How to avoid the No. 1 kind of regret people have when they die, from an Ivy League instructor

Of all the things I fear — spiders, needles, rejection — regrets take the cake. I have a deep-rooted fear of getting to the end and feeling woefully disappointed — not so much by the life I lived but by the life I didn’t live.

In many ways, I have my mother to thank for waking me up and helping me course-correct. She died at 58 with a litany of regrets. After losing her, I was gripped by the fear of dying with my own laundry list of “if onlys.” 

I committed to live a regret-free life or die trying. Now I’m hell-bent on helping us all make the most of our time while we’re lucky enough to be above ground. I want us to live regret-free lives we can feel proud of. 

That’s why I left my job as a corporate executive to become a “stop squandering your life” speaker and coach. It’s why, while I was in the University of Pennsylvania’s Master of Applied Positive Psychology program, I wrote a 101-page thesis about “reflecting on mortality to inspire vitality and meaning in life.” And it’s why I recently published my book, “You Only Die Once: How to Make It to the End With No Regrets.”

As terrifying as regrets are, they can be useful, because they can motivate us to change our behavior and improve our lives. That is, they can help us after we simmer in the uncomfortable awareness of what could have been if we’d only made a way better decision.

We tend to value regret more than any of the negative emotions out there, studies show, because we understand its value and power.

There are two main categories of regrets you want to pay attention to:

1. Regrets of commission: These include things we did that we wish we hadn’t done. We tend to be able to rationalize regrets of commission through the softening of time.
2. Regrets of omission: These include the paths we didn’t take, the things we wish we’d done that we never did. Regrets of omission tend to haunt us. 

Also known as hot regrets, regrets of commission tend to feel intense at first. They’re often stupid things we do that make us burn in the short run with shame, guilt, or remorse, and then cool off over time.

Here’s a true-crime sampler from my clients and workshop attendees: 

• “Being mean to Kandy on the schoolyard in sixth grade” 
• “Having an affair” 
• “Telling that client what I really thought of them” 
• “Getting a DUI” 
• “Leaving my vintage baseball card collection at home for my mother to later throw out” 
• “Giving Tom the finger after quitting in a huff” 
• “Eating three-day-old sushi” 

Also known as wistful regrets, regrets of omission can torment us until the end of time. 

Real-life client examples include: 

• “Not backpacking across Europe after college” 
• “Not running that marathon”
• “Not finishing law school” 
• “Not fixing my relationship with my brother” 
• “Not writing that children’s book”
• “Not ordering desserts just for myself; I wish I’d had more pieces of cake all to myself” 
• “Not telling my first crush I loved him”

Regrets of omission plague us mostly because these are paths not taken. They shine a glaring spotlight on the chasm between our actual selves and the person we’ve imagined as our ideal self, one that could make our dreams come true.

Anticipating our regrets before they come to fruition — or what I call our “pre-grets” — gives us a chance to live a life that feels right. 

In my book, I share several exercises, assessments, and tips designed to help you identify your pre-grets and figure out how to use them to your advantage. Here’s one way to start: 

• Get comfy in bed. Yes, for real — recline your body and take a deep breath. Imagine you’re lying on your deathbed. You’re not in pain. You feel lucid and at peace. You’re near the end and reflecting back on your life. Start to zero in on your regrets of omission — not the things you did do but rather the things you didn’t do. 
• Make a list of what comes up for you.
• Circle the entries that make your heart beat fast, or make it ache or skip a beat. Any heart-related reaction is a good indication that this one matters. 
• Pay close attention to the pre-grets that want to hide on the page because they’re fragile and afraid to be exposed. Perhaps you feel fear of failure or rejection or ridicule. That’s a sign that it’s important to protect and be kind to those dreams.
• Start brainstorming ways to take even one step forward. Better yet, write one down right now. 

An unflinching awareness of your pre-grets can change the trajectory of your life.

That’s because we don’t have to continue down the paths we’re on and resign ourselves to regrets of omission. We don’t have to merely imagine the paths not taken.

We can go down entirely different paths if we choose. We just have to recognize what matters deeply to us and take action.

Jodi Wellman is a former corporate executive turned executive coach. She has a master’s in applied positive psychology from the University of Pennsylvania, where she is an instructor in the master’s program and a trainer in the world-renowned Penn Resilience Program. She runs her own business, Four Thousand Mondays, and is the author of “You Only Die Once: How to Make It to the End With No Regrets.”

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