Freelance artists, writers, and other creatives often build rewarding careers without the safety net of employer-sponsored health insurance, paid leave, retirement benefits, or long-term financial protections. As health concerns, aging, disability, or caregiving responsibilities arise, navigating these challenges independently can feel overwhelming. A panel of health-care and benefits professionals, advocates, and fellow creatives shares practical guidance on protecting health, financial well-being, and creative longevity. Topics include health insurance, Medicare, Social Security, caregiving, long-term planning, burnout prevention, and strategies for maintaining a sustainable creative career at every stage of life. Panelists include Jennifer Arango (MHA, Syndicated Insurance Agency), Meghan Atilano (executive director of HR and training, Manna Development Group), Teresa Beckwith (Apricot Forest Acupuncture), Kelly Cooney (past president, National Association of Rehab Providers and Agencies), Matt Medeiros (president, Clelland and Company), and Fran Pillersdorf (client services, Alvino & Associates). Moderated by Karen Martin (The Princess Project). Q&A follows.