Health & Dental Insurance for the Self-Employed in Ontario

When you leave a job with benefits — or never had them — you quickly discover how much your employer’s health plan was quietly covering. Prescriptions, dental checkups, physio, new glasses: all now out of pocket, and none of it covered by OHIP for working-age adults.

Personal health and dental insurance rebuilds that safety net. Here’s how it works for the self-employed in Ontario.

What personal health & dental plans cover

These plans are modular — you choose the components and levels that fit your needs and budget. Typical coverage includes:

• Prescription drugs — a percentage of eligible drug costs up to an annual maximum
• Dental — checkups, cleanings, fillings, and often major work like crowns
• Vision — eye exams, glasses, and contacts up to a limit
• Paramedical — physiotherapy, chiropractic, massage, psychology/psychotherapy, and more
• Extras — often emergency travel medical, ambulance, and medical equipment

You can start basic and add coverage, so you’re not paying for things you won’t use.

Two types of plan: underwritten vs. guaranteed

Medically underwritten plans ask health questions. If you’re healthy, you get more coverage for less — but pre-existing conditions may be limited or excluded.

Guaranteed-acceptance plans ask no health questions and can’t decline you. They cost more and have lower limits, but they’re invaluable if you have existing conditions or have been declined elsewhere.

If you’re leaving a job, there’s also a third route: a conversion plan. Many insurers let you move from group coverage to an individual plan without medical questions if you apply within a set window (often 60–90 days) after your group coverage ends. Miss that window and you may have to answer health questions — so don’t wait.

What it costs

Premiums depend on your age, who’s covered, and the level of coverage. As a rough guide:

• Basic individual plans often start around $45–$60/month
• Comprehensive plans with strong drug, dental, and paramedical limits cost more
• Family plans scale up with the number of people covered

Because plans are modular, the smartest approach is to match coverage to your actual usage. If you take a regular medication and see a physio monthly, prioritize those. If you mainly want protection against big dental bills, weight the plan that way.

The tax advantage the self-employed often miss

Here’s a genuine perk of being your own boss. Through a Private Health Services Plan (PHSP) or a Health Spending Account (HSA), a self-employed person or incorporated business can often turn personal medical and dental costs into a deductible business expense — subject to CRA’s rules.

For some business owners, running health costs through an HSA is more tax-efficient than buying a traditional premium-based plan, especially if your expenses are predictable. It’s worth modelling both with your accountant. We can help you compare a conventional plan against an HSA approach.

How to choose the right plan

1. List your real health costs. Prescriptions, dental visits, physio, glasses — what do you actually spend in a year?
2. Decide underwritten vs. guaranteed. Healthy? Underwritten gives more value. Pre-existing conditions? Consider guaranteed or conversion.
3. Check the limits and co-insurance. A plan that covers “80% of drugs up to $1,000/year” is very different from one with a $5,000 limit.
4. Consider an HSA. If you’re incorporated or have steady costs, compare the tax-efficient route.
5. Compare insurers. Coverage, limits, and claims experience vary — that’s what we do for you.

Don’t stop at health & dental

Health and dental insurance covers everyday costs, but the self-employed have two bigger exposures worth addressing:

• Disability insurance — replaces your income if you can’t work. Usually the top priority for anyone self-employed.
• Critical illness insurance — a lump sum on a major diagnosis.

The bottom line

If you’re self-employed in Ontario, a personal health & dental plan covers the prescriptions, dental, vision, and paramedical costs OHIP and your (nonexistent) employer won’t. Choose the plan type that fits your health, size the coverage to your real usage, and ask whether an HSA could make it more tax-efficient.

Ready to compare plans? Get a free quote — we’ll build coverage around how you actually use health care, at the best price we can find.