{"podcast":{"title":"It Gets Late Early","slug":"it-gets-late-early-6096744","podcast_index_feed_id":6096744,"rss_url":"https://feeds.captivate.fm/it-gets-late-early/","website_url":"https://www.itgetslateearly.com/","image_url":"https://artwork.captivate.fm/dc4d6575-9642-4d43-94d5-225572b5cd9f/2026-IGLE-COVER-FINAL.png","author":"Maureen Wiley Clough","episode_count":73,"summary":"Have you ever looked around at work and realized you might be one of the oldest people in the room—and you’re not even 40 yet? It Gets Late Early is a show about what’s really happening to experienced workers as the rules of work change. We dig into layoffs dressed up as AI strategy, side hustles and portfolio careers, the quiet rise of workplace ageism, and the (sometimes harsh) reality of building a career in midlife and beyond. We connect the dots between corporate decisions, economic forces, and the real lives of people navigating a changing world of work to help make sense of it all…because the career playbook we all followed was for a game no one can win anymore. You’ll hear honest conversations, expert insights, and practical advice for people trying to figure out what comes next—all wrapped up in a healthy dose of dark humor. Because sometimes you have to laugh so you don’t cry. Hosted by Maureen Wiley Clough—corporate dropout and ex-journalist who won’t quit telling the truth about work.","last_synced_at":"2026-06-10T02:19:57.969761+00:00","page_url":"https://stenobird.com/podcast/it-gets-late-early-6096744"},"episode":{"title":"I Paid $48K for Health Insurance and Still Owed $10K—So I Built a Solution","slug":"i-paid-48k-for-health-insurance-and-still-owed-10k-so-i-built-a-solution","published_at":"2025-11-13T12:00:00+00:00","page_url":"https://stenobird.com/podcast/it-gets-late-early-6096744/i-paid-48k-for-health-insurance-and-still-owed-10k-so-i-built-a-solution","show_page_url":"https://stenobird.com/podcast/it-gets-late-early-6096744","url":"https://www.itgetslateearly.com/","audio_url":"https://episodes.captivate.fm/episode/4e08ddd0-f5ed-4144-ba12-3ec576aa28bc.mp3","summary":"With mass layoffs hitting tech, media, and corporate America, more professionals over 40 are being forced into freelance work, consulting, and solopreneur life—whether they planned for it or not. And here's a big problem with that: the moment you leave corporate, you lose access to affordable health insurance. Suddenly, you're staring down $4,000/month premiums, sky-high deductibles, and hospital bills that make you wonder what you're even paying for. In today's episode, I sit down with Crystal Jackson—also known as The Real Mrs. Poindexter—a former Intel engineer turned viral content creator with millions of followers. After 13 years in corporate, Crystal left to raise her kids, went back to work for the benefits, left again, and eventually found herself paying $48,000 a year for health insurance that barely covered anything. When she got sick and ended up with another $10,000 in medical bills, she'd had enough. So she did what any fed-up engineer would do: she co-founded EssentL Creator with her husband Chris to solve the problem no one else would touch—affordable, corporate-level health insurance for freelancers, gig workers, and solopreneurs. In this episode, we talk about: Why Crystal was paying $48K/year for health insurance and still owed $10K in hospital bills How the \"future of work\" is creating a wave of involuntary entrepreneurs (and what that means for you) What a PEO (Professional Employer Organization) actually is—and how it gives solopreneurs access to corporate-level benefits Why leaving corporate might be the scariest—and best—thing that ever happens to you How to protect yourself legally and financially when you go out on your own (LLCs, IP protection, contract red-lining) The mental health crisis among content creators—and why EssentL offers enhanced…","meta_description":"With mass layoffs hitting tech, media, and corporate America, more professionals over 40 are being forced into freelance work, consulting, and solopreneur…","key_points":[],"chapters":[],"topics":[],"duration_seconds":4485,"processing_state":"not_requested","actions":[{"name":"request_transcript","method":"POST","url":"https://stenobird.com/v1/public/podcasts/it-gets-late-early-6096744/episodes/i-paid-48k-for-health-insurance-and-still-owed-10k-so-i-built-a-solution/transcription-requests","description":"Idempotently request low-priority transcript generation for this episode."},{"name":"read_markdown","method":"GET","url":"https://stenobird.com/podcast/it-gets-late-early-6096744/i-paid-48k-for-health-insurance-and-still-owed-10k-so-i-built-a-solution.md","description":"Read the agent-friendly Markdown representation of this episode resource."}]}}