Decisions, Regrets, Hope: Wisdom from a Champion Poker Player and a Hospice Chaplain

The past decade has been tough for our family. My husband and I have had to play the hands we’ve been dealt, making many difficult decisions with incomplete information amid changing circumstances. Some undesirable outcomes have led to a lot of Monday morning quarterbacking on my part, a topic World Series of Poker champion and Ph.D. in cognitive psychology Annie Duke takes on in her book Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts.

Duke highlights a controversial play call by Seattle Seahawks coach Pete Carroll in the 2015 Super Bowl. With the Seahawks down by four points, Carroll made the decision to pass the ball on second down from the one-yard line instead of handing it off to their star running back. The play ended in disaster when New England intercepted the pass, clinching the Super Bowl victory.

Media reaction was overwhelmingly negative, with headlines denouncing the decision as the "worst call in Super Bowl history."

However, a few sports writers offered a more nuanced perspective, defending the play call and pointing out that interceptions in such situations were extremely rare. In fact, out of 66 similar plays that season, there had been zero interceptions.

Duke uses this example to call attention to the human tendency toward "resulting"—that is, our propensity to judge the quality of a decision based solely on its outcome. Had the pass been completed for a touchdown, the same media likely would have praised Carroll as a genius. Duke contends that Carroll made a strategically sound decision with a high probability of success but was unfairly criticized because the outcome was negative. She recounts this episode to raise several important questions about how we evaluate our decisions: “Why are we so bad at separating luck and skill?” she asks. “Why are we so uncomfortable knowing that results can be beyond our control? Why do we create such a strong connection between results and the quality of the decisions preceding them? How can we avoid falling into the trap of the Monday Morning Quarterback, whether it is in analyzing someone else’s decision or in making and reviewing the decisions in our own lives?”

My husband, Scott, has patiently listened to my Monday morning quarterbacking and my litany of regrets these past several years. A poker aficionado and a fan of Annie Duke, he pointed me to her book and the wisdom it contains.

Duke asserts that every decision is essentially a bet: “Thinking in bets starts with recognizing that there are exactly two things that determine how our lives turn out: the quality of our decisions and luck. Learning to recognize the difference between the two is what thinking in bets is all about.” 

In life, as in poker, Duke says, we must constantly make choices with incomplete information, uncertain outcomes, and varying degrees of risk. Duke argues that we should stop thinking in terms of absolute certainties and instead embrace probabilistic thinking.

But for me, the book's most powerful insight is the distinction between decision quality and decision outcome.

“Take a moment to imagine your best decision in the last year. Now take a moment to imagine your worst decision,” she writes. “I’m willing to bet that your best decision preceded a good result and your worst decision preceded a bad result.”

Duke posits that a good decision is about the quality of one’s thinking process, not the ultimate result. Sometimes, one can make an excellent decision with a high probability of success and still experience a negative outcome due to factors outside one's control.

Unfortunately, our natural inclination is to retrofit narratives to explain outcomes and to have difficulty accepting the role of chance in our decision-making. If a decision – even a reasonable decision based on solid thinking and intelligent analysis of the information available at the time – leads to a bad outcome, it’s easy to enter a cycle of regret, and that can be dangerous.

In her book On Living, hospice chaplain Kerry Egan recounts the story of a man named Albert. Albert’s wife, Ada, is non-verbal, immobile, dying. Every time Egan visits the couple, Albert tells Egan the exact same story in the exact same way: many years ago, their four-year-old son had been playing with the feet of their Thanksgiving turkey the night before the holiday, laughing uproariously and chasing Albert around pretending to scratch him with the talons, though it was the little boy who ultimately got scratched. The next day – Thanksgiving – the boy died suddenly of meningitis, his fever spiking before Albert and Ada even realized the seriousness of what was happening. Though every medical professional involved assured Albert that his son’s death had nothing to do with the scratch he got playing with the turkey feet, Albert was certain that it somehow did, certain that by letting the boy play with them, it had been his fault. Egan writes about her worry “when the story never changes” for people: “when there are never new connections with other things the speaker has seen or learned or thought or experienced, when there is never any reflection about what happened, when the person does not even seem to know I’m there as he tells the story again and again, the same way each and every time – that means that the story is stuck and the suffering is immobile. It means that there is no meaning to the loss. And if that loss is the story that defines your life, it can mean there is no meaning to life.”

The bereaved father, Albert, allowed his grief to calcify into regret. That regret stole meaning from his life, and presumably from his wife Ada’s life, too. If their son had not died of meningitis on that Thanksgiving day, the memory of him laughing and running around chasing Albert with the turkey feet might have been one of the happiest of their lives.

I have been in danger of letting my grief calcify into regret. I’ve spent a lot of time judging my decisions by their outcomes and engaging in harsh Monday morning quarterbacking rather than reflecting on my good intentions or the quality of my decisions based on the information I had available to me at the time. But while regret can be dangerous, Egan explains how its flip side is actually hope:

“Life is a million choices, and every choice is a choice not to do something else, and so regrets accrue with life. It’s inevitable. Thinking through those regrets, though, gives any one of us a chance to think about what we wish had been different. It’s a chance to think about what we feel is missing in our lives, what we hope could be different. Most important, even if just in a small way, it’s a chance to act on that understanding. 

“Hope is the belief that better things are possible. Regret shows us what those better things we hope for are. Regret hones hope, sharpens and clarifies the desire at the heart of it. If you’re alive, even if you’re on hospice, you can still work on making those hopes come true. 

“As a very young woman, I thought regret was a failure, something to avoid at all costs. It is, in fact, a window. It’s an unasked-for chance, an uncomfortable prompt, a painful encouragement to imagine what else could be. If you let it, regret can be a vehicle to hope. But you have to accept it first. You have to hold it up to the light streaming in from those leaded casement windows, in order to see clearly what it is that you wish was different in your life. 

“There may be thousands of regrets in a single life. Hope, though, can take millions of forms. Hope is a shape-shifter that can appear and grow in even the tiniest of cracks, at even the last hour.”

Life sometimes deals us bad hands. Life sometimes deals us good hands. We play those hands as best we can, making the smartest decisions we are capable of given the cards we hold – based on what is known to us at the time – not knowing what cards will come down in the flop or what others hold in their hands. Sometimes you get lucky with shitty cards. Sometimes, when the odds should be in your favor, you get beat holding ace-king. Duke teaches us to acknowledge the role of luck and examine the strategic quality of our decisions to tighten our future play. She cautions us not to get stuck in regret based on results.

Egan illustrates that if, like Albert, we dwell on a story with a terrible outcome, blaming ourselves and failing to recognize the elements at play outside our control, we can become mired. But if we find the courage to examine the stories we’re telling ourselves, our decisions and regrets can be gifts that point us toward what we still hope for, even amid grief, even at life’s end. 

Perhaps we can also eventually find gratitude in our hearts for the bad hands we’ve been dealt, the good hands we’ve been dealt and lost, and the decisions that didn’t go our way. Perhaps we can even find gratitude for our regrets. Because if we let them, they can guide our paths forward toward the longings of our hearts.