Hello Monday with Jessi Hempel

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.

Erin Halper, founder and CEO of The Upside, is a veteran consultant who shares her invaluable insights on thriving in the consulting world. She talks about finding your niche, the critical role of community support, and the importance of strategic planning. Erin offers practical advice on pricing your services and communicating your value succinctly. She also discusses the mindset shift required when transitioning from full-time work to consulting and emphasizes the 'three C's'—confidence, clarity, and curiosity—as keys to client engagement.

Nicaila Matthews Okome, a prominent creator and host of Side Hustle Pro, shares her journey from a corporate employee at NPR and Google to empowering Black women entrepreneurs. She delves into the importance of side hustles as a career safety net and strategies to transition these projects into full-time ventures. Nicaila discusses how to differentiate hobbies from businesses, manage time effectively to avoid burnout, and navigate the unique challenges faced by Black women in entrepreneurship. Her insights are a roadmap for anyone aspiring to turn passion into profit.

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.

Shannon Watts, the Founder of Moms Demand Action and author of 'Fired Up,' shares her inspiring journey from corporate PR to grassroots activism after the Sandy Hook tragedy. She emphasizes how starting before you’re ready can spark significant change, particularly for women and mothers. The conversation dives into the emotional resilience required in advocacy, how burnout can transform perspective, and the incredible power women have in driving societal change. Shannon's insights offer a motivating call to action for anyone ready to make a difference.

Paul Sullivan, journalist and founder of The Company of Dads, shares his journey as a primary caregiver championing a new definition of fatherhood. He discusses the rise of lead dads and the challenges they face in a workplace often biased towards traditional gender roles. The conversation dives into the importance of support systems for fathers and how openly communicating about emotional labor can alleviate resentment. Paul emphasizes the need for workplaces to adapt and support diverse family dynamics, advocating for a shift in societal perceptions of masculinity.

Kathleen deLaski, a social entrepreneur and founder of the Education Design Lab, discusses her book, *Who Needs College Anymore?*. She challenges the outdated belief that a four-year degree is essential for career success. Kathleen highlights the experiences of the 62% of Americans who don't complete a degree and advocates for the increasing importance of community colleges and skills-based programs. The conversation emphasizes the shift in mindset needed for students and parents as they navigate the evolving job market and educational landscape.

Darra Gordon, CEO of Family Equality, passionately advocates for LGBTQ+ families while juggling her own parenting journey. In this conversation, she emphasizes the necessity of visibility and community support during uncertain times. They discuss empowering children to embrace their identities and the importance of allyship beyond Pride Month. Darra shares personal experiences navigating the legal hurdles faced by queer families in adoption and foster care, highlighting the ongoing fight for equal rights and the joy within queer family dynamics.

Join Anna Kendrick, an accomplished actress known for her roles in Pitch Perfect and Up in the Air, as she takes a bold leap into directing with her Netflix film, Woman of the Hour. She shares her journey of stepping out of her comfort zone, confronting imposter syndrome, and the importance of trusting her intuition. The conversation dives into the emotional depth of storytelling, exploring themes of vulnerability, intimacy, and betrayal. Anna's insights on overcoming fears and the necessity of trustworthy feedback offer inspiration for anyone looking to reinvent their careers.

Caroline Wanga, President and CEO of Essence Ventures and co-founder of Wanga Woman, shares her journey from intern to corporate leader and her views on career mapping. She emphasizes that your next career move doesn't have to follow a traditional path and that embracing imperfection in your career map can provide clarity. Caroline discusses the power of authenticity in leadership, the necessity of self-compassion during uncertain times, and how reframing failure can lead to growth. Her insights inspire building a meaningful career that evolves with you.