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Why Chasing Success Can Leave You Feeling Stuck (with David Brooks)

Jan 19, 2026 36m 48s 34 insights
<p>It&rsquo;s easy to fixate on the usual markers of success &mdash; your resume, your net worth, or how &ldquo;impressive&rdquo; you seem on paper. But how much do those things really speak to our wellbeing? And what do we miss when we only focus on them?</p> <p>Author and cultural commentator David Brooks reflects on what he learned when he moved beyond ambition, and shares some practical ways to get unstuck.</p><p>See <a href="https://omnystudio.com/listener">omnystudio.com/listener</a> for privacy information.</p>
Actionable Insights

1. Prioritize Aspiration Over Ambition

Focus on aspiration—the goal of becoming a better person—rather than ambition, which is focused on outward success, as aspiration leads to a longer-lasting happiness boost.

2. Shift to Other-Centered Mindset

Actively turn your mindset from self-focus towards others, as service and connection are effective paths to developing deeper meaning and getting psychologically unstuck.

3. Cultivate Other-Centered Humility

Develop humility through radical self-awareness from a position of other-centeredness, allowing you to see yourself accurately and honestly without constantly seeking to impress.

4. Embrace Vulnerability in Pain

In moments of pain, choose to be ‘broken open’ by allowing yourself to be more vulnerable, as this is the only pathway to personal growth, rather than becoming invulnerable.

5. Master Making Others Feel Seen

Develop the ‘apex skill’ of making others feel seen, heard, and understood, treating it as a learnable skill that is crucial for meaningful connection.

6. Lead with Preemptive Vulnerability

Act in ways that are trusting and practice preemptive vulnerability, understanding that while occasional betrayal may occur, it generally pays off and fosters stronger connections.

7. Practice Character Daily

Develop character through small, everyday practice changes and habits, recognizing that character is forged incrementally, not through massive, sudden transformations.

8. Prioritize Your “Wanting System”

Pay attention to your ‘wanting system’ over your ’liking system,’ as it is more reliable for pursuing hard and challenging things that lead to deep fulfillment, even if the process isn’t always enjoyable.

9. Be Open to Being Seized

Cultivate a willingness to be ‘seized’ by interests or passions, approaching life like wandering through a bookstore, open to being captured by whatever genuinely interests you.

10. Initiate Positive Social Cycles

Actively make connections and try to see others, as putting good out there encourages reciprocation and builds more positive interactions and cycles.

11. Engage in Local Service

Look around your neighborhood to identify problems, discuss them, and then assess what unique skills you possess to contribute and help your community.

12. Commit to Showing Up

Consistently show up for others, even in the face of rejection, as this persistent presence can be identity-changing for both you and the person you’re supporting.

13. Cast Just and Loving Attention

Shift from self-centered attention to casting a ‘just and loving attention’ on others, seeing them with fair and compassionate eyes rather than evaluating them based on personal gain.

14. Practice Full Attention

Give your full attention to others, recognizing it as the ultimate act of generosity and a fundamental component of moral interaction.

15. Practice Powerful Listening

Actively practice listening, understanding that it is a tremendously powerful act in human connection and fostering deeper understanding.

16. Initiate Conversations with Strangers

Force yourself to start conversations with strangers, even if you anticipate boredom, as these interactions often prove more interesting and rewarding than expected.

17. Practice Deeper Vulnerability

Engage in deeper vulnerability by sharing things you might be embarrassed about or asking profound questions, as this often leads to surprisingly positive and connecting experiences.

18. Ask Personal Questions

Don’t hesitate to ask people questions about their lives, even personal ones, as people are often willing to share and appreciate being asked.

19. Value Small Connections

Do not underestimate the power of small moments of connection and brief acts of attention, as they can significantly impact relationships and overall well-being.

20. Reconnect with Childhood Desires

Reflect on your childhood to uncover dormant gifts or desires you left behind, as re-tapping into these can help you connect with a deeper sense of self and purpose.

21. Identify Core Desires

Ask yourself what you truly want deep down at the core of your being, as understanding your own desires is crucial for personal fulfillment.

22. Read Biographies of Admiration

Read books about people you admire to unconsciously adopt some of their admirable qualities and become a better person.

23. Surround with Admired Figures

Place postcards or portraits of people you admire on your wall to surround yourself with their influence, which can lift your spirits and inspire you.

24. Learn Basic Social Skills

Actively learn and practice basic social skills, such as how to sit with someone depressed, break up gracefully, ask for forgiveness, or end a conversation politely.

25. Improve Conversation Quality

Focus on improving the quality of your conversations, as this directly reflects and enhances the quality of your overall interactions with others.

26. Avoid Quantifying Human Beings

Be cautious and stop whenever you find yourself quantifying a human being, as the most important aspects of life, like determination and kindness, are not easily measurable.

27. Avoid Over-Autonomizing

Be mindful of ‘over-autonomizing’ by putting away phones and intentionally seeking connection, as excessive autonomy can lead to poorer long-term well-being despite short-term ease.

28. Challenge Selfishness Assumptions

Challenge the assumption that people are fundamentally selfish and avoid ascribing darker motivations to others, as this leads to a ‘dark world mentality’ that hinders trust and connection.

29. Provide Effective Care

Offer ’effective care’ by focusing on what the other person truly needs in a given moment, rather than what is comfortable or convenient for you.

30. Practice Aggressive Friendship

Engage in ‘aggressive friendship’ by actively connecting with and supporting your community, such as being the person who posts everything to keep neighbors informed.

31. Cultivate Daily Personal Depth

Engage in practices like reading spiritual books and attending religious services consistently to make yourself a little deeper each day.

32. Embrace Mixed Motives

Allow your actions to be driven by both selfish and altruistic reasons, recognizing this as a sign of a well-structured society and a healthy approach to personal growth.

33. Avoid Constant Busyness

Do not be constantly busy or have a ‘clock in your head’ during interactions, as this behavior can destroy relationships by making others feel unheard and undervalued.

34. Avoid Workaholism for Crises

Do not use workaholism as a coping mechanism for spiritual or emotional crises, as it is an ineffective therapy that only provides an outward appearance of success.