What if the very thing driving your success is quietly breaking you?

Brooke Taylor, Enneagram Three, career coach, and author of Healing the Success Wound, joins me for a searingly honest conversation about achievement, identity, and spiritual hunger.. Brooke grew up in Silicon Valley where worth was measured in gold stars, landed at Google by her early twenties, and found herself drowning in a success she couldn't feel. We talk about the success wound which, as Brooke describes it, is the pain that comes from mistaking productivity and achievement for self-worth — the deeply installed belief that the more you produce and achieve, the more worthy of love and belonging you become.

This wound isn't just for Enneagram Threes. It's a human condition — and it shows up differently depending on your type, your culture, your family system, and what "success" looks like in your particular world.

We talk through Brooke's five types of unfulfilled achievers — the grinder, the hider, the seeker, the work-hard-play-hard, and the pleaser — and I couldn't help mapping those to the Enneagram types in real time. We also get into the distinction between the true self, the wounded self, and the socialized (or protector) self — a framework rooted in Internal Family Systems and gestalt psychology that I think will resonate deeply with longtime Typology listeners.

Whether you're a Three or you love one, this episode is for you.

Guest Bio:

Brooke Taylor is a certified career coach, speaker, and the author of Healing the Success Wound. A self-identified Enneagram Three, Brooke built her coaching practice specifically for women navigating the intersection of ambition, identity, and fulfillment — though her framework applies broadly across genders. Her research includes a survey of more than 5,000 high-achieving professionals who identified as unfulfilled, which forms the empirical backbone of her five-type model of the unfulfilled achiever. A veteran of Google and a long-term member of recovery communities, Brooke brings both lived experience and rigorous research to her work. She is the founder of the Lined Ambition framework and writes and coaches at the crossroads of psychology, spirituality, and career development. Learn more at brooketaylor.co.

Healing the Success Wound is available now wherever books are sold.

Find Brooke at https://brooketaylorcoaching.com.

Have you ever known where you want to go—but felt mysteriously stuck getting there? In this episode of Typology, I sit down with Dr. Henry Cloud, clinical psychologist, leadership expert, and bestselling author of Boundaries, to talk about his new book, Your Desired Future: The Five Essential Steps That Take You Where You Want to Go.

Together, we explore the intersection of faith, psychology, the Enneagram, self-awareness, and personal growth, and how real transformation begins when we stop shaming ourselves for where we are and start getting curious about what's possible. Henry brings his characteristic wisdom, warmth, and clinical insight to a conversation about healing, purpose, emotional health, and the practical path from "here" to "there."

This is a thoughtful and hope-filled conversation for anyone who feels stuck, is navigating change, or wants to better understand the patterns that shape the life they're living.

"Emotions drive 90 to 95% of our unconscious decision-making."

Attia Qureshi is back — and this time, we go deeper.

After her first interview, Attia's insights on persuasion and negotiation were so helpful that Anthony put them to the test in a real-life negotiation and said, "they changed the game." So, we invited her back to go deeper into the ideas behind her book, Never Settle: Persuasion and Negotiation Skills to Get What You Want, and explore how each Enneagram type approaches one of the most important conversations we can have: asking for what we need.But, as Attia explains, negotiation isn't just something that happens across a boardroom table. It happens every day – with our spouses, our kids, our coworkers, our neighbors, and perhaps most importantly, within ourselves. Before we ever make an ask, we have to face the internal stories, emotions, fears, and assumptions that often keep us from speaking up in the first place.

In this episode, we explore how different Enneagram types navigate negotiation, conflict, emotional regulation, self-advocacy, and the art of creating value without damaging relationships. We unpack why some types avoid the ask, why others over-assert, why some need more clarity around what they actually want, and how every type can grow in confidence, courage, and self-awareness.

You'll learn:

• How emotions shape the way we ask – or don't ask – for what we need

• How to identify and label your emotions so they stop driving your decisions unconsciously

• The worst-case scenario exercise that builds resilience and inoculates you against fear

• What each Enneagram type brings to the negotiation table — where they shine, where they get stuck, and what to do about it

• A breathing technique that signals your nervous system it's safe before a high-stakes conversation

You can learn more about Attia and grab her free resource for Typology listeners, which includes a breakdown of each Enneagram type's negotiation strengths, blind spots, and exercises at https://attiaqureshi.com/typology.

Never Settle: Persuasion and Negotiation Skills to Get What You Want by Attia Qureshi and John Richardson is available now wherever books are sold.