How Edward Jones Investments Approaches the Checklist Before Leaving a Tech Job

Which equity due dates fall within 90 days of my last day?

Every vest, purchase and expiration date between your last day and 90 days after it needs a spot on your calendar before you give notice. Four types matter: RSU vests, ESPP purchase dates, option exercise windows and your final 401(k) paychecks. Each lives in a different document, and none of them moves because you resigned.

Take Carol, 48, a VP of engineering at a public cloud company (hypothetical, round numbers). Before she picks a resignation date she lists 4 due dates: a quarterly RSU vest on May 15, an ESPP purchase on May 31, a 90-day exercise window on her vested NSOs, and her last 401(k) paychecks. She planned to leave May 1 and hadn't connected any of them to that date.

Where does each date live? Vest dates are in the equity portal's release schedule. The ESPP purchase date is in the offering documents. The option window is in your grant agreement. Many agreements say 90 days, but some companies allow years, so read yours instead of trusting what a colleague remembers.

Here is a quick test. Look at any vest, purchase or expiration within 6 weeks of your planned last day. If one of them exceeds 1 month of your take-home pay, price the delay before you give notice. Carol's May 15 tranche alone was $80,000, many times a month's pay, so the test said stop and calculate.

Price the 2 weeks between notice and the next vest

Resigning May 1 would have cost Carol the $80,000 RSU tranche vesting May 15 plus a $2,250 ESPP discount, $82,250 in total. Waiting until June 1 keeps both and adds another month of salary. She moved her date to June 1.

The ESPP arithmetic is easy to check. She has contributed $12,750. If she stays through May 31, that buys $15,000 of stock at a 15% discount ($12,750 ÷ 0.85 = $15,000). If she leaves first, she gets the $12,750 back as a refund and loses the $2,250 difference.

Her rental income changes the 401(k) picture. Her condo's $30,000 annual net rent keeps coming after paychecks stop, but it isn't earned income, so it can't fund a 401(k) or an IRA. That is why she sets May deferrals high enough to use the $16,500 left of her $24,500 limit for 2026 (the IRS limit). Once the paychecks end, that room is gone for the year.

Edward Jones Investments sizes her stock sales after the last day from her spending, not her appetite for risk. She spends $150,000 annually; subtract $30,000 of rent and a $120,000 annual gap remains for her pre-set trading schedule to cover. That gap, not a risk questionnaire, says how much of her $3 million of employer stock must be sold and how much loss the rest of the portfolio can absorb.

Check how each account is taxed before your last day

The two largest costs in Carol's case come from dates, a vest and an exercise window, not from tax rates. Tax rates only change how much of the money you keep. A missed date changes whether you get it at all. The table assumes a planned last day of May 1.

RSUs are ordinary income at vest. The ESPP discount becomes taxable income in the year you sell the shares. With NSOs, the spread counts as income on the exercise date. 401(k) deferrals are taxed at withdrawal. Severance is taxed as wages, and the flat supplemental withholding can run below the actual bill if your bracket is higher.

One severance detail trips people up. Severance paid after employment ends usually doesn't count as pay for 401(k) deferrals. Ask payroll before you assume it does, because that changes how much room you must use in the final paychecks.

Where the standard exit advice breaks down

Common exit advice fails in four situations, and each one costs real money if you follow it blindly. The first is the rule to roll the 401(k) into an IRA. That is wrong for anyone leaving in the calendar year they turn 55 or later, because that employer's plan allows penalty-free withdrawals before age 59½ and an IRA doesn't.

The second involves company stock inside the 401(k). It may qualify for net unrealized appreciation treatment, but only through an in-kind lump-sum distribution. A rollover to an IRA gives that up, so look at it before you move anything.

The third applies to insiders like Carol, who sell only through a pre-set trading schedule. Read the schedule's termination terms and the company's insider policy. Many policies keep restrictions in place for a period after departure, so your sales may not be free to start the day you leave.

The fourth is the layoff. There the employer usually sets the date, and the checklist shifts to what the separation agreement accelerates or extends. A new employer's sign-on payment can also outweigh a forfeited tranche, so waiting isn't always worth it. Negotiating the separation agreement itself is a job for an employment lawyer, not this checklist.

Should a 48-year-old and a 57-year-old treat the 401(k) the same way?

No. Someone who leaves at 55 or later in the calendar year can usually take penalty-free withdrawals from that employer's 401(k) before 59½, while an IRA offers no such exception. Under 55, that advantage doesn't exist, and the plan-versus-IRA choice turns on costs and investment choices.

Carol, at age 48, gets nothing from the age-55 exception. Her choice between the old plan and an IRA turns on fund costs and investment choices, so she compares both lineups line by line.

Glenn, a hypothetical 57-year-old, holds $1.1 million in his 401(k). If he leaves at age 57, keeping the money in the plan lets him take withdrawals penalty-free until age 59½. Rolling to an IRA first and withdrawing $50,000 would add a $5,000 penalty (10%), plus the ordinary income tax he'd owe either way.

Use these thresholds to place yourself: the age 50 catch-up of $8,000 for 2026 (Carol isn't eligible yet), age 55 for the separation exception, age 59½ for IRA withdrawals, and up to 18 months of COBRA health coverage after you leave.

What does a missed exercise window or ESPP refund cost?

Letting the 90-day window lapse on Carol's vested NSOs forfeits the full $60,000 spread (hypothetical). Exercising or selling inside the window keeps it. Resigning before the purchase date turns the ESPP into a refund and loses the discount, $2,250 in Carol's case.

Giving notice 2 weeks before an RSU vest and an ESPP purchase would have cost Carol $82,250. The $80,000 tranche would be forfeited, and the $2,250 ESPP discount would come back only as a plain refund of her contributions. That is a two-week timing error, and nothing in the paperwork reverses it once the date passes. Her move to June 1 avoided it.

Other costs are slower. If you join a new employer in the same year, deferrals there count toward the same $24,500 personal limit. An excess deferral must come out by April 15 of the following year, or it is taxed twice.

Treating severance withholding as the full tax bill can leave a balance due at filing. Ask payroll for the withholding rate and set the difference aside. Sales of company stock after you leave also carry market risk, and the price can fall before you sell.

Do these first, then ask these questions

Work in this order. Pull the vest and purchase schedule. Read the grant agreements for exercise windows. Raise 401(k) deferrals for the remaining paychecks. Read the trading schedule's termination terms. Set the spending gap for the months without salary. Only then choose the last day.

That order matters because the last day is the one input that changes every other number. Fix it first and you're stuck pricing the damage afterward. These questions go to the plan administrator, your CPA and your advisor:

• Does my final paycheck count for the ESPP purchase?
• Is the employer match vested if I leave on this date?
• Is my severance eligible for 401(k) deferral?
• What happens to my trading schedule when my employment ends?
• How much extra tax should I set aside on severance?

What Edward Jones Investments checks first in your exit dates

Edward Jones Investments would first set every vest, purchase and expiration date beside your planned last day and price each one. It would then compare the spending gap after paychecks stop with what your accounts and any trading schedule can cover, before looking at the 401(k) choice and any company stock inside it. Clients nationwide meet with the firm by video or phone.