Christine Kieffer, Health Insurance Strategist

The Knowledge Library

Strategy Starts
With Education.

In-depth articles on health insurance strategy, tax optimization, and benefit architecture — written for entrepreneurs, 1099 professionals, and growth-minded business owners who want to think beyond the premium.

Also on LinkedIn: "What Your CPA Won't Tell You"

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Why Should I Apply for Private Health Insurance While I Am Healthy?

Many private health plans decide who can join based on a short set of health questions. When you apply while you are healthy, with no tests or procedures pending, you are far more likely to qualify for the plans with the best networks and value.

October 21, 2026Read Article

Tax Strategy 6 min read

The $15,000 Write-Off Self-Employed People Leave on the Table Every Year

If you are self-employed and paying for your own health insurance, the IRS allows you to deduct 100% of those premiums directly from your gross income — not as an itemized deduction, but as an above-the-line adjustment. Most people either don't know this exists, or they're not applying it correctly.

June 2025Read Article

HSA Strategy 5 min read

The Only Account in America With a Triple Tax Advantage — And Most People Are Missing It

There is one account in the U.S. tax code that gives you a deduction going in, tax-free growth while it sits, and tax-free withdrawals when you use it. Most self-employed professionals and entrepreneurs either don't have it — or are using it wrong.

June 2025Read Article

All Articles

The Full Library3 articles

Strategy Fundamentals 5 min readOctober 21, 2026

Why Should I Apply for Private Health Insurance While I Am Healthy?

Read

Tax Strategy 6 min readJune 2025 LinkedIn

The $15,000 Write-Off Self-Employed People Leave on the Table Every Year

Read

HSA Strategy 5 min readJune 2025 LinkedIn

The Only Account in America With a Triple Tax Advantage — And Most People Are Missing It

Read

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Strategy StartsWith Education.

Start Here

Why Should I Apply for Private Health Insurance While I Am Healthy?

The $15,000 Write-Off Self-Employed People Leave on the Table Every Year

The Only Account in America With a Triple Tax Advantage — And Most People Are Missing It

The Full Library3 articles

Why Should I Apply for Private Health Insurance While I Am Healthy?

The $15,000 Write-Off Self-Employed People Leave on the Table Every Year

The Only Account in America With a Triple Tax Advantage — And Most People Are Missing It

Get Christine's Insights Every Wednesday

Strategy Starts
With Education.