The Anxious Achiever

Which conversations have you been avoiding at work? In this classic episode, I sit down with Death, Sex & Money host Anna Sale to talk about why conversations about money, mental health, and personal struggles still feel so difficult in many workplaces. We discuss the shame that often shapes our financial decisions, how your upbringing influences the way you negotiate and advocate for yourself, and what to consider before telling your boss you're struggling. Anna also shares advice for setting boundaries, asking for what you need, and creating more honest relationships at work. Get ready to rethink the conversations that...

Would you take four months away from work? Have you ever wondered who you'd be without your job for a while? In this episode, I sit down with Harvard Business School lecturer and The Sabbatical Project founder Dennis “DJ” DiDonna to talk about why many of us keep pushing until burnout forces us to stop, how intentional time away creates space to reflect on what really matters, and why rest isn't about doing nothing. DJ also shares ways to plan a sabbatical, navigate the uncertainty that comes with slowing down, and return with a stronger sense of purpose. Get read...

Could the way you think about money have more to do with your childhood than your bank account? In this episode, I sit down with personal finance expert Shannah Game to talk about why your relationship with money is often shaped long before you earn your first paycheck. We dive deep into money trauma, the stories we attach to spending and saving, and how those patterns influence our careers, relationships, and sense of self. Shannah also shares ways to respond differently to financial triggers and build healthier habits that align with the life you want. Get ready to rethink...

How do you lead when the future refuses to give you certainty? In this episode, I sit down with leadership experts Scott D. Anthony, Lisa Kay Solomon, and Chris Shipley to talk about what leadership looks like when uncertainty becomes the norm. We dive into making decisions without having all the answers, why leaders need to let go of the illusion of certainty, and how curiosity, agency, and even play can help teams adapt to change. We also share ways to navigate uncertainty, manage anxiety, and create workplaces where people feel empowered to do their best work. Tune in...

Can loving your work make burnout more likely? In this episode, I sit down with Harvard Business School professor Jon Jachimowicz to talk about the downside of passion at work. Jon shares why passion isn't something you either have or don't have, but something that rises and falls over time. We also talk about why passionate employees often overwork, skip recovery, and become vulnerable to burnout, how organizations unintentionally exploit passion, and why leaders need a better strategy for helping people sustain meaningful work over the long term. Tune in to rethink what it really means to follow your...

How do you ask for what you need at work when the system still makes disability feel risky to name? In this episode, I sit down with attorney, author, and neurodiversity advocate Haley Moss to talk about the reality of being neurodivergent at work. Haley breaks down what the ADA actually protects, how reasonable accommodations work in practice, and why disclosure is still such a fraught decision for so many people. We also talk about masking, internalized ableism, the pressure to frame neurodivergence as a “superpower,” and MORE. Get ready to rethink disclosure, disability, and what real inclusion at work...

How much of yourself should work be allowed to cost you? In this episode, I sit down with author and former Deloitte partner Deepa Purushothaman to talk about what happens when ambition, bias, and chronic overwork are carried in the body. Deepa shares how a major health crisis forced her to rethink the way she worked, the way she defined success, and the ways women of color are taught to survive in workplaces that were never built for them. We talk about masking, hypervigilance, power, and why so many women can appear successful on paper yet feel depleted, silenced...

How do you stay grounded when technology is changing work faster than any of us can keep up with? In this episode, I sit down with journalist and CNN contributor Jacob Ward to talk about the emotional and psychological impact of living and working alongside increasingly powerful technology. Jacob shares why he believes the bigger threat isn’t just automation, but the way these systems shape your behavior, attention, and relationships at work. We talk about loneliness, agency, management, the pressure to keep producing, and what happens when more of our thinking gets handed over to machines. Get ready to...

Can achievement become a coping mechanism? In this classic episode, I sit down with entrepreneur, investor, and former Facebook and Twitter growth leader Andy Johns to talk about the connection between childhood trauma, anxiety, achievement, and self-worth. Andy shares how growing up with instability, loss, and trauma shaped his relentless drive to succeed, why panic attacks eventually forced him to confront his mental health, and how years of healing helped him realize that achievement and self-love are not the same thing. We also dive into PTSD, entrepreneurship, intrusive thoughts, overwork, and why so many successful people struggle to slow...

How do you build a meaningful career when AI is rewriting the future of work? In this episode, I sit down with New York Times investigative reporter Jodi Kantor to talk about why so many young professionals feel discouraged about the future, and how digital shifts are reshaping our modern workplaces. Jodi shares how she survived getting fired from her college paper and dropping out of law school, and how those setbacks paved her way back to journalism. We also dive deep into the realities of AI-driven hiring, the loss of workplace autonomy, and the formula for reclaiming your...

What if achievement doesn't have to come from suffering? I sit down with Congressman Adam Smith to talk about the complicated relationship between anxiety, achievement, and self-worth. Adam shares his journey through panic attacks, psychotherapy, chronic pain recovery, and the difficult work of building self-worth that isn't tied to performance. We also dive into why so many high achievers believe anxiety is the price of success, how trauma and stress shape the way we lead, and what happens when you stop using fear and self-criticism as your primary source of motivation. Get ready to discover a healthier path to...

Why does modern work feel impossible for so many families? In this episode, I talk with sociologist, former Navy pilot, and workplace researcher Dr. David Smith about why so many modern couples feel trapped in work-life conflict, how to navigate the structural stress of dual-career life, and the realities of modern caregiving. David breaks down the "Lead-Follow" relationship strategy used by highly successful couples. We also dive into the anxieties men face surrounding workplace allyship, why traditional mentorship scripts are broken, and how organizations must design work for a cross-generational workforce. Tune in to learn about the pressures modern...

How much of your life is being driven by fear without you even realizing it? In this episode, I sit down with Harvard Business School lecturer, entrepreneur, and former executive Martin Sinozich to talk about the pressure high achievers carry to prove themselves, stay successful, and never disappoint anyone. Martin shares about divorce, identity, workplace culture, and the freedom that comes from letting go of perfection and learning to trust yourself instead. We also break down the imposter feelings in elite environments, the anxiety of always needing to be “right,” and why so many ambitious people feel like they don’...

Have you started expecting therapy to do too much? In this episode, I sit down with therapist and writer Megan Cornish to talk about the pressure we place on therapy to solve problems that may actually stem from isolation, lack of community, and modern life itself. Megan shares that many of the struggles we now label as “mental health problems” were once held by friends, neighbors, faith communities, and everyday human relationships. She also breaks down ACT therapy exercises that can help you hold painful thoughts more lightly and reconnect to your values instead of chasing constant happiness. Get read...

This week we’re sharing a special episode from our friends at How To!, the 2026 Ambie Award-nominated “Best Personal Growth Podcast” that’s back with a new host and new topics to fuel your curiosity.  Each week on How To!, award-winning journalist Mike Pesca tackles a listener’s question – on topics ranging from travel and finance to health and relationships – with help from world-class experts who actually know what they're talking about. Think of it as eavesdropping on someone else's therapy session, without the co-pay or awkward silence.  And today, we’re sharing their recent episode “How To Ta...

Why do so many capable, high-performing people end up exhausted, and emotionally drained even when they’re doing everything “right”? In this episode, I sit with psychologist Dr. Thomas Greenspon to talk about perfectionism, shame, and self-worth. Thomas breaks down why perfectionism isn’t actually about excellence, then entrepreneur Eleanor Beaton shares how perfectionism shaped her leadership, ambition, and identity and what changed when she stopped chasing perfection and started embracing wholeness instead. Get ready to rethink the way you work, care for others, and define success. Check out our sponsors: Shopify - Sign u...

What if the problem isn’t your brain, but the systems you’ve spent your life trying to fit into? In this episode, I sit down with David Flink, founder of the Neurodiversity Alliance. We talk about what it means to navigate work, leadership, and identity as a neurodivergent person. David shares how he learned to stop forcing himself into systems that didn’t fit, how metacognition changed his life, and why today’s younger workers are approaching neurodivergence differently. Get ready to build your life around your strengths instead of constantly trying to fix your weaknesses.  <...

Why does AI feel so personal to so many professionals right now? In this episode, I talk with Nilay Patel, editor-in-chief of The Verge, about the emotional side of artificial intelligence and why so much of the fear around AI may actually be about work itself. We dive into how layoffs, shrinking trust in employers, “good enough” automation, and constant technological change are reshaping the way ambitious people think about stability, creativity, and their future careers. Nilay shares why humans naturally form emotional relationships with technology, why AI companions and chatbots can feel strangely comforting, and why today’s AI hyp...

What happens when a leader realizes the traits they spent years hiding are actually their greatest strengths? In this episode, I talk with Amy Streater Wilson, Chief Marketing Officer, who was diagnosed later in life with ADHD and autism. Amy shares the shame and confusion that can come with a late diagnosis, from struggling with “boring” tasks to feeling overwhelmed by sensory input and social dynamics at work. We also dive into negotiation and selling through a neurodivergent lens, why many neurodivergent people struggle with traditional power dynamics, and how understanding neurodivergence can transform the way you lead, negotiate, comm...

What happens when stress, uncertainty, and lack of control start to take over your brain? In this episode, I sit down with renowned behavioral economist Dan Ariely to talk about resilience, learned helplessness, anxiety, and why so many people feel overwhelmed right now. Dan shares how surviving severe burns, years in the hospital, and later facing conspiracy theories and death threats shaped his understanding of stress, resilience, and human behavior. We also dive into why uncertainty at work feels so psychologically destabilizing, how scarcity and anxiety reduce our mental capacity, why humans look for villains during stressful times, and...