We don't regret things we did
People at end-of-life rarely regret actions they took — they most commonly regret the things they did not do, particularly not living fully.
Snapshot · The School of Greatness
The Grief Expert Who Discovered a Sixth Stage | David Kessler
Explore episode
Aug 10, 2026
Where this was said
Grief, Love, and the Cost of Playing It Safe
At 16:10 · chapter starts 13:00
This chapter pivots from personal reflection to bold philosophy. Lewis asks whether someone can fully experience love if they are unwilling to go through grief at the deepest level — and Kessler's answer is unequivocal: grief and love are a package deal, non-negotiable, and anyone who tries to play it safe gets less of both [1] — David Kessler "What we run from pursues us and what we face transforms us." 50:32 . He connects this directly to his work at end-of-life: people lying on their deathbeds consistently express regret not for the things they did but for the things they never dared [2] — David Kessler "We don't regret things we did: People at end-of-life rarely regret actions they took — they most commonly regret the things they did not do…" 16:10 . Playing safe, he argues, is actually the scariest thing a person could do — what a waste of life to arrive at the end with risks untaken and love unexpressed. The exchange is charged with urgency, as both Lewis and Kessler acknowledge their own periods of playing safe and the price they paid for it.
The Balloon vs. the Beach Ball: Why Stuffing Feelings Costs You Everything
Avoiding grief isn't free — it's exhausting. Kessler's beach ball metaphor nails it: pushing a small balloon down is easy, but holding a massive beach ball underwater takes constant, draining energy. Unattended feelings don't disappear; they just consume you.
Similar snapshots
Medicaid 5-year look-back rule
When applying for Medicaid to cover nursing home costs, there is a 5-year look-back period that can disqualify applicants who gave away or spent down assets.
Pipe broke → hydrogen sulfide studio air
A broken pipe filled the Bad Friends studio with what the hosts identified as hydrogen sulfide — microscopic fecal aeroparticles — that the crew denied smelling.
Robot surgery: 10x less blood loss
Fei-Fei Li's father's liver surgery performed by a da Vinci robot resulted in 10 times less blood loss than a typical open liver surgery, thanks to laparoscopic precision.
115M US adults have prediabetes
Approximately 115 million adults in the US currently have prediabetes, most of whom are unaware, according to the Lingo sponsor segment.
Drug overdose deaths: 110K to 80K to 70K
Drug overdose deaths in the US fell from 110,000 to 80,000 in 2024, and then to roughly 70,000 — the largest single-year drop the CDC has ever recorded.
Men's overdose rate fell 27% in one year
Men's overdose death rate fell 27% in a single year, outpacing the 23% drop for women.
Ages 15–24 overdose deaths down 37%
The steepest decline in overdose deaths was among 15–24-year-olds, whose rate fell 37%.
Nurses walk miles per shift fetching items
Fei-Fei Li observed that on a given hospital shift, nurses walk miles just to fetch medicine and supplies, illustrating a clear use case for assistive robotics in healthcare.
Gabby Windey worked as ICU nurse
Before becoming the Bachelorette, Robby's wife Gabby Windey worked as an ICU nurse for years.
