One Year Self-Employed!!!

November 21, 2015 is the one-year anniversary of my last day as an employee. As a self-employed person, the last year has taught me more than I thought I was capable of learning. While these lessons may not be valuable to anyone but myself, I want to put them down for my own sake. Over the next couple days, I'll be sharing some of the biggest lessons I've learned over the last year.

Lesson One: Great Days and Terrible Days

As an employee, my work life was mostly boring. I didn't care about the work I was doing, so I punched in, punched out, and collected my paycheck. Eventually I grew to resent this and so most days defaulted into crappy days simply because I was at work. The actual bad days consisted of getting yelled at by clients, reprimanded by the boss, and being bored out of my mind, which in the grand scheme, doesn't seem all that bad.

As a self-employed person, there seem to be very few boring days. Days are typically either great or terrible. Great days consist of working hard while singing at the top of my lungs (most days), having indoor snowball fights, taking impromptu breaks to go sledding, or selling three cars in a single day and making enough to carry me through the next three months. Terrible days consist of making stupid mistakes like forgetting to cap my transmission lines and spraying transmission fluid all over the floor of the shop, improperly mixing the sealer and having it run off the surface of the car I was trying to paint, working for a full month on a car and making less than $500 on it, and buying a car that looked good, only to find out it had a bad motor and was going to cost me thousands more than I expected.

I've never felt more stupid on a regular basis than I have over the last year.

As an employee, my employer shielded me from the ups and downs of the market. Things could be going poorly for them, but I still received my paycheck. There were even times I made mistakes that cost my employer money, but it never came out of my pocket. Of course, if things would have gone bad enough for long enough, I might have been fired or laid off, but that never happened, and I was never even worried it would happen. In exchange for this insulation and security, I did whatever my employer asked and in turn submitted myself to a life of boring drudgery.

As a self-employed person, I immediately absorb every up and down the market throws at me. If people aren't buying cars, I don't make money. If the market says my cars are worth less then I calculated they should be, I make less money. If I make mistakes, they cost me money. All of my decisions directly impact my bottom line. It can be unnerving to say the least, but despite the inherent stress, the last year has been one of the best of my life.

If you're considering striking off on your own, the first of many questions you need to ask yourself is "What do I value more, freedom or security?" Freedom comes with some truly great days, but it also comes with truly terrible days as well. Security is rarely great or terrible. It's comfortable, but it's also boring. The correct answer depends on you. For me, the resounding answer is freedom. I would much rather suffer the emotional and financial roller coaster of being my own boss, than suffer the boredom and restraints of being an employee. While I admit it would be nice to have great health insurance and paid vacation days again, those pale in comparison to the fact that I'm taking a week off over Christmas to spend time with family, and I didn't have to get permission from anyone.

You'll see over the course of the next few days that life was actually a lot easier for me as an employee, but the freedom I've gained from becoming self-employed is far more valuable than the comfort my cushy corporate job provided.