I Asked ChatGPT How To Retire in 2026: Here’s What It Said

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Retiring next year sounds ambitious, but I wanted to know if it was actually possible, so I asked ChatGPT to lay out exactly what someone needs to do to retire in 2026. The AI treated the question seriously and broke down retirement into a step-by-step timeline.

The answer was more actionable than I expected. ChatGPT didn’t give generic advice about saving more money. Instead, it mapped out specific tasks for the final months before retirement with deadlines attached.

Calculate Your Number First

ChatGPT started by saying you need to know if your savings can support your lifestyle. The AI said the 4% withdrawal rule, which means you multiply your annual spending by 25 to get your target savings amount.

The chatbot gave examples. Someone planning to spend $40,000 a year needs roughly $1 million saved. A $50,000 annual budget requires $1.25 million. If you want to spend $70,000 yearly, you should have $1.75 million.

This calculation happens first because everything else depends on whether your numbers actually work.

Lock Down Income Sources Now

ChatGPT said 2025 should focus on confirming exactly where your retirement money comes from. The AI broke this into two categories.

First, Social Security. You need to create a My Social Security account to see your actual estimated benefit. ChatGPT pointed out that you can claim reduced benefits at 62, full benefits at your full retirement age (usually 66 or 67) or maximum benefits at 70. The chatbot suggested that if you retire in 2026 but wait to collect Social Security until 67 or 70, you live off savings temporarily but get much larger checks later.

Second, your actual savings. The AI said to list everything, including investments like your 401(k) plan, traditional and Roth IRAs, brokerage accounts, any pensions, annuities and even your HSA. This forms what ChatGPT called your income stack.

Build Your Retirement Paycheck

ChatGPT said that you need a withdrawal strategy before you retire, not after. The AI outlined how most people should pull money from different accounts at different ages.

From 59 to 65 before Medicare starts, withdraw from taxable brokerage accounts first. Keep your Roth IRA for later. Convert small amounts from your 401(k) or IRA to Roth to reduce future taxes. After 65 when Medicare begins, increase withdrawals from your 401(k) and IRA and start Social Security sometime between 65 and 70.

The chatbot emphasized that this sequencing matters for taxes and for making your money last.

Eliminate Three Things Before 2026

ChatGPT gave three non-negotiables for retiring safely. Pay off high-interest debt like credit cards and personal loans. Make sure your car is paid off or the payment is under $300 monthly. Don’t take out any new major loans in the final 18 months before retirement.

The AI did the math on this. Every $300 monthly payment you eliminate means needing $90,000 less in retirement savings over 25 years. That calculation shows why clearing debt matters so much.

Decide Where You’ll Live

ChatGPT said your housing decision shapes everything else about retirement costs. Location affects property taxes, insurance, utilities and overall cost of living. The chatbot made it clear this decision can’t wait until after you retire, and listed markets expected to remain affordable through 2026 and 2027:

• Albuquerque, N.M.
• Greenville, N.C.
• Kansas City, Miss.
• Knoxville, Tenn.
• Oklahoma City
• Omaha, Neb.
• Pittsburgh
• San Antonio

It also recommended the Raleigh, N.C. suburbs and inland neighborhoods of Jacksonville, N.C. neighborhoods.

Healthcare Is Critical

ChatGPT called healthcare the number one mistake new retirees make. The AI split this by age.

If you retire before 65, your options are Affordable Care Act marketplace plans, COBRA (which the chatbot said is usually too expensive) or health sharing plans (which it didn’t recommend unless you understand the risks). Subsidies can make ACA plans very cheap depending on your state.

If you retire at 65 or older, you need Medicare Part A and Part B, either Medicare Advantage or Medigap and a Part D prescription plan. ChatGPT estimated normal total costs at $350 to $600 monthly.

Build a Year of Cash

ChatGPT recommended holding one full year of expenses in cash or high-yield savings before retiring in 2026. If your budget is $50,000, save $50,000 in cash.

The AI said this protects you from market dips, unexpected healthcare bills and bad timing risk. The chatbot called this one of the smartest moves retirees make.

Actions To Take in the Six-Month Home Stretch

ChatGPT laid out a detailed checklist for January through June 2026. Six months before retiring, rebalance investments to lower risk, consolidate scattered funds, update beneficiaries on all accounts and create estate documents like a living will, power of attorney and healthcare directive.

Three months out, set your Social Security start date if applicable, select your health insurance plan and set up automatic withdrawals from accounts. One month before, notify your employer, take unused vacation days, confirm pension paperwork and set your final paycheck date.

The AI’s timeline was specific, and if you enter your exact information directly into ChatGPT, it can obviously get even more specific. It treated retirement like a project with milestones instead of something that just happens when you feel ready.

Editor’s note: While AI tools can assist in categorizing expenses and setting savings targets, they cannot replace the expertise and guidance of financial advisors.

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