Leading When Nothing Feels Certain With Scott D. Anthony, Lisa Kay Solomon, and Chris Shipley

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 could change your work and your life. Check out our sponsors: Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever Chime - Head to chime.com/achiever to sign up Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today. In this Episode, You Will Learn 00:00 The value of talking about hard things. 05:30 Which conversations are still taboo at work? 08:15 The shame that shapes our relationship with money. 12:15 Anna's experience with money anxiety. 15:45 The money mindset behind anxious achievers. 18:00 How do you negotiate without losing yourself? 20:30 How to set boundaries without apologizing. 22:45 A test before saying yes. 23:45 Negotiation advice for the start of your career.  27:30 Should you tell your boss you're struggling? 31:45 Choosing your wellbeing over your paycheck. Resources + Links Learn more about Anna Sale HERE Get a copy of Anna’s book Let's Talk About Hard Things HERE Listen to Death, Sex & Money HERE Get a copy of my book - The Anxious Achiever Watch the podcast on YouTube  Find more resources on our website morraam.com Follow Follow me: on LinkedIn @morraaronsmele + Instagram @morraam Follow Anna: on LinkedIn @annasale + Instagram @annasalepics

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 ready to rethink time off as an investment in the life and career you want to build. Check out our sponsors: Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever Chime - Head to chime.com/achiever to sign up Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today. In this Episode, You Will Learn 00:00 A new way to think about time away from work. 05:30 How sabbaticals create space for renewal instead of escape. 07:15 What is a sabbatical? 10:00 How burnout led DJ to rethink the life he was building. 15:00 Why achievement often comes at the expense of the people who matter most. 21:45 What are the benefits of stepping away from work? 26:45 When is the perfect time for a sabbatical? 32:15 What are the 3 types of sabbatical takers? 36:00 Why reconnecting with your craft can restore creativity. 41:00 How do you give yourself permission? 46:00 Are sabbaticals always relaxing? 49:00 How stepping away from work can make you a better leader. 53:00 Why taking time off is an investment, not an escape. 57:30 DJ's advice for planning your first sabbatical. Resources + Links Learn more about DJ DiDonna HERE Pre-order a copy of DJ DiDonna’s book Big Time Off HERE Learn more about The Sabbatical Project HERE Get a copy of my book - The Anxious Achiever Watch the podcast on YouTube  Find more resources on our website morraam.com Follow Follow me: on LinkedIn @morraaronsmele + Instagram @morraam Follow DJ DiDonna on LinkedIn: @djdidonna

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 your relationship with money. Check out our sponsors: Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever Chime - Head to chime.com/achiever to sign up Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today. In this Episode, You Will Learn 00:00 How childhood experiences shape your money habits and beliefs. 05:00 Why money is about so much more than dollars and cents. 07:15 How your money story influences your work and relationships. 12:00 A question that helps uncover your beliefs about money. 16:15 What is money trauma? 19:15 How to recognize your financial triggers before they take over. 22:00 How to interrupt unhealthy money habits with healthier thought patterns. 24:45 An exercise for changing your emotional response to money. 26:15 How do you build systems that reduce financial anxiety? 28:30 Why creating a regular "money date" builds confidence instead of fear. 30:00 What is financial self-actualization? 33:00 The 100-day challenge that helps you rethink every financial decision. Resources + Links Learn more about Shannah Game HERE Get a copy of Shannah’s book Unraveling Your Relationship with Money HERE Get a copy of my book - The Anxious Achiever Watch the podcast on YouTube  Find more resources on our website morraam.com Follow Follow me: on LinkedIn @morraaronsmele + Instagram @morraam Follow Shannah on Instagram: @shannahgame

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 to discover why the future belongs to leaders who are willing to learn, adapt, and grow. Check out our sponsors: Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever Chime - Head to chime.com/achiever to sign up Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today. In this Episode, You Will Learn 00:00 Why today's leaders need clarity instead of certainty. 03:15 What effective leadership looks like in an era of constant disruption. 08:15 Why clarity matters more than having all the answers. 11:00 Why learning often requires unlearning first. 12:45 How can you become more comfortable with uncertainty? 20:00 How mindfulness helps leaders stay grounded under pressure. 22:00 Why is agency one of the most important leadership skills today? 30:00 Why anxiety often leads people to avoid the work that matters most. 32:30 How to build psychological safety when everything feels uncertain. 39:00 How to create more joy, connection, and creativity at work. 44:45 Why appreciation and gratitude are essential for a thriving team. 53:45 Who are you when you take your job title away? Resources + Links Get your copy of Leading for Tomorrow HERE Get a copy of my book - The Anxious Achiever Watch the podcast on YouTube  Find more resources on our website morraam.com Follow Follow me: on LinkedIn @morraaronsmele + Instagram @morraam Follow Scott on LinkedIn: @scottdanthony Follow Lisa on LinkedIn: @lisakaysolomon Follow Chris on LinkedIn: @cshipley9

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 passion without sacrificing your well-being. Check out our sponsors: Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today. In this Episode, You Will Learn 00:00 Why following your passion isn't always the path to sustainable success. 04:00 How Jon's own loss of passion inspired his research. 09:00 Why passion can become one of the biggest drivers of burnout. 12:15 How passionate employees unknowingly skip recovery and overextend themselves. 15:00 Why do client and societal expectations trap high achievers into overperforming? 17:00 How do workplaces systematically confuse extroversion with passion? 23:15 Why performing passion can become emotionally exhausting. 27:15 How managers should lead passionate employees differently. 31:00 Why organizations often exploit passionate workers without realizing it. 35:15 Why current promotional career paths are broken for passionate workers. 39:15 How can companies help employees sustain passion? 43:45 The 3 different types of burnout and why they need different solutions. 45:30 Ways to recover when burnout comes from a loss of self-efficacy or cynicism. Resources + Links Get a copy of my book - The Anxious Achiever Watch the podcast on YouTube  Find more resources on our website morraam.com Follow Follow me: on LinkedIn @morraaronsmele + Instagram @morraam

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 should actually look like. Check out our sponsors: Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever Chime - Head to chime.com/achiever to sign up Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today. In this Episode, You Will Learn 00:00 Why talking about neurodivergence at work is still so loaded. 03:00 How Haley’s career shifted after becoming known as Florida’s first openly autistic attorney. 08:00 Why telling your own story matters more than letting other people simplify it for you. 11:30 What the ADA protects for neurodivergent employees at work. 13:30 How to understand reasonable accommodations and what counts as “essential functions” of a job. 16:30 What are the myths people still believe about workplace accommodations? 22:15 Why neurodivergent workers are often expected to do the emotional labor of culture change. 25:45 What happens when an accommodation exists on paper but not in practice? 29:30 What the “double empathy problem” shows about communication between neurotypical and neurodivergent coworkers. 35:00 What to do if you’re neurodivergent but don’t identify as disabled or don’t want to disclose formally? 39:15 What do you think about disclosing to get legal protection versus advocating informally? 41:45 How framing neurodivergence as a strength can be both empowering and strategic. 49:30 How meeting other neurodivergent people can shift your sense of identity and belonging. 50:45 Why Haley is intentionally expanding beyond autism as the center of her public identity. 53:45 How to make work feel safer for different brains and bodies. Resources + Links Get a copy of Haley Moss’s book, The Young Autistic Adult's Independence Handbook HERE Learn more about Haley Moss HERE Get a copy of my book - The Anxious Achiever Watch the podcast on YouTube  Find more resources on our website morraam.com Follow Follow me: on LinkedIn @morraaronsmele + Instagram @morraam Follow Haley: on LinkedIn @haleylmoss + Instagram @haley.moss

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, and disconnected from themselves. Get ready to challenge your assumptions about power, productivity, and the stories corporate culture has taught you to believe about yourself. Check out our sponsors: Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever Chime - Head to chime.com/achiever to sign up Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today. In this Episode, You Will Learn 00:00 What happens when workplace stress gets carried in the body? 04:45 Why high achievers often learn to ignore their bodies. 08:45 How illness can push you to rethink your purpose and priorities. 12:00 How to recognize when your body is sending you a warning sign. 16:00 How women of color can end up in a constant state of hypervigilance. 22:15 What happens when women report racism or bias at work? 24:45 The workplace delusions many women are taught to believe in order to survive. 28:30 Why have so many women been taught to see power as something aggressive or unsafe? 31:15 What does it actually mean to “shed” the beliefs that no longer serve you? 32:30 How to identify the old messages that still drive your anxiety and self-doubt. 36:15 Why toxicity at work isn’t just a mental health issue. 37:45 How to protect yourself while still pursuing ambition and success. 39:30 How redefining success can change the way you work and live. Resources + Links Get a copy of Deepa Purushothaman’s book, The First, the Few, the Only: How Women of Color Can Redefine Power in Corporate America HERE Learn more about Deepa Purushothaman HERE Get a copy of my book - The Anxious Achiever Watch the podcast on YouTube  Find more resources on our website morraam.com Follow Follow me: on LinkedIn @morraaronsmele + Instagram @morraam Follow Deepa: on LinkedIn @deepapuru + Instagram @deepa.puru

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 rethink productivity, management, and the value of human judgment. Check out our sponsors: Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever Chime - Head to chime.com/achiever to sign up Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today. In this Episode, You Will Learn 00:00 What is AI doing to your mind and mood? 04:45 Why technology is really a story about human behavior. 09:00 How “fast thinking” makes us easier to manipulate. 13:00 What an AI co-parenting tool reveals about convenience, conflict, and control. 15:15 Can technology really support mental health without replacing human care? 17:45 Why the systems built to help us often prioritize engagement instead. 20:00 What a more “human-free” workplace could mean for all of us. 26:45 The human skills at work that are most at risk of disappearing. 30:00 How to deal with the helplessness so many people feel about the future of work. 36:00 The Pope’s warning about AI, dignity, and human value. 43:30 Why trust matters so much when institutions are under pressure. 47:45 How to decide when to use AI and when to resist it. 50:00 Why the pressure to produce more can quietly trap high achievers. 54:30 How do you stay relevant without giving up your standards? Resources + Links Visit Jacob Ward’s website HERE Get a copy of Jacob’s book, The Loop: How Technology Is Creating a World Without Choices and How to Fight Back HERE Get a copy of my book - The Anxious Achiever Watch the podcast on YouTube  Find more resources on our website morraam.com Follow Follow me: on LinkedIn @morraaronsmele + Instagram @morraam Follow Jacob: on YouTube @byjacobward + Instagram @byjacobward

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 down even after they've reached their goals. Tune in to learn why healing is the most important achievement of all. Check out our sponsors: Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever Chime - Head to chime.com/achiever to sign up Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today. In this Episode, You Will Learn 00:00 What’s the connection between achievement and self-worth? 05:00 What "growth" really means in the startup world. 07:15 Why entrepreneurs are more likely to struggle with mental health conditions. 08:45 How anxiety can fuel exceptional performance and success. 15:00 Why speaking publicly about mental health felt so risky. 18:30 What are intrusive thoughts? 20:30 How childhood trauma can shape adult anxiety and depression. 25:15 The childhood experiences that contributed to Andy's PTSD. 30:15 When does achievement become an addiction? 34:15 How to recognize when overachievement is masking emotional pain. 35:45 Why mental health is about more than brain chemistry. 36:45 What is the biopsychosocial model of mental health? 38:15 How your experiences shape the way you think, feel, and live. Resources + Links Read Andy's writing at https://andyjohns.substack.com Get a copy of my book - The Anxious Achiever Watch the podcast on YouTube  Find more resources on our website morraam.com Follow Follow me: on LinkedIn @morraaronsmele + Instagram @morraam Follow Andy: on LinkedIn @andrewjohns + Substack @cluesdotlife

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 agency. Get ready to rethink what it truly takes to protect your career in a rapidly changing world. Check out our sponsors: Shopify - Sign up for a $1 per month trial, just go to shopify.com/anxiousachiever Chime - Head to chime.com/achiever to sign up Monarch - Use code ACHIEVER at monarch.com to get 50% off your first year Physician’s Choice - Use code PCPODCAST10 at physicianschoice.com to get 10% off your entire order Whatnot - Get free shipping on your first order. Just search W-H-A-T-N-O-T in the app store and start scoring amazing deals Pebl - Take advantage of Pebl’s limited-time offer before it’s gone. Visit hipebl.ai today. In this Episode, You Will Learn 00:00 What Jodi Kantor believes is one of the most important ingredients for a meaningful career. 04:15 How do you think about hope? 05:45 The question that Columbia students wanted answered during a year of campus turmoil. 09:45 How technology has reduced worker autonomy over the last decade. 14:45 Why AI is making the hiring process feel increasingly impersonal. 17:00 How do you define craft? 19:45 What's the relationship between strengths, interests, and building expertise over time? 24:00 Why career setbacks are often essential parts of growth. 27:00 How to stay focused on the work instead of public praise or criticism. 30:00 How to identify the problems, opportunities, or needs you want your work to serve. 31:45 Why AI won't eliminate the need for fresh talent and new ideas. 33:00 What colleges can do to better prepare students for today's workforce. 35:15 How universities can better help students find their life's work. 38:00 Jodi's advice for anyone starting their career today. Resources + Links Get a copy of Jodi’s book, How to Start: Discovering Your Life’s Work HERE Get a copy of my book - The Anxious Achiever Watch the podcast on YouTube  Find more resources on our website morraam.com Follow Follow me: on LinkedIn @morraaronsmele + Instagram @morraam Follow Jodi: on LinkedIn @jodikantor + Instagram @jodikantor