Cassidy Krug is a former Olympic diver, a writer, and brand and innovation strategist.
What’s the big idea?
After 20 years training to be an Olympic diver, Cassidy finally had her shot at a bronze medal during the 2012 Olympics. A mistake on her last dive landed her in 7th place, and her lifelong athletic career came to an unremarkable end. She felt uncertain, inadequate, and alone as she mourned the closing of that chapter and tried to figure out how to build a new life.
In pursuit of answers, Cassidy spoke with hundreds of people navigating massive transitions: exceptional athletes, new parents, people leaving jobs or religions or marriages, veterans, and people facing injuries or diagnoses or death. She found stories of people making impossible choices or coping with unimaginable loss and emerged with new wisdom and strength. Resurface shares the lessons she discovered for experiencing change with less pain, and more joy.
Below, Cassidy shares five key insights from her new book, Resurface: A Guide to Navigating Life’s Biggest Transitions. Listen to the audio version—read by Cassidy herself—below, or in the Next Big Idea App.
1. Unlearning is just as important as learning.
I grew up believing that life was cumulative. In sports, you build skills, lock them into muscle memory, and face tougher competition. School works similarly—each year builds on the last. Winning at life, I thought, came from carrying forward everything you’ve learned.
When I retired from diving at 27, I brought that mindset into the workplace. I assumed that the work ethic and goal setting that made me one of the best divers in the world would serve me just as well in advertising. I just needed to add new skills on top of my athletic foundation.
But it didn’t work like that.
In diving, everything was clear-cut: a rigid scoring system, established rules, and a coach who told me what was right or wrong. At work, there were no such guideposts. I became a strange kind of perfectionist, striving to get things “right” without knowing what “right” even meant. I agonized over emails, second-guessed every idea, and leaned too heavily on others for direction.
Molly, a former Olympic hockey goalie, told me, “My boss always says, ‘Perfect is the enemy of done.’” I instantly remembered my coach’s mantra: “Good is the enemy of great.” That’s when it hit me: the rules had changed. There was no perfect 10 here. My job wasn’t to impress a judge but to take ownership, make decisions, and move forward.
I learned valuable things from diving. But the idea that all learning is additive is a myth. Every new learning involves an element of unlearning. If you’re struggling with change, ask yourself what habits, assumptions, or mindsets you might need to let go of.
2. Grief isn’t about letting go. It’s about finding new ways to hold on.
For a decade after I stopped diving, one of the things that bothered me most was that I still missed it. I assumed a transition followed the laws of physics. Like the arc of a dive, you rise, you shift, you fall. I couldn’t understand why the yearning kept rising back up long after I’d left my sport behind.
“The size, shape, and color of grief are different for each of us.”
It shouldn’t have been so surprising. Psychologists define grief as the natural response to great loss. The more significant the loss, the more deeply we feel it. In speaking with nearly 100 friends, acquaintances, and strangers for this book, I found grief everywhere. Elie, who emigrated from Lebanon, grieved the country he’d left behind. Karie grieved the dream of having children after years of trying. Jimmy, diagnosed with early-onset Parkinson’s, grieved his pre-diagnosis self. But no one taught me more about grief than Dawn.
After Dawn’s mother died, she sank into a deep depression, barely managing the basics of daily life. Every day brought a fresh wave of grief. “It was too overwhelming to think about not having her forever,” she told me. “So I just kept saying, ‘she’s not here in this moment.’ Then the next moment, I’d say it again.”
For a long, long time, it was all she could do to put one foot in front of the other. But over time, she found comfort in the idea that some part of her mother lived on. She began to see love as an energy that couldn’t be created or destroyed. “Being aware that energy is always going to be alive and active—that was the real transition,” she said. Her mother received love, passed it to Dawn, and now Dawn offers it to others.
I used to think grief was about forgetting so you could move on. But according to grief expert Dr. Robert Neimeyer, it’s the opposite. “Grieving isn’t a process of letting go,” he said. “It’s a process of finding a new way to hold on.”
Dawn’s way may not be yours. The size, shape, and color of grief are different for each of us. But we can all retell the stories of what we’ve lost, rebuild our relationship with it, and acknowledge what we learned, finding a new way to hold on that fits our present and future.
3. Asking for help is its own kind of giving.
The strongest predictor of long-term well-being isn’t wealth, fame, or cholesterol levels—it’s the quality of our relationships. That’s the central finding of Harvard’s Happiness Project, which has tracked participants for over 80 years. “The people who were the most satisfied in their relationships at age 50 were the healthiest at age 80,” said study director Robert Waldinger.
But life transitions—moving, aging, loss—can sever us from our communities. How do we keep building meaningful connections? I learned a lot from my conversation with Becca.
“Asking for help connects us, and people are more likely to say yes than we think.”
Becca was an expert skydiver with 7,000 jumps under her belt when she had a horrible accident that shattered her C3 and C4 vertebrae, leaving her paralyzed from the neck down. Today, two and a half years later, she can swallow, shrug, turn her head, smile, and deliver a killer eye roll. But she can’t do many of the essentials. Her family members brush her teeth, empty her bladder, and scratch her ears when they itch. Tinder dates pour her beer into her mouth. Her friends suction her lungs. She maintains a list of the ways people can support her, with three tiers ranging from “insert a catheter” to “things you ask from the church ladies.”
Becca has to accept help in every aspect of her life. Most of her goals and accomplishments now center on finding ways to help others. After years of trying, she recently persuaded her parents to go to therapy. She’s taking sales courses in the hopes of someday being able to pay for her own care. She hates when friends keep their troubles to themselves: “You want me to unload my shit on you, but you’re not gonna do the same for me?” she said. “I’m not paying you to be my therapist. Don’t make me feel like I’m the only one with problems.”
Becca’s story is a reminder: humans are wired to give and receive. Giving brings us joy. Asking for help connects us, and people are more likely to say yes than we think. Organizational psychologist Vanessa Bohns found people are 48 percent more likely to help than we expect, even with truly weird requests, like committing small acts of vandalism.
If you need help, ask. If you’re feeling lost, offer help. Both are acts of connection. Both lead us back to each other.
4. You can move the goalposts.
In sports, the goalposts don’t move, but in life, they can and often should. Society offers many fixed definitions of success, including school grades, career promotions, religious milestones, and the relationship escalator of love, then marriage, then children. These frameworks can be so deeply ingrained that they are hard to question. For many, they provide meaning. But for others, they become traps—metrics that don’t reflect personal truth.
Too often, we adopt the institutional definition of success as our human reason for being. Businesses need to make money, but that doesn’t mean a person’s worth is defined by income. Schools give grades, but an A doesn’t capture your value. By committing this fallacy, we can break ourselves optimizing for the wrong metrics and still end up dissatisfied, whether we “succeeded” or not.
A conversation with Stanley brought this lesson to life. At age 24, Stanley went to prison, where he stayed for more than two decades. At 40, after 15 years inside, he was denied parole for the second time. It devastated him. “I didn’t know when I was gonna get out,” he said. “I had no wife, had no kids, had no money.” It wasn’t just the prospect of a longer sentence, but the fact that by every measure in his mind, he was a failure.
“Stanley’s story illustrates that there is no wrong time to redefine success.”
But a prison psychologist helped him reframe his experience. Over those years, Stanley had joined the prison church, led self-help groups, processed his trauma, and helped others grow. “Even though I wasn’t getting out,” he said, “I helped people who were—to leave with a better chance of succeeding.” He began defining success by his impact on others.
That mindset stuck. Years after release, when asked about marriage or kids, he laughs. “Do I need to get married? Do I need kids?” He’s done the work to be okay with himself, regardless. Stanley’s story illustrates that there is no wrong time to redefine success. Do it when you set goals, in the middle of chasing them, or while reflecting on the past. Let go of the status quo if it doesn’t serve you. Prioritize what gives you meaning and move your goalposts if you need to.
5. Let change carry you.
At the end of nearly every conversation, I asked the same question: “What advice do you have for others going through a major transition?” I was surprised to find that most gave some version of the same answer.
Nora, who had beaten cancer but was living with ongoing health issues, said, “Everything goes in phases. And they’re always going to change again, for better or worse.”
Shelby, who left the Mormon church and became a therapist for queer and non-monogamous people, told me, “Once you’ve transformed, you can’t go back into the cocoon. You have no other choice but to fly.”
I interviewed Heather, my childhood babysitter, who had recently been diagnosed with terminal cancer and given about a month to live. “Let it happen,” she said. “The angrier you get, the more minutes you lose. And now that we’re talking about minutes in my life, literally, those minutes are precious. Anger is like smoking a cigarette. You’re wasting your time.”
Essentially, they were all saying that change is inevitable. Don’t fight it, fear it, or try to control it. A large part of our suffering around navigating transitions is our resistance to them. It’s powerful to accept the feeling of living in the unknown and to recognize that, until we cross over in our last great adventure, the only constant is change. Let it carry you.
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