Transform Regret into Success! (Pt.2)

This is a 4-part series discussing 4 types of Regrets. Last week we talked about Foundational Regrets. You can read that newsletter edition here. This week we discuss what Boldness Regrets are, why we experience them, and how we can overcome them.

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Early in my marriage, I didn't make a lot of money. I was in my twenties working in an entry-level job with a young family to take care of. Around the same time, my life partner's business was in its infancy. We decided she would stay home and raise our two kids while becoming an entrepreneur. After doing some local work for a few clients, she landed a gig that would be a game changer. Her reputation as a creative photographer was growing, so a couple hired her to shoot their wedding in the Bahamas. We both immediately saw this as an opportunity to have a 'make-up honeymoon' since we couldn't afford a real one after our own wedding.

She received the first downpayment and we immediately bought our flight tickets. We then planned on using our own funds to book our accommodations and then use the other half of the payment to cover our regular bills. It was a great plan on paper. That was until I got cold feet (and it wasn't even my wedding!). I wasn't sure we'd be able to cover the rest of the vacation and our bills. The Bahamas was historically more expensive than other Caribbean locations, and I struggled to find affordable accommodations. So, I made the tough call to bow out of the trip. Just one problem: I had already purchased a plane ticket. But that was quickly resolved after selling my ticket to a good friend of my partner. They both went on to have a great trip.

I still remember seeing the photos after they got back and being filled with envy and jealousy. But the worst part was the feeling of regret. What I initially thought was the financially smart, responsible thing to do ended up?being feelings of fear. After receiving the second payment for her work, I realized we could have both enjoyed the trip. Would things have been tight? Yes. Could we have figured it out? Absolutely. But at the time, I allowed fear to cloud my better judgment. It would be another few years until we had enough to take a really nice all-inclusive vacation together. But to this day I still have regrets about not going.

That story outlines what Boldness Regret is. The term was coined by author Daniel Pink from his book The Power of Regret. It's when we look back over time and say to ourselves, "If only I had applied for that role... started that business... written that book... taken that vacation." It's the regrets we have from not taking a big risk and doing something significant. We stop ourselves because of what we see as limitations in time, money, or clear opportunity. And we convince ourselves that we'll make it happen someday in the future or that we're going to be just fine not pursuing it. The problems come years later when we start feeling personally unfulfilled, stagnant, or worse, harbor resentment towards people around us who have taken risks and accomplished great things.

But why does it matter? If we're healthy, honest, hardworking people who decide to live a steady life playing it safe and not chase dreams of grandeur, does that make our lives any less significant? Absolutely not. Maintaining a strong consistency in the things that matter most will mean more to our family and significant relationships. We don't chase bold ideas to gain worldly value or significance. But just like being consistent on everyday life issues has its benefits, taking risks to accomplish something big has cognitive benefits that we may not realize.

From a cognitive science perspective, being bold and taking big risks can lead to enhanced neural connections and plasticity in our brains. The new and challenging experiences prompt our brains to create new neural pathways and strengthen existing ones. The benefit? Neural pathways or neuroplasticity is the fundamental mechanism of how our brain adapts and learns. So when we stretch our limits through new and unfamiliar situations, we're actually strengthening our brain's ability and capacity to learn. From there, we begin to acquire new skills, broaden our knowledge, and grow our creative thinking. We become more self-confidence and improve our decision-making skills.

Being bold enough to travel to another country like the Bahamas on the surface might look like just personal downtime, but it's an opportunity to see different landscapes, try new foods, and learn about different cultures. An experience like that can have a profound impact on our unconscious biases about the world around us. Mark Twain sums this up beautifully in one of his writings, "Travel is fatal to prejudice, bigotry, and narrow-mindedness, and many of our people need it sorely on these accounts. Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one's lifetime."

Even with all those benefits, we still stop ourselves short from taking the leap, mostly due to the fear of failure and looking foolish if we fail. The opinions of others holding the social mirror double down on this idea, promoting a life free of risk and centered on personal security. But even if we do fail, we gain benefits through the process.

While risk-taking exposes us to the possibility of failure or setbacks, overcoming those challenges can boost our resilience. Dealing with failures can help us develop mental toughness, problem-solving skills, and the ability to bounce back from adversity. Resilience can also transfer to other areas of our lives, enabling us to approach future challenges with a positive mindset. There's always something to learn when applying for an internal job posting and not being selected. A business idea that doesn't pan out becomes a reference guide for what not to do on your next idea. Asking someone out and getting rejected at the very least lets you know where they stand instead of not trying at all.

Personal benefits aside, sometimes the strongest motivation we can have to combat boldness regrets is considering others. When our risk-taking is built on a purpose that can impact the well-being of others, we'll be less hesitant to move forward. Suddenly our fear of looking foolish takes a back seat to empathy and the fear of what might happen if we selfishly play it safe. World-changers like Nelson Mandela and others risked their lives for others. Our impact might not be on that level, but wanting to avoid the regret of not doing something can be a great motivator to initiate something significant in your company, community, and/or family.

The concept of Boldness Regret highlights the importance of taking risks and pursuing our dreams. It's about overcoming the fears and limitations that hold us back. By embracing boldness, we strengthen our cognitive abilities, broaden our perspectives, and gain valuable life experiences. Even if we encounter setbacks, the process of pushing our boundaries and learning from failures can lead to personal growth and resilience. Ultimately, being bold not only enriches our own lives but also has the potential to positively impact those around us. So let's seize the opportunities, chase our dreams, and live a life without regret!

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Sheldon Barrocks?is an author, freelance writer and?Award-winning?Supply Chain professional. Since 2010 he has published articles covering business, career advancement, creativity, pop culture, music, fashion, sports and more. He's provided creative solutions for major brands like?Mars, Kelloggs, General Mills, Conagra, B&G Foods, Ingredion, Henkel and more. Check out his book?Unstuck Mondays?and join his?mailing list?to level up in your creativity and career!