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.
--------
40:07
--------
40:07
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.
--------
33:39
--------
33:39
How One Mom Sparked a National Movement with Shannon Watts
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.
--------
34:41
--------
34:41
Masculinity, Work, and the New Fatherhood with Paul Sullivan
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.
--------
35:26
--------
35:26
Is College Still Worth It? Kathleen deLaski on Rethinking the 4-year Degree
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.
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.
France