The exit timing checklist
You've decided to leave. When you actually hand in notice can be worth thousands — a few weeks either way can mean a vested grant, a paid bonus, or a costly coverage gap. Map these dates before you set one.
Money on the table — don't leave it
- Equity vesting. Check your next vesting date and any cliff. Leaving a month before a cliff can forfeit a year of equity. For options, note the (often 90-day) post-departure exercise window and the cash/tax to exercise.
- Bonus payout. Many bonuses require you to be employed on the pay date. Quitting just after can be a large, easy win; quitting just before can cost the whole thing.
- Pension / employer match. Some 401(k) matches or pension benefits vest on a schedule — confirm you're not walking away from money days before it's yours.
- Accrued PTO / holiday. In many places unused leave is paid out; in others it's use-it-or-lose-it. Know which, and plan accordingly.
The coverage clock (especially US)
- Benefits end date. Find out exactly when health, dental and life coverage stop — often the end of the month you leave, sometimes the day you leave.
- COBRA's 60-day window. In the US you have 60 days to elect COBRA, and it's retroactive — so you can bridge a short gap. Line up an ACA plan vs COBRA before the old plan ends; leaving a job is a qualifying event.
- FSA balances. Use remaining flexible-spending funds before they vanish at termination.
Paperwork that's easy to forget
- 401(k) / pension rollover to an IRA or new plan — don't leave it stranded.
- References in writing and updated contact details for people who'll vouch for you.
- Personal files & access off work systems (within policy) before your accounts are cut.
- Notice period & handover — honor your contract; a clean exit protects the reference and any future boomerang.
The cheapest money you'll make this year might be waiting three extra weeks for a bonus or a vest. Map the dates, then pick your last day around them.
If there's any chance of a package
If a layoff or restructuring is in the air, timing can also mean severance. Understand what's typical where you are before you make the first move:
Estimate severance by country → How to negotiate it
Turn the dates into a plan
Drop your vesting, bonus and benefits dates into the transition planner so your exit is sequenced around them — not scheduled in a frustrated afternoon.