Free Strategic Guide — Guide 2 of 3

The 1099 Professional's Health Insurance Guide

Stop overpaying. Start strategizing. Everything independent contractors, freelancers, and consultants need to know about coverage options, tax deductions, and building a smarter health plan.

100%
Premium Deductible
$8,300
Max HSA (Family)
5
Coverage Options
GUIDE 2 OF 3
The 1099 Professional's
Health Insurance
Guide
By Christine Kieffer | Kieffer Insurance Group LLC
What's Inside
01Your Coverage Options as a 1099 Professional
02The Self-Employed Health Insurance Deduction
03Health Savings Accounts for 1099 Professionals
04Income Variability — The 1099 Challenge
05The 4-Step Strategic Framework
Free download — no credit card required

What You Will Learn

This guide is written specifically for independent contractors, freelancers, consultants, and gig workers. It covers every coverage option available to you, how to maximize your tax deductions, and how to build a health insurance strategy that actually serves your life and income structure.

5 coverage options available to 1099 professionals — ranked by cost-effectiveness
How to claim the 100% Self-Employed Health Insurance Deduction correctly
The HSA triple tax advantage strategy and how to use it as a retirement tool
How to navigate income variability and marketplace subsidy reconciliation
The 4-step strategic framework for building your optimal coverage plan
Why your CPA may be missing key deductions — and what to ask them
Example Tax Savings (22% Bracket)
Medical premiums ($9,600/yr)Save $2,112
Dental premiums ($1,200/yr)Save $264
Vision premiums ($360/yr)Save $79
HSA contribution ($4,150/yr)Save $913
Total Annual Tax Savings$3,368+
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