Cathy Thorpe is the CEO of Nurse Next Door and the author of Bold Kindness: A Caring, More Compassionate Way to Lead.
A few years ago, I stood in a theater watching my daughter dance, feeling proud and present—until a text message arrived that would alter the course of my life. It was from my husband, Harry. He’d been feeling off for a few days, and I’d nudged him to visit the ER. His message was brief and devastating: “They think I have cancer.”
That spring night, sitting alone in the dark with tears silently streaming down my face, I wasn’t just grappling with fear—I was gripped by a deeper, more unfamiliar feeling: regret. Regret for the conversations we hadn’t yet had. The trips we hadn’t taken. The ordinary days I’d taken for granted.
As leaders, we spend a lot of time looking ahead—toward the next quarterly result, the next strategic move, the next crisis to manage. But sometimes, it’s just as important to look back. Not to dwell in the past, but to learn from it. Daniel Pink’s book The Power of Regret outlines four core types of regret that show up in life and work: foundation, connection, moral and boldness regrets. After years of leading a global care company—and experiencing deep personal loss—I’ve seen firsthand how these regrets shape leadership decisions, team culture and business outcomes. Understanding them has made me a better leader. Let’s take a look at three of the four regrets and discuss how they might help you, too:
Foundation Regrets: The “I Should’ve Built Stronger Systems” Moments
These regrets are about the missed building blocks—like not saving enough, not prioritizing your health or ignoring early signs of burnout in your team. In business, foundation regrets sound like, “We didn’t invest in leadership development early enough,” or “We waited too long to fix our culture.”
At my company, we grew from 40 to over 400 franchises globally by obsessing over foundational systems: clear vision, self-led teams and our mission of “Bold Kindness” as our cultural bedrock. But it didn’t happen overnight. Early on, I remember walking into our shared kitchen daily only to find the sink full of dirty dishes—an unspoken reflection of deeper accountability issues. That small moment helped me realize that building a strong culture is about the micro-decisions we make every day. If you don’t start reinforcing values early, regret will follow.
Start with structure. Whether it’s investing in culture, personal habits or financial rigor—foundation regrets are often the easiest to prevent and the hardest to repair. A 2023 article from MGMA highlights that when an organization’s values align with its employees’ values, it results in a better work environment, increased productivity, higher job satisfaction and reduced turnover. This underscores the importance of proactively establishing strong foundational structures to prevent future regrets.
Connection Regrets: The Missed Conversations That Linger
These regrets haunt us with what we didn’t say, the relationships we didn’t repair or the team members we didn’t nurture. They might look like: “I wish I’d told her how much her work meant to the company,” or “I never checked in after his father passed.”
When Harry died, I realized just how crucial our connections are. The grief cracked me open. Instead of masking my pain as a CEO, I chose vulnerability. I told my team when I was having a hard day. I leaned on them more than I ever had before. And something surprising happened: Our company didn’t weaken—it got stronger. My openness gave others permission to bring their full selves to work, too.
At our organization, we have a shared philosophy: Our clients live one life—and so should our team. That means supporting the whole person, not just the professional role they play. In return, we see higher retention, deeper engagement and, yes, more human joy at work.
Don’t wait to send the thank-you note, make the call or ask the honest question. Business is built on relationships. Regret thrives where connection is missing.
Boldness Regrets: The “What If I’d Gone For It?” Syndrome
Among the four types, this is the one I hear most often from other leaders. The job not taken. The conversation avoided. The dream deferred. As Pink notes, people are far more likely to regret the chances they didn’t take.
After Harry passed, I found myself feeling lonely and in an unfamiliar phase of life. So I made a list of women I admired and reached out for coffee. It was terrifying. What if they said no? What if it was awkward? But nearly all said yes. Those connections have since become some of the most meaningful in my life.
That same boldness applies in business. We took big swings at my company—entering new countries, securing first-of-their-kind hospital partnerships—and not all of them worked. But the act of trying kept us alive and expanding.
Adopt a “What’s the worst that could happen?” mindset. Bold moves—whether personal or strategic—are where growth happens. Regret loves safety. On the other hand, a Cornell University study found that seeking out discomfort can enhance motivation, personal development and, ultimately, help individuals reach their goals.
As leaders, we often celebrate wins and analyze failures. But we rarely make space to reflect on regret. That’s a missed opportunity. Regret is a compass—it shows us what we value most. And it nudges us toward living and leading with more intention. If you want to build a life and business with fewer regrets, here’s my advice: Fortify your foundation, prioritize your people and choose boldness when fear wants you to stay still.
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