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 mental health and addiction coverage

If you've been laid off, are thinking about going solo, or are tired of paying insane premiums for garbage coverage, this episode is for you. Find a gift of 50% off the admin fee for It Gets Late Early listeners at https://essentlcreator.com/maureen.

Resources:

-Get Business Protection and Health Coverage at Solopreneur-friendly Prices - https://essentlcreator.com/maureen

-Free Guide to LinkedIn Job Hunting for the 40+ Crew - https://www.itgetslateearly.com/job-guide

Connect with Crystal Jackson:

-LinkedIn: https://www.linkedin.com/in/crystal-jackson-mba-8893b72bb/

-Website: https://essentlcreator.com/

Connect with Maureen Clough:

-LinkedIn: maureenwclough - https://www.linkedin.com/in/maureenwclough/

-Website: itgetslateearly.com - https://www.itgetslateearly.com/

-Instagram: @itgetslateearly - https://www.instagram.com/itgetslateearly/

-YouTube: @itgetslateearly - https://www.youtube.com/channel/UCGrHwk-y7ERaq7bCSjZYf1A?sub_confirmation=1

-Facebook: It Gets Late Early - https://www.facebook.com/people/It-gets-late-early/100088694515585/

Affiliate Disclaimer:

Hey there! Just a quick heads-up — some of the links we share in our show notes, YouTube videos, or episodes might be affiliate links. That means if you click on one and make a purchase, we might earn a small commission (at no extra cost to you).

We only shout out products, tools, or services we’ve actually tried, love, or think you’ll find genuinely useful. Still, it’s always a good idea to do your own homework before buying anything.

Using these links helps support the show and keeps It Gets Late Early rolling — so thanks a ton for being part of the community!