Stop People-Pleasing Danny Goldberg on Assertiveness, Boundaries & Being “A Little Bit Asshole”

Send us Fan Mail Danny M. Goldberg is a serial entrepreneur, speaker, trainer, and author who describes himself as a recovering people-pleaser. In this episode of the Remarkable People Podcast, Danny joins David Pasqualone to explore why always trying to be “nice” can cost you confidence, identity, time, money, and respect—and how to build healthier boundaries without becoming rude, selfish, or cruel. Danny shares practical lessons from relationships, corporate America, entrepreneurship, client work, parenting, faith, and his book A Little Bit Asshole. Together, David and Danny discuss the difference between being nice and being kind, why saying no does not always need an explanation, how to handle reasonable conflict, why people often undervalue themselves, and what it means to be assertive enough to earn respect while still treating people well. One of Danny’s central ideas is simple: “The goal isn’t to be nice. The goal is to be kind. The goal is to be respected.” If you struggle with people-pleasing, weak boundaries, overexplaining, or putting everyone else’s needs ahead of your own, this conversation offers practical ways to start changing that pattern. GUEST LINKS Book: https://littlebitahole.com/ LinkedIn: https://www.linkedin.com/in/dannymgoldberg/ X / Twitter: https://twitter.com/dannymgoldberg GoldSRD: https://goldsrd.com/ FULL SHOW NOTES + TRANSCRIPT: https://davidpasqualone.com/content-type-media/podcasts/the-remarkable-people-podcast/danny-goldberg-stop-people-pleasing-boundaries-respect/ WATCH ON YOUTUBE: https://youtu.be/GkP2d0AX-hM This episode includes personal stories, religious viewpoints, opinions, social commentary, and discussion of cultural issues. Statements made by the speakers represent their own perspectives and are not automatically independent factual findings of the podcast. Listen. Do. Repeat. For Life! Chapter Quick Links: 00:00 Welcome & Episode Setup 01:28 Why People-Pleasing Costs You 03:22 Danny Goldberg’s Story & Immigrant Upbringing 08:17 Faith, Family & Finding a Moral Foundation 10:37 Leaving Corporate America & Forging Your Own Path 12:28 Reprogramming the People-Pleasing Mindset 15:05 Boundaries in Relationships 16:18 Professional Boundaries & Knowing Your Value 20:35 Nice vs. Kind: Respect, Boundaries & Saying No 21:52 Think Long-Term in a Changing Job Market 27:47 AI, Technology & the Future of Human Connection 31:31 Communication & Critical Thinking in the AI Era 35:55 Why the Book Is Called “A Little Bit Asshole” 37:33 Echo Chambers, Conflict & Learning to Say No 41:44 Courage, Convictions & Difficult Conversations 52:07 The Book, Practical Application & Guest Resources 55:16 Final Advice: Have Faith Support the show THE NOT-SO-FINE-PRINT DISCLAIMER:  While we are very thankful for all of our guests, please understand that we do not necessarily share or endorse the same beliefs, worldviews, or positions that they may hold. We respectfully agree to disagree in some areas, and thank God for the blessing and privilege of free will. For more Remarkable Episodes, Inspiration, and Motivation, please visit https://davidpasqualone.com/remarkable-people-podcast/ now!