Finding Your Business Why — and Why Not: Taking Creative Risks

At age 23, Simone Biles already has an impressive list of accomplishments: four Olympic gold medals, five all-around world championships, four gymnastic skill moves named for her, and more. Biles says, “I’d rather regret the risks that didn’t work out than the chances I didn’t take at all.” What implications can Simone Biles’s attitude toward risk have on your business?

Life decisions often require a certain amount of risk and uncertainty, but what is often not highlighted is that creativity and risk are intimately linked and often misunderstood by rational thought. Why was Einstein — a creative giant and innovator — an avid sailor but couldn’t swim? And how are those seemingly contrasting points linked? 

Creative risk-takers fail, often extravagantly, but their greater output of attempts typically overcomes their failure rate. The successes of creativity depend on the brain making connections that are not immediately obvious to others, stretching and coupling subtle relationships and novel linkages. Each risk taken expands our fields of possibilities; it stretches the connections in our brains and creates conditions that are necessary for innovation. This trains the brain to recognize alternative options and see varied outcomes and, conversely, taking the certain path quite literally narrows our field of options. 

Spanx founder, Sara Blakely, is quick to acknowledge how taking risks has shaped her successes in life and business. She is often outspoken about her failures and the unconventional path she took to success. She went from selling fax machines door-to-door to creating Spanx and every piece of her journey created the puzzle of her success. Blakely says, “With every obstacle that has happened to me in my life, my brain immediately says, ‘Where is the hidden blessing?’ In starting a business and growing a business, every day is learning how to manage obstacles.” This comes from someone that is ranked #32 on The Forbes Most Powerful Women Entrepreneurs list in 2020, and at the age of 41, was crowned the world’s youngest self-made billionaire.

A recent study by the University of Chicago economist Steven Leavitt (author of Freakonomics) offered 20,000 participants facing a major life decision a virtual coin toss to make the choice for them. At a sixth-month follow-up, those who made the “riskier” choice reported feeling happier and more satisfied than those who “played it safe.” Another study at Northwestern University’s Kellogg School of Management found that most people tend to regret things they haven’t done more than things they have. These two studies highlight that happiness may have less to do with the actual decision but rather in making any decision and moving toward a possible unknown outcome. Sitting on the sidelines is a choice and the regrets are costly; “taking your shot” matters.

We do not bring these topics together as justification for making rash decisions, but rather to highlight the research that shows we should pay attention to that nagging dream or goal we have for our business or life. If the risk aligns with our long-term strategy, it may be one worth taking. If you face a difficult choice, maybe you should favor the option that takes your business in the direction of positive change or strategically driven development. 

If you’re wondering whether it’s time to make a change in your approach to your investments, your financial plan, or other important personal or business matters, we are here to provide professional, fiduciary advice geared to your unique situation. We would enjoy the opportunity to get to know you and find out what is most important to you.

To read our recent article, “Business Succession Planning: Why It Matters for Female Business Owners,” click here.