Living Without Regret

Living Without Regret

It is good to have an end to journey toward; but it is the journey that matters, in the end.

– Ursula K. Le Guin

Thanks for taking the time to look at a phenomenon that all of us experience at some point in our lives. In my research about this experience, I’ve learned that regret, or the anticipation of it, affects our decision-making in almost every area of our lives.

“Regret” comes from an Old French word meaning “to bewail the dead.” Over time, it evolved to mean feeling sad or disappointed about something you did or didn’t do. It’s like wishing you could go back and do things a bit differently.

There are many different kinds of regret:

  • Regret at not having done something we should have done. For example, not exercising your hip or knee to help the body get back to normal flexibility, resulting in stiffness that doesn’t go away.
  • Regret at having done something we should not have done. For example, speaking harshly with someone we love.
  • Regret for taking a long time to accomplish something that we think we could or should have done more quickly (see Sally’s story below).

In this article, we look primarily at work-related regrets.

In their 1986 seminal study about regret, Amos Tversky and Daniel Kahneman explored the psychological concept of regret in decision-making under uncertainty. It’s called “counterfactual thinking.” Counterfactual thinking is when we imagine different scenarios of what could have happened instead of what actually did happen. For example, after missing a bus, someone might think, “If only I had left the house five minutes earlier, I would have caught the bus.” This kind of thinking involves looking at past events and imagining different outcomes by changing some details, like our behavior, in our minds.

Tversky and Kahneman’s study shows how the fear of regret can shape our decisions. They found that not only do we feel regret after seeing the outcomes of our choices, but the mere thought of feeling regret can make us cautious before we even decide! Their research suggests that sometimes, to avoid the discomfort of regret, we might choose safer options, even if they’re not the best or the most logical ones.

Regarding regret, I’ve discovered something in coaching people over the past thirty-plus years. Some of them who come from a corporate culture and then become entrepreneurs face more difficulties than those who have never worked in corporate environments. Here’s why:

When you’re your own boss as an entrepreneur, it’s like needing to catch a fish each day if you want to eat that night. In contrast, when you’re part of a big company, missing a fish today isn’t a big deal—you’ve got until the end of the quarter to make up for it. There’s no instant pressure.

A lot of clients I’ve worked with weren’t ready for the shift to having to be the ones getting things done themselves. In corporate life, they had a team to help reel in the big deals. They could oversee things and delegate people to solve problems as they popped up.

However, when you start your own business, it’s a whole different “kettle of fish.” Suddenly, you’re the one learning to do everything! This need to learn entrepreneurial skill sets can really ramp up the stress. And, at times, regrets about the results of this move to a different kind of business are not far behind.

Here’s a story about one of my coaching clients, who I’ll call Sally, to protect confidentiality. Sally was a successful corporate professional who decided to transition into entrepreneurship. Her story is one that many of us can relate to, as it’s about regretting the steps she took from having a corporate job to being an entrepreneur.

Sally: When I left my corporate job as a leader, it never occurred to me that I’d have to learn so much about how to operate a small virtual assistant company from start to finish. There were so many unforeseen difficulties. For example, a friend of mine who worked at a corporation looking for a reliable virtual assistant business got me an interview with the HR manager, who asked me to submit a proposal. I didn’t know the first thing about how to do it and so I waited two weeks before getting back to her. By that time, they’d already signed a fairly big contract with another virtual assistant group.

I regret that missed opportunity! If I’d learned sooner what it takes to submit an offering, I would have had a great start. In addition, and I know it sounds naive, I didn’t realize I had to have a business license. In addition, my business plan was overly optimistic because I’d forecast higher revenue and profit within the first year. It finally occurred to me to hire a business consultant who began to show me how to be a successful entrepreneur! She saved me from regretting that I’d left my corporate job!

I have my own example of regret about writing a book to be published by a well-known book company. It happened about 26 years ago, before all of the advances in technology that we might take for granted today.

There I was, having been picked up by this publishing house. I had promised to deliver my first draft of the book in six months. All went well until:

  • My computer broke down as I was writing Chapter 3, and I hadn’t saved it to a “floppy disc” along with Chapters 1 and 2! Mind you, this was in the days before iCloud or similar services, and I had to write all three chapters over again. Luckily I had my old notes, and, I have to say, the three chapters were better than my first draft of them had been.
  • It was determined that I had to buy a new computer. Luckily, I had the funds to do it, but it took an extra two weeks to receive it and then have someone sync it with the old one so that all my notes and previous chapters were saved.
  • The editor the publishers gave me did well for a few weeks. We were on the same page in so many ways.  However, around six weeks into this project, she was offered a higher-paying job at a publishing house.
  • It took at least two weeks more before we found the perfect editor! She didn’t quit. Her dedication and support were crucial in keeping me motivated and focused on my goal.
  • It took at least seven days to meet and orient her to the project.
  • At that point, I was behind the projected timeline by about eleven weeks.
  • I thought no one went through similar unexpected difficulties when starting their book project, so I imagined it should have gone more quickly and that I had done something wrong in the process. I regretted having told the publishers it would be done by the projected date. At one point, I even regretted that I promised to write the book! But that was short-lived.

Everything turned out well. The manuscript was delivered almost three months later than I had projected. The publishers were pleased with the work. But at each of the above points, I was sure that I was doing something wrong. As a matter of fact, I began to call these points my ” OSPs,” which stands for the Oh S–T point. That’s because our first reaction to something that happens and makes us deviate from our plan usually sounds like: Oh, S–T! Right?

However, this is what I learned, and in order for you to see what it was, I ask you to use your imagination. If at all possible, please get a clean piece of paper and a pen that’s easy to use. If you don’t have any, just imagine what I’m saying without closing your eyes.

Draw a stick figure representing you on the left corner at the bottom of the page. Next, put something that could represent a goal in the upper right-hand corner. Make it a clear example, like a book, a revised website, a trip, or something easy to recognize.

Now draw a straight line from the stick figure to the goal. Next, you’re going to draw a wavy line that wanders back and forth over the straight line but continues to advance toward that goal. However, from our subjective experience, every time it deviates from that straight line, it becomes an OSP.

So, this is what I saw as I continued to write despite the breakdowns. The straight line was the path I thought I would take toward the goal of a book manuscript delivered on time. It was the one I predicted would happen. However, I soon found that this wasn’t how life actually works.

The wavy line turned out to be the actual path! I found that there will always be deviations from our projected outcomes!  Life doesn’t run in a straight line. It was useless to regret the breakdowns that happened. They were a regular occurrence, and rather than being a setback, they were a sign that I was moving forward! 

Once I saw the above, I began to relax. Any further deviations from the plan actually taught me something about the world of writing. I saw how to shift from seeing unforeseen events as obstacles to seeing them as opportunities to learn more about what it takes to be a persistent writer, no matter what happens.

Does all of this ring a bell? Do you have regrets about a particular business idea or a dream that you gave up on? If it’s not about business at this time, think about any goal, such as a journey, learning to play an instrument or anything that once captivated you before you stopped yourself.  

Here’s what you can do to handle regrets:

  1.  About a goal that you reached but with more time and energy than you thought it would take or 
  2. Didn’t reach because you gave up at some point thinking there was something wrong with all the twists and turns it was taking. 

Clarify what the regret is all about. For example, if you’re looking at a business venture or goal, what did you do or not do? Be specific.

  1. Identify any regrets if you achieved your goal. Consider aspects like time, cost, or excessive attention to detail. Write these regrets down. This helps to confront them. Be specific.
  2. Reflect on lessons learned from the experience and document them. Allow yourself to acknowledge these insights generously.
  3. Find something to be grateful for in the situation, as there’s always an aspect to appreciate. This is an essential part of dealing with the situation from all aspects of it.
  4. If you didn’t achieve your goal, list your specific regrets so that you can see and acknowledge them.
  5. Determine if you’re ready to try again to achieve your goal. If so, plan your next small, achievable step.
  6. If you’re not pursuing the original goal, choose a new, manageable goal to focus on and take action toward it.
  7. Consider if you need to ask anyone for forgiveness related to the situation and plan how to do so gently and appropriately. If direct contact isn’t suitable, think of a generous act you can do for someone else.

One sure way to handle regret is to assess if it is genuinely warranted. One way to let go of regret that you didn’t do everything you thought you should have done is to consider the following: 

The minute you start toward a goal or dream, you will always experience OSPs along the way. They are not an occasion for regret. They are a validation of you!

Until next time!

P.S. Make sure you listen to my podcasts, The Energy Of Money and Coach Training Podcast, both offering their own unique insights that I’m sure you’ll enjoy.

​​If you are also looking for coaching, please contact me at Monica@acecoachtraining.com.

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