Eight readers share their stories of taking risks

Ted Young: I started by painting my neighbor’s shed to be able to buy groceries, then my other neighbor’s house. I started with no equipment, no supplies and no network, just a need to make something happen. From that small start, I was able to support my family for almost 20 years and the company is still doing well today. Taking a risk impacted my life in that something came from nothing, and we are still benefiting from that risk-taking behavior to this day.

Alicia Hollis: I used to be a single mom pursuing a bachelor’s degree in teaching and had barriers of child care, bills, and education funding. It took me three years at MCC and three years at UCM. Now, I’m a passionate high school counselor helping teens to discover their talents and work towards their dream. I learned that it doesn’t matter how long the journey takes, because in the end, no one really asks about that.

Steven Martin: On July 3, 1997, I was the COO and EVP of a $20 million high tech company. On July 4, I cleaned out my office and put a letter of resignation on the CEO’s desk. I had no plan. My natural tendency toward being risk-averse flavored everything. My dedication and commitment were significant barriers to leaving the job, not to mention the fact that we had no other source of family income. At age 53, I started a consulting business, have been self-employed and have not experienced a bad boss since 1997.

Anna Wasescha: I resigned from a senior management job without having another one. I moved to New England from the Midwest, met people I now regard as close friends, learned a lot about a new place and its customs, succeeded in my new job, and increased my self-confidence by leaps and bounds.

Yvette Connor: Had I not taken the risk, including leaving a 14-month-old baby girl behind with my in-laws while I commuted 300 miles away to make ends meet and build my career, and had I not possessed the courage to do what many working moms fear, I would not be where I am today. I have set an example for my daughter and also for the women I mentor or lead professionally.

Enoch Stiff: I took over the reins of a small Midwest construction equipment manufacturer with $28 million in sales and 125 employees. We had an idea about changing the way America built buildings. Twelve years later, our sales were $600 million with almost 1,800 employees and nine facilities, $400 million of which was directly attributable to indigenous growth through innovation.

Jennifer Connolly: I was unhappy with the situation at work and my life seemed stuck in a rut. Then came the opportunity to continue with the same nonprofit but in a different state. I put my house on the market and moved into a little house in a new town in Massachusetts all by myself for the first time in my life. That was 16 years ago, and the area has become home. I have made new friends, become the executive director of the nonprofit and put down roots. I know I am more fulfilled than I would have been had I not taken the opportunity, or risk, moving away and starting over. I have met wonderful people and had amazing experiences. I learned that I can be successful on my own and that I am more resilient than I ever thought I could be.

Fred Ledley: Starting a company never seemed to be a risk, though by any objective criteria leaving my position to join the first company, and leaving the first soon after it completed an Initial Public Offering to start the second were certainly high risk endeavors. Each company embodied something I wanted to do, something I was good at, something I thought I could accomplish and something that I believed needed to be done. My investors joked that I was ‘risk-oblivious,’ but I never felt that way. I was doing something that that I was good at, something I loved.

“The Risk Optimistic” is about belief: the assurance that taking a chance is worthwhile, even without knowing the outcome. It’s also the belief that if we value and support risk – in policy, community, and culture – we benefit from each person’s ability to make choices to achieve success. With this initiative, Kauffman kicks off 2020 with insights, stories, and opportunities to explore what it means to take risks, and own your own success, however you choose to define it.