Boldness, regret and the roads not taken
By Homer H. Hillis
One of the most fascinating things about President Trump is that he seems determined to avoid what Daniel Pink calls a “Boldness Regret.”
Homer H. Hillis
Whether you agree with him or not, he continues to act, speak and push forward. He does not appear to be someone who wants to wake up late in life and say, “I was a mouse. I played it safe.”
Much of that mindset can be traced to the influence of Norman Vincent Peale, author of “The Power of Positive Thinking.” Peale preached confidence, action, and the belief that people often underestimate what they can accomplish. Trump has frequently cited Peale as an influence, and his public statements often reflect that philosophy.
Daniel Pink argues that many of our deepest regrets come not from actions we took, but from actions we never took. The business not started, the question not asked, the opportunity not pursued. These are what Pink calls Boldness Regrets. Of course, bold action is not without risk.
Sometimes people take chances they later wish they hadn’t. Research suggests that roughly one in five people eventually regret at least one of their tattoos. That’s a reminder that boldness and wisdom must travel together. The movie “We’re the Millers” gave us the memorable line, “No ragrets.” It’s funny because everyone knows the truth: life comes with regrets. The real question is which regrets we choose. Do we regret trying and failing, or do we regret never trying at all? Pink’s research suggests that, over time, most people make peace with their failures. What lingers are the roads not taken. Whether in business, relationships, travel, creativity, or public life, many of our greatest regrets come from caution rather than courage. Perhaps the goal isn’t to live with “no regrets.” Perhaps the goal is to have fewer regrets born of fear and more stories born of action.
About Homer H. Hillis Jr.
Homer H. Hillis Jr. is an entrepreneur, storyteller, product designer, and lifelong student of human behavior. Since 1988, he has built businesses in jewelry, accessories, manufacturing, and wholesale distribution through HHH Enterprises. After reversing his Type 2 diabetes through lifestyle changes and significant weight loss, Homer became an advocate for personal responsibility, continuous improvement, and the idea that small daily actions create extraordinary long-term results. His interests range from business and philosophy to journals, bolos, art, travel, and the power of stories to connect people.
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“There’s little art in making money, but how you spend it is pure art.” — Homer H. Hillis Jr.
