7 Documents to Have in Order Before You Retire

March 9, 2026

You can’t fully retire until you’ve answered one question: “If I can’t make a decision tomorrow, who can?” That means documents—a lot of them. Not just the fun money stuff. Medical decisions. Legal authority. The things that keep life running when you can’t.

Here’s what you need to pull together, ideally 6 months before you stop working.

1. Will or Living Trust

This is how your estate gets divvied up. A will goes through probate court (could take 6 months to 2 years depending on your state). A trust bypasses probate, which is faster and cheaper. Either way, you need one. And you need to update it every few years or when something major changes (marriage, death of a beneficiary, asset changes).

2. Healthcare Power of Attorney

This document names who can make medical decisions for you if you can’t. This is different from a living will (which tells doctors when to let you go). You need both. Healthcare power of attorney is active immediately if you say so, or only if you’re incapacitated—you decide. This is the most commonly used document in retirement, statistically.

3. Financial Power of Attorney

This names who can manage your money if you can’t: pay bills, move assets, handle tax returns. Make sure whoever you pick actually wants this job. And specify when it takes effect (now, or only if you’re incapacitated). A durable financial power of attorney is active even after you die, which is usually what you want.

4. BENEFICIARY DESIGNATIONS (Updated)

Your life insurance, IRAs, 401(k)s, and some brokerage accounts let you name a beneficiary. These pass directly to whoever you name—they skip probate and override your will. If your beneficiary designation still says your ex-spouse and your will says your new spouse gets the money, your ex-spouse gets the money. Update these now. (Seriously. Most people don’t.)

5. List of Accounts and Passwords

This doesn’t need to be fancy. Your executor or successor trustee needs to find your money. List every financial account: bank, brokerage, crypto, credit cards, loyalty programs (yes, airlines have value). Add passwords in a secure password manager (1Password, LastPass, Bitwarden) and give your successor trustee access. If you keep it in a document, it’s too easy to lose.

6. Insurance and Social Security Info

Document your health insurance plan details, life insurance policy number, disability coverage (if any), and your Social Security statement. You can grab your latest Social Security statement on ssa.gov. Include your employer’s benefits contact info and any pension plan details. Your heirs won’t know where to look.

7. Debt and Monthly Bills Inventory

List every debt: mortgage, car loan, credit cards, loans from family. Include the lender’s contact info, account number, and balance. Also list monthly bills: utilities, insurance premiums, subscriptions. This is what your executor needs to pay off or cancel. Missing a debt doesn’t make it go away—it comes out of your estate.

The Real Timeline

Start pulling these documents 6 months before you retire. Talk to an estate attorney if you have anything complicated: a business, blended family, lots of assets, or a child with special needs. Expect to spend $1,500–$3,000 in attorney fees. That’s way cheaper than your heirs fighting it out in court.

Retiring means protecting the people you leave behind.

Free planning tools and Transition Navigator at lumeway.co

This post is for informational purposes only and does not constitute legal, financial, or medical advice. Consult a licensed professional for guidance specific to your situation.