Summary of ADHD-ish Podcast Episode:

How to Stop People Pleasing and Manage ADHD Rejection Sensitivity at Work
Host: Diann Wingert
Guest: Dave Greenwood
Date: June 24, 2025

Episode Overview

In this episode, Diann Wingert welcomes back ADHD coach and author Dave Greenwood to unpack the challenges of people pleasing and rejection sensitivity at work—especially for neurodivergent entrepreneurs and professionals. Using lessons from the book The Courage to Be Disliked (by Ichiro Kishimi and Fumitake Koga, inspired by Alfred Adler), they explore mindset shifts for self-acceptance, managing interpersonal dynamics, and embracing the liberating possibility of being "disliked" in the pursuit of authentic living and sustainable success.

Their candid, sometimes irreverent conversation mixes practical strategies, real-life stories, and provocative insights about self-concept, burnout, and how to cultivate deeper agency in life and work.

Key Discussion Points & Insights

1. The Courage to Be Disliked: Introduction & Relevance

• [01:42] Dave introduces The Courage to Be Disliked and discusses Alfred Adler’s philosophy.
• The book isn’t ADHD-specific but contains universal lessons, especially resonant for people with ADHD.
• Facing the challenge of self-acceptance vs. striving for change.

Dave Greenwood [01:57]: “There were so many pieces of the book that literally stop me in my tracks… Not only resonated with people with ADHD, but just like stopped me thinking, this guy’s living with me.”

2. Separation of Tasks: You’re Not Responsible for Others’ Emotions

• [04:06] Adler’s "separation of tasks" challenges the notion we must manage others’ feelings.
• Diane and Dave connect this to ADHDers’ tendency to people-please and fear rejection in professional settings.
• You are responsible for your actions, not others’ interpretations or emotions (e.g., being late to a meeting).

Dave Greenwood [06:57]: “Your task is not to be responsible for or manage the emotions of others.”

• [07:10] Cultural conditioning teaches us otherwise (“don’t take the last cookie, you’ll make people feel bad”).

3. People Pleasing, Burnout, and Relationship Dynamics

• [07:50] People pleasing often arises from desire to be liked and insecurity.
• Adler’s focus on equality: All relationships should be horizontal, not vertical/hierarchical.
• Diane links chronic people pleasing to burnout—especially when one neglects personal boundaries to meet external expectations.

4. Inferiority, Fixed vs. Growth Mindset

• [09:53] The difference between momentary feelings of inferiority and an inferiority complex.
• Comparison with others can be used either as self-defeat or motivation.
• Diane highlights the importance of rejecting “outsourcing your self-esteem” and moving toward growth and contribution.

Diane Wingert [11:53]: “Our job is not to compete. Our job is to accept ourselves, accept others, and contribute.”

5. Can We Really Change? – Pushing Back on Limits

• [14:49] Emphasizing the Adlerian idea: change is possible, but it’s a process—not magic.
• Challenges when clients seek coaching but aren’t ready to do the work (“the magic pill” fantasy).
• The danger of relying on diagnosis or history as unchangeable excuses.

Diane Wingert [16:07]: “You have to be willing to believe to some degree that you can change. Otherwise, why engage the services of someone whose skill set is largely devoted to helping people change so they can reach their goals?”

6. Timing, Burnout, and Readiness for Change

• [18:56] Many seek help when they hit a breaking point (burnout), but aren’t necessarily ready or able to engage in change.
• Healing requires patience, not just urgency or despair.
• Diane emphasizes the repeated, lifelong nature of these challenges for ADHDers.

7. Interpersonal Problems: The Root of Most Struggles

• [22:53] Adler’s “all problems are interpersonal” thesis—endorsed with nuance by both.
• Majority of stress and anxiety at work or home relate directly to concern over other people’s judgments, expectations, or reactions.

Dave Greenwood [24:02]: “Unless you are on a deserted island and starving, generally speaking our day to day challenges are those with other people.”

8. Expectations & The Four Tendencies

• [24:35] Diane references Gretchen Rubin’s Four Tendencies to explain how most people are “obligers”—meeting others’ expectations while letting themselves down, fueling people pleasing and potential resentment.

9. ADHD and Relationship Complexity

• [28:31] ADHD can add layers of difficulty to relationships (though not always; sometimes it’s a strength, e.g. in sales).
• Scar tissue from misunderstood childhood experiences can fuel adult sensitivity and rejection fears.
• Achieving peace often means confronting and accepting these patterns—and giving up the comfort of feeling misunderstood.

Diane Wingert [30:55]: “Learning to approve of ourselves no matter what… and staying in the present moment… is probably the hardest work any of us could ever attempt.”

10. Present Moment Awareness & Self-Acceptance

• [31:49] Meditation and reversing the traditional self-help order: accept yourself first, then develop self-awareness.

11. Burnout, Assholes, and Imposter Syndrome

• [34:20] Dave jokes that “assholes don’t burn out,” because people-pleasers are typically those susceptible to burnout, as they care deeply about others’ opinions.
• Narcissists and true impostors don’t have imposter syndrome; those who worry are often genuinely competent.

12. Superiority Complex, Masking, and Division

• [39:21] Some in the neurodivergent community use “you don’t understand me” as a distancing or protective mechanism—which can backfire by increasing isolation and reducing support.
• Diane expands on the costs of defaulting to “no one gets me,” both at work and in burnout.

13. Where to Start? – Practical Takeaways

• [44:13] Dave’s advice for listeners who want to experiment:
  • Don’t just accept advice blindly—engage with critique, skepticism, and curiosity.
  • The audiobook version of The Courage to Be Disliked is recommended for its dialogic format and emotional nuance.
  • Cultivate self-awareness and openness to being “gobsmacked” (hit with new, challenging perspectives).
  • The ultimate promise: freedom and peace of mind, not just efficiency or popularity.

Dave Greenwood [46:48]: “It’s not a self-help book, but it does help you… like a work of fiction but with a fuck-ton of wisdom wrapped in the storytelling.”

14. The Most Controversial Take: Anger as Control

• [46:58] The book’s assertion: Anger is often used to control others—regardless of neurotype. This is flagged as a topic deserving further personal reflection.

Notable Quotes

• Diane Wingert [03:06]: “It is an act of courage to be willing to be disliked... Being willing to be who you really are—even if people dislike you, reject you, don’t want to hire you, that’s OK.”
• Dave Greenwood [07:50]: “There is a direct connection between people pleasing and wanting to make sure the other person feels good and doesn’t dislike me.”
• Diane Wingert [11:53]: “Our job is to accept ourselves, accept others, and, and contribute… if we could do anything to approximate that mindset, it would solve a lot of problems.”
• Dave Greenwood [21:12]: “We actually do tell ourselves things that are untrue… we are pretty good at giving ourselves a narrative that can be disproven.”
• Diane Wingert [34:20]: “Assholes don’t burn out… people who care what others think are the ones who burn out.”
• Dave Greenwood [46:58]: “We use anger as a way to control others.”
• Diane Wingert [47:24]: “If that doesn’t make you curious… I don’t know what would.”

Key Timestamps

• [01:42] – Introduction to The Courage to Be Disliked and its relevance
• [04:06] – Separation of tasks and people pleasing
• [09:53] – Inferiority, mindset, and comparison traps
• [16:07] – “Magic pill” coaching and change readiness
• [22:53] – The primacy of interpersonal problems
• [24:35] – Gretchen Rubin’s Four Tendencies & expectations management
• [28:31] – ADHD and relationships
• [31:49] – Self-acceptance vs. self-awareness (and why order matters)
• [34:20] – Burnout, narcissism, imposter syndrome
• [39:21] – Using “no one understands me” as both protection and isolation
• [44:13] – Practical ways to experiment with ‘the courage to be disliked’
• [46:58] – Anger as a tool of control (controversy)

Tone & Style

• Conversational, frank, and full of wit.
• Willingness to tackle controversial or challenging topics, occasionally with explicit language for emphasis.
• Use of real-life anecdotes and client stories to ground theory in practice.
• Encouraging skepticism, self-compassion, and experimentation.

Action Steps for Listeners

1. Read or listen to The Courage to Be Disliked—preferably the audiobook for its engaging dialogue.
2. Reflect on personal patterns of people pleasing and rejection sensitivity, especially around work and professional relationships.
3. Experiment with the “separation of tasks”—notice when you take responsibility for others’ feelings, and try letting go.
4. Practice self-acceptance before self-awareness to reduce fear of introspection.
5. Be open to moments that “gobsmack” you—sometimes profound change begins with discomfort or challenge.
6. Check the show notes for links to related episodes and coaching offerings.

This episode is a call to embrace the “messy middle”—for ADHDers and anyone else—of managing relationships, boundaries, and self-concept, in service of authentic, less anxious living.