How does the Retirement Gap Finder work?

The Retirement Gap Finder is a free 3-question assessment that takes about 2 minutes. First, select your retirement timeline. Second, check which of 10 critical areas your current plan addresses. Third, identify your top 1-2 retirement concerns. Grace AI then generates a personalized Gap Report showing covered areas, gaps by severity (critical, moderate, emerging), and prioritized focus areas. You can email the report to yourself.

What are the most common retirement planning gaps people miss?

The five most common gaps: (1) Medicare enrollment timing — missing the 7-month window triggers permanent 10% annual penalties. (2) Social Security claiming strategy — 62 vs 70 can mean a 76% difference in lifetime benefits for couples. (3) Tax-efficient withdrawal sequencing — wrong order triggers unnecessary taxes and higher Medicare premiums. (4) Healthcare cost bridging — COBRA gap costs $12,000-$24,000. (5) Purpose and identity — 40% of new retirees experience identity crisis in the first two years.

Is the Retirement Gap Finder really free?

Yes, completely free with no credit card, no account signup, and no obligation. Answer 3 questions, get your personalized gap report immediately on screen, and optionally email it to yourself. The tool is provided by My Plan Keeper as a free public resource.

How is this different from other retirement calculators?

Most retirement calculators ask 'Do I have enough money saved?' The Retirement Gap Finder identifies what your plan is MISSING across 10 critical areas. It covers healthcare cost bridging, tax-efficient withdrawal sequencing, Social Security timing, Medicare enrollment, long-term care, purpose planning, health planning, and partner alignment — the areas where people lose tens of thousands to avoidable mistakes.

Retirement Gap Finder™

Find what your retirement plan is missing.

Most retirement plans focus only on savings. Grace looks at everything else too — and it only takes three questions to see what yours could be missing.

Loading the Retirement Gap Finder™…

What is the Retirement Gap Finder?

The Retirement Gap Finder is a free retirement planning assessment tool that identifies missing pieces in your retirement plan across 10 critical areas. Most retirement plans focus only on savings, but ignore 9 other areas where costly mistakes happen: withdrawal strategy, healthcare costs, Medicare timing, tax planning, Social Security claiming, long-term care, purpose and identity, health planning, and partner alignment.

How It Works

Select your timeline — How close are you to retirement?
Check your coverage — Which of 10 critical areas does your current plan address?
Identify concerns — What keeps you up at night about retirement? Grace AI generates your personalized Gap Report.

The 10 Areas Checked

Savings & Investment Plan
Withdrawal Strategy & Sequencing
Healthcare Cost Estimation
Medicare Enrollment Planning
Tax-Efficient Withdrawal Planning
Social Security Claiming Strategy
Long-Term Care Contingency
Purpose & Identity Planning
Health & Wellness Planning
Partner Alignment

Why Retirement Gaps Matter

Missing Medicare enrollment = permanent 10% penalty per year delayed
Social Security timing (62 vs 70) = up to 76% difference in lifetime benefits for couples
COBRA healthcare bridge = $12,000–$24,000 unbudgeted
Tax-inefficient withdrawals = thousands in unnecessary taxes and higher Medicare premiums
Purpose & identity crisis = affects 40% of new retirees

Who Should Use This Tool

Anyone within 10 years of retirement, recently retired, or helping a family member plan. Especially valuable if you have savings but haven’t mapped out healthcare, taxes, Social Security timing, or what you’ll actually do in retirement. Free, no signup required, takes 2 minutes.