GROW · VOLUME 2 OF 3 · STRATEGIESRetirement shelf
Retirement Income & Implementation
The second retirement volume turns a plan into practice: moving money into Roth accounts, saving as a self-employed worker, using an HSA for healthcare in retirement, choosing when to claim Social Security, covering health insurance before and after 65, and planning for long-term care. Every limit and threshold is dated and sourced.
Chapters8
Reading time50 min
Worked examples0
Updated2026-10-01
What you will be able to do
- Judge whether a Roth conversion this year is likely to save tax, and size it to a bracket.
- Run a clean backdoor Roth and tell whether your 401(k) allows a mega backdoor Roth.
- Choose between a SEP-IRA, a SIMPLE IRA and a solo 401(k) for your own business.
- Compare Social Security claiming ages for yourself and a spouse.
- Plan health coverage from leaving work through Medicare, and price the risk of long-term care.
Contents
8 CHAPTERS · ABOUT 50 MIN- 01Roth Conversions: When Paying Tax Early Pays Off A conversion trades tax now for tax-free money later, and it pays only when today's rate is lower than tomorrow's or the tax comes from outside the account. How to size one to a bracket, and the Social Security, Medicare and subsidy costs it can trigger.7 min
- 02The Backdoor Roth and the Mega Backdoor Roth Two legal routes into Roth accounts for people whose income is too high to contribute directly: a nondeductible IRA contribution converted to Roth, and after-tax 401(k) money moved to Roth. The pro-rata rule, Form 8606, and what your plan must allow.7 min
- 03Retirement Plans for the Self-Employed: SEP-IRA, SIMPLE IRA and Solo 401(k) How contributions are worked out from self-employment income, what each of the three plans allows and costs to run, and the traps when you also have a job with a 401(k) or want a backdoor Roth.6 min
- 04The HSA as a Retirement Account Who can contribute to a health savings account, the 2026 limits, and how investing it and saving receipts turns it into tax-free money for healthcare in retirement. What changes at 65 and when you enroll in Medicare.5 min
- 05Social Security Claiming for Singles and Couples How your benefit is built from your earnings record, what claiming between 62 and 70 does to it, what the break-even age shows and misses, and how spousal, survivor and divorced-spouse benefits change the decision for couples.7 min
- 06Health Insurance Before Medicare Covering the years between leaving work and 65: COBRA, the ACA marketplace and Medicaid, how the premium tax credit and its 400% cliff work for 2026, and how your choice of withdrawals sets the income the credit is based on.6 min
- 07Medicare: The Four Parts, Enrollment and Premiums What Parts A, B, C and D cover, the enrollment windows and lifelong penalties for missing them, the choice between Original Medicare with a supplement and Medicare Advantage, and the income-related premiums that look back two years.7 min
- 08Long-Term Care: Costs, Insurance and Medicaid How likely you are to need help with daily living and what it costs, why Medicare does not pay for it, how Medicaid's spend-down and look-back rules work, and the choice between self-funding, traditional, hybrid and partnership insurance.6 min
CALCULATORS USED IN THIS BOOK