You left the corporate world for freedom. Your health insurance strategy should match that ambition — not trap you in a plan designed for someone else's life. Kieffer Insurance Group designs coverage strategies built specifically for freelancers, independent contractors, and self-employed professionals.
100%
Premium Deductible
Triple
HSA Tax Advantage
Private PPO
Gold Standard Coverage
Nationwide
Doctor Access
Shopping by premium alone and ignoring total out-of-pocket exposure
Not taking the self-employed health insurance deduction
Choosing a narrow-network plan that limits access to preferred doctors
Skipping gap coverage and leaving income unprotected during illness
Failing to open an HSA when eligible — leaving triple tax savings on the table
Not reviewing coverage annually as income and health needs change
Premium individual health insurance with nationwide access to top doctors and specialists — no referrals required. The gold standard for 1099 professionals who demand quality and flexibility.
Best for: High-income 1099 professionals who want premium coverage
Pair a high-deductible health plan with a Health Savings Account (HSA) to pay for medical expenses with pre-tax dollars. Triple tax advantage: contributions are tax-deductible, growth is tax-free, and withdrawals for medical expenses are tax-free.
Best for: Healthy 1099 professionals focused on tax efficiency
As a 1099 professional, you can deduct 100% of your health insurance premiums from your taxable income — reducing your adjusted gross income dollar for dollar. This is one of the most powerful tax deductions available to the self-employed.
Best for: All 1099 professionals and self-employed individuals
Supplement your primary coverage with accident insurance, critical illness coverage, and hospital indemnity plans that pay cash benefits directly to you — protecting your income when you can't work.
Best for: 1099 professionals without employer sick leave or disability
We start by understanding your health history, income structure, preferred doctors, and financial goals — not just your budget.
We map your business structure to identify every available health insurance deduction — self-employed premium deduction, HSA contributions, and more.
We recommend a specific coverage architecture — not just a plan — that aligns your protection with your income and tax position.
We handle enrollment and stay with you as a strategic partner — reviewing your coverage every year as your income and needs evolve.
Explore how 1099 coverage connects with your broader financial strategy.