ChooseFI Podcast Summary

Episode 574: Top Five Regrets of the Dying (Book Club with Frank Vasquez and Ginger)

Release Date: November 24, 2025
Guests: Frank Vasquez (Risk Parody Radio), Ginger (Host)

Episode Overview

This episode dives deep into the human experience of regret, inspired by Bronnie Ware’s book, The Top Five Regrets of the Dying. Ginger and Frank Vasquez use the lens of FIRE (Financial Independence, Retire Early) to question how future-oriented financial strategies interact with living a life of meaning, self-expression, and strong relationships. Together, they break down the five major regrets revealed in Ware’s memoir, relate them to their personal experiences, and extract actionable insights for the FI community.

Key Discussion Points and Insights

The Value of Regret and Inversion Thinking

• Regret as a Guide:
  Regret is both a way to understand past decisions and a motivator for making better choices now to avoid future regrets.
  • "Instead of asking what would be a good life or what would make me happy, let's talk about what would be a bad life or what would I regret..." (A, 01:41)
• Inversion (Charlie Munger’s Advice):
  Rather than focusing only on optimizing for happiness or success, ask, "What should I avoid to prevent an unfulfilling life?"

FIRE and Death: Why It’s a Taboo Topic

• Future-Orientation of the FI Community:
  Frank theorizes that those in the FIRE or personal finance space tend to avoid death-related topics because they are emotionally invested in planning for a never-ending future.
  • "By continuing to plan for the future, it's almost saying like, well, if I could just keep planning for the future, maybe I'll live forever..." (A, 03:49)

Book Summary: The Top Five Regrets of the Dying

Frank provides a brief summary:

• The book is a memoir by Bronnie Ware, a palliative care nurse who observed common end-of-life regrets.
• Rather than data-driven, its value lies in shared human themes that resonate across cultures and generations. (A, 10:25)

The Five Regrets, Explored

1. "I wish I had the courage to live a life true to myself, not the life others expected of me."

• Example: John, a lawyer by parental expectation, wished he'd pursued art (A, 13:53).
• Key Points:
  • Requires courage to break societal or familial molds.
  • FI offers the freedom to rediscover early passions, creative pursuits, or non-monetized interests (A, 15:27).
• Notable Quote:
  • "Oftentimes the people who are closest to you are the least helpful about this...you'll shoot your eye out." (A, 18:33)
• Ginger (Counselor’s perspective):
  • Often, fear of disappointing others is self-imposed; openness brings unexpected support (B, 19:39).
• Actionable Insight:
  • Don’t wait for permission; don’t over-optimize for productivity or monetization (A, 20:57).

2. "I wish I hadn't worked so hard."

• Example: Grace regretted her husband's work-centric life and its toll on family (A, 21:34).
• Key Points:
  • Sacrificing family or personal time for career, especially among careerists/baby boomers, leads to estranged relationships.
  • It's not about completely avoiding work, but being intentional about boundaries and priorities (A, 25:35).
• Notable Quote:
  • "Spoiler alert. None of the top five regrets were, I didn't make top sales." (B, 29:00)
• Actionable Insight:
  • Recognize the cost of always climbing. Prioritize experiences and relationships alongside (or above) workplace achievements (A, 26:02).

3. "I wish I had the courage to express my feelings."

• Example: Margaret hid her true emotions for family peace; a common regret among women of older generations (A, 31:29).
• Key Points:
  • Bottling up feelings to maintain harmony often backfires.
  • More relevant for those raised with strong caretaker roles, but likely less prevalent in FI circles (A, 32:44).

4. "I wish I had stayed in touch with my friends."

• Example: Rosemary, an isolated widow, mourns lost friendships (A, 33:23).
• Key Points:
  • Relationships (old and new) are central to end-of-life satisfaction.
  • FI provides both means and need to actively nurture relationships.
• Listener Email (Susan):
  • "To me, people and relationships are the things that really matter. I'm the one who generally makes or accepts invitations to nurture our relationships..." (B, 35:40)
• Frank:
  • "Friendships are formed not by perfection, but vulnerability and responding with care." (A, 41:29)
• Notable Quotes:
  • "No one wants to be friends with a perfect person...it's the moment where you actually reveal that you're not perfect that brings people to us." (B, 41:31)
• Actionable Insights:
  • Nurture existing friendships and make new ones through shared activities, vulnerability, and “bids” for connection—even if it means spending money (A, 47:06).
  • Prioritize spending on relationships over rigid budget adherence (A, 50:48).

5. "I wish I'd let myself be happier."

• Example: Harold stayed in an unfulfilling job and marriage out of routine (A, 53:12).
• Key Points:
  • Happiness requires conscious, sometimes courageous, choices—awareness of your own needs and joy.
  • “I am a saver” can be a dangerous identity if it leads to postponing joy or connection (A, 55:43).
• Listener Email (Adley):
  • "It's amazing how easily I can cheer on others...yet still wrestle with fully allowing myself to be happy and at peace with who I am." (B, 59:50)
• Listener Email (Charlotte):
  • "It is also important to appreciate the ordinary so that it becomes extraordinary..." (B, 63:35)
• Notable Quote:
  • "At some point, you need to be really focused on what's important to you, and it may not be something that other people think is important." (A, 72:13)
• Actionable Insight:
  • Notice and value small joys; being present-focused enhances happiness (A, 63:39).

Timestamps for Key Segments

• Opening/Intro to Regret and Inversion Thinking: 00:38–02:57
• Why FI Avoids Death Discussion: 03:49–05:34
• Book Structure and Five Regrets Introduced: 10:25–12:58
• 1st Regret - Living True to Yourself: 12:58–20:57
• 2nd Regret - Working Too Hard: 21:21–30:58
• 3rd Regret - Expressing Feelings: 31:22–32:44
• 4th Regret - Maintaining Relationships: 33:23–47:06
• Friendship, Bids, and Vulnerability: 38:06–45:51
• Spending Money on Friendship: 47:06–52:51
• 5th Regret - Happiness and Identity: 53:12–58:18
• Listener Stories (Adley, Charlotte) & Ordinary Joy: 59:50–64:13
• Death, Presence, and Learning from Loss: 64:16–74:48
• Recommended Reading / Additional Resources: 75:38–77:02

Notable Quotes & Memorable Moments

• "Oftentimes the people who are closest to you are the least helpful about this...you'll shoot your eye out." – Frank, on living your own life (18:33)
• "Spoiler alert. None of the top five regrets were, I didn't make top sales." – Ginger (29:00)
• "No one wants to be friends with a perfect person...it's the moment where you actually reveal that you're not perfect that brings people to us." – Ginger (41:31)
• "Friendships are formed not by perfection, but vulnerability and responding with care." – Frank (41:29)
• "At some point, you need to be really focused on what's important to you, and it may not be something that other people think is important." – Frank (72:13)
• "It is also important to appreciate the ordinary so that it becomes extraordinary." – Charlotte (Listener Email) (63:35)

Book & Resource Recommendations

• Books:
  • Falling Upward – Richard Rohr
  • Second Mountain – David Brooks
  • Strength to Strength – Arthur Brooks
  • Midlife: A Philosophical Guide – Kieran Setiya
• Podcast:
  • Frank’s Risk Parody Radio, episode 436 for further book suggestions (75:51)

Episode Takeaways

• Courage is Central: All regrets involve missed courage—be bold in self-expression and relationships.
• Relationships Matter Most: Invest time, effort, and even money in building and maintaining connections.
• Don’t Over-Optimize: It’s not about maximizing wealth or workplace awards; it’s about living fully.
• Happiness is a Choice: Don’t just cheer on others—give yourself permission for joy and fulfillment.
• Death Brings Focus: Acknowledging mortality can reshape what you prioritize in life.

Final Message:
Reflect on the five regrets—and let them inspire you to make intentional, courageous choices now, so your future is rich not just in finances but in meaning and connection.