Switching Jobs Checklist

A new job is a raise and a reset — and a moment when small oversights quietly cost real money. Run this checklist in the 30 days before and after you switch so a better salary doesn't come with hidden losses in benefits, retirement, or taxes.

Negotiating the full compensation package

Base salary is one line on a multi-line offer. Before you accept, look at the whole package: signing bonus, equity, annual bonus target, 401(k) match, PTO, remote flexibility, and title. Many of these are negotiable even when base isn't, and a strong match or equity grant can be worth more than a few thousand dollars of salary. Get the final offer in writing before you resign.

Rolling over your old 401(k)

Don't leave it orphaned or — worse — cash it out (that triggers taxes and an early-withdrawal penalty). You generally have three options: leave it in the old plan, roll it into the new employer's plan, or roll it into an IRA. Use a direct rollover (funds move trustee-to-trustee) to avoid mandatory withholding and the strict 60-day deadline that comes with taking the check yourself.

Health insurance gap planning

Coverage doesn't always continue seamlessly. Confirm exactly when your old plan ends and the new one begins. If there's a gap, your options usually include COBRA (continuing your old coverage for a limited period, but paying the full premium yourself) or a marketplace plan. Don't go uninsured, even briefly — one accident in the gap can erase the whole raise.

Equity, vesting, and what you leave behind

Know your vesting schedule before you give notice. Unvested equity and unvested employer 401(k) contributions are typically forfeited when you leave, so timing your exit around a vesting date can be worth real money. If you hold stock options or RSUs, understand the tax treatment and any deadlines to exercise after departure.

Updating W-4 withholdings

Your new employer needs a fresh W-4, and changing jobs mid-year is a classic cause of under-withholding — two partial-year incomes can push you into a higher bracket than either job assumes. Use the IRS withholding estimator to set it correctly so you're not surprised at tax time.