Claiming Your Baggage with Kier Gaines | Booked, Blonde & Busy w/ Olivia Ponton
September 21, 2026
AI Summary
5 min read“I’m not in a rush to say it’s over.” That line from licensed therapist Kier Gaines lands about halfway through his conversation with Olivia Ponton on Booked, Blonde & Busy, and it captures the episode’s central tension. Gaines, a therapist and author of It All Starts When You Do: How to Do the Real Work of Self-Healing, pushes back against the idea that healing is a finish line you cross. Instead, he argues, it is a continuous process of claiming your baggage—not discarding it—and learning to walk with it differently.
The Pebble in Your Shoe
Gaines introduces a metaphor that structures much of the conversation: the pebble in your shoe. It is something that hurts but does not kill you, so you keep walking. Over time, the pain grows, and even after you remove the pebble, the soreness lingers. The pebble is not a catastrophic problem—it is the small, persistent discomfort you ignore until it becomes unavoidable. For Gaines himself, the pebble right now is being present. He admits that sitting in the moment and internalizing it in real time is not how his brain works. His brain is wired for reflection, not immersion. So he has adapted: his version of presence is reflective, not immediate. After a high-emotion event, he slows down and processes the memory of it. He forces himself to eat slowly, to ask what the food tastes like, what it reminds him of. He is not trying to
Continue reading the full summary in the app — free to try.
Read Full Summary →Free • No credit card required
Never miss an episode of Booked, Blonde & Busy w/ Olivia Ponton
Get every new episode summarized in your inbox — free, ~5 minutes to read.
No spam. Unsubscribe anytime.
What you'll learn
- 1 (00:00) **Opening & Guest Introduction** - Ad for Toy Story 5, then Olivia introduces Kier Gaines, a licensed therapist and author of *It All Starts When You Do*.
- 2 (02:10) **Guest Background & Misconception About Aggression** - Kier explains his role as a therapist and content creator, and shares that people often mistake his resting face for aggression rather than simply being in his own business.
- 3 (04:07) **60-Second Book Pitch: Claiming Your Baggage** - Kier summarizes his book's core message: separating feelings from identity, interrogating thoughts, and taking accountability for your own "baggage" (flaws, history) as the path to healing.
- 4 (07:14) **The Pebble in the Shoe: Being Present** - Kier explains the "pebble" metaphor (a small, persistent annoyance that grows painful), and reveals his current pebble is difficulty being present in the moment—he is more reflective than experiential.
- 5 (10:37) **Restorative Practices for Public Figures** - Olivia shares her struggle to slow down; Kier challenges her to cater restorative practices to her unique public-facing life, and they discuss the pressure of always being "on" for fans.
- 6 (14:07) **How to Say No in Public** - Kier describes practicing saying "no" in low-stakes situations (e.g., mall kiosks) to build confidence, then applying it to fans asking for photos during difficult moments. He emphasizes that people usually understand.
- 7 (16:06) **Social Media’s Effect on Men vs. Women** - Olivia asks how social media targets men differently; Kier outlines three male archetypes (looksmaxxers, fitness bros, red-pill relationship content) and explains how they weaponize insecurity about masculinity.
+ Full timestamped outline available in the app
Show Notes
Hey Angels!
Today I'm sitting down with a licensed therapist who has DEFINITELY been on your For You page - the one and only Kier Gaines!
His new book It All Starts When You Do: How to Do the Real Work of Self-Healing just came out, and it had me rethinking my own life choices (in the best way)...
We get into claiming your baggage, why "have healed" hits different than "healed," and I get real about a friendship breakup I still can't shake. Then I put Xaden, Maven and Johnny on the therapy couch, and Kier does NOT go easy on our book boyfriends.
You DO NOT want to miss this one!
xoxo,
Olivia
Timestamps
Intro/Bev of the Day
00:29-01:39 Sour Apple Is Bad ?
01:40-02:42 Who is Kier Gaines?
02:43-03:33 The biggest misconception about Kier
03:37-06:41 60-second pitch of It All Starts When You Do
06:42-09:34 What's your pebble?
09:35-11:04 How do you slow down in NYC?
11:05-12:42 Getting asked for a pic mid-fight
12:43-14:17 How to tell a fan "not right now"
14:18-15:03 Practice saying no
15:04-18:05 How social media targets men vs women
18:06-20:23 Men with feminine energy
20:24-21:16 Most of Kier's clients are women?!
21:17-23:07 Why men talk shoulder to shoulder
23:08-24:17 What do men vs women talk about in therapy?
24:18-26:50 "Healed" vs "have healed"
26:51-27:53 Living with depression
27:57-30:30 Olivia's friendship breakup
30:31-33:22 Kier's follow-up questions
33:23-34:01 Drinking friends vs sober friends
34:02-36:09 Should Olivia reach back out?
36:13-37:10 What is a book boyfriend?
37:11-39:37 Book boyfriend 1: Xaden (Fourth Wing)
39:38-41:01 Book boyfriend 2: Maven (Red Queen)
41:02-43:25 Book boyfriend 3: Johnny (Binding 13)
43:26-44:28 The best-friend-of-the-month friend
More from this podcast
Booked, Blonde & Busy w/ Olivia Ponton →