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Overcoming Your Kryptonite and Making the Leap into Entrepreneurship

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Editor’s Note: With the goal of humanizing entrepreneurs, this monthly series from entrepreneurship group Empact profiles young founders as they deal with the trials and tribulations of starting up.

Evan Kirkpatrick had the life we all think we dream of -- complete with job security, above-market salary and the thrill of managing multi-million dollar deals. It was the kind of life where you wonder how a person would dare want more.

Kirkpatrick began his career in finance at age 22 for a Fortune100 Seattle-based investment company and quickly became a senior investment consultant for a boutique wealth-management and corporate-benefits firm.

Four years later, the still-young Kirkpatrick began to worry about burning out. Working more than 85 hours a week with no personal time to do things like respond to calls from friends and family would surely take its toll eventually. He knew he wanted to make a change but also harbored doubts and insecurities -- specifically over his young age.

These insecurities became his Kryptonite.

We all have our own version of Kryptonite -- age, lack of experience, some feeling of inadequacy from being different than our peers. It’s a little different for everyone, but the result is the same: insecurity. How we overcome these fears is what helps an entrepreneur be born, and subsequently, rise to the top.

To be sure, the decision to give up the life that he had built for himself and start Wendell Charles Financial wasn’t easy. Nor was it immediate. There wasn't an “ah-ha” moment or a light bulb that magically flickered on compelling him to march into his office and quit on the spot. It was a process that mostly entailed overcoming insecurities.

“For a time, I believed that I was too young and it led to issues of being too serious, trying to be too technical and not being myself and letting my personality show," says Kirkpatrick. “Overcoming this insecurity and letting my confidence shine outweighed any doubts anyone had about my age.”

Kirkpatrick wasn’t around any spiders. He wasn’t born on Planet Krypton and wasn’t infused with Adamantium. So how did he do it? Here are his three tips for overcoming fear and insecurity:

1. Seek education and self-training to build confidence.

Kirkpatrick’s advice on breaking free from a life of contentment is to push your limits on what you think is possible through education and self-training. His advice? “You don’t necessarily need 20 years of physical experience if you have the same knowledge as your peers.”

To gain this insight, he went to every single conference, read every industry white paper, spent nights and weekends learning about the business and listening to inspiring talks and books.

After spending all of this time absorbing, it started to really sink in. “It finally clicked," says Kirkpatrick. "I could run a financial-services practice and sit at the same table as my peers who were managing a billion dollars at the age of 45 and I wasn’t intellectually intimidated by it.”

2. Choose the right community.

Though he's compelled to prove those who say he can't wrong, he also couldn't have done it alone. Kirkpatrick credits much of his success to his support system. His parents were small-business owners and understood his compulsion to venture out on his own.

Being an entrepreneur can be a lonely journey but there are many others out there on similar journeys. Evan’s advice is to “search for like-minded peers and communities that will positively encourage you to persevere but who will also be upfront with you about when to pivot”.

3. Get a little experience.

Depending on the industry, it can be very wise to get some experience before starting.  When Kirkpatrick first graduated, he had no idea how to run a financial company or perform at the level of his competitors so it was necessary for him to find mentorship and get involved in a company that was successful before launching one on his own.

The question for him then became, what is a "little" experience? How do you know when you really need experience versus when you’re just too scared to leave? The answer is different for everyone, but accomplishing points one and two (above) will point you in the right direction.

No entrepreneur is a superhero, even though it sometimes appears that way. We hear a lot about the overnight success stories but what you don’t hear about is the constant battle against each entrepreneur’s Kryptonite.

The three steps above helped Kirkpatrick navigate the battle that led to his now successful private wealth management firm, Wendell Charles Financial.

Sarah Green

Written By

Sarah Green is a social entrepreneur and consultant dedicated to economic empowerment through entrepreneurship around the world. Green has been acknowledged by President Obama for her work as a young leader in entrepreneurship in America. She has also been named one of 100 "Global Leaders of Tomorrow" by the St Gallen Symposium in Switzerland and named as a 2013 Top 99 Under 33 Foreign Policy Leader. Green's work as an entrepreneur has been featured in prominent media outlets including Forbes, Entrepreneur,, MSNBC, ABC, Yahoo! Finance and Fox Business.