How to Pick the Right Retirement Date

Employer 401(k) matches and bonuses. Most employers match contributions throughout the year, says Carol Sladek, head of work-life consulting at Aon Hewitt, but a few make a single contribution in December. Profit-sharing and bonuses are generally awarded at year-end. If you're due a cash payment, set your retirement date accordingly.

Unused vacation. At most companies, vacation days accrue over the course of a year. To get paid for any days you didn’t use, retire at the end of the year; otherwise, you may not be compensated for those days. If your employer is one of the few that still allots your full vacation at the beginning of the year and lets you take it at any time, ask your benefits manager whether you’ll be fully compensated by retiring after January 1.

Medical benefits. Be sure to use all the money you’ve contributed to your medical flexible spending account before you leave the company; otherwise, you’ll lose it. While you’re still on employer group coverage, take care of doctor visits and necessary medical procedures.

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