In this episode of Almost Got It, we dive deep with Will Rocklin — former Google & YouTube Product Manager turned comedian, screenwriter and still product manager — about the chaos, comedy, and clarity of navigating a midlife career reinvention.
Follow the hosts and guest:
Dilan: https://x.com/dilan
Ben: https://x.com/realbentauber
William: https://x.com/willrocklin
Timestamps:
00:00 – Intro: Transhumanism, AI & Comedy Collide
01:09 – Who Is Will Rocklin?
02:35 – Why Will Left Tech for Comedy
05:34 – What “Going All In” Really Feels Like
07:15 – The Truth About Art and Authenticity
08:46 – Does Will Actually Want to Be a Comedian?
10:17 – Comedy as a Healing Tool
13:03 – The Universe Has a Sense of Humor
16:18 – Relationships: Seriousness vs Play
18:49 – The “Finger in the Butt” Rule
21:06 – Parenthood & Playfulness
24:05 – The Moment That Could’ve Broken Me
26:01 – Can You Actually Change a Pattern in the Moment?
29:02 – Why Conventional Therapy Might Not Work
31:02 – Blame, Bananas, and Emotional Ownership
33:00 – Living with Anxiety in a High-Performance World
36:20 – Thought Work vs Nervous System Rewiring
39:10 – Childhood, Identity, and the Myth of Fulfillment
41:10 – Ideal Parent Figure Protocol
42:16 – Coaching Mode: How to Rewire Your Brain
43:32 – Dario Amodei’s AI Job Loss Prediction
46:04 – Mass Panic vs Present Reality
49:14 – The Responsibility of Tech Leaders
50:56 – Who Do We Trust on AI?
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