The Social Security Playbook · Companion Library
All 75 Answers. On Video. Free.
Every question in The Social Security Playbook has a short companion video, organized by the 7 Big Decisions — so you can jump straight to the one you need. New videos are added as rules change.
Decision 1 When to Claim 7 of 12 available
The biggest decision — 62, full retirement age, or 70.
- 2What is the break-even age for claiming early vs. waiting? Coming soon
- 3Does my health and life expectancy affect when I should claim? Coming soon
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Also on this question:
Took Social Security Too Early? Here’s How to Fix It & Boost Benefits! - 7Do pensions affect my Social Security retirement benefit? Coming soon
- 10How do I set up direct deposit securely? Coming soon
- 12What is my Full Retirement Age, and how do delayed credits work? Coming soon
Decision 2 Working While on Benefits 7 of 10 available
The earnings test, what counts, and getting withheld money back.
- 16How do I report expected earnings to SSA? Coming soon
- 18How does self-employment income affect Social Security benefits? Coming soon
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Social Security Overpayment Bill: Limiting Collections From 50% to 10% - 20What records should I keep for SSA? Coming soon
Decision 3 Spousal & Ex-Spousal Benefits 9 of 10 available
The 50% rule, the 10-year divorce rule, timing two claims.
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Also on this question:
Divorced? You Can Still Claim Your Ex’s Social Security Benefits!
How Long Must You Be Married to Get Spousal Social Security Benefits?
50% of Divorced People Are Missing Out on Social Security Benefits!
Will My Ex Know If I Claim Their Social Security Benefits?
Divorced? You Can Still Claim Your Ex’s Social Security Benefits! -
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Can Multiple Ex-Spouses Claim the SAME Social Security Benefits? YES! -
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My Ex Remarried—Can I STILL Get Their Social Security Benefits? YES! -
Also on this question:
What is Full Retirement Age for Spousal Benefits? (Don’t Claim Early!) - 31What documents do I bring for spousal claims? Coming soon
Decision 4 Survivor Strategies 9 of 10 available
What a widow or widower is entitled to — and the switch most people miss.
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My Spouse Died—Do I Get Both Social Security Checks? -
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My Spouse Died—What Happens to My Spousal Social Security Benefits? - 39How do I choose the best effective month? Coming soon
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Also on this question:
Divorced? You Can Still Claim Your Ex’s Social Security Benefits!
Decision 5 SSDI vs. Early Retirement 1 of 8 available
How disability and early retirement interact, and why order matters.
- 44What is Substantial Gainful Activity (SGA) and the Trial Work Period? Coming soon
- 45Can I collect disability and retirement benefits? Coming soon
- 46How does SSDI affect when my Medicare starts? Coming soon
- 47What if my SSDI claim is denied — should I appeal? Coming soon
- 48What evidence should I include with my SSDI claim? Coming soon
- 49Can I work part-time while on SSDI? Coming soon
- 50How does SSDI back pay work? Coming soon
Decision 6 Taxes & Withholding 5 of 10 available
Provisional income, the thresholds, and keeping more of your check.
- 54How do Required Minimum Distributions and Roth conversions affect taxes? Coming soon
- 55Can qualified charitable distributions (QCDs) help me? Coming soon
- 57What if I got a surprise tax bill last year? Coming soon
- 58Do states tax Social Security benefits? Coming soon
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Also on this question:
Social Security 2026 COLA: 2.8% vs Medicare: 12% INCREASE? - 60Where do I find the exact IRS thresholds? Coming soon
Decision 7 Medicare Timing & Social Security 8 of 10 available
Enrollment windows, penalties, IRMAA, coordinating start dates.
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Also on this question:
Still Working at 65? THIS Medicare Mistake Could Cost You THOUSANDS -
Also on this question:
You Have 26 DAYS to Appeal Your IRMAA Medicare Increase - 66What forms do I need for SEP? Coming soon
- 69How do I fix a Part B start-date error? Coming soon
Special Situations Part II 2 of 5 available
Public sector, self-employment, divorce timing, living abroad, children.
- 71Public sector or teacher? What the WEP/GPO repeal changed Coming soon
- 72Self-employed or gig worker — how do Social Security credits work? Coming soon
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Also on this question:
50% of Divorced People Are Missing Out on Social Security Benefits! - 74Living abroad & totalization — can I receive benefits? Coming soon
The book behind the videos.
7 Big Decisions and 75 Essential Answers — plus a numbers guide we refresh every year.