The Avoidable Regret of "Playing it Safe"
You don't have to go bungee-jumping to reap the rewards of taking risks
My father is 93 years old, alone, and confined to a nursing home. He seldom leaves his tiny apartment except for medical appointments. He is drowning in regrets.
He regrets not venturing off the beaten path throughout his life and exploring slightly risky adventures. He never learned to roller skate, dance, or shoot a bow and arrow. Tragically, he never learned to take his guard down and reach out to people for fear that they might reject him. He is reluctant to tell people that he loves them.
I don’t want my last years on this planet to be like my father’s, and I don’t think you want that for yourself, either. There is a better way.
Two flavors of regret.
First, let me distinguish between two kinds of regret.
The first is the regret we feel for things we have done in the past. This letter is not about that type of regret.
The other form of regret is the kind associated with what we didn’t do but wish we had. That is what I’m talking about here.
Build a better “risk radar”.
Risk covers a lot of territory, so rather than looking at it generally, let’s begin by considering the specific experiences we want to invite into our lives. Risk is a relative assessment. How you assess risk is different from how I do it. And there are different kinds of risk—physical, emotional, financial, etc…
Getting caught up trying to evaluate risks at this point is a creative roadblock not worth dealing with.
So, rather than get tied up into a knot trying to figure out risks, let’s simplify things. Let’s generate a list and assign risks to each item when finished.
Here’s an example of a list.
Let’s say that I dream of the following experiences that I believe would contribute to a more fulfilling life.
Dancing the waltz with my spouse or partner at a romantic venue.
Singing a Carol King song while playing the guitar.
Hiking to the top of Yosemite Falls with a friend and soaking up the view.
Writing a series of love letters to my romantic partner,
Writing and reciting poetry at an independent bookstore.
Getting a two-hour massage.
Calling each of my friends and telling them how much I love them.
Visiting the Louvre with a tour group led by an artist.
Traveling to the Tetons and working alongside a professional photographer.
Attending a meditation retreat in the mountains.
Visiting a holy place and sitting in silent prayer.
Viewing the Northern Lights.
When you create your list, it’s important not to limit yourself unnecessarily at this stage. Many of us are so risk-averse that the “I can’t do that” voice shuts us down before we start.
You need to turn off your “risk radar” for a bit.
Now is the time to think strategically, not tactically. What do I mean?
Strategic vs Tactical Thinking.
When you craft a life strategy, you take the 10,000-foot view—the big picture. Strategies are only effective if they inspire—otherwise, it’s a recipe for disappointment.
Tactical thinking, on the other hand, is concerned with details. If you get bogged down in details while envisioning the landscape of your life, you risk sabotaging your dreams. Don’t do it.
With your “strategic thinking hat” on, review your list and prioritize the experiences from most important to least important. Which experiences make your heart leap in your chest?
If you don’t feel anything when you imagine yourself dancing with your wonderful partner, then either choose a different dream or get a different partner (I'm just joking).
Here are two questions to ask yourself as you go through your list:
How would I feel at the end of my life if I had taken the risk and made that experience happen?
How would I feel if I didn’t have that experience?
Most people regret the risks they did not take. I can’t think of a single time in my life when I took a risk that I now regret. Not one.
Sometimes, being risk-averse can lead to misery and loneliness, not joy.
When I did this exercise, I couldn’t stop. I felt like a kid let loose in a toy store at Christmas with a credit card. Almost everything on my list involved others or made me a better person.
Here’s a not-so-gentle hint:
If the things on your list are all about you, then ask yourself if you want to die alone. That’s pretty blunt, sorry. Our relationships are of fundamental importance to our experience of genuine happiness and contentment. Don’t ignore them.
Take a minute to watch this TED Talk by Dr. Robert Waldinger, director of the Harvard Study of Adult Development, about what matters most to people at the end of their lives.
Yes, loving relationships are absolutely crucial. But they aren’t everything. Sometimes, there are things we wish to bring into our lives that have nothing to do with other people. These things give us a sense of accomplishment, invite awe and wonder, or inspire us. They are worthy additions to your list, and it’s up to you to prioritize them.
Here’s my two cents…
My relationships are healthier and more vibrant when I nurture my mind, heart, and spirit. I am more available to others when firmly grounded and fully alive. The time I spend alone doing things that bring me joy is an investment in my life and the lives of the people I love.
If you look at the list I gave you, you will see that I included a massage, silent meditation, and silent prayer as experiences I wanted to have. These involve other people but only tangentially. I would not want to look back and regret not having sat quietly in Notre Dame or The National Cathedral.
Now, it’s time to think tactically.
Making dreams come true: Thinking tactically.
Dreams are nice, but sometimes they can be difficult to pay for. Or maybe you have a health condition that makes travel a challenge. These are real obstacles. However, like most problems, they often have solutions.
Thinking tactically is all about the details—the nitty gritty.
Visiting the Louvre as part of a guided tour may be way too expensive. But before I write that one off, I’ll consider all the ways I could afford to make that trip.
Could I forgo the guided tour and go it alone? Could I price shop on discount airline sites and get a deal? If time wasn’t an issue, could I accumulate points on a credit card to pay for it? Could I get a part-time job to earn enough to go to Paris?
If one of your dreams is outlandishly expensive, you may have to choose a Plan B. I would love to take a trip around the world on a cruise ship, but there are alternatives to that scenario. I may not see as many countries if I decide on a budget-friendly option, but I can see some remarkable places.
Creating a Plan B is not a failure. It’s pivoting.
Remember, you aren’t compiling a list of “nice to do” experiences—you are sculpting a life, your life. Peruse that list and select the “no regrets must-haves.” Trekking in Nepal with my camera gear was really high on my list. The emotional and spiritual resonance of that experience ranks really high and, as a result, I will make it happen next May (really).
A book worth reading.
If you want to learn more about the motivating power of avoiding regrets, read Daniel Pink’s book The Power of Regret: How Looking Backward Moves Us Forward (not an affiliate link).
The beautiful thing about life is that our list of inspiring experiences always evolves. We discover a new magical place and add it to our list. We are introduced to a new experience, and it captivates us. Some experiences lose their magnetic appeal over time and drop off the list entirely.
My wish for you is that when you pass from this life, you exit with a warm heart, a peaceful soul, a smile on your face, and surrounded by people you love. The time to create that scene is now.