In this episode of The School of Greatness, grief expert David Kessler discusses his proposal for a sixth stage of grief—finding meaning—which he developed after experiencing the loss of his own son. Kessler expands on Elisabeth Kübler-Ross's original five stages, explaining how grief applies to any unwanted change and how the stages don't follow a linear path. He explores how unprocessed grief manifests through triggers, self-sabotage, and emotional suppression, draining energy and preventing authentic living.
Kessler and Lewis Howes examine the relationship between grief and love, with Kessler asserting that avoiding grief requires avoiding love and life itself. The conversation covers the importance of witnessing and connection in healing, the role of vulnerability in creating authentic relationships, and how processing grief unlocks presence and deeper living. They also discuss how success cannot mask unprocessed pain and emphasize that genuine connection exists only in the present moment.

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David Kessler explains that Elisabeth Kübler-Ross identified five stages of grief—denial, anger, bargaining, depression, and acceptance—by observing patterns in people experiencing loss. Kessler expands this framework beyond death, defining grief as a reaction to any unwanted change, including breakups, job losses, and divorces. He emphasizes that these stages are not linear or hierarchical; people may revisit them in different orders and experience acceptance at various points throughout their grief journey.
After losing his son, Kessler found acceptance insufficient—it felt flat and purposeless. This led him to propose a sixth stage: finding meaning. Drawing on Viktor Frankl's work, Kessler clarifies that meaning is not found within the tragedy itself but in how we respond and who we become afterward. Meaning can take many forms: cherishing life's brevity, creating change to help others avoid similar suffering, expressing love more openly, or transforming pain into purpose. Kessler shares that recognizing his son would want his death to expand rather than restrict his father's work motivated him to continue his mission. He acknowledges that finding meaning takes time—it was about two years after his son's death before he began to glimpse life and hope again.
Kessler explains that healing from grief cannot happen in isolation; it must be witnessed by another person. This act of acknowledgment—having someone recognize and hold space for our experience—restores connection during deep isolation. Effective witnessing is a two-step process: first, acknowledging the person's pain with empathy, and second, witnessing their capacity for growth and transformation even when they cannot see it themselves.
Connection is essential in grief recovery. Kessler emphasizes that grief groups provide uniquely healing environments by allowing people to share experiences with others who truly understand. His Tender Hearts online grief groups offer specialized matches for different needs, with no one turned away for lack of funds. However, Kessler warns against seeking empathy from those unprepared to give it, comparing it to searching for milk in a hardware store.
Lewis Howes describes how disclosing his childhood sexual abuse, initially terrifying, ultimately deepened his connections rather than destroying them. When he published his story publicly, thousands responded with their own experiences, demonstrating how vulnerability creates safe spaces for healing. Kessler notes that authentic discussion of feelings brings people closer, not apart, and that in grief groups, members often laugh and cry more than outsiders would expect, experiencing both the hardest pain and the greatest relief.
Kessler describes triggers as maps that guide us to unresolved wounds. Howes shares his own experience of disproportionate anger during pickup basketball games, which frequently escalated into altercations. When his best friend distanced himself due to these outbursts, Howes realized the issue was within himself—a recognition that became a wake-up call for personal growth. Kessler notes that such intense reactions often signal unprocessed trauma, as the response doesn't fit the present moment but maps directly to deeper, unacknowledged pain.
Suppressing emotions requires constant energy, like holding a beach ball underwater. Kessler explains that running from feelings leaves people drained and unable to fully engage with life. He discusses the modern phenomenon of "half-felt" feelings, where people suppress their pain because they believe others have it worse. However, escape through achievements or addictions provides only temporary distraction. Kessler emphasizes, "What we run from pursues us and what we face transforms us."
Kessler explains that bargaining—constantly ruminating on "what ifs" and "if onlys"—delays acceptance and constructive action. This defense mechanism can persist long after initial understanding, as Kessler experienced even years after his son's death.
Unprocessed grief can lead to self-sabotaging behaviors regardless of external success or fame. When individuals don't acknowledge everyday disappointments and changes, these feelings accumulate and overwhelm their ability to cope. Kessler notes that anger often serves as a mask for underlying grief, acting as a bodyguard for deeper pain. Recognizing anger as an expression of grief allows for compassion and sets the stage for authentic healing.
Kessler states, "You can only avoid grief by avoiding love—and avoiding life." When Howes asks if someone can truly experience love at its greatest level without being willing to go through deep grief, Kessler is unequivocal: it is impossible. He shares that the greatest tragedy would not have been his son's death, but never to have loved and known him at all.
Processing grief, especially long-held trauma, frees up energy and allows for greater authenticity. Howes notes that after speaking about his own abuse, listeners commented that his podcast responses changed, reflecting deeper presence and authenticity. Kessler reinforces that embracing and moving through grief brings about fuller, more vibrant living rather than narrowing one's world to avoid pain.
Both emphasize that living fully is a daily choice not dictated by circumstances. Kessler recounts consciously deciding not to become "the grief guy that never left his house again" after his son's death. He notes that end-of-life regrets rarely concern what people did but center on experiences not taken and lives not fully lived.
Kessler calls success "a great deodorant"—effective at masking pain but incapable of addressing unprocessed grief. Howes shares that accumulating achievements didn't fill his sense of emptiness or make him feel more lovable; in fact, it amplified anxiety and distrust. This realization opens the opportunity for genuine emotional healing unhindered by illusions of success as a cure-all.
Finally, Kessler and Howes highlight the present moment as the only space where authentic love and connection can manifest. Anxiety about the future and rumination on the past prevent genuine presence with ourselves and others. Kessler teaches that loving connection happens only "in the now," and the goal becomes to process grief and fear so we can return to this space where life's richest love and most profound connections are found.
1-Page Summary
David Kessler explains that Elisabeth Kübler-Ross, famous for her work in hospice and grief, did not invent but rather observed the five stages of grief: denial, anger, bargaining, depression, and acceptance. She noticed these patterns as a kind of natural progression people seemed to go through, similar to the consistent rising and setting of the sun.
Kessler expands on how grief extends beyond death, defining it as a reaction to any change we did not want. He points out that the framework applies to breakups, job losses, divorces, and other significant life transitions. Large companies consult with him on grief because, fundamentally, it is about managing unwanted change. Those who adapt to change effectively are generally happier in life. If someone gets stuck in a state of loss—whether the death of a loved one, a breakup, or losing a job—they are likely to suffer as they cannot move through that change.
Kessler stresses that these stages are not linear or hierarchical. People do not move through the stages in a set sequence and may revisit them in different ways. Acceptance is not a singular moment but occurs in small and large ways, and individuals may experience acceptance at different points or multiple times throughout their grief.
Kessler emphasizes that after his own devastating loss—the death of his son—reaching acceptance did not feel sufficient. Acceptance alone felt flat, merely recognizing that life was now irrevocably changed without offering purpose or hope. This realization led Kessler to propose a sixth stage of grief: finding meaning. Inspired by Viktor Frankl’s work in "Man’s Search for Meaning," Kessler suggests that meaning allows people to move beyond mere survival after major loss.
Crucially, Kessler clarifies that meaning is not found within the tragedy itself—there is no inherent meaning in loss, death, or horrific events—but rather in how we respond and who we become afterward. Meaning emerges from the changes people make, how they live their lives, and the ways they help others or transform their pain into something positive.
Kessler identifies many forms that meaning can take. After loss, some people are struck by the brevity of life and resolve to make the most of their time. Others channel their pain into creating change—such as advocating so that others do not experience the same loss—or finding new sources of gratitude. Sometimes, meaning involves expressing love more openly or ensuring others feel valued in the present rather than waiting for loss to prompt such expressions. Kessler recounts his own story: by sharing the story of his son and helping millions, he transforms suffering into a sense of purpose.
Six Stages of Grief: Finding Meaning
Grief, by its nature, involves separation and loss. David Kessler explains that healing from grief cannot be done in isolation; it must be witnessed by another person. He says that if you are grieving, you need someone to acknowledge your pain, such as hearing, "That job meant a lot. I'm so sorry that happened to you." Grief is a severance, and connection mends the disconnection. To process loss, our attachment, pain, and love require validation in another’s eyes. This act of witnessing—having another recognize and hold space for our experience—restores worth and connection during times of deep isolation.
When others share and acknowledge our grief, we see ourselves mirrored in their concern and empathy. As Lewis Howes shares, being safely witnessed in his own grief allowed him to start healing unresolved pain, gradually easing the isolation that loss created. In grief, people find healing by recognizing their experiences in each other’s stories, which strengthens bonds and supports recovery.
Effective witnessing of grief is a two-step process. Kessler outlines that the first essential step is acknowledging a person’s pain with empathy, validating the unfairness and hardship in their experience. For example, statements like "I see the pain. You loved your wife, it's so unfair," or recognizing a deep betrayal, help the grieving person feel truly seen. This offers reassurance rather than dismissing or shaming emotions.
The second step is to witness the person’s capacity for growth and transformation, even when they cannot see possibility for improvement themselves. Kessler emphasizes saying, "I know you though. I know you can turn this around. You might not see it right now, but I know who you are." Witnessing pain and then believing in a person's ability to recover plants seeds of hope. Acknowledging not just what’s broken but their inherent capacity for resilience supports the painstaking work of healing.
Throughout history, grief groups have existed to provide exactly this kind of supportive witnessing and connection. Kessler likens the need for support in grief to buying insurance for tires: we should invest in supporting ourselves when we experience emotional blowouts. Connection is "everything"—whether it’s through a therapist, a friend, a group, or even helping others through volunteering, any form of supportive human interaction is crucial.
Grief groups are uniquely healing because they let people share and connect through similar losses. Specialized matches—such as groups for sibling loss, anticipatory grief, faith-based experience, or even specific time zones—remove access barriers and offer an audience that truly "knows." Kessler’s Tender Hearts online grief groups provide options for different needs, with no one turned away for lack of funds. These groups show that there isn’t just one voice or one way to grieve—the variety of stories enriches the communal process and ensures that everyone’s pain can be seen and discussed.
However, not every audience is supportive. Kessler warns of seeking empathy in those unprepared to give it, comparing it to searching for milk in a hardware store. Grief-illiterate communities can invalidate or retraumatize, so it is essential to choose supportive, grief-literate spaces for sharing, rather than persisting with those who dismiss or shame feelings.
Being vulner ...
The Role of Connection and Witnessing In Healing
Grief often expresses itself through unexpected triggers, automatic reactions, and even self-sabotaging patterns. In conversation, Lewis Howes and David Kessler illustrate how unprocessed pain shapes emotions and behaviors, sometimes long after the original loss or trauma.
David Kessler describes triggers as personal maps that guide us to our areas of pain, attention, healing, and ultimately, freedom. He encourages people to notice their triggers, as these reactions often point to unresolved wounds within. Kessler explains that efforts to avoid triggers—such as steering clear of specific people, places, or even asking others to change their behavior—are forms of emotional avoidance. This does not eliminate pain but merely causes it to linger internally, as "it's running out with you" wherever you go.
Lewis Howes provides an example from his own life. For years, he found himself getting easily triggered and quickly enraged during friendly pickup basketball games—escalating frequently into altercations, sometimes even into fistfights. This disproportionate anger felt automatic, beyond conscious control. The situation became evident when his best friend Matt distanced himself, citing Howes' ongoing outbursts even in low-stakes situations. Howes realized the real issue was within himself, not others. This recognition became a wake-up call for personal growth.
Kessler notes that such disproportionate anger often signals unprocessed trauma. The intensity of the response usually doesn’t fit the present moment, but instead maps directly to deeper pain that has not been acknowledged or healed.
Suppressing emotions requires constant energy, much like holding a beach ball underwater. Kessler explains that while it is possible to push feelings down, doing so leaves people drained and unable to fully engage with life. Both experts agree that running from feelings—as many do for years—exacts a hidden toll and never leads to genuine relief.
Kessler discusses the modern phenomenon of "half-felt" feelings, where guilt or self-judgment prevents legitimate emotional processing. People may feel that they shouldn’t be angry or sad, as others may have it worse, so they suppress their own pain and live burdened with unfelt emotions. Howes adds that many seek to escape pain through achievements or addictions, from workaholism to substance use, but these are only temporary distractions. Kessler reiterates, "What we run from pursues us and what we face transforms us." True release and freedom only come from allowing oneself to feel and process the full range of emotions.
One of the key defense mechanisms after loss, Kessler explains, is bargaining—constantly ruminating on "what ifs" and "if onlys" as a way to avoid the randomness and lack of control in life. This can happen after a divorce, job loss, or the death of a loved one. Bargaining delays acceptance and constructive action because the mind prefers endless analysis over sitting with painful feelings and moving forward.
Kessler shares that even after years of personal growth, he found himself returning to bargaining long after his son’s death. The process of revisiting bargaining illustrates that this stage of grief can persist and return, even after initial understanding. Only when one moves beyond ...
How Grief Manifests as Triggers, Reactions, and Self-Sabotage
Grief, often misunderstood as solely a source of pain and loss, emerges in this conversation between Lewis Howes and David Kessler as a profound and necessary experience for living and loving fully. Their dialogue explores how grief’s presence in life enables deeper love, richer connections, and a more authentic, meaningful existence.
Howes and Kessler agree that grief and love exist as a package deal. Kessler states, "You can only avoid grief by avoiding love—and avoiding life," underscoring that to sidestep grief is to also sidestep the possibility of joy and deep connection. When Howes asks if someone can truly experience love at its greatest level without being willing to go through deep grief, Kessler is unequivocal: it is impossible. Grieving deeply after losing a loved one allows the survivor to appreciate the fullness of what they had. Kessler applies this to his own experience with the loss of his son, sharing that the greatest tragedy would not have been his son’s death, but never to have loved and known him at all.
Acknowledging grief, instead of suppressing or avoiding it, broadens one’s emotional spectrum. Processing loss can lead to a greater appreciation for life and more meaningful relationships. Kessler observes that people are often told, explicitly or implicitly, not to seek happiness after loss, yet he affirms that feeling worthy of joy and love again is not only possible but necessary for healing and continued engagement with the world.
The act of processing grief, especially long-held or childhood trauma, frees up energy and allows for greater authenticity and creative potential. Howes notes a personal transformation when he began to integrate and speak about his own experiences of abuse. He describes a noticeable shift in the way he engaged on his podcast: listeners commented that his responses and interactions changed, reflecting a deeper presence and authenticity. Releasing suppressed emotions enabled a more honest connection with his audience and the world.
Kessler reinforces that allowing the full range of feelings—grief included—expands life. Rather than narrowing one’s world to avoid pain, embracing and moving through grief brings about fuller, more vibrant living. This process shifts the energy of relationships and public engagement, as seen in Howes’s podcast experience.
Both Kessler and Howes emphasize that living fully is a daily choice and is not dictated by one’s circumstances. Kessler recounts the aftermath of his son’s death, noting he consciously decided not to become "the grief guy that never left his house again." He chose instead to remain engaged with life, to “show up” even in adversity. This message transcends grief from death alone—everyone faces daily decisions about whether to sink into withdrawal or to re-engage with life.
Kessler’s work with the dying affirms that end-of-life regrets rarely concern what people did, but far more often center on experiences not taken, risks not embraced, and lives not fully lived. Playing it safe, he says, is the most frightening waste, and people often reach the end wishing they had been more open, adventurous, and authentic.
Howes and Kessler dissect a common illusion: that success, whether financial, social, or professional, can heal wounds or grant lasting peace. Kessler calls success “a great deodorant”—effective at masking pain, but incapable of addressing unprocessed grief or deep questions of worthiness. Howes shares that accumulating achievements did not fill his sense of emptiness or make him feel more lovable. In fact, it amplified anxiety and distrust.
Kessler references Freud’s preference for working with wealthy clients, since they had already discovered happiness is not found in money. For those still struggling, the hope that external achievements will solve inner pain persists—until it doesn’t. This realization can be liberating, as ...
Grief: A Gateway To Living and Loving Deeply
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