dad is more than likely subscribed to), 2 million Americans a month are leaving their fulltime jobs to go find something much better for themselves. Where are they all going? A large portion of these dissatisfied folk are setting out on the path to go and become their own bosses. Anything is better than working for someone else again…right?

2 years ago, I quit my own fulltime job. I was working a job that I honestly didn’t care for much at all, but the money was good at the time, so I focused on the huge plus that that was to my life. It was the most money I had ever had in my young life, so it was easy for me to be lured in and fixate on the paycheck.

I knew that the work I was doing was not exciting for me, and that it wasn’t anywhere near the line of work I always dreamed of doing, but the people I worked with were great, the work wasn’t difficult, and that dream I always had of being a writer and doing only that for a living would always be there. After a while, I knew that I couldn’t kid myself anymore and that I wasn’t moving toward my goal at all. I wanted to write, but I knew very well that I wasn’t doing anything about making that goal come closer.

In the beginning, I told myself that I would work in the day and write at night –that way I can do both! Easy-peasy, but like most of us who have consoled ourselves with a lie like this, it never worked out the way I planned: I would come home from work and be “too tired” to write. I would tell myself that I would just write more tomorrow to make up for it. Even on my days off of work, I never wrote a thing.

After a while, I knew that the only way that I was going to make my goal of authentically being able to call myself a writer would be to prioritize it. I talked to my family (who has always been unrelentingly supportive, thank God), and I talked to my friends about what I should do about it, and they all agreed with what I proposed as a next step –quit my job, set up a time frame and actually go all in –no more excuses or cop-outs.

So that’s what I did. I had more than enough money in the bank to support myself through a season of genuinely trying to build myself up as a writer who worked for himself and no-one else, and a deadline of when I needed to make some serious traction by. My reasoning was that if I was nowhere better than where I started by this particular date, then I would go back to working fulltime again. That kind of heat and pressure seriously keeps you motivated, especially if you really don’t want to go back to being an employee again.

When I first got started, I didn’t have much to work with in the sense of serious “resume candy”, but I worked with what I had –a series of campus news articles that I wrote during my time at my high school and college newspaper. It wasn’t much, but it was much better than nothing, and when it came down to it, that’s really all it takes. That, and a plan to get it into the hands of the right people.

I worked for free for a long time. When you’re starting pretty much from scratch and trying to create a business that eventually can becomes a source of genuine income, you have to start somewhere and expect to not make it big anytime soon. I reached out to dozens of places at a time, sending content managers my published works (if you can call high school newspaper articles “published work” to anyone not in your home-room class) and expressed to them that I would write for them for free in exchange of simply publishing me. To content managers, this is some serious appeal, and many of them don’t turn these kinds of offers down, but even still, many did.

I worked that way for a long time, trading free content in exchange for publishing. After a while, I was writing for quite a few publications, and let me tell you — It. Was. Awesome.

Yes, I wasn’t making serious money just yet, but I got what I wanted, I was a writer with actual writing work to do! I sat there at my little desk and marveled at the white board that I set up on my wall that chronicled the various projects that I had to complete. I had a fine little list of articles to write, and I couldn’t have been prouder, and the best part was that I had no one on my back about when and where I should get started on it. It was all up to me… and that was when reality kicked in.

For years, I had always had a manager breathing down my neck about when to get started on this, when to get this portion of the work done by, when to make this call happen –and now all of that was gone. Yes, I hated having to be reminded all of the time to do my job and even be told exactly how to do it, but take that series of reminders away, and it honestly is a bucket of ice water getting dumped over your head.

Deadlines creeped up to being just hours away, and I was not any closer to being done than I was when I first wrote the reminder to get started on my white board a week ago. Nobody tells you that when you work for yourself, you really are all alone when it comes to managing yourself.

Obviously I got the hang of managing myself after many desperate scrambles to make deadlines, but being your own boss is not all it’s cracked up to be. You really have to be in complete charge of your situation, and say “No” to things you would sometimes much rather be doing (like rewarding yourself with a Netflix break just for finally coming up with a catchy title to that article that is due next week). Yeah you’ve probably had bosses that micromanage the hell out of your work day, but honestly, that kind of a boss is a cakewalk compared to the boss you need to be over yourself.

Knowing myself, and a lot of other full time freelancers that I chat with from time to time –we are our own bosses, and more often than not, we would fire ourselves as employees.


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