#16: Stoic Beauty, 16 Questions of Habit Change, and Trump vs. Socrates

PLUS: Seneca on embracing the end like a sage

Welcome, Stoics.

Dive into the art of living well with a Stoic twist—ponder life's big questions and fine-tune your daily habits with wisdom from the past.

In today’s Nous

  • ☠️ How embracing the Stoic mindset can transform your approach to life's final act and everything leading up to it.

  • 🙋‍♂️ A deep dive into Russell Brand's modern take on the classic 12-step program for breaking free from life's hang-ups.

  • 🗣️ A creative spin on what a chat between Donald Trump and Socrates might look like.

Read time: 8 minutes

Editor’s Picks

🏹 Stoic Wisdom Arrows

🪞 Did the Stoics get their Theory of Beauty Wrong?: Check out this 30-minute talk from Massimo Pigliucci where he discusses the Stoic theory of beauty: Watch here.

😇 How a Stoic Becomes a Saint: Allan from What Is Stoicism? created a potent video that serves as a reminder of Marcus Aurelius’s Stoic belief that “we exist for the sake of one another.” Watch here.

🔨 The 5 Iron Rules of Productive Output: Enjoy part 3/5 in my free productivity course where Eric Brown and I discuss principles to increase your output in all that you do. Watch here.

Technique Try-Out

🧰 The 16 Questions of Habit Change

I have recently begun reading a book called "Recovery" by Russell Brand. This book explores the concept of achieving freedom from addiction through the renowned 12-step program popularized by Alcoholics Anonymous.

Brand attempts to simplify the 12 steps so anyone can use them for almost any ailment, not just addictions. He describes the 12 steps in his own language as follows:

  1. Are you a bit f*cked?

  2. Could you not be f*cked?

  3. Are you, on your own, going to ‘unf*ck’ yourself?

  4. Write down all the things that are f*cking you up or have ever f*cked you up and don’t lie or leave anything out.

  5. Honestly tell someone trustworthy about how f*cked you are.

  6. Well that’s revealed a lot of f*cked-up patterns. Do you want to stop it? Seriously?

  7. Are you willing to live in a new way that’s not all about you and your previous, f*cked-up stuff? You have to.

  8. Prepare to apologize to everyone for everything affected by your being so f*cked-up.

  9. Now apologize. Unless that would make things worse.

  10. Watch out for f*cked-up thinking and behavior and be honest when it happens.

  11. Stay connected to your new perspective.

  12. Look at life less selfishly, be nice to everyone, help people if you can.

In the first step, “Are you a bit f*cked?”, Brand provides 16 questions we can work through to truly find out the answer to this question.

Here’s the practice:

Think of a craving or bad habit you have and with that in mind journal through the following 16 questions. You’ll find that this is time incredibly well spent.

Question 1: What do I want to change?
  • Take a moment to reflect on your life and identify the specific area or aspect that you are eager to change. Consider why this change is important to you and how it could potentially improve your life.

Question 2: What pain is associated with this change?
  • Reflect on the difficulties and challenges that might come with making this change. Are there fears or anxieties associated with it? Try to understand and acknowledge the pain that might come with the process.

Question 3: What pleasure am I getting out of not changing?
  • Think about the current state of your life and how maintaining the status quo might be providing you with comfort or pleasure. What are the short-term benefits you’re experiencing from not changing?

Question 4: What will this cost me if this doesn’t change?
  • Reflect on the long-term consequences of not making this change. How might your life be affected negatively? What opportunities might you miss out on?

Question 5: What are the benefits I can get from having this changed?
  • Envision the positive outcomes that could result from making this change. How could your life improve? What new opportunities or experiences might become available to you?

Question 6: Has this problem made my home life unhappy?
  • Consider how this issue has impacted your personal life, particularly within your home and family. Has it created tension or unhappiness?

Question 7: Has this problem caused any type of illness?
  • Reflect on whether this issue has had any impact on your physical or mental health. Has it contributed to any illnesses or conditions?

Question 8: Do I turn to the type of person who practices this behavior, or to companions who enable me?
  • Consider the social influences in your life. Are there individuals who encourage the behavior you’re trying to change? How do they impact your actions?

Question 9: What part of the problem do the people who care about me object to most?
  • Think about the perspectives of your loved ones. What aspects of this issue do they find most concerning or objectionable?

Question 10: What type of abuse has happened to me and others due to this problem?
  • Reflect on the potential harm this issue has caused, both to yourself and to others. What forms of abuse or negative consequences have arisen?

Question 11: What have I done in the past to try and fix, control, or change this area of my life?
  • Recall your previous attempts to address this issue. What strategies or actions have you taken? What worked, and what didn’t?

Question 12: What are the feelings, emotions, and conditions I've tried to alter or control by indulging in this behavior?
  • Identify the emotional or mental states that have driven you to engage in this behavior. What have you been trying to avoid or alleviate?

Question 13: How has this problem put my important relationships in jeopardy?
  • Consider the impact of this issue on your relationships with family, friends, and other loved ones. How has it strained or damaged these connections?

Question 14: Have I lost respect from people due to this problem?
  • Reflect on your social standing and reputation. Has this issue led others to lose respect for you? How has it affected the way people perceive you?

Question 15: If this is so important, why haven't I changed?
  • Delve into the reasons behind your resistance to change. What has held you back from making the necessary adjustments in your life?

Question 16: Am I willing to do the work to change?
  • Finally, assess your readiness and willingness to embark on the journey of change. Are you prepared to put in the effort required to transform your life?

New Ways of Seeing

🤖 Donald Trump Meets Socrates

Donald Trump, a wealthy business tycoon and former influential world leader, is a figure whose views and values warrant scrutiny.

Let us imagine a scenario where he accidentally time-traveled back to Ancient Athens and encountered Socrates, engaging in a thought-provoking discussion. This is how their interaction might unfold:

Socrates: Greetings, stranger. It is not often we see such... peculiar attire in the Agora. From whence do you hail?

Trump: I'm from a place that's the best, the greatest—you wouldn't believe it. Suddenly, I'm here. It's like I've stepped into history. Tremendous!

Socrates: A most extraordinary claim. And what knowledge do you bring from this 'greatest' place?

Trump: I know how to win. I've built empires, shaped destinies. People love me, and I have very, very good ideas.

Socrates: It is a fine thing to build and to win, but tell me, what is the nature of 'winning'? How does one truly 'win' in life?

Trump: Winning? It's about having more. More money, more buildings, more power. When you're rich, they let you do it. You can do anything.

Socrates: And yet, can a man who has more than he needs truly be happy if he desires more still?

Trump: Of course! Happiness is having a billion dollars in the bank.

Socrates: Perhaps. But consider this: if a cup is already full, does adding more water not simply cause it to overflow? Maybe there is more to happiness than material wealth.

Trump: Overflowing sounds like winning to me. If the cup overflows, you just get a bigger cup. A golden cup!

Socrates: A golden cup, you say? Yet if the gold does not quench your thirst, what use is the cup?

Trump: You’re not making sense. Everyone wants gold. Gold is power. Gold is... everything.

Socrates: It appears we value different kinds of 'gold,' my friend. I seek the gold of knowledge and virtue. Tell me, have your riches brought you peace?

Trump: I've got the best of everything. The best buildings. The best companies. Peace is having everyone agree with you, or making them agree.

Socrates: Ah, but agreement is not the same as truth, and peace of the soul is not won by agreement, but by understanding. Tell me, does the wise man not seek truth over consensus?

Trump: Maybe that's your truth. I have my own truth. It’s worked for me so far.

Socrates: Indeed, a man may have his own truth, but wisdom is knowing the difference between what we believe to be true and what is universally true. Shall we explore this further?

Socrates 1 - Trump 0

Turning Theory Into Skill

🧘 The Wise Man Does Nothing Unwillingly

I’ve just started reading How to Die: An Ancient Guide to the End of Life from the Ancient Wisdom for Modern Readers collection. I’m really loving it so far, and I wanted to share a quote that stuck out for me:

Accept this assurance from me – I shall never be frightened when the last hour comes; I am already prepared and do not plan a whole day ahead. But do you praise and imitate the man whom it does not irk to die, though he takes pleasure in living. For what virtue is there in going away when you are thrust out? And yet there is virtue even in this: I am indeed thrust out, but it is as if I were going away willingly. For that reason the wise man can never be thrust out, because that would mean removal from a place which he was unwilling to leave; and the wise man does nothing unwillingly. He escapes necessity, because he wills to do what necessity is about to force upon him. Farewell.


Seneca's words resonate with a powerful message: to live without fear of life's final curtain, prepared for its inevitable descent at any moment.

It's a call to embrace the present with vigor while holding the knowledge of life's transience close to our hearts.

Imagine life as a captivating book—while we're engrossed in each page, we're aware that the final chapter will come, and we're prepared to close the book with a sense of fulfillment, not regret.

To weave this Stoic contemplation into the fabric of our daily lives, consider a simple daily reflection:

Each day, take a moment to ponder the aspects of life you cherish, acknowledge their impermanence, and meditate on the acceptance of their eventual conclusion.

This practice isn't about fostering fear but about cultivating gratitude and peace with the present, an equilibrium that prepares us for the ebb and flow of existence.

I created a Death of Seneca guided contemplation that will help you put this idea into practice. Listen to it here:

Off The Beaten Path

📆 Self-Improvement To-Do List

  Hack: If you have an iPhone turn on “Access Control” to make it impossible to switch to other apps. I love this feature for reading and studying.

Read: The British psychological illusionist and author of Happy, Derren Brown has an extensive reading list. Here are 25 top picks you can start with.

Contemplate: Here are 50 maxims from Alain De Botton. Which is your favorite?

Organize: Lately I’ve been using Milanote to organize my life. Here’s a great overview of the features by Tiago Forte.

All Things End

🤝 Friend of Wisdom

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Thank you for reading. As Stoics, we understand that the future is uncertain, so let's say…

I’ll speak to you again next Wednesday if fortune allows.