Key Moments
He Interviewed 65 Dying People. Here's What They All Regretted.
Key Moments
Dying people regret not spending time with family over wealth, and men often prioritize being seen as successful over genuine connection, leading to emptiness.
Key Insights
The most common regret among 65 dying individuals interviewed was not spending enough time with family, citing missed milestones like children's first steps.
A man who amassed over half a billion dollars regretted not attending his sons' baseball practices, stating, 'Can I have three of them?'
Vanity is identified as filling an 'existential vacuum' when core needs like safety and family are neglected, leading men to optimize for external validation.
The 'red pill' space is criticized for performative masculinity and catering to insecurities, often lacking genuine emotional depth and promoting a 'trolling' or 'meme' based approach to discourse.
True masculinity is defined as the 'willingness to shoulder responsibility,' a breadth that has expanded beyond financial provision to include emotional support for family and loved ones.
Only about one-fifth of millionaires genuinely enjoy and utilize their wealth, with many experiencing stress, imposter syndrome, or fear of losing it, indicating money doesn't equate to happiness.
The profound impact of 65 deathbed interviews
At just 19, Kyree Oliver embarked on an ambitious project: interviewing 65 dying individuals. Initially seeking self-understanding, the goal evolved into gathering '43,000 years of life experience' by leaning into genuine, often meandering conversations. He found older individuals, particularly those facing terminal illness, were more open with their wisdom and regrets than his peers. This intensive, self-directed research laid the foundation for his later work helping men navigate challenging self-conversations and understand the trajectory of their lives through the lens of deep regret and fulfilled purpose.
Family time: The ultimate, universal regret
The most pervasive regret voiced by the dying individuals was the lack of time spent with family. This wasn't about a general sentiment, but specific, poignant moments missed, such as a child's first steps, birthdays, or weddings. One particularly striking example was a man who had amassed over half a billion dollars. When asked what he would change, he wished for the opportunity to have attended 'one of each of my sons' baseball practices.' This man, who hadn't seen his three sons in 12 years and died shortly after the interview, had met only one of his nine grandchildren and none of his great-grandchildren. His wealth, by his own admission, offered no solace for these missed familial connections. The narrative around him was one of profound loneliness and emptiness, underscoring that financial success, when it comes at the expense of relationships, leads to an unfulfilling end. This emphasis on family regret highlights a critical generational shift in what constitutes a 'good father,' moving beyond mere financial provision to active presence and emotional investment.
The trap of prioritizing being 'seen' over being
A significant theme emerging from the interviews is the danger of optimizing for vanity and external validation over genuine being. Oliver explains the concept of an 'existential vacuum' – a void created by unmet core needs (safety, family, relationship) that gets filled with superficial pursuits like money, status, and attention. Vanity is particularly insidious because it can be easily performed. For entrepreneurs, the 'mask of being a family man' can become a vanity metric, driven by a desire to be 'seen as a good father' rather than actually *being* a good father. This distinction is crucial: optimizing for the performance of virtue attracts attention and applause, but it hollows out the genuine experience. The core question posed to figures like Mike Cernovich is whether one wants to be the good father or be seen as the man who is a good father. True presence, goodness, and honesty occur when one is not focused on the 'YouTube optimized version' or the 'thumbnail,' but simply *is*. This pursuit of authentic being stands in stark contrast to a culture that often rewards only the most performative aspects of masculinity and success.
When men stop believing they can change
A critical turning point for many men, as observed by Oliver, is the internal declaration that 'it's too late for me to change.' This belief system, often unacknowledged, leads to men taking their 'hands off the wheel,' surrendering agency and defining themselves by a static identity. Even when faced with negative consequences—divorce, estranged children, lack of deep friendships—they remain entrenched in this self-perception. The narrative becomes, 'This is just who I am now,' making it nearly impossible for external realities to break through the self-imposed limitations. This fatalism prevents them from adapting or seeking new paths, even when the current one is demonstrably failing them.
Red pill culture and the performance of masculinity
The discussion touches upon the 'red pill' space and its portrayal of masculinity, which is critiqued as often being performative and pandering. While acknowledging an audience exists for these narratives, Oliver suggests it often stems from men using insecurity as armor. The rapid-fire delivery, hot takes, and manipulative communication styles can captivate a vulnerable audience, offering an easier path than honest self-reflection. This space is seen as creating echo chambers where participants are either surrounded by those who agree or are constantly battling perceived enemies, fostering a lack of genuine discourse. The tendency to focus on 'marketable' surface-level opinions, or 'hot takes,' rather than nuanced, heartfelt beliefs, is highlighted as a significant issue. The danger lies in these figures becoming spokespeople, allowing audiences to outsource their thinking rather than engaging in introspection.
Masculinity redefined: The willingness to shoulder responsibility
Kyree Oliver defines true masculinity not by archaic notions of sole financial provision, but by the 'willingness to shoulder responsibility.' This responsibility has a widened breadth today, encompassing not just financial security but also emotional support for partners, children, and even friends. It involves holding space for others' difficult emotions, supporting loved ones through personal struggles, and generally taking ownership of the well-being of those who rely on them. While past generations might have equated masculinity with being the sole breadwinner, contemporary masculinity requires a more complex emotional intelligence and active participation in the lives of those around him. This broader definition includes aspects previously considered 'feminine,' such as nurturing and emotional attunement, emphasizing a holistic approach to care and leadership within relationships.
The path of meaning and purpose over vanity metrics
Oliver advocates for prioritizing meaning and purpose over the accumulation of wealth or external validation. He argues that while chasing money can be 'super fucking fun,' deifying it as an end goal is dangerous. True fulfillment doesn't stem solely from financial success, as evidenced by millionaires who remain depressed or anxious. The lesson from those who have it all but still feel empty is that the true treasures are often found 'scattered along the way'—the relationships, the experiences, and the personal growth. The pursuit of wealth without a foundation of meaning leads to a hollow victory. The advice for young men is to define who they want to be in 20 years, not just what they want to achieve, and to focus on becoming that person, aligning actions with core values and purpose rather than chasing superficial metrics.
Building a fulfilling future starts with small, intentional actions
Ultimately, growth and fulfillment are achieved through consistent, intentional action. Oliver often guides individuals, particularly young men, to start with small, manageable habits, like cleaning their room, as an exercise in control and order in a chaotic world. If one is convinced that nothing matters, then no small step will seem significant. The key is to *decide* that things matter, to force that conviction, and then to act accordingly. This involves taking on challenges that are 'a little bit too big' to foster growth, treating life like a controllable narrative, and continually recalibrating one's vision of their future self. The antidote to nihilism and emptiness isn't necessarily grand gestures, but the quiet, consistent effort to make everything matter, fostering competence, control, and ultimately, a meaningful existence.
Mentioned in This Episode
●Books
●People Referenced
Shifting from Performance to Presence
Practical takeaways from this episode
Do This
Avoid This
Common Questions
The most common regret among dying individuals is not spending enough time with family and loved ones. This includes missing significant life events like children's first steps, birthdays, or weddings, and not being present for the people who matter most.
Topics
Mentioned in this video
A book by Viktor Frankl that discusses finding meaning in life, even in the direst circumstances, and introduces the concept of the existential vacuum which the speaker relates to modern man's pursuit of external validation.
A book by Jordan Peterson that advocates for adopting small, intentional habits as a foundation for building structure and control in one's life, seen as a practical starting point for personal growth.
Mentioned in the context of a conversation on Tucker Carlson's podcast where Cernovich discussed an ayahuasca journey and the distinction between wanting to be a good father versus wanting to be *seen* as a good father.
Host of a podcast where Mike Cernovich was a guest, discussing the difference between genuine fatherhood and the perception of being a good father.
Mentioned as an example of a polarizing figure who uses a stripped-down, often provocative approach to communication, similar to comedians who use controversial hooks to draw audiences in and guide them through a narrative.
Mentioned as another example of a polarizing figure who, like Andrew Tate, is adept at using online communication strategies that can be performative rather than authentic, potentially lacking genuine personal belief.
Cited as an example of someone who has honed their communication by creating impactful, short 'quotes' or snippets to capture audience attention, which the speaker contrasts with a desire for depth and authenticity in online content.
Mentioned for his book '12 Rules for Life,' which emphasizes starting with small, mundane habits that people might resist, as a way to build order and control in one's life, particularly for young men seeking self-improvement.
More from Grant Owen
Ask anything from this episode.
Save it, chat with it, and connect it to Claude or ChatGPT. Get cited answers from the actual content — and build your own knowledge base of every podcast and video you care about.
Get Started Free