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. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks. Apply for 1-on-1 Coaching with Barrett: https://barrettbrooks.com/coaching Subscribe to Tiny Leadership Lessons: https://barrettbrooks.com

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. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks. Apply for 1-on-1 Coaching with Barrett: https://barrettbrooks.com/coaching  Subscribe to Tiny Leadership Lessons: https://barrettbrooks.com

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. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

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. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

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. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.Apply for 1-on-1 Coaching with Barrett: https://barrettbrooks.com/coaching Subscribe to Tiny Leadership Lessons: https://barrettbrooks.com

This week, I talk with Parker Palmer in one of the most intimate and expansive conversations I’ve had on Good Work. Parker is an author, activist, and teacher whose ideas have shaped generations. But what moves me most is his honesty. We talk about the winding path that led him from academic life to community organizing to a Quaker learning community where he rebuilt his inner world. We explore discernment, solitude, “Circles of Trust”, and what it means to listen to the voice of your soul—especially in seasons of burnout or heartbreak. At 86, Parker reflects on aging, democracy, vocation, and his belief that the heart can break in two ways: it can shatter, or it can break open into greater capacity. If you’ve ever felt pulled toward a path you “can’t not do,” or if your inner life is asking more of you right now, this conversation is for you. Let’s get to it! In this episode: (00:00) – Intro (00:42) – “Deep in the oatmeal” and the role of humor in a serious life (02:11) – How Parker’s spiritual life slowly took shape (13:08) – Choosing to stay at Pendle Hill—and what that meant for Parker’s family (23:45) – How to tell the difference between a passing idea and a true calling (31:40) – A radically different way of being in community (40:45) – Why presence matters more than fixing (52:35) – The unlikely beginnings of the Center for Courage & Renewal (01:05:17) – What 30 years of building an organization has taught Parker (01:15:06) – Solitude, nature, and marriage as sustaining practices (01:22:31) – Aging, loss, and staying open to what’s next (01:30:39) – The two ways a heart can break Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

This week, I talk with Jeff Sheldon, designer and founder of Ugmonk. Jeff’s story is about more than building a successful brand—it’s about choosing craft over scale and staying true to what you love. We talk about why he turned down Shark Tank at the peak of a viral Kickstarter, how his childhood love of drawing grew into a career in design, and what he’s learned about perfectionism, entrepreneurship, and the emotional cost of mastery. We also explore the quieter parts of his journey: the role his marriage has played, his philosophy of work and life, and how he continues to create intentionally 16 years in. If you’re trying to make meaningful things without losing yourself in the process, this conversation is for you. Let’s get to it. Partner Deals Proper: Save $500 off onboarding when you mention Good Work at https://workwithproper.com. In this episode: (00:00) – Intro (01:55) – Why Jeff turned down Shark Tank (04:35) – The foresight behind saying no (06:59) – Jeff’s philosophy of work and life (10:04) – First steps into design (13:08) – Nurturing creativity (19:13) – Why Jeff doesn’t call himself an entrepreneur (25:49) – A relentless standard of excellence (34:46) – The emotional cost of mastery (42:48) – Doing vs. learning on the internet (46:43) – Partnership and support (54:15) – Keys to a lasting relationship (01:01:00) – Winning his first t-shirt contest (01:04:31) – From $18k goal to $430k raised (01:08:06) – Gather vs. Analog (01:16:08) – Success without wealth (01:22:30) – The tradeoffs of a bespoke business (01:25:03) – Lessons from early struggles (01:32:36) – Holding to an ethos in a bigger culture (01:35:56) – Becoming world-class (01:39:34) – Jeff's most beautiful future (01:40:35) – Who Jeff is becoming Get full show notes and links at https://GoodWorkShow.com.Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

This week, I talk with Dr. Emily Anhalt—a clinical psychologist, founder, and writer who’s spent the past 15 years exploring what it really means to be emotionally healthy. You might know her from her TED Talk or her work at Coa, but in this conversation, we go deeper. We talk about growing up in Silicon Valley, the pressure of being a high-achieving kid, and why so many successful people still carry unresolved grief. Emily shares how ADHD shaped her early life, what led her to leave pre-med for psychology, and how emotional patterns from childhood often resurface in our work and relationships. We also dive into what actually makes therapy effective and why hitting your goals doesn’t always bring peace. If you’ve ever built something meaningful but still felt unsettled, or questioned what’s really driving your ambition, I think this episode will speak to you. Let’s get to it. In this episode: (00:00) - Intro (02:52) - How a beanbag chair and snacks helped Emily unlock her best work (08:01) - Growing up inside the Silicon Valley success machine (09:45) - Why high performers need a different kind of therapy  (11:53) - The story of Emily’s parents and how they ended up in the Valley (13:54) - Reframing ADHD as a strength, not a stigma (16:33) - The early experiences that shaped Emily’s emotional lens (23:40) - How Emily chose psychology—and what kept her going (28:40) - The moment therapy stopped being about symptoms (33:06) - Why grief is a necessary companion to growth (38:21) - The origin story of a company built around emotional fitness (42:30) - What changes when you go from therapist to founder (45:27) - The qualities of high-integrity therapy (51:26) - How Emily knew it was time to write a book (58:20) - What really keeps entrepreneurs stuck—and how to get unstuck (01:02:09) - What it feels like when success leaves you empty (01:05:32) - How to rebuild when your goals stop making sense (01:07:44) - Why achieving meaning isn’t the same as feeling it (01:11:06) - Why therapy often gets harder before it gets better (01:12:47) - Abandoning hard feelings before healing happens (01:13:40) - The isolation of success—and how to find support (01:21:17) - How overachievers get trapped in burnout (01:29:26) - Healthy ways to process anger (01:33:46) - What makes Emily world-class? (01:34:09) - Emily's most beautiful future (01:34:49) - Who Emily is becoming Get full show notes and links at https://GoodWorkShow.com.Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

This week, I talk with Mark Manson—best known for The Subtle Art of Not Giving a Fuck—about what success really costs and why it often leaves us wanting more. Mark and I go deeper than I’ve heard him go before: we explore his upbringing, the complex role faith and community have played in his life, and how he’s learned to follow his internal compass—even when it meant walking away from huge opportunities. After climbing to the top of the publishing world and getting a taste of Hollywood, Mark has returned to where he started: creating online for the joy of it. This conversation is about more than career moves—it’s about identity, meaning, and the choices that define a thoughtful life. If you’ve ever achieved a big goal and asked, “Now what?”—this one’s for you. Let’s get to it. In this episode: (00:00) – Intro (02:32) – The golden egg mindset that changed Mark's career (04:49) – Lessons from a “high-volatility” childhood (09:46) – Mark’s secret to depth (and viral hits) (13:51) – Losing faith—and what Mark misses most (17:58) – The loneliness no success can solve (28:09) – What real friendship looks like (31:19) – How to go deeper with the people who matter (36:51) – What happens after success? (41:47) – Chasing Hollywood—and hitting a wall (45:38) – Why Mark turned away from traditional media (49:23) – The lingering pull of prestige and the trap of status (50:48) – Why Mark is still in LA—and what he found there (51:40) – How to know what to say yes to (and what to walk away from) (56:27) – What Mark is optimizing for today (59:02) – The one thing Mark wants to be excellent at (01:02:35) – The “shit sandwich” Mark’s happy to eat (01:03:58) – Turning down a seven-figure book deal (01:18:28) – YouTube vs writing (01:21:34) – How much thought goes into Mark’s content (01:25:04) – Is the business sustainable? (01:27:03) – Reinventing the podcast—again (01:33:19) – Mark’s most beautiful future (01:36:33) – Who Mark is becoming Key Takeaways Be the goose, not the egg hunter. Rather than chasing after “golden eggs” of success, become the kind of person who can generate them consistently. Mark’s father taught him that real security and fulfillment come from developing your own capacity to create value again and again—not from trying to protect or hoard what you’ve already made. Choose depth over status when building community. Mark reflects on how true community—like that found in religious, family, or workplace settings—is built on commitment and shared legacy. Recreational groups and hobbies, while enjoyable, often lack the deeper sense of belonging. If you’re feeling lonely or disconnected, consider what you’re willing to commit to. Build a life that prioritizes fun over status. After years of high-profile projects and burnout, Mark realized that chasing prestige wasn’t worth the cost. His new rule: if it’s not fun, he doesn’t do it. With success comes more invitations to chase status—but the most fulfilled people are those who stay grounded in what brings them joy and meaning. Don’t confuse cultural clout with real impact. Despite already having a massive online audience, Mark admits being drawn to traditional media for its perceived prestige. He ultimately found that building directly with his audience—via his creator business and YouTube—was more rewarding and impactful. Recognition is nice, but it shouldn’t dictate your creative choices. The best relationships are honest, non-transactional, and earned through time. Deep friendships grow through vulnerability, shared values, and a willingness to say the hard thing. In a world increasingly shaped by status, the relationships that matter most are built on trust, not utility. Get full show notes and links at https://GoodWorkShow.com. Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.

This week, I talk with someone who’s been on my dream guest list since day one—Ami Vitale. Ami is a National Geographic photographer and filmmaker whose work has taken her from war zones to wildlife sanctuaries, always in pursuit of the deeper story. But this conversation goes far beyond her remarkable resume. We talk about how picking up a camera transformed her from a shy, introverted kid into one of the world’s most powerful visual storytellers. Ami opens up about what it really means to bear witness, the emotional cost of telling the truth, and why she eventually turned her lens away from conflict and toward hope, healing, and our connection with the natural world. This episode is about dignity, presence, and the quiet leadership that comes from listening well and seeing clearly. I promise, you’ll never look at a photograph the same way again. In this episode: (00:00) - Intro (03:06) - How picking up a camera gave Ami a voice (05:06) - Why introverts might see the world more clearly (06:21) - Knocking on doors with a camera (12:32) - Wanting to be a photographer—and being told “no” (16:27) - Leaving a steady job to bet on herself (23:30) - What war zones taught Ami about storytelling (29:26) - The moment Ami knew she had to walk away from war zones (38:08) - From grief to hope: finding a new kind of story (51:26) - The story that changed everything (59:42) - Why wildlife stories are human stories (01:07:22) - One image that moved the world: Steve Winter’s P-22 (01:13:41) - Capturing moments with dignity and depth (01:15:59) - The relationships behind the photographs (01:25:51) - Reflecting on a life of good work (01:28:02) - Barrett on the fears and hopes behind Good Work Get full show notes and links at https://GoodWorkShow.com.Watch the episode on YouTube: https://www.youtube.com/@barrettabrooks.