No More Living Small
How I wound up talking to Oprah & Daniel Pink about my regrets
One word in the email jumped out at me the instant I opened it. Regret.
It felt like a dirty word in my mouth. I wanted to pretend I’d never met regret before. We’re strangers, really, from opposite ends of the world. I’m optimistic, positive, and grateful. Regrets are bad. “I don’t have regrets,” I scoffed to myself.
But the email gave me permission to really ask the question.
“Do I regret anything?” I asked, settling into the silence, listening closely for the answer.
“I think I might,” a small, quiet voice said from somewhere down deep. Once you hear that voice, it’s nearly impossible to pretend you didn’t. My eyes went back to the email.
The producers were looking for people to talk about their regrets with author Daniel Pink and Oprah. With research from over 26,000 participants, in his book, The Power of Regret: How Looking Backward Moves Us Forward, NY Times bestselling author Daniel Pink formulated a way to identify and use regret as a catalyst for helping achieve the life they want.
A light flickered in a dusty old closet in my mind where I’ve shoved boxes of “What ifs.” If there was ever a time to unpack them, now is it. I wiped off the cobwebs and took them out to examine them one by one.
I married my high school sweetheart in my early 20s and never finished college. I was a brand new wife to an Army officer during 9/11, so it was never even a question of whose career to prioritize. Years later, my now ex-husband earned two master’s degrees while we were married, and I was home with our infant, it made sense. He had the career. My art and writing could be sculpted and molded around everything else as I parented, cooked, cleaned, and entertained guests. Or at least I tried.
I willingly made myself small. I felt that what I was doing was important and fulfilling - and it was. However, when my ex-husband left me, and our marriage ended, I was in shock and not at all prepared for the life that followed. I wasn’t prepared to make myself a priority in my own life.
It didn’t initially feel like regret because I’ve always been grateful for the people brought into my life and positive experiences during those years, but I’ve struggled to make peace with the aftermath. More than ten years later, I’m still haunted by the “What ifs.”
What if I finished my degree before I got married?
What if I started a career in my 20s instead of trying to make my art and writing small enough to fit into that lifestyle?
What if I recognized the early signs of fracture in my marriage?
What if I listened to my intuition when stories didn’t add up?
What if I was prepared for the unexpected? (Financially and emotionally)
What if I recognized my own value to the marriage and stood up for myself, prioritizing my own growth?
What if I wasn’t afraid to use my voice?
What if I didn’t sit in the passenger seat for all of my 20s and half of my 30s?
I have often thought about what I would tell my younger self. It always circles back to not allowing myself to become small. Even now, in my mid 40s, I’m still unknotting the mess that came from it. I’ve struggled to find balance. If I were stronger, then would I be less afraid to step into my life fully and do things like publish my book and do more with my art?
I’m grateful, but I do regret not seeing myself as a full, talented, capable person early on in adulthood.
I’ve come to this moment before when I’m right on the ledge of taking a leap of faith, but instead of leaping, I find myself hopping in place. Hopping is not leaping. There is movement and a moment when your feet leave the ground, but the end result of where you wind up is completely different.
I struggled to call these “what ifs” regrets because I’ve walked away from every decision with some experience or introduction to a person who has enriched my life so much. But by giving myself permission to redefine the hauntings as regrets, allows me to use them to propel myself into a more authentic, fulfilling, and meaningful future, and that is exactly what I want.
So I said yes to the email, sent back my responses, and sat back for a moment to be proud of taking a leap toward an incredible opportunity.
…which, of course, was quickly followed by panic. What if I make a fool of myself? What if I fumble through it and say the wrong thing or make an awkward guest? What if I chicken out and can’t be vulnerable? What if? What if? What if?
I was terrified. Not because I didn’t want to do it, but because I was afraid I’d miss the opportunity to really be present in it. To take advantage of the wisdom and experience of these two remarkable people
But I did it.
For 6 minutes, actually more but not all of it made it into the final cut, I had an amazing conversation with Daniel Pink and Oprah.
I spoke about my regret of making myself small for so much of my 20s and 30s, and how, even now, in my mid-40s, I struggle to put myself out there.
Daniel Pink identified it as a “boldness regret.”
“What would it mean for you to not be small right now? Not an emotion, but an action - what step would you want to take?” he asked me.
The air sucked from the room in a split second. I hesitated. I knew the answer — my book. I want to publish my book.
“Don’t mess this up, Kell. Speak up.” said the version of me from long ago, slightly louder than before, and standing next to the dusty box of “What ifs,” covered in cobwebs and regrets.
So I did.
And then Daniel Pink jumped in. Mind you, he is the author of A Whole New Mind: Why Right-Brainers Will Rule the Future, a book that, a few years ago help make me feel valuable because of my creativity not in despite it. To see his excitement and enthusiasm and to watch both he and Oprah talk about it was… indescribable. You just have to watch it!
“What would a mediocre guy in your situation do?”
“You need to be out there and doing everything you can to get this book out there so you can be a guest on season 3 of this podcast!”
“The best time to plant a tree is 20 years ago. The second best time is now.” Chinese proverb.
“Use that spear of regret as a catalyst for starting now.”
Then the conversation moved to Oprah, noticing my paintings on the wall behind me. “You mentioned your art. Is that your painting behind you?” she asked.
Never once did I think that I’d be talking about my paintings with Oprah and Daniel Pink.
My heart swelled.
“Congrats on finishing the book. That’s an amazing thing. Now, get it out to the world. You owe it to the world to do it. You have a moral obligation to put it out in the world.”
“Get in the driver’s seat, Kelly.” Oprah said, and then in her sing-song voice, “Kelly, take the wheel!”
My eyes burned. And once they cut to the next guest, I sat in disbelief as my checks dampened with a few runaway tears.
I was speechless. Actually, I didn’t even absorb those words in the moment. It didn’t sink in until now, as I watch the episode. There have been over a million views at this point. Not a speck of dust or cobwebs remained. My regrets were no longer hidden away, but out on display for me to help me orientate how I want to move through the next stages of my life.
After the recording ended, and I turned my screen off, I realized that I hadn’t asked Daniel Pink the question that I had spoken to the producers about: Can gratitude and regret coexist? But I think I already know the answer. Absolutely,
Do I wish I had done things differently at different points in my life? Yes. But I am grateful for the life I’ve had so far, and I will keep collecting past versions of myself to better direct the present me into an unknown future. That’s all any of us can do.
So, thank you, Oprah and Daniel Pink, for the opportunity to explore my regrets with both of you. Thank you for the kind words about my art and for the encouragement to get my book out there! And a great big thank you to the team of people behind the scenes of Oprah’s new podcast, especially Erinn.
*Watch the full podcast at: How Regrets Can Move You Forward | Oprah & Daniel Pink, or listen wherever you subscribe to podcasts.
**A few selected pieces of my art are available at Chroma Fine Art Gallery’s current show, Sigillaria.
Ah-MAZING!!! Regrets turned into purposeful action. So inspiring 🫶🏻👏🏻👏🏻👏🏻👏🏻
I will borrow those words of encouragement about your book 📖 and believe them for myself as well in this liminal space of agent-querying, Kelly! Thank you SO MUCH for sharing!