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.
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Caregiving Is Work — We Just Don’t Treat It That Way
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.
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How to Be a Consultant—and Actually Make It Work
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!
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From Side Hustle to Main Meal: How Nicaila Matthews Okome Scaled Her Passion Project
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.
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Reclaim Your Joy and Overcome High Functioning Depression with Dr. Judith Joseph
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.
Ever wish you had a pal who could break down the biggest ideas of the new world of work and distill them into actionable insights you could apply to your own life, right away? Meet LinkedIn's Hello Monday with Jessi Hempel! Each week, Jessi explores the changing nature of work and how that work is changing us. Jessi welcomes big thinkers to share their best ideas: everyone from game-changing entrepreneurs like Aurora James, to research-based experts like Daniel Pink, to notable figures like Megan Rapinoe and Bozoma Saint John. Start your week by joining us every Monday for a dose of fresh ideas, then join us in community and conversation on LinkedIn.
New episodes weekly.
Ireland