Why Work For Yourself?



One of the boldest steps a human can take is going out on their own. Whether it’s moving away from their parents, buying a car, or starting a business, the cocoon being torn open is always a shock to the system; but when done right can be the best move you can ever make.

I didn’t do it right. But I did do it.


My mom used to have copies of Entrepreneur and other business magazines lying around the house when I was growing up. I was always more creatively inclined (my career choices ranged from astronaut to chef to computer animation and I STILL want to go to space) but the “being your own boss” aspect of it was intriguing; one way or another I was going to go into business for myself, it was just a matter of “when” and “doing what”. I knew wearing a suit was a part of the deal but that and leadership were the only things I knew that applied to entrepreneurship. And I didn’t own a suit!

Fast Forward to around August 2013

Ship life was gradually wearing on me even though I kick ass at being a DJ. The living conditions didn’t suck and it was what freelance musicians call “a really good gig”. But being “TEN YEARS WITH ZE COMPANY, WOOOOOOO” didn’t feel right to me. I wanted more.

Being out on the seas brought beautiful sights and wonderful people into my field of vision, but my vision is the size of the solar system we live in. Eventually, I was going to have to make a choice about what happens after the really good gig and get back into the land-based world where I could really shake things up how I wanted to.

I had to think… bigger.

Coming off of a bootstrapped (read: self-financed) DJ tour where most of the cash funds got blown to smithereens, I tried my hand at a “regular” job doing sales consulting at a local fitness chain. This lasted about six days. The entire six days, I learned cool sales techniques with the caveat that I was going to apply them to my own outside operations. That job only lasted that long because I was having a internal debate about what I was actively doing versus what I actually wanted to do. The long hours cut into the things I felt I needed to be doing (music, writing, creating, building, etc) and I didn’t see this business relationship lasting terribly long (I initially gave it 3 months). Being right all the time isn’t all it’s cracked up to be, as it turns out.

On the sixth day, I created a bullshit excuse stating contractual obligations and returned my work uniform to them. Standing outside trying to persuade people to get gym memberships they’d give up within a month of signing up was not my idea of a good time OR helping to achieve my goals, though I admired the business model that it was built upon. I’m a mercenary at times (everyone who ever lived is, whether they accept that or not) but even I have my limits as to what I’ll put up with for cash.

So I left.

You would think that I’d end up a man-cave dwelling beast playing Xbox and drinking PBR watching my bank account sink while my stomach and beard hit new levels of inflation after that. What actually happened was a lot less romantic.

The next month and a half leading up to the new year was comprised of thinking, self-searching and ruminating on how I was going to get everything financially taken care of  as well as get back on track with my music career (which can be considered stagnant if you’re not out and amongst the people, which I was NOT for 14 months) and goals. Just so we’re keeping a timeline, this all happened after I returned from that intercontinental tour I set up in October. So mid-November and December, I started researching potential revenue streams. For those who don’t know, that means I explored the legal options on how to get paid (illegal almost always ends badly unless you quit while you’re ahead) while still keeping my time and sanity to myself (I was less concerned with the sanity because I heard you can buy that.) and I ended up finding quite a few. For the amount of freedom I’d have, the only thing I would need is what amounts to coffee, gas and spontaneous dinner money to make the necessary purchases and willingness to do the work and apply myself. One person’s pocket change can be the next person’s fortune it seems.

I’ve operated as a freelance DJ for about… 5-8 years so far but DJ work is spotty and I needed something more consistent than gigs in entertainment but still played to the countless other skills I’ve picked up in life. To take the “make or break” pressure off, I framed it as an experiment; Worst come to worst, I’ve already earned my Bachelor of Sciences and I’d use that as a cushion if everything else fell apart (spoiler alert: everything else is not falling apart and will not as long as I draw breath). There was also that voice in the back of my mind that I finally decided to heed when I quit that job, shout out to that guy.

My hypothesis; running myself as a DJ business or any other opportunity outside of being an employee gave me enough experience, foresight and knowledge to apply the same framework (knowing how to trade my services/goods for money, keep track of where everything’s coming from and going, repeat) and see what happens. The internet’s big enough to show how to do everything with books and video tutorials and when in doubt, I’d outsource it to a professional!

Here’s what I picked up for pointers and references:

                   The Four-Hour Workweek fourhourworkweek Ca$hvertising Things They Don’t Teach You In Business School richard-branson-like-a-virgin-secrets-they-wont-teach-you-at-business-school So far it’s been an interesting ride watching business grow like a many-tentacled plant. And I’ve got time to do more music! Which is coming in the next post. Stay tuned!


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