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How to Handle Medical Expenses as a Self-Employed Person

Medical costs hit self-employed people harder than employees. Learn the high-deductible health plan strategy, HSA optimization, and every available tax deduction for freelancer medical expenses.

By FlowFund TeamJune 28, 20263 min read

Medical Costs Hit Freelancers Harder

Without employer insurance, freelancers pay more for health coverage and face higher out-of-pocket exposure. Understanding your options reduces both the cost and the financial shock of medical events.

The High-Deductible Strategy

For healthy freelancers in the US: A High Deductible Health Plan (HDHP) combined with a Health Savings Account (HSA) is often the optimal approach.

HDHP: Lower monthly premium than traditional plans. Higher deductible ($1,600+ individual in 2024).
HSA: Pre-tax contributions (up to $4,150 individual in 2024). Invest the HSA balance in index funds. Use HSA funds tax-free for medical expenses.

Net effect: Lower monthly premium, tax-advantaged savings for medical expenses, and a growing invested balance for future medical costs.

The Medical Emergency Fund

Beyond your regular emergency fund, maintain a separate medical emergency fund equal to your annual out-of-pocket maximum ($8,050 for individual HDHP plans in 2024).

This ensures a major medical event does not blow up your general emergency fund.

Tax Deductions for Medical Expenses

Self-employed health insurance premiums: 100% deductible off adjusted gross income (US).

HSA contributions: Fully deductible (US).

Medical expense deduction: Medical expenses exceeding 7.5% of AGI are deductible as an itemized deduction. For most, this threshold is too high to reach. But worth calculating in a high-expense medical year.

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