The Anxious Achiever

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.

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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...

What happens when the version of success you built your life around suddenly stops working? In this episode, I sit down with Meredith Arthur to talk about ego death, anxiety, nervous system healing, and what it means to let go of the need to prove yourself. We talk about career humiliation, social media comparison, identity, chronic pain, and the process of realizing that the things that once made you feel successful or special no longer fit who you are becoming. Meredith shares how ego death is about surrendering control and accepting that your worth cannot come from achievement, productivity...

Think imposter syndrome means something is wrong with you? Think again. In this episode, Basima Tewfik shares research on anxiety, self-doubt, and the traits high achievers often try to “fix.” She breaks down how workplace imposter thoughts can actually make you more effective, especially when it comes to how you show up with others. We also talk about why people who experience imposter thoughts are often better listeners, more thoughtful collaborators, and more attuned in conversations. Remember, not everything you label as a flaw is actually holding you back.

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Feeling unsure about your role in a world where AI seems to know more than you do? In this episode, Charlene Li is back to talk about how the most effective leaders today are letting go of the need to have all the answers and instead stepping into curiosity, experimentation, and honest leadership. Charlene shares her 90-day AI framework, why so many companies are stuck in pilot mode, and how to move your team from fear into confidence faster than you think. Get ready to lead through AI change without needing all the answers.

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What if burnout isn’t something you fix with better habits, but something built into the way we work? In this episode, I’m bringing back one of my favorite conversations because it gets at something I think we still don’t talk about enough. I talk with Rita McGrath, Poornima Luthra & Andrew Barnes about what actually makes work feel sustainable and human, why getting people back into the office doesn’t fix anything, how lack of control and fairness quietly drive stress, and why so many well-intentioned solutions miss the mark. Get ready to rethink burnout and see what act...

What if the difference between reacting and responding was just a few seconds? In this episode, I sit down with executive coach Dina Denham Smith to talk about what really happens when you get triggered at work and how to handle it. Dina breaks down a framework to help you understand what emotions actually are, how they show up in your body, and how to interrupt the automatic reaction cycle. Tune in to learn how to pause in the moment, regulate your nervous system, and respond with clarity instead of stress, anxiety, or overwhelm.

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What if the habits you rely on to cope with anxiety are keeping you stuck? In this episode, we explore what it really means to be “mentally healthy” and why most of us were never given the language or tools to get there. Kent Coules shares his story of high-functioning alcoholism and what happened when he stopped drinking after decades of using it to manage anxiety. We talk about why so many high achievers rely on coping mechanisms like alcohol, overwork, or constant problem-solving, and more. I also speak with educator Donna Volpitta about mental health literacy and why unde...

What if better performance at work didn’t come from pushing harder, but from being more honest? In this episode, Dan Simons shares how he built a $100M+ restaurant group by doing something most leaders still resist. Dan explains how honesty at work actually helps people show up more present, make better decisions, and perform at a higher level. We also talk about how you can get better results, stronger retention, and more focused teams by creating a workplace where people don’t have to hide what’s going on with them. Tune in to discover how to turn radica...

Is your overthinking actually helping you or draining your energy? In this episode, I talk with Meredith Arthur, Chief of Staff of the Pinterest Innovation Lab, about what it means to live with anxiety you don’t even recognize. Meredith shares how anxiety shows up in unexpected ways, from physical symptoms like migraines to subtle patterns like overworking and lack of boundaries. We talk about what happens when you push through without understanding your internal signals, how overthinking can disguise itself as productivity, and MORE. Tune in to learn how to step out of overthinking loops and build a he...

What if the qualities that make you successful are the ones keeping you from getting the help you need? In this episode, I talk with General Gregg Martin, a retired U.S. Army two-star general, about what it’s like to lead at the highest levels while living with bipolar disorder. Greg shares how the same energy, drive, and creativity that propelled his career were also symptoms of a condition that went undiagnosed for decades. We also dive into the cost of high performance, why success can mask serious mental health struggles, and how bipolar disorder often shows up in...

What if your anxiety isn’t just something you feel, but something you’ve been practicing? In this episode, I talk with psychiatrist Dr. Jud Brewer and Charles Duhigg about the science behind why anxiety sticks, how your brain confuses worrying with problem-solving, and why willpower alone isn’t enough to change your patterns. We break down how anxiety can become a habit loop and why so many high achievers unknowingly reinforce it through overwork, worry, and constant mental effort. Tune in to learn how to replace unhelpful patterns with ones that actually support your focus, energy, and mental health...

What if success isn’t about fitting in, but about creating something that fits you? In this episode, I talk with astrophysicist Dr. Jessica Schonhut Stasik about what it takes to succeed when your brain doesn’t match the systems around you. Jessica shares her experience of being late-diagnosed with autism and ADHD, the burnout and rejection that nearly ended her path in science, and the moment someone recognized her potential when she couldn’t see it herself. We also talk about what it looks like to design your work around how you think, not how you’re expected to think...

Are you actually more productive when you work longer hours or just more exhausted? In this episode, I talk with Christopher Barnes, Professor of Management and the Michael G. Foster Endowed Professor at the Foster School of Business at the University of Washington, about the ingrained belief that sacrificing sleep is the price of success and why that belief is costing you more than you think. Chris shares how leaders create “sleep-deprived cultures” through their behavior, from late-night emails to rewarding constant responsiveness. We break down what really happens to your brain when you’re sleep-deprived, the vicious cycle betwee...

What if the problem isn’t your focus, your discipline, or your productivity, but the way you’ve been taught to work? In this episode, I talk with Ennis Olson, Global Innovation Lead at Google, about what changes when you truly understand how your brain operates. Ennis shares how his late diagnosis of ADHD and autism helped him make sense of a career built on creativity, curiosity, and constant reinvention and why those same traits can create friction in traditional work environments. We break down how to navigate days when your brain won’t cooperate, how to design your work a...

Is entrepreneurship making your anxiety worse, or is it actually revealing something deeper about how you work and cope? In this episode, I talk with entrepreneur Chris Brogan and writer Ada Calhoun about the complicated relationship between freelancing, mental health, and the illusion of stability. Chris shares what it’s really like to build a career while living with depression, why success and struggle can coexist, and how he’s learned to “negotiate” with his mental health instead of letting it define him. Ada also breaks down the emotional and financial realities of freelance life, and the fears many of us ca...

What if happiness isn’t something you feel, but something you learn? In this episode, I talk with Dr. Arthur Brooks about why anxious achievers often struggle with happiness, and how emotions are data we can use to build better lives. Arthur shares how our emotional “profiles” shape leadership, why anxiety is really unfocused fear, and how to turn late-night spirals into something actionable. We also dive into what’s broken about how we live today and why that’s making it harder to find meaning. Get ready to rethink happiness, understand your anxiety, and learn how to build a life tha...

Is your anxiety something you need to eliminate or something you need to understand better? In this episode, I talk with psychologist Alice Boyes about the everyday patterns that can make anxiety worse. Alice shares why trying to control anxiety often backfires and how common traps like perfectionism, rumination, avoidance, and impulsive decision-making keep anxious high achievers stuck. We also break down ways to create distance from anxious thoughts, handle feedback without spiraling, and make better decisions. Tune in to learn how to work with your anxiety instead of constantly fighting it.

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Are today’s college students really in a mental health crisis, or are you misunderstanding what it’s always been like to grow up? In this episode, I talk with Dr. Alexis Redding, a Harvard developmental psychologist and editor of Mental Health in College. Dr. Redding shares that feelings like anxiety, loneliness, and uncertainty are often normal parts of growing up, especially during major transitions like starting college or entering the workforce. We also talk about what has actually changed for young people, from rising college costs and financial stress to the complexity of modern career paths and what hasn...

What if the anxiety you feel walking into a meeting, networking event, or conference isn’t a personal flaw, but social anxiety? In this episode, clinical psychologist Dr. Ellen Hendriksen talks about the psychology behind social anxiety and why avoidance keeps it alive. She breaks down the belief at the core of social anxiety and tools to challenge anxious thoughts, manage shame, and build confidence even when anxiety is still present. Then, entrepreneur and former LinkedIn executive Arvind Rajan shares what it’s like to build a successful career while living with social anxiety. Tune in to learn how to m...

What if the skill that makes you a stronger leader is the same skill that protects free speech? In this episode, I’m joined by Greg Lukianoff, First Amendment attorney, to talk about emotional reasoning, why discomfort isn’t the same as danger, and what happens when we start treating speech as violence. Greg shares how his own battle with depression and suicidal thoughts led him to CBT and how learning to question his thoughts transformed both his mental health and his leadership. Get ready to rethink what makes us mentally strong and why protecting speech may also mean prot...

What if the stress you feel at work isn’t just about deadlines or difficult bosses, but about your attachment style? In this episode, I’m joined by Dr. Jack Hinman, founder and executive director of Engage Young Adult Transitions, to talk about how the patterns you develop in early childhood show up in your leadership, ambition, anxiety, and burnout. We break down secure, preoccupied, and avoidant attachment styles, how they influence the way you handle feedback and uncertainty, and why your “relationship operating system” doesn’t stop at home. Tune in to understand your patterns and learn how to lead fr...

What if the biggest obstacle to your performance isn’t your workload or your leadership challenges, but your own mind? In this episode, I sit down with Shirzad Chamine, founder and CEO of Positive Intelligence, to talk about the habits many anxious achievers rely on to succeed (i.e. hypervigilance, perfectionism, control, and constant striving), but that can drain energy, clarity, and confidence over time. Shirzad breaks down how overused strengths turn into self-sabotage, and the 10-second practice that helps you shift from stress and reactivity into calm, focused leadership. Get ready to learn how to work with your mi...

Do difficult conversations keep you up at night, or do they make you want to avoid conflict altogether? In this episode, I sit down with workplace conflict expert Amy Gallo, author of Getting Along, to talk about how healthy conflict actually strengthens trust, decision-making, and leadership confidence. We dive into how our brains get emotionally hijacked during difficult conversations, how avoidance creates “conflict debt,” and why learning to stay grounded in discomfort may be one of the most important leadership skills we can build. Tune in to learn how to face conflict calmly to reduce anxiety and make you a mo...

For years, leadership has been associated with charisma, confidence, and speaking the loudest in the room. But what if some of the most powerful leadership traits are actually quiet ones? In this episode, I’m joined by leadership expert and author Jennifer Kahnweiler to talk about the strengths of introverted leaders. We break down the misconceptions around introversion, why many successful leaders are secretly introverted, and how preparation, listening, and thoughtful presence can become leadership superpowers. Tune in to rethink what effective leadership looks like and learn how quiet strengths can create lasting influence.

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