Edward Jones Investments does early retirement planning for tech employees who want to stop working before age 65 while much of their net worth still sits in one employer's stock. You receive a written playbook of about 10 pages after 3 meetings over roughly 6 weeks. It shows, year by year from your last paycheck to age 75, which account pays your withdrawals and which tax year each block of company stock gets sold in.
The question usually comes from home. A spouse or an adult son asks, "If you stop at 60, what do we live on until Social Security? And who gets your 401(k) if something happens?" You know the account balances and the share count, but you don't have a dated answer. This page follows Glenn, a hypothetical engineer facing those same questions, and shows what the work looks like at each point.
What does early retirement planning cover when most of your money is one stock?
Early retirement planning means working backward from the amount you want to spend to a stop date, then checking which accounts can pay for it. Take Glenn, 57, a divorced principal engineer at a large public software firm with one grown son.
He has bought ESPP shares every period for 15 years and now holds $900,000 of company stock with a cost basis near $200,000, plus $1.1 million in his 401(k). He wants to stop at age 60 with $120,000 annually in withdrawals (hypothetical, round numbers). The plan starts from that spending number. It doesn't pick a date and hope the portfolio stretches.
The bridge years come first. Between the last paycheck and Social Security at age 67, and with Medicare not starting until age 65, the portfolio pays almost everything. Glenn's paid-off condo, inherited from his mother, nets $24,000 annually in rent. So from age 60 through 66 his portfolio covers $120,000 − $24,000 = $96,000 annually, and $96,000 × 7 = $672,000.
Here is where our position shows up in practice. Edward Jones Investments decides how much of the portfolio can take a 40% drop by reading the withdrawal schedule. A risk questionnaire doesn't set that number. The $672,000 Glenn needs for the bridge is money that cannot take that drop, so it comes out of the $900,000 of company stock first. Any investment, the company stock included, can fall below what you paid for it. That is why we protect the bridge money before anything else.
Planning like this starts to matter about 3 to 5 years before the target date, so age 57 for a stop at age 60. Selling $900,000 of stock with a $200,000 basis means about $700,000 of gain. Spread over several tax years, that sale costs less than one big sale in your last working year. Spreading needs calendar time, and each year of delay leaves one fewer December to sell in.
Start now if a severance offer, a final ESPP period or a divorce is on the calendar
A severance offer comes with a clock. Employees age 40 and older who are offered a group separation agreement generally get 45 days to consider it and 7 days to revoke it after signing. That window is your due date for deciding whether early retirement starts now, so the first meetings need to happen inside it, not after it.
Your last ESPP purchase period and last RSU vest each add shares to a position that is already too big. Decide before they land whether those shares are sold soon after purchase or vesting. If you wait, the stock percentage keeps climbing while you debate it. A big run-up in the share price works the same way: it raises the gain locked inside the stock and makes the case for spreading sales over more tax years before you stop.
Divorce brings a paperwork trap. Glenn's divorce is final, but his 401(k) beneficiary form still names his ex-wife, and under federal plan rules that form overrides the divorce decree. His $1.1 million would go to her instead of his son. While he is alive, the fix is one new form filed with the plan administrator. After his death it usually can be undone only if the ex-spouse agrees to disclaim, and nobody should count on that. Glenn files the form in week one.
Which 401(k), Social Security and Medicare dates decide when you can stop?
Four dates matter most: age 55 for the 401(k), age 65 for Medicare, age 67 for full Social Security, and age 75 for required withdrawals if you were born in 1960 or later. If you separate from your job during the year you turn 55, or in any year after that, you can draw from that employer's plan without the 10% penalty.
Roll that plan into an IRA before age 59½ and the exception is gone. Anyone stopping before age 55 should look at substantially equal periodic payments (72(t)) and check its strict rules first.
Social Security is the next lever. Full retirement age is 67 for people born in 1960 or later, and claiming at age 62 cuts the benefit by 30%. The SSA earnings test for 2026 is $24,480 a year for wages and self-employment income. Net rental income generally doesn't count toward it, which matters for Glenn's condo.
Glenn expects $36,000 annually at age 67. Claiming at age 62 pays 30% less, or $25,200. That shrinks the bridge by $25,200 × 5 = $126,000, from $672,000 to $546,000, but it costs $10,800 every year after age 67. At age 67 his withdrawals fall to $60,000 either way the claim goes. Find the age where the running benefit of waiting passes the $126,000 running cost, which is about 78 to 79.
Medicare adds a lookback. Eligibility begins at age 65, and IRMAA uses your MAGI from 2 years earlier. The 2026 standard Part B premium of $202.90 a month rises to $284.10 for single filers above $109,000. The quick test: if you expect to enroll at age 65, any large stock sale in the calendar year you turn 63 or later raises your premium 2 years later, so schedule the biggest company-stock sales in the years before age 63. Glenn's 401(k) also faces required withdrawals from age 75.
| Glenn's age | Running cost of waiting to 67 | Running benefit of waiting to 67 |
|---|---|---|
| Age 66 | $126,000 | $0 |
| Age 70 | $126,000 | $43,200 |
| Age 75 | $126,000 | $97,200 |
| Age 78 | $126,000 | $129,600 |
| Age 85 | $126,000 | $205,200 |
What does an Edward Jones Investments early retirement playbook look like on paper?
The playbook is about 10 pages, and page 1 states two numbers: your spending figure ($120,000 annually for Glenn) and your risk capacity. That second figure is how far the portfolio can fall before withdrawals would have to be cut, shown in dollars, not as a risk score. Glenn's page 1 doesn't ask whether he feels brave. It shows what a 40% drop does to the schedule.
The middle pages hold a year-by-year withdrawal schedule from age 60 to age 75. Each year shows which account pays (taxable stock, 401(k) or rental income) and the estimated federal tax. Before any block of company stock is sold, Edward Jones Investments estimates the tax due on that sale and records it next to the year of the sale. You see the cost before the trade, not on a January tax form.
The last pages hold the Social Security claim-age comparison, which is the break-even table above, with the IRMAA lookback years flagged in red. A titling and beneficiary checklist covers the 401(k), the brokerage account and the condo, and that is where Glenn's ex-wife would have shown up.
The limits are plain. The playbook does not choose a health insurance plan, draft a will or file tax returns, so your CPA and an estate attorney still have work to do. It is also usually not worth paying for while the stop date is more than 10 years away. If you're 45 and wondering about 60, keep saving and come back around age 52 to 55.
Gather these statements before your first call with Edward Jones Investments
Four documents cover most of what the first meeting needs: * a brokerage statement showing lot-level basis for the company stock * the latest 401(k) statement with its beneficiary page * your Social Security estimates * last year's rental income figures, plus any severance letter Glenn pulls them together in an evening, and each one answers a specific question.
Lot-level basis decides which shares are sold first and what each sale costs in tax. The 401(k) balance sets the later withdrawal years, and the beneficiary page shows right away whether an ex-spouse is still named. The Social Security estimates feed the break-even table and the bridge-year math. Net rental income reduces the bridge withdrawals, and a severance letter's due date sets how fast the first meetings must happen.
There is no published phone number, so reach out through the request form. We discuss the fee openly when we first talk, then put it in writing before any work starts. Edward Jones Investments meets clients nationwide by video and phone. To become a client, you need at least $500,000 in investable assets.
- Brokerage statement listing every ESPP lot with purchase date and cost basis (the Form 3922 data)
- Latest 401(k) statement plus the beneficiary confirmation page
- Social Security statement from ssa.gov with estimates at age 62, 67 and 70
- Schedule E from your most recent tax return for any rental property, plus any severance letter
What people ask about early retirement planning
Can I take money from my 401(k) without the 10% penalty if I leave my job at age 56?
Yes, if you leave that employer in the calendar year you turn 55 or later, withdrawals from that employer's 401(k) skip the 10% additional tax, though ordinary income tax still applies. The condition is that the money stays in that plan. Rolling it to an IRA before age 59½ gives up this access.
How many years of withdrawals should sit outside company stock when I stop working early?
Cover every year from your last paycheck until Social Security and Medicare begin, and keep that money out of company stock. For a stop at age 60 with Social Security at age 67, that is 7 years. In the hypothetical Glenn example, those 7 years of withdrawals come to $672,000.
Why pay for early retirement planning when free online retirement calculators exist?
A calculator gives you one average result. It won't tell you which year each block of ESPP shares gets sold, what each sale costs in tax, or how a stock sale at age 63 changes your Medicare premium at age 65. A playbook puts those dates and dollar amounts on paper. If your money is mostly in index funds, a calculator may be enough.
What covers health insurance between leaving work at age 60 and Medicare at age 65?
Most people in this gap buy individual coverage, such as a marketplace plan, or use COBRA for a limited time after leaving the employer. Medicare starts at age 65. Your income in those years affects plan costs, so the withdrawal schedule matters. A playbook doesn't choose a health plan, so an insurance specialist or your CPA should help with that choice.
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This material is general information only and does not address any individual's investment, tax or legal situation. Investing involves risk, including possible loss of principal. Before acting on any information here, speak with a financial advisor, tax professional or attorney about your circumstances.