Who we help

You are the employer now. Nobody explained what that costs.

Working for yourself means the plan, the premium and the paperwork are all yours. Here is what is actually available, and what it costs before anyone tries to sell you something.

The moment you left a W-2 job, a benefit you never thought about became a line item you pay in full. There is no employer covering seventy percent of the premium, no open-enrollment email, and no one to ask which plan is the sensible one.

Most people in this position do one of two things. They take the first marketplace plan that looks affordable and discover the deductible on their first real claim, or they go without and hope. Both are decisions made without the information that would have made them decisions.

What you can actually get comes down to three things: your household income for the year, your county, and your health. Those three inputs change the answer completely, which is why nobody can quote you honestly from a webpage.

Get your free quote

Six fields, about a minute. We come back with what is actually available where you live.

This form is not connected to a submission endpoint yet. Until it is, please book a call or email Troy@legacystrategies.co.

Please do not submit account numbers, Social Security numbers, policy numbers or other sensitive financial details through this form. Detailed information is gathered later through a secure process.

What applies to you specifically

Marketplace subsidies are based on income you estimate

Self-employed income is uneven, and the subsidy is calculated on what you project for the year. Estimating badly in either direction has consequences at tax time. This is worth getting right rather than guessing.

Health premiums may be deductible

The self-employed health insurance deduction exists, with conditions — including that you are not eligible for a plan through a spouse's employer. Whether it applies to you is a question for your accountant, not for us, but it is worth asking them.

Underwritten plans are sometimes far cheaper

If you are healthy and paying full price without a subsidy, short term and multi-year medical plans can cost meaningfully less. They are also not comprehensive coverage, and we say which category a plan is in before we say what it costs.

Income protection matters more without an employer

No sick pay, no group life, no short-term disability. Coverage that replaces income is doing a job here that a salary used to do quietly in the background.

Questions we get asked

Is the marketplace always the cheapest option for me?
Not always. If your income qualifies you for a subsidy, it usually is. If it does not, an underwritten plan can be cheaper — though it is a different kind of coverage with different limits. The comparison is worth running rather than assuming.
My income changes every month. How do I even estimate it?
You estimate the year and you can update it during the year if it changes materially. Getting this wrong in either direction affects what you owe or get back at tax time, so it is one of the things we walk through rather than leaving you to guess.
What if I miss open enrollment?
Outside open enrollment you generally need a qualifying life event — losing coverage, moving, marriage, a birth. Most supplemental products are available year-round, and some underwritten medical plans are too, depending on the state.

This page is general education, not individualised financial, tax, legal or investment advice. Product availability, pricing and eligibility vary by state, county, age and health. Nothing here guarantees any particular outcome, cost or result.

Next step

Fifteen minutes, and you will know where you stand.

A review is a short conversation about the coverage and savings you already have. We look at what you pay, what it covers, and whether there is a better fit available where you live. No cost, no obligation, and no pitch if nothing needs changing.