Good Work with Barrett Brooks

The Stories We Tell Ourselves That Keep Us Stuck with Jenny Wood

This week, I talk with Jenny Wood, who spent 18 years at Google, rising through the ranks and building global programs used by tens of thousands of employees. From the outside, Jenny had the kind of career many people aspire to—prestige, influence, and steady advancement inside one of the world’s most admired companies. But over time, she began to realize that the very habits that fueled her success—relentless drive, constant striving, and an obsession with achievement—were also taking a personal toll. In this conversation, we talk about ambition and when it becomes a trap, the pressure to keep chasing the next milestone, and the challenge of celebrating wins along the way. We also explore money, identity, imposter syndrome, motherhood, and the fear that comes with walking away from something impressive to build a life that feels more aligned with who you truly want to become. Let’s get to it! In this episode: * (00:00) - Intro * (00:44) - How Jenny became a pilot—and what flying gives her * (02:59) - What flying represents in Jenny’s life * (04:25) - The importance of finding an escape * (06:57) - Optimizing for leisure versus optimizing for productivity * (14:06) - Jenny’s early interest in psychology * (19:15) - Packaging compelling ideas without losing what’s true * (22:09) - When obsession helps—and when it starts holding you back * (25:54) - Jenny’s years inside Google * (28:54) - Anticipatory grief and the psychology of impact bias * (34:19) - Balancing career, health, family, and the leap into * entrepreneurship * (41:29) - Leaving the comfort zone and taking a leap of faith * (44:06) - The moment Jenny decided to leave Google * (52:00) - Jenny’s journey into parenthood and being a career mom * (56:29) - How slowing down changed Jenny’s relationship with her kids * (01:01:47) - Chasing the New York Times bestseller list * (01:07:32) - How this conversation between Barrett and Jenny came to be * (01:12:33) - How Jenny is making a living today—and what’s next * (01:15:05) - Jenny’s ambitious family travel plans * (01:17:31) - Building a business that supports a life of travel * (01:20:37) - Trusting that stepping away for a year will work out * (01:26:11) - What makes Jenny world-class? * (01:26:54) - The change Jenny hopes to create through her work * (01:28:40) - Who Jenny is becoming Get full show notes and links at https://GoodWorkShow.com [https://goodworkshow.com]. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks [https://www.youtube.com/@barrettabrooks]. Apply for 1-on-1 Coaching with Barrett: https://barrettbrooks.com/coaching [https://barrettbrooks.com/coaching]  Subscribe to Tiny Leadership Lessons: https://barrettbrooks.com [https://barrettbrooks.com]

Capturing Wonder: Jon McCormack's Journey Through Photography and Technology

This week, I talk with Jon McCormack, the leader behind the iPhone camera at Apple—the most widely used camera in human history. But Jon’s story goes far beyond technology. He grew up on a farm in rural Australia without full-time electricity, dropped out of a PhD to chase an unexpected opportunity in tech, helped build Kindle, and founded schools in Kenya that now serve thousands of children. Along the way, he developed a body of photographic work rooted not in spectacle, but in wonder. We talk about letting go of camera snobbery, building technology that empowers rather than exploits, and why beauty and awe make us more generous and connected. If you’ve ever wrestled with the tension between ambition and meaning—or wondered how to use your success in service of something deeper—this conversation is for you. Let’s get to it! In this episode: * (00:00) Intro * (00:41) From camera snobbery to something deeper * (03:34) When Jon realized photography isn’t about the gear * (06:22) What a photograph means in the age of AI * (13:11) The unseen work behind meaningful images * (15:51) Beauty, stewardship, and why the environment matters * (28:39) Returning to the same landscape—and learning to see * (32:16) Growing up in Australia and the roots of Jon's vision * (34:38) How colorblindness shaped Jon’s sense of pattern and form * (36:07) Dropping a PhD and stepping into tech * (38:06) A one-way ticket to Seattle—and an unexpected path * (40:10) Building products that connect people to what matters * (47:45) The double helix of art and technology * (52:46) Leading the iPhone camera and democratizing storytelling * (59:56) From safari camp conversation to schools in Kenya * (01:11:50) Why Jon stayed quiet about his philanthropy until now * (01:15:49) Wonder as a daily practice * (01:21:44) Where Jon has become world-class * (01:23:11) Filling gaps and shaping a more beautiful future * (01:26:53) Rewriting your algorithm with beauty * (01:27:53) Who Jon is becoming Get full show notes and links at https://GoodWorkShow.com [https://goodworkshow.com]. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks [https://www.youtube.com/@barrettabrooks]. Apply for 1-on-1 Coaching with Barrett: https://barrettbrooks.com/coaching [https://barrettbrooks.com/coaching]  Subscribe to Tiny Leadership Lessons: https://barrettbrooks.com [https://barrettbrooks.com]

The Quiet Grief Behind the Growth with Sam Vander Wielen

This week, I talk with Sam Vander Wielen—entrepreneur, author, and founder of a multi-million-dollar legal education business. We talk about what happens when the life you built for safety no longer fits—and when success and grief collide at the same time. Sam shares how childhood survival strategies shaped her career, how a scrappy food blog became the bridge out of law, and why listening deeply to customers changed everything in her business. We also explore the parallel track of her personal life: losing both of her parents while scaling her company and signing a book deal. At its core, this conversation is about agency—about recognizing that even after trauma, even after achievement, you still get to choose who you’re becoming. It’s a conversation about grief, reinvention, and the courage to build a life that’s truly your own. Let’s get to it! In this episode: * (00:00) - Intro * (00:44) - The story of “Sourdough Joe” and what it reveals about vision versus follow-through * (03:35) - Why community matters so much * (06:44) - Moving to Long Island and building a calmer life * (09:01) - Childhood chaos vs. adult stability * (12:55) - Tools for regulating the nervous system * (16:52) - How survival shaped Sam's personality * (18:29) - Why law felt like safety—and the only viable path forward * (21:28) - The moment that forced Sam to confront her career * (26:31) - Starting a food blog * (29:02) - The spark behind her pivot * (32:04) - Turning law into leverage * (36:42) - Building the business * (40:18) - Doing the unglamorous work * (45:44) - “Mac & cheese” marketing * (55:01) - Deciding what to share publicly * (01:06:55) - Signing a book deal during tragedy * (01:08:25) - Building through grief * (01:14:18) - Building a team that creates stability and trust * (01:16:29) - Sam's mental model for hiring * (01:22:01) - Defining roles as the business evolves * (01:24:06) - The systems and discipline behind consistent, high-quality content * (01:26:33) - How Sam is thinking about the next chapter * (01:30:53) - The risk of telling the truth * (01:37:29) - Where Sam has become truly world-class * (01:38:06) - Who Sam is becoming Get full show notes and links at https://GoodWorkShow.com [https://goodworkshow.com]. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks [https://www.youtube.com/@barrettabrooks].

Beyond Productivity: Tiago Forte's Journey of Growth and Transformation

This week, I talk with Tiago Forte about far more than productivity systems or note-taking. This one is about what happens after success—when the systems that once fueled your growth start working against you. We talk about burnout, anger, embodiment, and how listening to the body can become a doorway to deeper clarity and determination. Tiago shares the personal journey that shaped Building a Second Brain, why he made the difficult decision to wind down a wildly successful business, and what he’s learned by redesigning his life around alignment rather than optimization. We also explore the changing value of audience, community, and creativity in the age of AI, and why real connection—both locally and globally—matters more than ever. This conversation is about the inner work required to build a life, not just a career, that actually fits. Let’s get to it! In this episode: * (00:00) - Intro * (00:54) - Tiago on " highly fit, middle-aged dads" * (03:29) – Moving beyond intellect into emotional and somatic awareness * (05:37) – How physical pain forced Tiago to listen differently * (08:46) – The books, thinkers, and experiences that reshaped Tiago's understanding of healing * (13:43) – What changed when Tiago learned to express anger instead of repressing it * (17:03) – How a healing system unexpectedly became Building a Second Brain * (20:57) – Knowing when success no longer fits * (24:27) – Facing the “now what?” phase after shutting down a successful business * (28:46) – Why audience size doesn’t mean what it used to * (30:32) – Balancing lived fulfillment with the need to stay profitable * (32:29) – The psychological transition that comes with midlife * (34:41) – How Tiago is organizing work in this next chapter * (37:20) – The decision that led Tiago and his family from LA to Mexico * (42:11) – How changing environments reshaped Tiago's family relationships * (45:22) – Rediscovering cultural identity through place and presence * (47:39) – Why where you live may matter more than the goals you set * (54:33) – Holding joy and slowness alongside AI-driven productivity * (01:00:15) – Using AI as leverage without losing meaning or direction * (01:05:08) – What AI is revealing about the future of “good work” * (01:07:31) – Creating in a world where value is rapidly shifting * (01:10:53) – How AI is changing the way Tiago writes—and edits—his next book * (01:15:34) – Navigating local and global communities at the same time * (01:18:48) – Creating spaces for real connection and intimacy * (01:21:17) – The deeper principles behind Tiago’s masterminds * (01:23:46) – The loneliness that sparked a desire to bring people together * (01:26:09) – The practices that consistently create the deepest bonds * (01:30:10) – How Tiago is working to make the future more beautiful * (01:31:45) – Who Tiago is becoming Get full show notes and links at https://GoodWorkShow.com [https://goodworkshow.com]. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks [https://www.youtube.com/@barrettabrooks].

Finding Your Voice: How to Outgrow the Need to Prove Yourself with Michael Gendler

This week, I talk with Michael Gendler about what it really takes to communicate at a high level without losing yourself in the process. Michael’s story is more than “learn public speaking.” It’s the journey of a shy Russian immigrant kid with a deep drive to prove himself, who eventually realized that the breakthrough isn’t technique — it’s self-acceptance. We talk about how grit can be both a gift and a cage, why striving doesn’t always lead to happiness, and what happens when you start pursuing excellence from peace instead of pressure. We also unpack Michael’s inside-out approach to speaking: flow over performance, presence over perfection, and why the ability to handle pressure is the real foundation of high-stakes communication. Let’s get to it! In this episode: * (00:00) Intro * (00:33) Freestyle rap, improv, and learning to create on the fly * (03:52) “Mamba mentality”: when proving yourself becomes your identity * (08:27) Redefining happiness when achievement stops working * (13:37) The hidden cost of growing up as an immigrant (and staying shy) * (15:40) The “magic” of unlocking skills people already have * (18:57) Grit is powerful… until it turns into a cage * (37:38) The simple way to end strong (and why people remember the ending) * (44:33) The moment Michael froze in a meeting—and everything changed * (57:52) What Ultraspeaking is really teaching * (01:02:23) Why most speaking advice fails (inside-out vs outside-in) * (01:13:31) The real obstacle isn’t skill—it’s self-consciousness * (01:16:04) What makes a keynote actually work * (01:24:13) Teaching what you see: turning intuition into frameworks * (01:34:41) The Accordion Method, and how great speakers expand + compress ideas * (01:35:57) What Michael is world-class at * (01:40:42) Building a future where people feel more free to express themselves Get full show notes and links at https://GoodWorkShow.com [https://goodworkshow.com]. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks [https://www.youtube.com/@barrettabrooks]. Apply for 1-on-1 Coaching with Barrett: https://barrettbrooks.com/coaching [https://barrettbrooks.com/coaching] Subscribe to Tiny Leadership Lessons: https://barrettbrooks.com [https://barrettbrooks.com]