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

ChooseFI

Brad Barrett | Choose FI Media

Business, Careers, Investing

4.8 • 5K Ratings

🗓️ 24 November 2025

⏱️ 78 minutes

🔗️ Recording | iTunes | RSS

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Summary

Join Ginger and Frank as they dive into the impactful concept of regret, exploring insights from Bronnie Ware's The Top Five Regrets of the Dying. Discover how these regrets can shape a life of fulfillment and happiness, and learn how to embrace self-expression and relationships to achieve true satisfaction.

Episode Summary:
In this episode, the hosts explore the concept of regret and its role in shaping meaningful lives. Inspired by Bronnie Ware's work, they discuss the common regrets of those at the end of their lives and provide insights on living authentically, nurturing relationships, and prioritizing happiness. Listeners are encouraged to reflect on their lives and make intentional choices to avoid future regrets.

Key Topics Discussed:

Introduction to Regret (00:00:00)
- Understanding the concept of regret and its implications for personal fulfillment.
Charlie Munger's Inversion Strategy (00:01:15)
- Utilizing inversion as a technique to clarify what leads to a fulfilling life by considering what leads to regret.
Overview of Bronnie Ware's Book (00:02:01)
- Discussion on The Top Five Regrets of the Dying and the importance of reflecting on these regrets to live better now.
First Regret: Living Authentically (00:12:32)
- "I wish I had the courage to live a life true to myself, not the life others expected of me."
- Importance of self-expression and the courage to defy societal expectations.
Second Regret: Courage to Express Feelings (00:20:52)
- "I wish I had the courage to express my feelings."
- The emotional costs of not sharing our feelings and the impact on personal relationships.
Third Regret: Maintaining Relationships (00:22:54)
- "I wish I had stayed in touch with my friends."
- The significance of nurturing friendships and relationships.
Fourth Regret: Nurturing Friendships (00:23:07)
- The necessity of continual effort in maintaining connections as life evolves.
Fifth Regret: Allowing Happiness (01:40:22)
- "I wish that I'd let myself be happier."
- The barriers to joy and the importance of allowing oneself to seek happiness.
Conclusion (01:04:19)
- Encouraging listeners to choose courage over complaint and to take proactive steps toward authentic living.

Key Quotes:

"Live true to yourself, not others' expectations." (00:12:32)
"Rekindle your childhood passions beyond societal expectations." (00:16:30)
"Build friendships by starting with acquaintances and shared interests." (00:28:04)
"Choose courage over complaint." (01:04:19)

Actionable Takeaways:

Reflect on what makes you truly happy and take steps to pursue it.
Invest time and resources in fostering meaningful relationships.
Practice sharing your emotions to deepen connections.
Engage in self-reflection to identify passions that were set aside.

Related Resources:

Discussion Questions:

What actions can you take today to align your life more closely with your authentic self?
How can you prioritize relationships in your daily life?
What does happiness mean to you, and how can you pursue it more actively?

Transcript

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0:00.0	Before we get started, I keep this podcast entirely ad-free for two reasons. First, this is a five
0:16.5	podcasts and I don't want to promote products that I don't want you to buy in the first place.
0:20.6	And second, I really like the clean listening experience of a show where you don't want to promote products that I don't want you to buy in the first place. And second, I really like the clean listening experience of a show where you don't have to fast forward ads.
0:26.2	To keep it ad-free, all I ask of you as a listener is the next time you open a travel rewards credit card,
0:31.6	go to choosefI.com slash cards.
0:34.6	And with that, onto the show.
0:38.2	Hey, everyone, it's Ginger, and I am here today with Frank Vasquez of Risk Parity Radio.
0:44.5	And we are here to talk about death. Or more specifically, we're going to talk about regret today.
0:51.8	And I think regret is interesting for this community and for all humans for a
0:57.4	couple reasons, right? One is, it's a way for us to understand our lives, right? It helps us to say,
1:04.3	here's why I feel this way. I did something and I should have done something else. And understanding that story helps me to reconcile my feelings that I have now.
1:15.2	But of course, we can also understand regret kind of on the back end to say, what do I want to do now so that I can ensure I'll have more positive feelings in the future that I won't experience that regret. And I suppose
1:28.8	that's a little bit why we would talk about that in this community, right? Because we're all about
1:33.8	how can we optimize our lives? How can we live good lives? And part of that is, can I avoid the big regrets?
1:41.9	Yeah. And what this is really an example of is what Charlie Munger talks about
1:47.1	if you want to really understand a question. What you should do is invert the question. And often that's
1:53.4	the easier way to get to good answers. So instead of asking what would be a good life or what would make me happy, let's talk about
2:03.8	what would be a bad life or what would I regret or what would make me unhappy. And oftentimes
2:09.8	that is a much easier way to focus on if we just get rid of some of these things or get rid of
2:17.0	some of these regrets, then it will
2:20.1	elevate us to a higher level just by getting rid of the regrets, even if we don't have a clue
2:27.0	as to what else is going to make us happy. Yeah, that makes sense. So for instance, if my question is,
	...

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