Words of wisdom on taking risks, overcoming failure

Highlights from the Oct. 6 Fearless Focus conversation on risk-taking

By Emily Kestel

Any business owner, CEO – or really anyone who is in an elevated or visible position within a community – will admit that getting to where they are now required a few risks. 

Saying yes to a position outside of your wheelhouse. Saying no to a safe bet because you had a hunch that a brighter horizon was ahead. Standing up for what you believe in. 

But knowing that risk-taking is a necessary ingredient for success, why do we avoid it? How do you overcome a fear of failure? Why are women more risk-averse than men? How can we encourage risk-taking? 

Those are some of the questions we asked our panelists at our Fearless Focus virtual event earlier this month. 

Panelists were: 

• Kirsten Anderson, author and advocate.
• Katie Hoff, team leader, Cyber Security Operations, Wellmark Blue Cross Blue Shield. 
• Connie Wimer, chairman, Business Publications Corp. 

Below are quotes from the conversation that I consider to be cream-of-the-crop. Sometimes it’s useful to have a little inspiration to refer to before you do something out of your comfort zone. I hope these comments help give you that boost you may need.

Wimer: Taking risks is like a muscle. The more you use it, the stronger it gets. 

Anderson: When I think about the unknown, I think about “What’s the worst that could happen? If I take this risk, what’s the worst that could happen to me?” 

Hoff: [Overcoming a sense of failure] is about the small steps you have to do. It’s the small things you do to just keep pushing forward. 

Wimer: Do a tremendous amount of research. Go into [something] knowing what the risks are. Prepare for the worst that could possibly happen, but expect the best. The optimism of expectation is equally as important as the preparation if the bottom falls out. 

Anderson: Don’t let the risk and decision-making paralyze you. Don’t get caught up in the what-ifs. If you take a risk, make a choice and it goes badly, make another choice to take the lessons from it and take another risk and decide the other way tomorrow. 

Wimer: Failure is another form of learning. Make the changes to adapt, and move on. 

Hoff: Build your support system. They will take the time to help guide you. They will be the ones to help you through your risks, your failures and your successes. 

Wimer: If you don’t have a women’s group, form one. There’s power in having that total freedom to ask questions and not worry about sounding dumb. 

Hoff: From the perspective of being in leadership or management, it’s up to us to create that safe space or place where women can fail. 

Anderson: We need to get over trying to be perfect, period. Uniqueness and imperfection will lead to failures, and that’s OK. 

View the full replay of the event.