Health Insurance and Benefits When You Work Alone (Book + Operator Toolkit)
You left the job. The benefits didn't come with you.
Health insurance, disability coverage, life insurance, paid leave: your employer used to handle all of it. Now you are the employer, and 2026 is one of the most complicated years ever to buy your own coverage. The enhanced marketplace subsidies have ended, the 400% income cliff is back, and repayment of excess subsidies is no longer capped.
This book shows how each piece works, with the arithmetic laid out, so you can make your own choices for your household, your income, and your state.
What's inside the book (206 pages, US Letter PDF + EPUB):
- Part One — The day coverage ends: the sixty-day clocks, COBRA without the myths, a spouse's plan and the end of the "family glitch," Medicaid and CHIP, and a first-year benefits budget.
- Part Two — The marketplace when income isn't steady: how the 2026 premium tax credit is calculated, the cliff, estimating income you haven't earned yet, reconciliation without a repayment cap, legitimate levers on MAGI, and choosing a plan by what it will really cost.
- Part Three — The tax tools: the self-employed health insurance deduction (and the spouse rule that trips people up), HSAs under the 2026 rules including bronze plans and direct primary care, and spouse-employee and S-corp arrangements.
- Part Four — The rest of the safety net: disability insurance, life and long-term care, dental and vision, the alternatives to ACA coverage, state paid leave, what to do when a bill or claim goes wrong, and household changes.
- Part Five — Medicare, outside the US, and every year: the bridge to 65, notes for Canada, UK, Australia, EU, and Asia, and an October review you can repeat every fall.
- Five hands-on workshops that work through each part with four fictional households in Colorado, Georgia, New Jersey, and Arizona.
- Appendices: glossary, 32 common questions, a state table of exchanges, Medicaid expansion, state subsidies, mandates, and paid leave, toolkit sample pages, and primary sources.
The Operator Toolkit ($44 version), 12 tools:
Every tool has a filled example (matching a workshop in the book) and a blank version for you.
- Quick Start (your first hour)
- Marketplace Subsidy and Cliff Estimator (2026 and 2027 tables, levers)
- Income Projection and Repayment Risk Tracker (monthly, quarterly, scenarios, benefits budget, October review)
- COBRA versus Marketplace Comparator
- HSA Planner
- Self-Employed Health Insurance Deduction Worksheet
- Disability and Life Coverage Needs Calculator
- Coverage Calendar (deadlines, life events, problem log, calendar export)
- Medicare Bridge Timeline (single and couple)
- Spouse-Employee Health Plan Template (draft for professional review)
- Broker and Navigator Question Brief
- AI Prompt Library: 30 prompts written for the tasks in this book
Who it's for: adults in their late 30s to early 60s working alone, often with AI tools doing part of the work: laid off and years from Medicare, married to someone with job benefits, a single parent, or earning in bursts rather than paychecks.
Please note: This is education, not insurance, medical, tax, legal, or financial advice. All examples use fictional people and hypothetical numbers; they are illustrations, not quotes, predictions, or promises of any result. US rules are primary, with notes for other countries. Figures are current as of October 2026.
Digital download. No physical item will be shipped.
