Chronic Boss Unfiltered

What do the women accused of witchcraft centuries ago have in common with women navigating chronic illness today? More than you might think.

In this spellbinding episode of Chronic Boss Unfiltered, Lilly sits down with Pam Grossman, acclaimed author, host of The Witch Wave podcast, and practicing witch, to explore the fascinating history of witch persecution, the power of modern witchcraft, and what it really means to reclaim your magic.

From the historical silencing of women's knowledge to the medical gaslighting women still experience today, Lilly and Pam explore the enduring relationship between women's bodies, power, and the right to be believed.

While this conversation draws on the past, it's also about embracing what makes us different, finding strength in our experiences, and using creativity to build a life on our own terms.

Drawing on her book Magic Maker: The Enchanted Path to Creativity, Pam shares how everyday rituals, imagination, and a little magic can help us reconnect with our creativity, overcome self-doubt, and recognize the unique gifts we have to offer the world.

Whether you're witch-curious, navigating chronic illness, or simply looking to reconnect with your own power, this episode is a reminder that you don't have to change who you are to create something extraordinary.

Episode Highlights

Connect with Pam Grossman:

Connect with Chronic Boss:

🖤 chronicboss.com

Connect with Lilly:

🖤 lillystairs.com

What does it look like to build a six-figure business while raising two kids, holding down a marriage to an active-duty Air Force pilot who's gone 70% of the year, and finally treating an anxiety disorder you white-knuckled for two decades? In this episode, host Lilly Stairs sits down with Beth Ann Hart, founder of Hart Health Consulting & Co and the operational engine behind both Chronic Boss and Patient Authentic, for a conversation that starts with food stamps and ends in boardrooms.

Beth Ann got pregnant with her daughter at 19, a sophomore in college. She was back at work at three weeks postpartum, writing papers with her daughter on her chest, and bought her first house by 21. She found Chronic Boss through a cold application on Upwork. Last summer, over dinner at Lolita in Boston, Lilly pulled out her phone, did some quick math on Beth Ann's rates, and told her she was undervaluing herself. That one conversation is the reason Beth Ann has since tripled her salary and is on track for multiple six figures in 2027.

Beth Ann and Lilly also get into the chronic half of Chronic Boss. Beth Ann has lived with anxiety since childhood and didn't start treating it with medication and therapy until last year, after realizing she couldn't keep white-knuckling her way through irrational fears. They talk honestly about what it took to get there, what changed once she did, and why being sure of yourself might be 90% of the job.

What You'll Learn:

Episode Highlights (topic markers below — send over the final cut and I'll convert these to real timestamps)

Connect with Beth Ann Hart & Hart Health Consulting:

Connect with Chronic Boss:

🖤 chronicboss.com

Connect with Lilly:

🖤 lillystairs.com

Ten days before my wedding, I sat down with the two women who are going to be there capturing every moment of it.

Mariah Gale and Andrea Schwanbeck aren't just my wedding photographers. They've been part of the Chronic Boss community since the very beginning. Mariah shot our first brand shoot before we even launched. Andrea was there at our launch party (yes, including the moment her hair caught fire). They've watched this whole thing grow, and I've watched them grow too, through studio closures, a new baby, insulin pod emergencies in the middle of Boston, and some really hard questions about who they are outside of their work.

This episode is going to air while I'm on my honeymoon, which feels right. Because this conversation was one of those ones I'll be thinking about for a long time.

We got into:

Mariah said something that I keep coming back to: "It's not failing. It's just learning and growing in an accelerated way." And Andrea's definition of chronic boss might be the most honest one I've ever heard on this show.

This one is for anyone who has ever tied their worth to their work, or wondered whether they can have a business AND a chronic condition AND a full life. You can. These two are proof.

Connect with Mariah 

 🖤 / instagram.com/mariahgalecreative

Connect with Andrea 

 🖤 / instagram.com/brasstacksphotography

Connect with Chronic Boss:

🖤 / https://chronicboss.com/

 Connect with Lilly:

🖤 / https://lillystairs.com/

What does it look like to build a company while your body is working against you? In this episode, host Lilly Stairs sits down with two Chronic Boss Scholarship recipients who are doing exactly that — and doing it brilliantly. Jolie Wyatt, founder of If the Shoe Fits and newly minted Babson grad, is revolutionizing the footwear industry with custom-fit heels built from 3D foot scanning technology. Amanda Berk, co-founder of Liora Health, is building a digital platform that matches women with chronic conditions to care advocates who show up with them — literally and figuratively — before, during, and after medical appointments. Both women are students, entrepreneurs, community builders, and chronic illness patients navigating it all at once.

What makes this conversation so special is how candidly Jolie and Amanda talk about the intersection of chronic illness and entrepreneurship — not as a liability, but as a lens. They cover the very real tension of scheduling your week on a Monday when your Thursday body is completely unpredictable, why stress is the common thread connecting conditions as different as hidradenitis suppurativa and chronic migraine, and how learning to block time for rest (not just work) has been a game-changer. They also share the moments that almost stopped them — including the belief that they weren't "sick enough" to deserve this scholarship — and why they applied anyway.

This episode also gets into the power of mentorship and community in a way that will light you up. Both Jolie and Amanda share the relationships that have changed everything for them — from cold DMs that turned into advisory board seats, to connections forged at the Chronic Boss launch party that are still going strong. If you've ever wondered whether putting yourself out there is worth it, this episode is your answer.

WHAT YOU'LL LEARN

[00:00] — Welcome & Episode Introduction Lilly sets up the episode and shares why the Chronic Boss Scholarship has been the most rewarding part of running Chronic Boss.

[01:30] — Introducing Jolie Wyatt and Amanda Berk Quick intros on both guests: Jolie's custom-fit heels company If the Shoe Fits and Amanda's patient advocacy platform Liora Health.

[02:01] — Jolie's Chronic Boss Elevator Pitch Jolie introduces herself, describes the technology behind If the Shoe Fits, and shares her diagnosis of hidradenitis suppurativa at age nine.

[02:54] — Amanda's Chronic Boss Elevator Pitch Amanda walks through her journey from Hashimoto's to chronic migraine, from healthcare communications to grad school, and how it all led to co-founding Liora Health.

[04:24] — Managing Chronic Conditions While Building a Business Both guests get honest about day-to-day impact — flare cycles, mental health as a chronic condition, and the emotional weight of being a "doer" whose body doesn't always cooperate.

[06:26] — Why Mental Health Belongs Under the Chronic Illness Umbrella Lilly makes the case for reframing mental health conditions as chronic conditions — and why that framing gives them the visibility and depth they deserve.

[10:01] — The Monday/Thursday Problem Every Chronic Entrepreneur Knows Jolie names something so many founders feel but rarely say out loud: how you feel and what you can do on Monday is not the same as Thursday, and there's no way to calculate that.

[11:20] — Practical Hacks for Juggling Entrepreneurship, School & Chronic Illness Time blocking for breaks (not just tasks), listening to your body before a flare hits, and why rest is a business strategy — not a weakness.

[13:51] — The Power of Community and Radical Transparency Amanda and Jolie on being open about their conditions — with friends, founders, and followers — and how that honesty unlocks connection rather than closing doors.

[16:55] — Jolie's Origin Story: How If the Shoe Fits Was Born From a business dress day in high school to a prototype she built by hand in Johannesburg — the full arc of four years, multiple pivots, and a manufacturer in New York City.

[25:15] — Amanda's Origin Story: How Liora Health Came to Be The four-month migraine flare that changed everything, the realization that women with chronic conditions shouldn't have to navigate the healthcare system alone, and the case for patient advocacy as a sustainable business model.

[31:36] — The Role of Mentorship: Jolie & Emily Levy How a cold LinkedIn message before the Chronic Boss launch party turned into one of Jolie's most important mentorship relationships — and the "sit under a tree" advice that still resonates.

[38:57] — The Role of Mentorship: Amanda & Alex Wilderson How Amanda cold-DM'd a podcast host she admired, and how that casual FaceTime turned into an advisory board seat, a South by Southwest partnership, and a friendship.

[44:05] — The Chronic Boss Scholarship: What It Meant to Each of Them Both guests share how they found the scholarship, the self-doubt that almost kept them from applying, and what it meant to finally feel seen.

[52:25] — What Does Being a Chronic Boss Mean to You? Closing reflections from both guests on wearing your chronic illness on your sleeve, the superpowers it gives you, and what it means to live fully — not just between flares.

Connect with Jolie & If the Shoe Fits:

🖤 / linkedin.com/in/joliewyatt 

🖤 / iftheshoefits.co

Connect with Amanda & Liora Health: 

🖤 / instagram.com/liorahealthadvocates 

🖤 / liorahealth.io 

🖤 / linkedin.com/in/amanda-berk

Connect with Chronic Boss:

🖤 / https://chronicboss.com/

 Connect with Lilly:

🖤 / https://lillystairs.com/

What if your mental health struggles weren’t holding you back, but actually shaping you into a stronger, more intentional leader?

In this episode of Chronic Boss Unfiltered, Lilly sits down with Lauren Perna, founder, multi-entrepreneur, storyteller, and Chief Community Officer of Chronic Boss. Together, they unpack what it really looks like to build a business while living with anxiety, depression, and the pressure to constantly do more.

From launching her agency during uncertainty to redefining success on her own terms, Lauren shares how she has learned to work with her mental health instead of against it, and why honoring your limits might be your greatest advantage.

You’ll hear why:

And perhaps most powerfully of all, Lauren explains why building a business that protects your nervous system is just as important as building one that grows your revenue.

This conversation is part founder story, part mental health reality check, and part permission slip to build a life that actually works for you.

If you’ve ever wondered:

This episode is for you.

1:16 Lauren’s “chronic boss” elevator pitch and living with anxiety and depression

Attend the Mentally Fit Founder Event May 14, 2026

https://www.eventbrite.com/e/an-evening-of-founder-stories-stories-reflection-and-guided-conversation-tickets-1986648187207

Connect with Lauren:

✨/ Mentally Fit Founder: https://mentallyfitfounder.com/ 

Connect with Chronic Boss:

🖤 / https://chronicboss.com/

 Connect with Lilly:

🖤 / https://lillystairs.com/

What if your chronic illness wasn’t a liability—but one of your greatest leadership advantages?

In this episode of Chronic Boss Unfiltered, Lilly sits down with Jess March, pharmaceutical executive, patient advocate, mom, and longtime leader in the rare disease space. Together, they unpack what it really looks like to build a meaningful, high-impact career while living with multiple chronic conditions—and why lived experience belongs in the room where healthcare decisions get made.

Jess shares how waking up paralyzed at 29 with multiple sclerosis forced her to reimagine everything she thought her life would be—and how that journey ultimately sharpened her ambition, deepened her leadership, and transformed the way she thinks about work, advocacy, and impact.

You’ll hear why:

And perhaps most powerfully of all: Jess explains why chronic illness didn’t take her ambition away—it clarified it.

This conversation is part career conversation, part leadership lesson, and part reminder that chronic illness may change your path, but it does not define your potential.

If you’ve ever wondered:

Can I still be ambitious after a diagnosis?

This episode is for you.

In This Episode, We Cover:

 1:17 Jess’s MS diagnosis and waking up paralyzed at 29

Connect with Jess March

Mentions

Connect with Chronic Boss:

🖤 / https://chronicboss.com/

 Connect with Lilly:

🖤 / https://lillystairs.com/

What if chronic illness wasn’t a burden—but the foundation of a whole new economy?

In this episode of Chronic Boss Unfiltered, Lilly sits down with Michelle Irving, chronic founder, career visionary, and the mind behind the term “the chronic economy.” Together, they unpack how millions of people living with chronic conditions are reshaping work, leadership, entrepreneurship, and the future of business—often without realizing it.

Michelle shares how being diagnosed with a life-threatening autoimmune condition forced her to redesign her career from the ground up—and how that journey led her to build two global businesses, advise executives, and create frameworks that help people pursue ambition without burning their bodies to the ground.

You’ll hear why:

And perhaps most jaw-dropping of all: Michelle takes one full week off every month—no meetings, no email, no guilt—and explains exactly how she built a business that doesn’t need her to survive.

This conversation is part big-picture vision, part practical roadmap, and part permission slip for chronic founders, professionals, and leaders who know there has to be a better way.

If you’ve ever wondered:

This episode is for you.

In this episode of Chronic Boss Unfiltered, our host Lilly Stairs opens up about her journey from chronic illness patient to powerhouse advocate and entrepreneur. With colleague and friend Lauren Perna stepping in as interviewer, listeners get a raw, honest look at the experiences that shaped Lilly’s mission-driven career.

Lilly’s story begins with early diagnoses—psoriasis at age seven and OCD during her teen years—and takes a life-altering turn when she is diagnosed with psoriatic arthritis and Crohn’s disease at 19. These challenges sparked her passion for patient advocacy at a time when the field was still largely undefined.

Throughout the episode, Lilly traces the evolution of her career: establishing herself in advocacy, launching her consultancy Patient Authentic to elevate patient voices in healthcare, and creating Chronic Boss, a community for ambitious women navigating chronic conditions while pursuing big goals.

The conversation highlights core themes of Lilly’s work—owning your narrative, prioritizing mental health, recognizing burnout, and redefining ambition through a chronic illness lens. It’s a powerful reminder that resilience and drive can coexist, and that women with chronic conditions deserve space to lead, build, and thrive.

Themes: 

OCD is widely misunderstood and often hidden in plain sight.

A lack of autoimmune awareness propelled her into patient advocacy.

Patient advocacy remains an emerging—and deeply needed—field in healthcare.

Lilly founded Patient Authentic to help organizations meaningfully engage patients.

Daily routines and boundaries are essential for chronic illness entrepreneurs.

Chronic Boss was built to empower ambitious women living with chronic conditions.

Owning one’s story creates personal and professional strength.

Burnout awareness is crucial for protecting mental health.

Timestamps:

Connect with Chronic Boss:

🖤 chronicboss.com

Connect with Lilly:

🖤 lillystairs.com

In this episode of the Chronic Boss Unfiltered Podcast, Our host Lilly Stairs sits down with Meg Block, the incredible powerhouse behind Boston Moms. Meg gets real about what it was like to build and scale a business in the middle of a global pandemic while battling the debilitating pain of trigeminal neuralgia. We dive into the messy middle — the sleepless nights, the pressure of motherhood, and the weight of carrying a brand on her back while her body was begging her to slow down.

Meg opens up about how deeply her identity became intertwined with her company, and the moment she realized that staying in constant hustle mode was costing her her health. Her decision to sell Boston Moms wasn’t a step back; it was a radical act of self-preservation and clarity.

This conversation is such a powerful reminder for every woman — especially my fellow chronic bosses — that caring for ourselves isn’t optional. It’s the foundation. Meg’s story is a testament to what happens when we choose connection, community, and our own wellbeing over the narrative that we have to do it all, all the time.

If you’re navigating chronic illness, entrepreneurship, or simply trying to keep all the plates spinning, Meg’s journey will speak straight to your soul.

Themes:

How Meg built Boston Moms in the middle of COVID chaos — and found purpose through the uncertainty.

Behind the scenes, she was carrying intense chronic pain from trigeminal neuralgia.

Growing a business while managing a chronic condition pushed her to her limits.

Self-care wasn’t a luxury — its a lifeline.

Community wasn’t just part of her mission; it was part of her own healing.

She had a powerful realization: her identity had become too wrapped up in her business.

Being a chronic boss isn’t about doing everything — it’s about proving to yourself that you can rise, even in the hard moments.

Chapters

Timestamps: 

00:00 Building Boston Moms Amidst Chaos

14:57 Navigating Chronic Pain and Motherhood

29:45 The Turning Point: Selling the Business

45:11 Self-Care and the Journey to Healing

29:04 Finding Balance: The Dangers of Identity in Work

30:38 The Summer of Mama: Prioritizing Family Over Work

33:26 Realizations and Reflections: What is Enough?

36:44 The Decision to Sell: Finding Peace in Transition

41:00 Navigating the Exit Process: Women in Business

47:20 Advice for Chronic Pain Warriors: Prioritizing Self-Care

51:14 Embracing the Journey: What it Means to be a Chronic Boss

Connect with Meg Block:

✨LinkedIn: https://www.linkedin.com/in/meghan-saunders-block/ 

✨Instagram: https://www.instagram.com/itsmegblock/ 

Connect with Chronic Boss:

🖤 chronicboss.com

Connect with Lilly:

🖤 lillystairs.com

This episode of Chronic Boss Unfiltered brings a deeply resonant conversation between host Lilly Stairs and Amanda Goetz, a two-time founder and author of Toxic Grit. Together, they explore the collision of high ambition, chronic stress, and the wake-up calls that force leaders — especially women — to rethink how they’re operating.

Amanda shares her transformational health journey, including the moment she went from the boardroom to the ER, and how that experience cracked open a deeper understanding of burnout and the pressure to “do it all.” The discussion digs into character theory, a powerful tool for understanding the different roles we embody, and how embracing intentional imbalance can create a more sustainable, fulfilling rhythm of life.

Listeners will walk away with a redefined perspective on success — one that prioritizes intention over hustle, honors personal capacity, and encourages reclaiming time before the body demands it. This conversation is a refreshing, unapologetic call to rewrite the scripts that keep so many chronic bosses stuck in cycles of depletion.

What You’ll Learn:

Early signals of burnout must be recognized and respected to protect long-term well-being.

Character theory offers a framework for understanding the various identities individuals occupy throughout their lives.

Intentional imbalance allows space for shifting priorities based on season, energy, and personal needs.

Reclaiming time shouldn’t be reserved for weekends; it’s essential for daily fulfillment.

Smooth transitions between life roles require awareness, rituals, and boundaries.

Toxic grit is defined as hustling without clarity, alignment, or intention.

Success should never be one-dimensional — a holistic view is both healthier and more empowering.

Personal operating rhythms help build a grounded, sustainable lifestyle.

Examining the “scripts” shaping decisions leads to more agency and authenticity.

Timestamps:

00:00 — Introducing Amanda Goetz + The Story Behind Toxic Grit

01:54 — From the Boardroom to the ER: Amanda’s Health Crisis

07:35 — Burnout’s Warning Signs and Why They Matter

10:43 — Character Theory Explained

18:22 — How Intentional Imbalance Creates Space for What Matters

23:54 — Reclaiming the Five-to-Nine Beyond the Workday

28:34 — Rituals and Awareness for Transitioning Between Characters

34:03 — Understanding the True Meaning of Toxic Grit

37:24 — “Having It All” — But in the Right Season

43:18 — Practical Steps Toward Sustainable, Aligned Ambition

Connect with Amanda Goetz:

✨Toxic Grit Book: https://www.amazon.com/toxic-grit-have-actually-love/dp/146423325x 

✨LinkedIn:  https://www.linkedin.com/in/amandagoetz/ 

✨Instagram:https://www.instagram.com/theamandagoetz/ 

✨Newsletter: https://amandagoetz.kit.com/posts

✨Website: https://www.amandagoetz.com/ 

Connect with Chronic Boss:

🖤 chronicboss.com

Connect with Lilly:

🖤 lillystairs.com