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Regret-Free Living

In life, we have a lot of decisions to make. Some decisions are small (PB&J or a BLT?). Some decisions are large (corporate or entrepreneur?). So, how do you know if you’re making the right decision or a decision that will ultimately result in regret? Without fail, every single person whom I’ve had the honor […]

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In life, we have a lot of decisions to make. Some decisions are small (PB&J or a BLT?). Some decisions are large (corporate or entrepreneur?). So, how do you know if you’re making the right decision or a decision that will ultimately result in regret? Without fail, every single person whom I’ve had the honor to enroll in our programs has shared this exact same worry. This fear of being wrong creates decision-making paralysis. In the absence of a strategy to overcome fear, our lives and careers become stagnant as our agency and sense of control withers. But thankfully, for you and me, I have learned a little something about regret-free living that I hope will free you from the prison of your own fears.

Here’s the lowdown: modern psychology breaks down regrets into two categories. You can experience regrets of commission, which means to regret something you did, or regrets of omission, which means to regret something you did not do.

Regrets of commission are understandably painful. You do something wrong. You find out, get found out, or come to terms with the fact that you did something wrong. You endure some type of consequence. You experience regret and (hopefully) repentance for what you did wrong. And the experience is over. Done. Dusted. On to the next. This sort of cycle hap- pens all the time when people make what they deem to be bad decisions. The process usually follows the same predictable stages: you decide, take action, get punished, regret what you did, and move on.

These kinds of regrets all share that similar closed-loop structure—a beginning, middle, and end. Yes, the outcome often sucks. That’s part of regret. But at the end of the day, there is a resolution you can (eventually) reconcile. Acceptance and reconciliation may be difficult, but they are possible.

And it’s precisely that possibility that distinguishes between these two types of regrets.

The second type of regret is impossible to forget because it inherently lacks resolution. Regrets of omission—regret for things you did not do—have no final or tangible outcome. No consequence. Or so it seems . . . More accurately, they have an infinite number of possible outcomes or potential resolutions. It is precisely this uncertainty—the unanswerable what-ifs— that elevates this type of regret over the other. The brain loves closed loops. Regret without resolution can haunt you for a lifetime, simply because of the lack of clear resolution. In the absence of a known outcome, the brain continues to fruitlessly search for one. In search of resolution, your mind clings to all the different possibilities, so you regret what you omitted not just once but over and over and over again.

By letting fear of an outcome that you can’t predict guide your decision-making, you’ll take the exact route through life that produces more regrets, not fewer. You may feel as though you’re protecting yourself from the regret of career failure by playing it safe. But choosing not to try opens you up to a cycle of regrets that could go on forever.

I ask that as you progress through this process, you embrace this lesson as it pertains to your career. Take your meaningful shot at the stars, whatever that may be. Fear, the most primal and visceral hurdle, keeps us from finding meaningful, fulfilling work. Everyone’s fear base is different, but the result is the same. Lifelong, crippling regret about the things we never did, and how we wish we had been brave enough to try. Don’t let this happen to you. Take your shot, knowing that even if you fail, you’ll never regret the failure more than not trying at all.

Paralysis by analysis, or the art of not deciding, is a choice in and of itself. It’s also a habit that many find challenging to break. To begin shifting this mindset, I offer you a couple of tips. First, make a what-if list. Think back on your major life decisions: relationships you started or ended, conversations that did or didn’t take place, places you did or didn’t move to, communities you got involved with or left, and so on. Which what-ifs still remain? What do you wish you knew the answer to? What do you struggle to let go of when you’re falling asleep at night? The angst this list creates will likely be enough to encourage you to make proactive decisions going forward and provide some incredibly powerful motivation. Practice your new decisive mindset by committing to newer, stronger, forward-focused decision-making.

Another trick, and my personal favorite, is to imagine yourself in your twilight years. The next time you have a deci- sion to make, imagine yourself as an elderly person looking back on your life. When I do this, I’m ninety-plus years old, sitting on a porch in a rocking chair, with an afghan draped over my shoulders and a cat sitting quietly in my lap. I ask that version of myself, “Will I regret this decision?” or “Will I regret not doing this?” I’m proud to report that Granny Tracy has been right 100 percent of the time.

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