Before You Quit: The Paperwork Checklist

Before you quit your job to stay home, work through the paperwork in this order: health insurance first (how your family will be covered from day one after your last day), then retirement accounts (what happens to your 401(k) and any employer match), then use-it-or-lose-it money like FSA balances, then the calendar check for vesting and bonus dates that might be worth waiting a few weeks for — and finally, a written list of questions for HR while you still have an employee badge. None of this is glamorous. All of it is money. Here’s the checklist, with the right questions for each line.

One rule up front: this post is a map of what to ask, not advice on what to choose. Your HR department, your plan documents, and a fee-only financial planner are the sources for the actual answers — the ranges and rules vary too much by employer and state for anyone’s blog to decide for you.

1. Health insurance — the deal-breaker line

If your job carries the family’s coverage, this is the first thing to solve, before any resignation date gets penciled in.

• Ask your partner’s HR: can the family join their plan, what does it cost per month, and does quitting count as a “qualifying life event” for mid-year enrollment? (It generally does, but confirm the deadline — these windows are short.)
• Ask your own HR: exactly when does my coverage end — my last day, or the end of that month? The difference can be worth timing your exit around.
• Price the bridge: if there’s a gap, ask about continuation coverage (COBRA) and check marketplace options. Get real quotes; guessing is how people end up uninsured for a month with a toddler.

2. Retirement accounts — don’t orphan the 401(k)

Your 401(k) doesn’t vanish when you quit, but it does need a decision: leave it, roll it into an IRA, or move it to your partner’s plan if allowed. Each has trade-offs beyond this post’s pay grade — the planner question. What’s firmly on your checklist:

• Check your vesting date. Employer-match money often vests on a schedule, and quitting weeks before a vesting date can forfeit real dollars. Ask HR for your exact vested balance and next vest date.
• Ask about the match timing. Some employers deposit matches annually — leaving before the deposit date can mean leaving a year’s match behind.
• Plan the spousal IRA. Staying home doesn’t have to mean zero retirement savings; a working spouse can generally fund an IRA for a non-earning partner. Ask the planner how it fits your situation.

3. Use-it-or-lose-it money

The small print that quietly eats hundreds if ignored:

• FSA balances are often forfeited at termination — ask what your deadline is and schedule the eligible spending (glasses, dental, stocked-up prescriptions) before your last day.
• Vacation payout: ask whether unused PTO pays out at termination in your state and company — policies differ, and the answer might change which week you resign.
• Tuition or certification reimbursements sometimes claw back if you leave within a set window of using them. Check the agreement you signed, not your memory of it.

4. The calendar check

Lay your target resignation date against: the next vesting date, the bonus payment date (paid, not just earned — many plans require you to be employed on payout day), the match deposit date, and your insurance end-of-month rule. Sometimes shifting your notice by two or three weeks changes the math by a lot. This is the least emotional and most profitable hour of the whole exit.

5. The HR meeting — go in with the list written

Book a benefits conversation before you announce anything (framing it as “reviewing my benefits” is normal and honest), and leave with answers in writing where you can get them. You lose easy access to every one of these answers the day you stop being an employee.

This checklist is one month of the full six-month two-incomes-to-one plan, and it assumes the budget side already passed the affordability test. Once the paperwork is clean, the only step left is the human one — resigning gracefully, especially if your exit follows a maternity leave.

FAQ: the pre-quit paperwork

What’s the most commonly missed item before quitting?

Vesting dates. People know their 401(k) balance but not how much of the employer match is actually theirs yet — and quitting a month early can forfeit a chunk of it. Ask HR for the exact number; it’s a five-minute email.

Do I lose my FSA money when I quit?

Often, yes — unspent health FSA balances are typically forfeited at termination, though plan rules vary. Ask for your plan’s exact cutoff and spend eligible dollars before your last day.

Should I time my resignation around insurance dates?

Frequently worth it: if coverage runs to the end of the month you leave, resigning on the 3rd versus the 28th can buy your family nearly a free month of coverage during the transition. Confirm your plan’s rule with HR first — it’s not universal.

Who should actually answer the money questions in this post?

HR for anything about your employer’s plans and dates; a fee-only financial planner for the choices (rollover versus leave, IRA strategy, runway sizing). This checklist’s job is making sure you ask, not telling you what to pick.