Chronic Boss Unfiltered is the podcast where ambition meets women’s health. Hosted by Lilly Stairs—two-time founder and three-time autoimmune patient—this show dives deep into what it really takes to build a business or climb the career ladder while living with chronic illness. Each week, Lilly sits down with powerhouse women who are chasing big dreams while navigating flare-ups, fatigue, and everything in between. Expect raw, unfiltered conversations that move from the hospital bed to the boardroom, giving you both inspiration and practical insights to balance health and ambition.
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Chronic Boss Unfiltered is the podcast where ambition meets women’s health. Hosted by Lilly Stairs—two-time founder and three-time autoimmune patient—this show dives deep into what it really takes to build a business or climb the career ladder while living with chronic illness. Each week, Lilly sits down with powerhouse women who are chasing big dreams while navigating flare-ups, fatigue, and everything in between. Expect raw, unfiltered conversations that move from the hospital bed to the boardroom, giving you both inspiration and practical insights to balance health and ambition.
The Truth About Work, Sex and Chronic Illness with Ali DiGiacomo
Chronic Boss Unfiltered
59 minutes
1 month ago
The Truth About Work, Sex and Chronic Illness with Ali DiGiacomo
Diagnosed with rheumatoid arthritis at 15, Ali thought her athletic career was over. Instead, she built a global following by embracing authenticity, humor, and resilience.
Episode Overview
Ali DiGiacomo—known as Another Day with RA—shares how she went from teenage athlete to patient advocate, trainer, and creator of the “Fuck It, Let’s Slay” fitness app. She opens up about building a 160K+ social following, freelancing struggles, intimacy and pelvic health, and why humor and resilience are her superpowers.
What You’ll Learn
How Ali turned her RA diagnosis into a platform for advocacy and empowerment.
Why authenticity and humor resonate more than “perfect” highlight reels.
The realities of freelancing and health insurance with chronic illness.
Tips for traveling and working while managing RA.
Why breaking the silence around intimacy and pelvic health matters.
Timestamps
(00:00) Introduction – Lilly welcomes Ali to the podcast. (00:46) Meet Ali – From “Another Day with RA” to trainer and advocate. (02:07) Diagnosis at 15 – Balancing RA with competitive swimming. (05:24) Losing Swimming, Finding Fitness – Rediscovering movement through inspiration online. (07:39) Becoming a Personal Trainer – The path back to fitness. (08:14) Launching “Fuck It, Let’s Slay” – Creating workouts for chronic illness. (11:35) Community Feedback – Stories of transformation from users. (12:53) Building a Social Following – Growing to 160K with raw honesty. (14:48) Authenticity & Dark Comedy – Why humor resonates online. (18:27) Setting Boundaries – Managing DMs, burnout, and online pressure. (22:47) Freelancing Realities – Wearing many hats and navigating insurance. (32:19) Nomadic Lifestyle – Living in an Airstream and traveling with RA. (38:13) Travel Hacks – Meds, injections, and business on the road. (42:14) Attitude as a Superpower – Resilience and rolling with the punches. (47:29) Getting real about sex & intimacy – Talking openly about pelvic health. (55:46) Authentic Women’s Health Conversations – Breaking taboos. (57:18) What Being a Chronic Boss Means – Ali’s empowering definition.
Connect with Ali:
✨/ https://www.instagram.com/anotherdaywithra/
✨/ https://www.tiktok.com/@anotherdaywithra
✨/ https://www.anotherdaywithra.com/
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
Links
Ali’s Fitness App: https://my.playbookapp.io/ali-digiacomo
Chronic Boss Unfiltered
Chronic Boss Unfiltered is the podcast where ambition meets women’s health. Hosted by Lilly Stairs—two-time founder and three-time autoimmune patient—this show dives deep into what it really takes to build a business or climb the career ladder while living with chronic illness. Each week, Lilly sits down with powerhouse women who are chasing big dreams while navigating flare-ups, fatigue, and everything in between. Expect raw, unfiltered conversations that move from the hospital bed to the boardroom, giving you both inspiration and practical insights to balance health and ambition.
