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.

Prefer to Read About the Episode:

When Ali DiGiacomo-known online as Another Day with RA-was diagnosed with juvenile rheumatoid arthritis at just 15, she had no idea it would become the launchpad for a wildly empowering and hilarious journey of advocacy, entrepreneurship, and chronic boss energy. On this episode of Chronic Boss Unfiltered, host Lilly Stairs sits down with the unfiltered powerhouse herself to talk about turning pain into purpose, creating inclusive fitness, and why it’s time we start talking about pelvic health and intimacy with the same candor we do medication.

How RA Became Her Platform for Empowerment

Ali was a competitive swimmer on track to swim in college when RA sidelined her plans. “I didn’t even tell anyone in high school,” she admits. “I was in denial.” But years later, after spotting someone online working out with the same medication she was on, she had a lightbulb moment: maybe she could return to fitness-this time on her own terms. That spark led to her becoming a personal trainer and launching her own fitness app tailored for chronic illness warriors.

Her message is clear: “You don’t have to ‘get over’ your illness to start living. You can build something powerful with it.”

Authenticity Over Perfection

Ali’s rise to becoming a content creator with over 160,000 followers didn’t come from curated highlight reels. It came from realness. “I post the good, the bad, and the ugly. I’ll make fun of myself, cry, and then make a reel about it,” she laughs. Whether she’s doing makeup while educating about methotrexate or creating darkly funny skits about joint pain, Ali connects with her community through radical honesty and humor.

The Realities of Freelancing and Health Insurance

Ali doesn’t sugarcoat the freelance life. “Health insurance in this country is a nightmare,” she shares candidly. After leaving a traditional job, she bounced between her partner’s insurance and Medicaid, navigating all the red tape just to access the medications that keep her functional. Her advice to aspiring freelancers with chronic illness? “It’s not easy, and you need a plan. But it can be worth it.”

Tips for Traveling While Managing RA

Now a full-time nomad living out of an Airstream, Ali shares her hacks for managing RA on the road:

• Portable Fridge: “Don’t suffer like I did with ice boxes. Get a fridge that plugs into your car for injections.”
• Flexible Work Schedule: She tailors her workload to her energy levels-filming content in the mornings and collaborating with her partner on production work later in the day.
• Embrace the Chaos: “It’s not easy. But the challenge keeps me feeling alive.”

Opening Up About Sex, Intimacy, and Pelvic Health

Ali isn’t just transforming how we think about fitness-she’s breaking the silence on intimacy and chronic illness. As an ambassador for a vibrator company and a fierce advocate for pelvic floor therapy, she’s on a mission to normalize conversations around sex, pain, and pleasure. “Nobody warned me that methotrexate could kill your sex drive,” she says. “We deserve better education and support around this.”

Ali’s Secret Sauce

In true Chronic Boss fashion, Ali wrapped the episode by naming her “Secret Sauce”: blending her skill for content creation that makes people laugh with the resilience chronic illness has given her. “Even when I’m in pain, I can make someone laugh. That’s my power.”

What Being a Chronic Boss Means to Ali

“Being a chronic boss means being an epic badass,” Ali says. “It means taking your chronic illness and turning it into something powerful. And cheering on other chronic bosses while you’re at it.”

Follow Ali on Instagram and TikTok @anotherdaywithra and check out her fitness app for inclusive, modified workouts you can do from a bed, chair, or wherever you are.

Want to discover your own Secret Sauce? Download the free worksheet at ChronicBoss.com and learn how to blend your skills and superpowers into a thriving career with chronic illness.

Connect with other Chronic Bosses at the Chronic Boss Monthly Mastermind. A monthly strategy room for ambitious women building businesses while honoring their health.