Taste might be the most valuable skill in business today. But what is it, exactly? And how do you know if you have it? In this episode, Jessi Hempel sits down with legendary retail executive Mickey Drexler to explore the magic behind great taste—and how it shapes products, brands, and careers. Mickey is known as the “King of Retail.” Over his decades-long career, he transformed Gap into a 1990s style powerhouse, invented Old Navy, revitalized J.Crew, and launched Madewell. Today, he’s the co-founder of Alex Mill, a fast-growing apparel brand he started with his son. Jessi and Mickey discuss: • Why taste is more than pattern recognition—and why AI can’t replicate it • How intuition, curiosity, and listening fuel creativity and business success • Lessons from building and reinventing iconic fashion brands • How to rebound after career setbacks • The role of taste in spotting products that move markets and shape culture • How to cultivate your own taste, no matter your field Continue the conversation with us at Hello Monday Office Hours! Join us here, on the LinkedIn News page, this Wednesday at 3 PM EST.

We’ve all had conversations that go sideways. Not because we said the wrong thing, but because we weren’t speaking the same language. In this week’s episode of Hello Monday, Jessi Hempel sits down with Charles Duhigg, the Pulitzer Prize-winning journalist and bestselling author, to unpack the science of great communication. Charles's latest book, Supercommunicators, explores how anyone—yes, anyone—can get better at having meaningful, impactful conversations. Whether you’re pitching an idea at work or trying to connect more deeply at home, Charles offers tools to help you bridge the gap between intention and understanding. Jessi and Charles discuss: The three types of conversations: practical, emotional, and social—and how to recognize them Why most of us are bad at predicting how conversations will go Why listening in real time matters more than planning what to say How to practice your way into being a better communicator How to talk so people will listen and listen so others feel heard This is a must-listen for anyone who wants to communicate more clearly, build stronger relationships, or become a better leader. Continue the conversation with us at Hello Monday Office Hours! We’re live on the LinkedIn News page every Wednesday at 3 PM ET.

We spend so much of our lives chasing goals: big ones, small ones, some we barely remember choosing. But what if the goals we’re working toward aren’t really ours? This week on Hello Monday, Jessi Hempel sits down with neuroscientist and author Anne-Laure Le Cunff to talk about how we really achieve the lives we want to live. Anne-Laure is the founder of Ness Labs, a popular online school focused on mindful productivity for knowledge workers. Her new book, Tiny Experiments: How to Live Freely in a Goal-Obsessed World, offers an alternative to rigid goal-setting: a flexible, curiosity-driven approach to figuring out what matters most—through trial, reflection, and self-compassion. In today’s episode, Jessi and Anne-Laure discuss: • Why we put too much pressure on “capital P” Purpose • How to design tiny experiments to better understand yourself • The role of curiosity in redefining ambition • The “Head, Heart, Hand” framework for navigating uncertainty • How to make peace with evolving priorities • The dangers of hustle culture, and how to opt out This conversation is a gentle invitation to slow down, reflect, and explore new ways of working that are more aligned with who you are rather than who you think you’re supposed to be. Continue the conversation with us at Hello Monday Office Hours—live on the LinkedIn News page, every Wednesday at 3 PM ET.

Most of us spend the majority of our lives at work — but how often do we pause to ask whether our days are actually fun? In this episode of Hello Monday, host Jessi Hempel sits down with Bree Groff, a senior advisor at SYPartners and author of Today Was Fun: A Book About Work (Seriously), to talk about how fun, mischief, and human connection can radically improve our work lives. Bree’s work centers around workplace transformation and employee experience. She’s advised companies like Google, Microsoft, Pfizer, and Calvin Klein on how to build work cultures where people thrive. And her approach is surprisingly joyful. Jessi and Bree unpack: Why fun belongs at the center of great workplace culture How professionalism can strip us of our humanity — and how to get it back The emotional toll of over-identifying with our jobs How “Do Nothing Days” unlock creativity and innovation The radical power of micro-mischief and music in the workplace Friendship at work and why it matters more than we think This episode is for anyone feeling worn down by workplace norms or wondering if work has to feel so serious. Bree offers fresh, practical strategies to build a work life that’s more joyful, more connected, and yes, more productive. Continue the conversation with us at Hello Monday Office Hours! Join us this Wednesday at 3 PM ET on the LinkedIn News page.

You shouldn’t have to choose between showing up for your job and showing up for your family and loved ones. Caregiving is a growing part of modern work life — and it’s largely invisible. In today’s episode of Hello Monday, host Jessi Hempel talks with Jennifer Levin, author of Generation Care, about what it means to care for others while juggling a career, and how we can better support caregivers at work and beyond. Jennifer began caregiving for her chronically ill father in her early thirties, long before her peers were navigating similar responsibilities. Struck by how few people were talking about it, she created Caregiver Collective, a Facebook group for Millennial and Gen X caregivers. Her new book, gives voice to a generation of caretakers, and confronts the increasingly urgent crisis of caretaking in the U.S. Jessi and Jennifer discuss: • The emotional toll of caregiving and why so many of us feel alone in it • Why caregiving should be treated as real, valuable work • How to support colleagues who are quietly balancing care responsibilities • Why policy change must recognize caregiving as core to the future of work • How managers and leaders can create cultures that acknowledge and support caregiving • The power of talking about caregiving — with friends, with employers, and in public This episode is for anyone who’s ever whispered, I’m sandwiching today. Whether you're deep in it now or likely to take on a caregiving role in the future, this conversation offers clarity, comfort, and community. Continue the conversation at Hello Monday Office Hours. Join Jessi and Senior Producer Sarah Storm this Wednesday at 3PM ET on the LinkedIn News page to talk about caregiving, trade-offs, and what support really looks like in today’s workplace.

More professionals than ever are rethinking what’s next. For many mid-career and senior-level workers, consulting is the best path forward. But how do you actually make the leap? In this week’s episode of Hello Monday, host Jessi Hempel sits down with Erin Halper, founder and CEO of The Upside, a vibrant community for consultants. Erin shares what she’s learned from years of working independent consulting and coaching others through the same transition. From pricing and positioning to finding your first clients and building support systems, Erin and Jessi walk through what it really takes to thrive as a consultant. They also tackle the big questions: How do you know if consulting is right for you? What’s the best way to price your work? How do you talk about what you do in 10 words or less? What role does community play in solo success? How do you shift between full-time work and consulting as your career evolves? Whether you're just starting out or thinking about a pivot, this episode offers practical advice, clarity, and confidence for building your independent career—especially in an uncertain job market. 🔗 Join us for Office Hours. We’re continuing the conversation on Wednesday at 3PM ET on the LinkedIn News page. RSVP here!

Millions of professionals are balancing side hustles alongside their full-time jobs. But what does it take to turn that extra project into something bigger? In this episode from the Hello Monday archives, Jessi Hempel sits down with Side Hustle Pro creator and host Nicaila Matthews Okome to explore how side work can lead to a meaningful, lasting career. Nicaila didn’t always see herself as an entrepreneur. She built her résumé with big-name employers, earned her MBA, and followed a traditional career path. But she kept testing new ideas on the side — and eventually turned her podcast into a full-time business. Now, she helps others navigate the same transition. If you’ve ever dreamed about turning your passion project into something more, this conversation is for you. Jessi and Nicaila discuss: Why side hustles can be a smart career safety net How to know when a side project is ready to grow The difference between hobbies and businesses Building a brand while holding a day job How to manage your time for real progress without burnout What stability looks like when you’re your own boss Nicaila also shares her journey from NPR and Google to building Side Hustle Pro, a thriving platform for Black women entrepreneurs. Keep the conversation going at Hello Monday Office Hours. Join us on the LinkedIn News page this Wednesday at 3 PM ET.

You’re showing up, doing the work, checking the boxes, but something feels…off. You’re not falling apart, but you’re not really okay either. And you’re certainly not alone. This week on Hello Monday, Dr. Judith Joseph joins Jessi Hempel to name and unpack this experience: high functioning depression. Dr. Judith is a board-certified psychiatrist, researcher, and educator at Columbia and NYU. Her new book, High Functioning: Overcome Your Hidden Depression and Reclaim Your Joy, offers a roadmap for understanding and addressing a kind of mental health struggle that often goes unnoticed—and untreated. Together, Dr. Judith and Jessi explore: • What high functioning depression looks like—and how to recognize it in yourself and others • The five Vs method for healing: Validation, Values, Venting, Vitals, and Vision • The power of naming hard feelings like anhedonia • Why we must treat mental health as proactively as physical health • How small steps can help us reclaim joy This episode is a starting point for anyone who feels stuck in the motions but wants more from their life.

Twelve years ago, Shannon Watts was folding laundry when breaking news stopped her in her tracks: a mass shooting at Sandy Hook Elementary. The next morning, she woke up with a fire inside her, and turned her grief and rage into action. That action became Moms Demand Action, now part of Everytown for Gun Safety, the largest gun violence prevention organization in the country. In today’s episode, Shannon joins Jessi Hempel to reflect on the grassroots journey that began in her kitchen and grew into a national movement. Shannon’s new book, Fired Up, is a call to action for women everywhere who are ready to turn their spark into action, but aren’t sure where to start. Jessi and Shannon discuss: Shannon’s journey from corporate PR to grassroots activism The power of starting before you feel ready Why burnout can be a turning point How women, especially mothers, are the hidden engine of societal change Lessons from more than a decade of advocacy and organizing Join the conversation at Hello Monday Office Hours. Catch us Wednesday at 3 PM ET on the LinkedIn News Page. See you there.

More dads are becoming lead parents. What does that mean for work? When we talk about parenting, the spotlight usually falls on mothers. In this week’s episode of Hello Monday, we’re shifting that focus, and talking about what it means to be a lead dad. Our guest is Paul Sullivan, journalist, author, and founder of The Company of Dads, a media platform and community for fathers who are primary caregivers. Paul shares his personal journey, from columnist at The New York Times to lead parent and now advocate for redefining fatherhood at work and at home. Paul and Jessi unpack: • What it means to be a lead dad and why more men are taking on caregiving roles • How gender roles and workplace expectations often clash • Why support systems for dads are essential, and still hard to find • The origin story of The Company of Dads • How to teach people how to treat you when you don’t fit traditional molds • What employers can do to better support working parents, regardless of gender This conversation is thoughtful, timely, and packed with insight for anyone navigating work and family life. Whether you’re a dad, a partner, a manager, or someone rethinking how caregiving shows up at work, this episode is for you. Join us for Hello Monday Office Hours, live on the LinkedIn News page this Wednesday at 3PM ET to continue the conversation.

The belief that a four-year degree is the only path to a good job is baked into our culture. But what if that narrative is outdated? In this week’s episode of Hello Monday, host Jessi Hempel sits down with Kathleen deLaski, social entrepreneur, author, and founder of the Education Design Lab. Kathleen’s new book, Who Needs College Anymore?, challenges the assumption that a bachelor’s degree is the default route to economic mobility. Together, Jessi and Kathleen discuss how we can better support shorter, more flexible learning paths to success for the majority of Americans who don’t pursue or finish a four-year degree. Jessi and Kathleen talk about: Why the four-year college degree is no longer the only path to a “good job” What happens to the 62% of Americans who don’t complete a four-year degree The growing role of community colleges, bootcamps, and skills-based programs How government and employers are starting to rethink credentialing and career readiness The mindset shift parents and students need to make in 2025 and beyond Whatever your age, this episode is a roadmap for how to navigate the changing landscape of education and work. Continue the conversation with us at Hello Monday Office Hours — Wednesdays at 3 PM ET on the LinkedIn News page.

Pride is more than a celebration, it’s a call to action, especially for queer families navigating today’s uncertain political landscape. This week on Hello Monday, Jessi Hempel sits down with Darra Gordon, CEO of Family Equality, to talk about protecting LGBTQ+ families, raising resilient kids, and why visibility and community are more vital than ever. Darra is a longtime advocate and nonprofit leader who works every day to ensure all families, especially those with LGBTQ+ parents, have equal rights and protections. She’s also a working mom, navigating the same daily chaos as many of us: career, childcare, dinner plans, and existential anxiety about the future. Jessi and Darra discuss: • How LGBTQ+ families can stay safe and visible in uncertain times • How to raise kids who are proud of their identity and inclusive of others • The joy and strength of queer families, and the role of community in liberation • Why allyship is more than a rainbow flag during June • How everyone, queer or not, can support family equality year-round Whether you're part of the LGBTQ+ community, love someone who is, or just want to build a more inclusive world — this episode is for you. Join us for Hello Monday Office Hours, live on the LinkedIn News page this Wednesday at 3PM ET. It’s a welcoming space to keep the conversation going.

What does it take to make a bold career pivot after decades of doing the expected? This week, we’re resurfacing our conversation with the multi-talented Anna Kendrick, whose journey from acclaimed actor to first-time director offers invaluable insights for anyone thinking about making the leap into something new.  Anna shares the story behind her directorial debut with Netflix’s Woman of the Hour, a true-crime drama. Far removed from the lighthearted films that Anna is known for, Woman of the Hour chronicles the stranger-than-fiction story of a 1970s aspiring actor and a serial killer whose lives collide when they're cast on a dating game show. Together, Jessi and Anna discuss: The courage it takes to step out of your comfort zone How to follow your intuition when making creative decisions Dealing with imposter syndrome Learning to lead What good feedback truly looks like This episode offers not just a behind-the-scenes look at Anna's latest project but also inspiration for anyone seeking to reinvent their own career. Watch Woman of the Hour on Netflix now, and tune in to hear how Anna Kendrick is embracing the next chapter of her career. Continue the conversation with us at Hello Monday Office Hours! RSVP here to join us on the LinkedIn News page this Wednesday at 3 PM EST.

It’s easy to feel lost in your career, especially as the world around us keeps shifting. Whether you’re starting over, seeking purpose, or just unsure what your next move is, this episode is for you. This week, Jessi Hempel sits down with Caroline Wanga, president and CEO of Essence Ventures and co-founder of Wanga Woman. Caroline is a dynamic leader and an unapologetic champion of authenticity. She joins Jessi to share her approach to building a career map – not just once, but continuously throughout your life. Before leading Essence, Caroline spent 15 years at Target, rising from intern to C-suite executive. Today, she’s focused on democratizing authenticity through her personal purpose, her leadership, and her new memoir, I’m Highly Percent Sure. Jessi and Caroline dig deep into: Why your “next right move” may not look like anyone else’s Why playing with your career map, not perfecting it, leads to clarity How, and when, Caroline has created her own career maps The role of authenticity in leadership and life What it really takes to live and work with personal purpose Tools and mindsets for building a meaningful career in today’s world Don’t miss Caroline’s practical wisdom on shaping a professional life that evolves with you. This episode was filmed live in-studio. LinkedIn Premium subscribers can watch the full video version here. Want to keep the conversation going? Join us at Hello Monday Office Hours, live on the LinkedIn News page this Wednesday at 3 PM EST.

Debbie Millman and Roxane Gay know a thing or two about building creative lives. Debbie is a legendary designer, writer, and podcast host. Roxane is a bestselling author and cultural critic. Together, they’ve built a partnership rooted in discipline, love, and slow growth. On this week’s episode of Hello Monday, Jessi Hempel welcomes the couple back to the studio to talk about their new book, and what it really takes to live a meaningful creative life. Their book, Love Letter to a Garden, is both literal and metaphorical. It’s about vegetables, sure. But it’s also about how we learn, how we fail, and how we grow. Debbie shares stories of her journey from struggling gardener to seasoned grower, an arc that mirrors her creative life. Roxane contributes recipes she’s crafted using the produce Debbie grows.  Jessi, Debbie, and Roxane dig into the kind of growth that takes time, and the work required to nurture it. They discuss: • The invisible years behind every “overnight” success • How to keep going when you fail again and again • Why your hope must be slightly bigger than your shame • What it means to save your best energy for what matters most • The difference between meaningful work and making work your meaning Continue the conversation with us at Hello Monday Office Hours! Join us here, on the LinkedIn News page, this Wednesday at 3 PM EST.

In this special Thursday bonus episode, we’re returning to Jessi Hempel’s conversation with Suzy Welch, a professor at NYU Stern School of Business, business advisor, and three-time NYT bestselling author. Suzy’s latest book, Becoming You, came out this week, in which she synthesizes her wildly popular NYU course of the same name. In conversation with Jessi, Suzy shares her insights on the importance of values, authenticity, and personal growth. She emphasizes the need to align our professional lives with our deepest values and aptitudes to achieve true satisfaction and happiness. Suzy and Jessi discuss: The importance of living an authentic life How values shape our career decisions The role of authenticity in finding career satisfaction Navigating the tension between personal and professional values This episode is a must-listen for anyone trying to find fulfillment and live authentically at work and beyond.

How do you live well when life falls apart? Suleika Jaouad has a powerful answer. In this deeply moving episode of Hello Monday, host Jessi Hempel sits down with Suleika Jaouad, bestselling author, speaker, and cancer survivor, to uncover what it truly means to live well in the face of uncertainty. From her fight with leukemia to her remarkable creative journey, Suleika has learned to turn adversity into art, and pain into purpose. Her latest work, The Book of Alchemy, is a soulful invitation to embrace creative practices that help build resilience, joy, and connection, even in our darkest moments. Jessi and Suleika dive into topics that challenge conventional ideas of success and encourage listeners to live more intentionally.  They discuss: Why curiosity and play can be powerful daily rituals How a 100-day journaling challenge sparked a creative breakthrough What it means to redefine productivity through values like kindness and bravery The healing power of deep friendships and chosen family How creativity helps us process adversity and transform it Continue the conversation with us at Hello Monday Office Hours! Join us here, on the LinkedIn News page, this Wednesday at 3 PM EST.

If you have found your way here right now, you are most likely at a turning point in your career, maybe in your life. Layoffs are a challenging and often unexpected part of our careers. In today's episode, Jessi Hempel dives deep into the emotional and practical aspects of navigating layoffs. Whether you're facing a layoff yourself or supporting someone who is, this episode offers valuable insights and actionable advice. Tune in to gain valuable insights and support for navigating your career journey during challenging times.

We’ve been taught to chase fancy job titles and large salaries, but what if we aimed for moral ambition instead? In this week’s episode of Hello Monday, host Jessi Hempel sits down with historian and best-selling author Rutger Bregman to explore moral ambition: the idea that the core metric of a successful career should be the positive impact we have on the world. Rutger’s new book, Moral Ambition: How to Stop Wasting Your Talent and Start Making a Difference, calls on all of us to rethink what we’re really working for. If you’ve ever felt like there should be more to your job than climbing the ladder, this conversation is for you. Jessi and Rutger dive into: What moral ambition is—and why we need more of it Why “follow your passion” is the wrong advice How to shift from success-driven to service-driven work Why young professionals are funneled into finance and consulting The real-world heroes solving the world’s biggest problems How to build coalitions and collaborate for impact This episode is a call to action for anyone who wants to do good—and do it well. Join the conversation at Hello Monday Office Hours! We’ll be live on the LinkedIn News page this Wednesday at 3PM EST. Bring your questions and your curiosity; we’d love to hear what moral ambition looks like for you.

Age bias is everywhere: online, at work, even in the stories we tell ourselves. Ashton Applewhite wants us to see age not as a limitation, but as a source of strength. In today’s episode, Jessi Hempel sits down with the anti-ageism activist to unpack the hidden ways ageism shapes our workplaces, and how we can push back. Ashton is a leading voice in the age equity movement. She’s the author of This Chair Rocks: A Manifesto Against Ageism and founder of the Old School Hub, a resource center filled with free tools to combat age bias. In this conversation, she shares practical strategies for navigating ageism at work, whether you’re feeling “too old,” “too young,” or just underestimated. Jessi and Ashton discuss: • Why age has less to do with competence than we think • How internalized ageism holds us back, and how to recognize it • What managers can do to build age-diverse teams • How to tell your story in a way that challenges bias • Tips for job seekers facing age-based assumptions • The power of language in shaping workplace perceptions Continue the conversation with us at Hello Monday Office Hours! Join us on the LinkedIn News page this Wednesday at 3 PM ET.