The Joy of Jumping into the Entrepreneurial Abyss

by / ⠀Personal Branding Startup Advice / August 18, 2012

This summer I chose to not follow the herd and trust my intuition. After interning for three different companies over the past two years I came to the realization that I could learn more on my own. I knew I wanted to be an entrepreneur and finally embraced the abyss.

For several months I watched creative individuals launch projects on Kickstarter. I awed over their ambition and was inspired to embark on a project of my own. The only thing that stood in front of me was a fork in the road. I had to choose between interning for another company or engaging in something entrepreneurial. It was much deeper than that though. I chose to be different. I chose to be myself. People who are closest to me were skeptical about my decision. However, it was pretty black and white for me. I couldn’t keep passing up the opportunity to create something. As they say, you have to swing the bat to hit the ball. Personally, I would rather fail one-hundred times in a row following my heart and trusting my intuition, than be successful living someone else’s life.

Never have I consistently woken up each morning as excited as I have been the last six weeks because I am finally doing what I want to do. My Kickstarter project has been a huge eye-opener for me. It subtly hit me in the head with a brick, and brought to my attention the insane amount of time that is required to make anything worthwhile happen. Without question, it has been the most challenging form of self-discipline in my entire life. My project is a tribute to the late great Steve Jobs. He is my icon as well as my inspiration and I have thoroughly enjoyed designing posters in his honor. I plan to launch my project, the “Billion Dollar Hippie” within the next month.

To anybody who has had thoughts about doing something entrepreneurial I highly recommend to dip your toes in by starting with a project of some sort, rather than a company (or initially approach the idea you have for a company as a project). Start small, think big. Whether it be a small design project on Kickstarter, building basic websites for people, or starting a themed blog. It’s a great way to experiment and see if you are willing to remain disciplined throughout the entire process and overcome constant adversity. I have had past thoughts about starting a company and I am so glad that I started with a Kickstarter project because after experiencing how challenging, time consuming, and involved my project has been I now have the slightest idea of how crazy starting a company probably is. And I am still probably nowhere near ready.

Going rogue can be risky. No, going rogue is risky. More than likely your project or company won’t generate enough money to solely support yourself at first. Finding work that is flexible, but provides you with enough time and money to support yourself and your dream is critical. To support my decision to go rogue I have been working at a restaurant which is far from glamorous, but pays surprisingly well. Most importantly it allows me to have a flexible schedule so I can stay up into the wee hours of the night working. I am confident my biological clock is no longer normal. But then again I’ve never heard of anyone refer to an entrepreneur as normal either.

P.S. ~ Don’t follow the sheep. Embrace the abyss. Swing the bat.

I am an undergraduate student studying computer science at San Francisco State. I am passionate about graphic design, music, and innovation of all sorts. I hate the status quo. twitter @jaredhalpert

About The Author


Matt Wilson is Co-Founder of Under30Experiences, a travel company for young people ages 21-35. He is the original Co-founder of Under30CEO (Acquired 2016). Matt is the Host of the Live Different Podcast and has 50+ Five Star iTunes Ratings on Health, Fitness, Business and Travel. He brings a unique, uncensored approach to his interviews and writing. His work is published on, Forbes, Inc. Magazine, Huffington Post, Reuters, and many others. Matt hosts yoga and fitness retreats in his free time and buys all his food from an organic farm in the jungle of Costa Rica where he lives. He is a shareholder of the Green Bay Packers.

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