Retirement Planning Guide
Timing Your Retirement Date
Your last day is a financial decision, not just a calendar choice. Confirm these five checkpoints before you pick a final workday.
Five Checkpoints to Map Out
Work through these in order. The right exit date usually falls just after the last one that matters to you.
Checkpoint 1
Incentive Pay
When does your bonus, commission or deferred compensation vest, and when does it actually hit your account? Leaving a week early can forfeit a full year of incentive pay.
Checkpoint 2
Pension Anniversary
A single extra month of service can raise a pension formula or reach the age for an unreduced benefit. Confirm your exact eligibility date in writing.
Checkpoint 3
Health Coverage & 401(k)
Find out the day medical coverage stops and how much COBRA would cost to bridge the gap. Check whether any employer match or profit-sharing is still unvested.
Checkpoint 4
The December 31 Cutoff
Every dollar paid by year-end counts toward this year's taxable income. Final payouts that slip into January may be taxed at a lower rate.
Checkpoint 5
Social Security & Medicare
Claiming Social Security is its own decision, separate from your final workday. Your Medicare enrollment window opens around your 65th birthday, so line up coverage before employer benefits lapse.
Comparing Exit Seasons
Every window involves trade-offs. Weigh them against your own pay schedule and tax picture.
Year-End Exit
Leave in December
Full-year pay and benefits earned; pension credits may round out at year-end.
Final payouts can push this year's income into a higher bracket.
Early-Year Exit
Leave in February or March
Light income in the new year can be taxed in lower brackets; may capture a bonus paid in Q1.
Requires working a few extra weeks into the new year.
Mid-Year Exit
Leave between April and June
Bonus cycle typically complete; partial-year salary keeps taxable income moderate.
Health coverage gap may be longer before Medicare; plan COBRA costs.
Before You Resign: Get Answers On
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Rigden Tip
Ask HR to confirm key dates in writing, then let us model two or three exit dates side by side before you commit.
A short planning session can help compare bonus, pension, and tax outcomes across different dates.
Important Disclosure