Chronic Boss Unfiltered

The Chronic Economy is the $100B Market Hiding in Plain Sight with Michelle Irving

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:
30%+ of the workforce lives with chronic conditions—and why calling them a “burden” is wildly outdated
The chronic economy is already worth billions (and still invisible to most leaders)
Most chronically ill professionals are overcompensating, not underperforming
Sustainable work isn’t about accommodations—it’s about redesigning how work gets done
AI may actually make chronic work strategies mainstream for everyone
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:
Can I be ambitious and chronically ill?
Is it possible to build a business or career that actually works with my body?
What does sustainable success really look like?
This episode is for you.
In This Episode, We Cover:
4:11 What the chronic economy is—and why it’s just getting started
13:05 Chronic founders, entrepreneurship, and redefining ambition
20:07 Boundaries, pricing, and saying no without burning bridges
25:03 Why “performing wellness” is draining talent at work
27:32 How AI is changing capacity, admin, and leadership
40:01 What it really means to be a chronic boss
Connect with Michelle Irving
✨ Websites: https://www.chronicillnessatwork.com/
✨ http://careerandchronicillness.com/
✨ LinkedIn - @michelleirvingofficial
✨Instagram: @michelleirvingofficial
Mentions
Leadership Series: https://www.careerandchronic.com/chronicleadership (Feb 2026)
Ambition Program: https://www.careerandchronic.com/ambition

Meet the Woman Behind the Mic: From Hospital Bed to CEO with Lilly Stairs

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: 00:00 — Introduction 01:59 — Early Health Journey: Psoriasis and Childhood Resilience 04:06 — Mental Health in Focus: Understanding OCD 08:32 — Age 19: Diagnoses That Shifted Everything 12:21 — The Spark of Patient Advocacy 14:02 — Building a Career Rooted in Advocacy 18:00 — The Launch of Patient Authentic 21:44 — Patient Authentic’s Mission and Impact 24:32 — The Creation of Chronic Boss 27:32 — Empowering Ambitious Women with Chronic Illness 29:29 — Entrepreneurship, Flexibility, and Balance 33:38 — Burnout, Boundaries, and Mental Health 36:24 — What’s Next for Chronic Boss
 
Connect with Chronic Boss:
🖤 chronicboss.com🖤 Instagram🖤 LinkedIn🖤 TikTok
 
Connect with Lilly:
🖤 lillystairs.com🖤 LinkedIn🖤 Instagram
 

The Exit That Saved Me: Building & Selling a Business Through Chronic Pain with Meg Block

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🖤 Instagram🖤 LinkedIn🖤 TikTok
 
Connect with Lilly:
🖤 lillystairs.com🖤 LinkedIn🖤 Instagram

Toxic Grit: Why Your “Success” Might Actually Be a Panic Attack with Amanda Goetz

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🖤 Instagram🖤 LinkedIn🖤 TikTok
 
Connect with Lilly:
🖤 lillystairs.com🖤 LinkedIn🖤 Instagram
 

The Business Strategy No One Talks About…That Built My Entire Career

This solo episode digs into the transformative power of giving—especially for women navigating career growth, advocacy, and the realities of living with autoimmune conditions. Through personal stories and lived experience, the conversation explores how authentic, aligned giving can open doors, build community, and spark meaningful change. It also highlights the importance of protecting mental health and honoring boundaries, reminding listeners that giving is most impactful when it comes from abundance rather than obligation. By weaving together advocacy, business strategy, and self-care, the episode encourages women to lead with their values, share their stories, and use generosity as a catalyst for both personal and professional growth.
 
Themes:
Giving can be a powerful force for opportunity and change.
Authentic generosity thrives when it comes from abundance, not pressure.
Advocacy often begins with personal lived experience and expands into broader impact.
Community building is a cornerstone of meaningful, sustainable advocacy.
Showing up authentically can accelerate career growth and deepen connection.
Clear boundaries protect mental health and prevent burnout.
Empathy and intuition are powerful assets in business and leadership.
Self-care is part of the giving equation—pouring into yourself matters.
Infusing generosity into business strategy can drive deeper success and alignment.
00:00 — The Power of Giving
02:05 — Balancing Giving and Self-Care
05:44 — Reflection and Integration of Giving
 
Connect with Chronic Boss:
🖤 chronicboss.com🖤 Instagram🖤 LinkedIn🖤 TikTok
 
Connect with Lilly:
🖤 lillystairs.com🖤 LinkedIn🖤 Instagram

The Car Accident that Changed Everything: Tiffany Yu on Rewriting Disability and the Anti-ableism Movement

In this conversation of the Chronic Boss Unfiltered Podcast Tiffany Yu shares her inspiring journey as the founder of Diversability, a disability-owned community business. She discusses her personal experiences with disability, the evolution of her identity, and the importance of community in fostering disability pride. Tiffany reflects on the key moments that shaped Diversability from a student club into a global organization, and she highlights the impact of her TikTok series and the Anti-Ablism Manifesto in advocating for disability rights and inclusion. In this conversation, Tiffany Yu shares her journey of navigating life with a disability, her advocacy work, and the creation of her book, 'The Anti-Ablest Manifesto.' She discusses the importance of community, the impact of her content on the disability community, and her aspirations for the future. Tiffany emphasizes the need for action-oriented advocacy and the significance of finding magic in one's identity, while also addressing the challenges faced by individuals with disabilities. What You’ll Learn: The importance of community in embracing one's identity.
The proverb 'the nail that sticks out gets hammered down' shaped her understanding of identity. Diversability started as a student club and evolved into a global organization. Key inflection points for Diversability included community events and leadership transitions. The pandemic prompted a shift to virtual events for Diversability. Tiffany's TikTok series on disability has gained significant traction and views. Content creation has connected Tiffany with others in the disability community. The Anti-Ablest Manifesto aims to empower individuals and organizations. Community is essential for personal growth and acceptance. Grief and gratitude can coexist in the journey of self-acceptance. Tiffany's book serves as a legacy for disability advocacy. The importance of action-oriented advocacy in creating change. Rediscovering joy and playfulness is vital for well-being. Finding their unique voice and community. Success is defined by self-acceptance and integrity.
 
Timestamps:
00:00 Introduction to Tiffany Yu and Diversability
03:15 Tiffany's Personal Journey and Identity
10:31 The Evolution of Diversability
22:55 The Anti-Ablism Manifesto and TikTok Success
24:57 Navigating Life with a Disability
25:53 Creating Content for the Disability Community
28:12 The Journey to Writing a Book
30:34 The Anti-Ablest Manifesto: Purpose and Impact
35:45 Finding Magic in Disability
41:16 Legacy and Future Aspirations
 
Connect with Tiffany Yu:
✨Website: https://www.tiffanyyu.com/bio
✨ YouTube Channel: https://www.youtube.com/@imtiffanyyu
✨Facebook: https://www.facebook.com/imtiffanyyu
✨Instagram: https://www.instagram.com/imtiffanyyu
 
Connect with Chronic Boss:
🖤 / https://chronicboss.com/ 
🖤 / instagram.com/chronicbossco/ 
🖤 / https://www.linkedin.com/company/chronic-boss/ 
🖤 / https://www.tiktok.com/@chronicbossco
 
Connect with Lilly:
🖤 / https://lillystairs.com/ 
🖤 / https://www.linkedin.com/in/lillystairs/ 
🖤 / https://www.instagram.com/lillystairs

The Four Rs to Rebuild Your Health After Autoimmune Diagnosis with Dr. Kara Wada

In this insightful and empowering episode of Chronic Boss Unfiltered, host Lilly Stairs sits down with Dr. Kara Wada — quadruple board-certified physician, autoimmune warrior, and founder of the Immune Confident Institute. As both doctor and patient, Kara bridges two worlds with empathy, expertise, and authenticity.
Diagnosed with Sjogren’s syndrome after years of symptoms and normal lab results, Kara experienced firsthand how challenging it can be to navigate chronic illness — even as a medical professional. What began as a personal health struggle has evolved into her mission to transform the patient experience and redefine what it means to thrive with autoimmunity.
Together, Lilly and Kara unpack the intersection of medicine, mindset, and self-advocacy. They discuss Kara’s Four Rs framework for healing, the “Perfect Storm” concept behind autoimmune disease, and how Kara built a values-driven medical practice rooted in compassion and connection. This episode is a masterclass in resilience, authenticity, and reclaiming your health on your own terms.
 
 What You’ll Learn:
How Kara’s journey from physician to patient reshaped her approach to medicine
Why Sjogren’s syndrome is often missed — and how to advocate for answers
The multifactorial nature of autoimmune disease and the “Perfect Storm” concept
How Kara’s Four Rs framework empowers patients to take back control of their health
The importance of aligning your career and purpose with your personal values
Why community and mentorship are essential for women in healthcare and entrepreneurship
How authenticity and vulnerability foster deeper trust between doctors and patients
Timestamps:
(00:00) – Introduction(02:40) – From Physician to Patient: Kara’s unexpected diagnosis and personal awakening(05:38) – Understanding Sjogren’s Syndrome: Misdiagnosis, symptoms, and stigma(08:42) – Women and Autoimmunity: Why women’s health is often overlooked(11:43) – Shifting Perspectives: How chronic illness deepened Kara’s empathy as a doctor(14:42) – Building a Patient-Centered Practice: The birth of the Immune Confident Institute(20:34) – The Perfect Storm Concept: What triggers autoimmunity and how to manage it(33:01) – The Four Rs Framework: A roadmap for healing and empowerment(38:54) – Entrepreneurship with Purpose: Balancing medicine, business, and motherhood(45:45) – Authenticity in Healthcare: The power of sharing your story
Connect with Dr. Kara Wada:
✨Website: https://www.drkarawada.com/
✨ YouTube Channel: https://www.youtube.com/@drkarawada
✨LinkedIn: https://www.linkedin.com/in/karawadamd/
✨Instagram: https://www.instagram.com/drkarawada/
 
Connect with Chronic Boss:
🖤 / https://chronicboss.com/ 
🖤 / instagram.com/chronicbossco/ 
🖤 / https://www.linkedin.com/company/chronic-boss/ 
🖤 / https://www.tiktok.com/@chronicbossco
 
Connect with Lilly:
🖤 / https://lillystairs.com/ 
🖤 / https://www.linkedin.com/in/lillystairs/ 
🖤 / https://www.instagram.com/lillystairs

Turning Pain Into Punchlines: Life As A Comedian With Type 1 Diabetes with Ivana Bonetti

“I make fun of it on stage. I call it the “Betes”. The pump doesn’t wear me—I wear the pump.”
In this hilarious and heartfelt episode of Chronic Boss Unfiltered, host Lilly Stairs sits down with Ivana Bonetti, Italian-American stand-up comedian, storyteller, and proud Type 1 diabetic. A Boston native from the North End, Ivana brings her sharp wit and resilience to the stage—transforming her chronic illness into comedy gold.
Diagnosed with Type 1 diabetes at 17, Ivana’s world shifted overnight. What began as a medical challenge became the foundation for her humor, advocacy, and perspective on life. From growing up in a food-loving Italian family to performing at legendary venues like the Laugh Factory and Apollo Theater, Ivana shares how she’s turned her “sweet” condition into a superpower.
Together, Lilly and Ivana dive into the healing power of laughter, the importance of representation in chronic illness spaces, and how comedy can bridge the gap between vulnerability and empowerment. This episode is a beautiful mix of humor, heart, and hard-earned wisdom—proof that even life’s toughest moments can be punchlines in disguise.
 What You’ll Learn:
How Ivana transformed her Type 1 diabetes diagnosis into comedic inspiration
The cultural role of food in her Italian-American upbringing—and how she navigates it with diabetes
Why support from family and community is essential for chronic illness management
How humor builds resilience and breaks down stigma
The lessons chronic illness teaches about adaptability, identity, and authenticity
Why embracing your story—messy parts and all—can empower both you and your audience
What it means to be a Chronic Boss when your life literally depends on balance
Timestamps:
(00:00) – Introduction: Meet Ivana Bonetti, comedian, storyteller, and Chronic Boss. (04:47) – Navigating Life with Type 1 Diabetes: Diagnosis, shock, and self-discovery. (10:08) – From Medicine to Microphone: The career pivot that changed everything. (14:54) – Building a Comedy Career: Finding her voice, her audience, and her punchlines. (19:54) – Living with Diabetes: Daily management and emotional resilience. (25:00) – Comedy as Advocacy: Turning medical moments into laughter and awareness. (30:11) – The Secret Sauce of a Chronic Boss: Humor, heart, and unshakable grit.
 Connect with Ivana:
 
✨Instagram
✨Tik Tok
✨Youtube
 
Connect with Chronic Boss:
🖤 chronicboss.com🖤 Instagram🖤 LinkedIn🖤 TikTok
 
Connect with Lilly:
🖤 lillystairs.com🖤 LinkedIn🖤 Instagram

Transforming Chronic Illness Into Your Sales Superpower with Justine Beauregard

“When people meet me they always go you are so organized, you are like systems oriented, youve got frameworks for everything and im like  Ive literally trained myself to have these skills because of my chronic illness”
In this inspiring episode of Chronic Boss Unfiltered, host Lilly Stairs sits down with Justine Beauregard, powerhouse sales strategist, entrepreneur, and Chronic Boss Collective member. Justine has helped hundreds of clients generate millions in revenue through her innovative approach to “feel-good sales.” But what makes her work extraordinary is how she’s woven her experience with multiple chronic illnesses into her sales philosophy.
Together, Lilly and Justine unpack what it means to lead with authenticity, why chronic illness can be a secret advantage in business, and how entrepreneurs can embrace frameworks that reduce sales anxiety. Justine shares her own journey of embracing vulnerability, building sustainable systems in business, creating boundaries, and cultivating a supportive community that empowers rather than drains. This conversation is equal parts strategy, wisdom, and soul
.What You’ll Learn:
Justine has worked with 700+ clients, helping them generate millions in revenue.
Vulnerability and openness about her chronic illnesses became a powerful branding asset.
ADHD reframed as a superpower: hyperfocus, efficiency, and system-building.
Sales anxiety can be reduced through frameworks that allow authenticity.
Business sustainability comes from flexibility, not rigid hustle culture.
Community recommendations are more powerful than Google searches—especially for health
Defines a Chronic Boss as someone who fully integrates ambition and chronic illness
Timestamps:
(00:00) – Introduction ambition meets chronic illness in the world of entrepreneurship.
(02:19) – Chronic Illness as a Mirror of Entrepreneurship  How flare-ups and uncertainty prepared her for the highs and lows of business.
(03:14) – Leading with Vulnerability Why Justine decided to openly share her conditions on her website and the impact on her clients.
(06:49) – Relating Through Authenticity  Opening up as a business strategy that deepens client trust and relatability.
(07:41) – Reframing ADHD & Other Conditions Turning hyperfocus and efficiency into strengths.
(10:07) – Confidence as an Output How confidence is built through action, not a prerequisite.
(13:37) – Process as a Superpower How medical routines taught Justine the power of systems and accountability.
(16:56) – Feel-Good Selling Defined Frameworks that empower entrepreneurs to sell authentically without anxiety.
(23:31) – Building a Business that Supports Health Sustainability, systems, and learning through trial and error.
(27:31) – Community as Medicine Why Chronic Boss connections provide both health and career solutions.
(37:25) – Finding Your Inner Circle The power of supportive, challenging, and uplifting friendships.
(43:40) – Having the Hard Conversations Growth through discomfort, curiosity, and open dialogue.
(46:16) – The Magic of Chronic Boss Networking Leading with vulnerability to create instant connection.
(51:59) – What Being a Chronic Boss Meansm Embracing all of yourself—conditions and business—as one whole identity.
 
Connect with Justine: 
✨/ SellWithJustine.com
✨/MonthlySpeedNetworking.com
✨/ https://www.instagram.com/sellwithjustine/#
✨/ https://www.linkedin.com/in/sellwithjustine
 
Connect with Chronic Boss:
🖤 / https://chronicboss.com/ 
🖤 / instagram.com/chronicbossco/ 
🖤 / https://www.linkedin.com/company/chronic-boss/ 
🖤 / https://www.tiktok.com/@chronicbossco
 
Connect with Lilly:
🖤 / https://lillystairs.com/ 
🖤 / https://www.linkedin.com/in/lillystairs/ 
🖤 / https://www.instagram.com/lillystairs 
 

When Wall Street Ambition Meets the Reality of Chronic Illness with Alex Wildeson

I didnt want to let me chronic illness take that away from me so during my medical leave I decided to launch three businesses
Episode Overview
In this candid and energizing episode of Chronic Boss Unfiltered, host Lilly Stairs sits down with Alex Wildson—venture capitalist, entrepreneur, podcaster, and fierce chronic illness advocate.
Alex’s story is one of resilience and reinvention. From her early days in oil and gas investment banking to private equity, to becoming a VC partner and launching her own ventures, Alex has navigated a demanding career while living with multiple chronic illnesses and undergoing major surgeries. Today, she’s the founder of Calling In Sick, a fast-growing podcast and platform redefining what it means to live and lead with chronic illness.
Lilly and Alex dive deep into the power of pivoting, creating community, redefining ambition, and building sustainable systems with boundaries and delegation. Alex also shares advice on starting a podcast, using technology to overcome limitations, and why success should be measured in more than just revenue
What You’ll Learn
How Alex went from investment banking grind to leading in venture capital and creative ventures.
Surviving a botched spinal surgery and used recovery time to launch three businesses.
Built Calling In Sick, a safe space for chronic illness community with hope and connection.
Advocates for boundaries, time blocking, and delegation to sustain entrepreneurship.
Redefined success away from revenue toward impact and meaningful connections.
Secret Sauce: pairing an analytical finance brain with high EQ storytelling
Timestamps
(00:00) – IntroductionLilly sets the stage: ambition, women’s health, and chronic illness.
(03:12) – Leaving Wall Street Dreams Surgeries, hospitalizations, and realizing work couldn’t be her whole identity.
(04:44) – Pivot to Pensions Rebuilding a $5B venture book at the Texas Teachers Retirement System.
(05:33) – A Botched Spinal Surgery Waking up paralyzed, hospital stay, and stepping away from traditional finance.
(07:29) – Finance Meets Creativity How storytelling and numbers-thinking became her edge.
(09:47) – The Birth of Calling In Sick A TikTok video goes viral, sparking a new platform.
(11:22) – A Safe Space, Not Trauma Dumping Building community around hope, joy, and connection.
(13:21) – Seeds of Hope Why Alex refuses to resign to “just being sick.”
(17:34) – Boundaries & Delegation Protecting energy, knowing her work hours, and building a team of chronically ill women.
(20:40) – Letting Go of Guilt Owning your time, not responding to every DM, and the $/hour mindset.
(25:25) – Redefining AmbitionFrom promotions and bonuses to impact and human connection.
(31:04) – Alex’s Secret Sauce Analytical brain + high EQ fueled by chronic illness = magic in social media growth.
(33:51) – Advice for Entrepreneurs Find environments that celebrate your superpower.
(34:37) – What’s Next for Alex Growing Calling In Sick, launching a new app, and pitching a TV show.
(39:21) – What Being a Chronic Boss Means Making little Alex proud: honoring past versions of herself and embracing the whole identity.
 
Connect with Alex: 
✨/ https://www.instagram.com/AlexandraWilderson/
✨/ https://www.tiktok.com/@alexandrawildeson
✨/ https://www.justmediahouse.com/podcasts/calling-in-sick
✨/ https://open.spotify.com/show/1FbzAVRNAYGWW8l8IPQew5?si=64a284c358a94e75
 
Connect with Chronic Boss:
🖤 / https://chronicboss.com/ 
🖤 / instagram.com/chronicbossco/ 
🖤 / https://www.linkedin.com/company/chronic-boss/ 
🖤 / https://www.tiktok.com/@chronicbossco
 
Connect with Lilly:
🖤 / https://lillystairs.com/ 
🖤 / https://www.linkedin.com/in/lillystairs/ 
🖤 / https://www.instagram.com/lillystairs