Early Retirement Readiness Checklist: 20 Items Before You Leave Your Job
Most people who are ready to retire early have done the math. They know their FI number. They've run the 4% rule calculation. What tends to derail plans isn't the number — it's the implementation details that weren't locked in before the last paycheck arrived.
This checklist covers 20 items across five areas: the portfolio math, pre-59½ account access, healthcare before Medicare, tax sequencing, and estate protection. A solid plan has all 20 addressed. Most people approaching their FIRE date have 14–17 checked and a few genuine gaps worth resolving before they leave.
Category 1: The Portfolio Numbers
Does your nest egg math hold up under pressure — not just on an average-return spreadsheet?
Category 2: Pre-59½ Account Access
Most early retirees need access to tax-advantaged accounts before the standard 59½ threshold. The wrong move here is irreversible.
Category 3: Healthcare Before Medicare
Healthcare is the most common financial gap in early retirement plans — the costs are real and the subsidy math is precise.
Category 4: Tax Sequencing
The "golden window" between retirement and Social Security/RMDs is when lifetime tax savings are won or lost. Most of the planning happens here.
Category 5: Estate & Protection
Early retirees with large portfolios and no W-2 income need specific coverage and legal documents that working people often defer.
What the gaps usually look like
In practice, most people approaching their FIRE date have categories 1 and 2 solid — they've done the number and thought about account access. The gaps concentrate in categories 3 and 4: healthcare and tax sequencing. Specifically:
- ACA coordination is the most common gap. Planning retirement income without modeling the ACA MAGI cliff means either leaving substantial subsidies on the table or getting surprised by $1,500/month premiums when you expected $150. The subsidy cliff is a hard threshold — a few thousand dollars of income in the wrong direction costs $10,000–$20,000 in annual premiums.
- The Roth conversion window is time-limited and people underestimate it. The 10–15 year "golden window" before Social Security and RMDs close the conversion opportunity is when most lifetime tax savings are made — but only if conversions are sized correctly each year across all four constraints simultaneously (12% bracket, 0% LTCG threshold, ACA cliff, IRMAA lookback).
- Pre-59½ access is often half-planned. People know they need a strategy but haven't verified whether Rule of 55 still applies (has the 401(k) been rolled yet?), whether the Roth ladder is started in time, or whether the taxable account bridges the full gap.
Relevant calculators and guides
- Safe Withdrawal Rate for Early Retirement — 30 to 50-year horizons
- Sequence of Returns Risk — simulator and bond tent strategy
- Roth Conversion Ladder Calculator — timing, rungs, and ACA coordination
- Rule of 55 — qualification checker and the rollover trap
- 72(t) SEPP Calculator — three IRS methods, commitment period
- Taxable Brokerage Bridge — coverage years and 0% LTCG draws
- Healthcare Before 65 — ACA, COBRA, MAGI coordination
- Tax-Efficient Withdrawal Order — four-cliff framework
- Social Security Timing — zero-earnings penalty and break-even
- Taxes in Early Retirement — the golden window and estimator
- 7 Early Retirement Mistakes — the common plan-killers
- How to Choose a Financial Advisor for Early Retirement
Get your plan reviewed before you pull the trigger
If you found items you haven't fully resolved, the time to work through them is before your last day — not after. A fee-only advisor who specializes in early retirement can model the ACA coordination, size the Roth conversion sequence, verify the pre-59½ access strategy, and pressure-test the sequence-of-returns math. No commissions. Free match.
Sources
- IRS Revenue Procedure 2025-32. 2026 ordinary income brackets and standard deduction: 10% bracket $0–$12,400 (single)/$0–$24,800 (MFJ); 12% bracket to $50,400/$100,800; standard deduction $16,100/$32,200; 0% LTCG threshold $49,450/$98,900 taxable income.
- HealthCare.gov — MAGI and ACA Premium Tax Credits. 400% FPL cliff determines PTC phase-out; 2026 approximate thresholds single ~$63,840, MFJ ~$86,640 based on HHS 2026 FPL tables. Roth conversions and capital gains both count as MAGI for ACA purposes.
- IRS — Exceptions to Tax on Early Distributions. IRC § 72(t)(2)(A)(v) Rule of 55: penalty-free 401(k) distributions for employees who separate from service in or after the year they reach age 55. IRA rollovers eliminate this exception for the rolled amount.
- SSA — Retirement Age and Benefit Reduction. Zero-earnings years: SS benefit is based on 35 highest-earning years; years below 35 count as zero. Early retirees with fewer than 35 working years can see 15–30% reductions relative to projected benefits. FRA for those born 1960+ is age 67.
- Medicare.gov — IRMAA and Medicare Part B/D Premiums. IRMAA determines Medicare surcharges based on MAGI from 2 years prior. 2026 Part B base premium + IRMAA tier-1 threshold $109,000 single / $218,000 MFJ per SSA POMS. Ages 63–64 Roth conversion decisions directly set Medicare costs at age 65.
Values verified June 2026. ACA MAGI thresholds approximate 400% FPL for a 1-person household (single) and 2-person household (MFJ); actual amounts vary by household size per HHS annual FPL tables. IRMAA thresholds per SSA POMS, subject to annual adjustment. Tax values per IRS Rev. Proc. 2025-32.