4 Questions You Must Answer About Ditching Your 9 to 5

If I stayed at the 9-5 job, what was the best case scenario?

I'd climb the fickle corporate ladder. I'd see incremental financial increases. Different words would be embossed on my business cards (which only meant more responsibility and stress). I'd probably never be truly happy.

If I stayed at the 9-5 job, what was the worst case scenario?

I'd either work there for the next 30 years and be miserable or at some point I'd be let go, I'd have no income, I'd be scared, and I'd find some other mediocre 9-5 job. I'd definitely be unhappy.

If I left the 9-5 job, what was the best case scenario?

I'd be my own boss. I'd call my own shots. I'd reap the rewards of all the hard work. My financial success would be limited by only my ideas, work ethic, and ability to sell something great. I'd also never have to commute to work, put on pants in the morning, or sit through absolutely mundane meetings. I'd be happy!

If I left the 9-5 job, what was the worst case scenario?

My new business venture would fail, I'd have no income, I'd be scared, and I'd find some other way to make money (doomsday scenario: find some other mediocre 9-5 job). I'd probably be unhappy, but I'd learn a crap-ton from the experience.

What I realized once I answered these questions was that I had so much more to lose by staying at the 9-5 job. Yeah, there are lots of other factors and details that could arise, but the overarching worst case scenarios were nearly identical. I'd be a fool not to try to start my own business and see where that journey would take me.

By staying in that secure job, I was not only sitting on a ticking time bomb of unhappiness but also ignoring my potential. I could be the next Bill Gates. I could be the next Steve Jobs. Hell, I could even strive to be the next Evan Spiegel (the way that kid turned down billions for Snapchat is inspiring--and crazy).

Don't get me wrong. I'm not saying I'm a software genius, product marketer extraordinaire, or creator of the next huge app. What I'm saying is that the potential for those things is in each of us. If we never give ourselves a chance to unleash that creative potential, that's a bigger prospective loss than what might happen if you try and fail. I'd so much rather be trying to do things that give me unbridled financial freedom and happiness than staying somewhere "secure" and miserable.

"You miss 100 percent of the shots you never take." -- Wayne Gretzky

It's a cliché, but it's so true. If you don't take the shots, you don't stand a chance of achieving so much more in life. If you do take the shots, you'll probably miss a bunch of times, but a couple of those makes will be so gratifying in so many different ways.