Clearwater, FL

Clearwater health insurance for people leaving a job to go out on their own

Clearwater has plenty of people who just walked out of a company job to start something of their own. The first question is always the same: what do we do about health insurance now?

Sam Jaber, licensed health insurance broker

Hi, I'm Sam Jaber, a licensed broker who helps people buy their own health insurance. I'm in Tampa, right across the Courtney Campbell from Clearwater. Clearwater is the county seat of Pinellas, so the plans you pick from are the county's.

The Clearwater calls I get most often come from people who just left a job. A marketing director who went freelance, a dental hygienist who opened a mobile practice, an IT manager turned consultant. Phone and video calls are how I work, here and across the 36 states where I'm licensed. See my Tampa page for the rest of the bay.

Leaving a job doesn't mean losing your PPO

Many people leaving a company had a PPO there and assume they'll have to give it up. On the Pinellas marketplace, the one PPO for sale costs well over double the alternatives. Outside the marketplace, a private PPO with a nationwide network is available through me, and for a healthy person paying full price it's often the closest thing to what they had at work.

Three clocks start when you give notice

The first clock is your last day of coverage, which your employer sets. The second is COBRA, which lets you keep the same plan for a while if you pay the full cost yourself. The third is your special enrollment window, generally 60 days after job coverage ends, to buy a marketplace plan.

The Pinellas plan file lists 149 medical plans from 6 insurance companies, with only 14 PPOs. On silver, at age 40, the marketplace PPO with the smallest premium still costs 138% more than the smallest-premium silver plan on any other network. That's why the PPO question deserves its own quote.

Scenario 1 of 3

A manager leaving a Clearwater company to consult

Picture a 48-year-old operations manager who just gave notice at a company near the Gulf to Bay corridor. He'll consult for two former clients. His wife is self-employed too. They've had the same doctors for years, and their cardiologist is affiliated with Morton Plant Hospital, which has served Clearwater since 1916.

They have three choices on the table: stay on COBRA, buy on the marketplace, or apply for a private PPO. If they're healthy and the first year of consulting will pay too well for a credit, I'd price the private PPO against COBRA first. It's underwritten, so their health answers decide if it's offered. If it fits, the nationwide network often feels like what they're leaving.

Scenario 2 of 3

Year one of the business will be lean

A new business often pays its owner very little at first. If your first-year income lands in the tax credit range, a marketplace plan is usually the most affordable way to stay covered, and COBRA rarely competes with that. We'd file inside your 60-day window and choose a plan that keeps your doctors.

Scenario 3 of 3

Someone in the family is in active treatment

If you or your spouse is mid-treatment, the safest move is usually to keep continuity first. That can mean staying on COBRA through the treatment, or moving to a marketplace plan that includes your doctors. Marketplace plans must accept you no matter your health and can't raise your rate because of it. A private plan can't promise that.

Where the figures on this page come from

  • Clearwater is the county seat of Pinellas County Source
  • BayCare Morton Plant Hospital, at 300 Pinellas Street in Clearwater, was founded in 1916 Source
  • The 2026 federal plan file lists 149 individual medical plans for Pinellas County, which includes Clearwater, from 6 insurance companies (counted by company; Florida Blue files under two names and is counted once); 14 are PPOs, all from one insurer Source
  • In Pinellas County, the lowest-priced silver marketplace PPO for a 40-year-old costs 138% more than the lowest-priced silver plan of any other network type, before any subsidy Source
  • Losing job-based coverage opens a special enrollment period, generally 60 days, to buy a marketplace plan outside open enrollment Source

Questions from Clearwater's new business owners

Straight answers, no sales pitch.

Should I take COBRA when I leave my job in Clearwater?

Sometimes. It keeps your exact plan, but you pay the full cost. Compare it with a marketplace plan and a private PPO before you decide.

How long do I have to buy a plan after leaving my job?

Losing job coverage generally opens a 60-day special enrollment window for the marketplace. A private plan doesn't need that window but needs time to approve you.

Can I keep a PPO after leaving my employer?

Yes. COBRA keeps your old plan for a while, and a private nationwide PPO is an option for healthy people paying full price.

Do I pay you anything?

No. You won't get a bill from me; the insurance company pays my commission.

Leaving your job in Clearwater? Call me first

Tell me your last day, what COBRA would cost, who's on the plan and what you expect the new business to pay you this year. I'll lay out every path with the dates that matter.

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