Your Complete Pre-Retirement Checklist: Last Steps to Financial Freedom

You’ve spent decades saving, investing, and planning. Now retirement is just around the corner and it’s time to make sure every piece of your financial and personal life is in place for a smooth transition. Think of this as your pre-retirement launch sequence: a final walk-through before you step confidently into financial freedom.

This empowering checklist covers everything you should review or finalize before you retire from budgeting to healthcare, estate planning to insurance, and more.

1. Build (and Test) Your Retirement Budget

Before you leave the workforce, make sure your lifestyle is sustainable.

List fixed expenses: Housing, utilities, insurance, groceries, taxes.
Account for variable costs: Travel, gifts, hobbies, home repairs.
Factor in inflation: Costs will rise over time build in a 2–3% annual increase.
Run a test month: Live off your projected retirement budget for 30 days.

Bonus: Use budgeting apps like You Need a Budget (YNAB) or Empower to track your numbers.

2. Lock In Your Retirement Income Plan

You need predictable, tax-efficient income to replace your paycheck.

Claim Social Security: Decide when (age 62, 67, or 70?) for optimal lifetime benefits.
Withdraw from retirement accounts: Set a drawdown plan (e.g., Roth first, then traditional).
Consider annuities or pensions: If applicable, determine payout options.
Model your Safe Withdrawal Rate: Use tools or an advisor to test 3–4% withdrawal strategies.

Tip: Diversify your income sources (e.g., a mix of Social Security, IRAs, and a rental property).

3. Double-Check Healthcare and Insurance Coverage

Healthcare is often the biggest wildcard in retirement.

Enroll in Medicare: Sign up at age 65 to avoid penalties. Consider a Medigap or Medicare Advantage plan.
Bridge the gap (if retiring before 65): Explore COBRA, ACA marketplace, or a spouse’s plan.
Review long-term care options: It’s easier to qualify before your 70s.
Update life insurance: Decide if you still need it or if it’s time to reduce coverage.

Consider: A Health Savings Account (HSA) is a great tax-free tool to cover future medical costs.

4. Finalize Estate Planning Documents

Secure your legacy and ensure your wishes are respected.

Create or update your will
Assign a financial and medical power of attorney
Establish a living will or healthcare directive
Consider a trust (especially for complex estates or privacy)
Name (and review) beneficiaries on all accounts

Note: Beneficiary designations override wills keep them current.

5. Evaluate Housing Needs

Your home should support your financial and lifestyle goals.

Consider downsizing: Smaller home = lower costs and maintenance.
Pay off your mortgage: Or decide if keeping it makes sense.
Think location: Stay close to family? Move for better weather or lower taxes?
Explore senior-friendly upgrades: Grab bars, no-step entries, and smart home features.

Tip: Test your new living situation with a 3-month trial rental before making a permanent move.

6. Optimize Taxes and Investment Strategy

Minimizing taxes in retirement helps your savings last longer.

Review Roth conversion opportunities
Harvest tax losses while you still have income
Strategically withdraw from taxable vs. tax-deferred accounts
Use Required Minimum Distribution (RMD) calculators (starts at age 73)
Rebalance your portfolio to match your lower-risk retirement glide path

Smart move: Set your investment withdrawals to minimize moving into a higher tax bracket.

7. Prepare Mentally and Emotionally

Don’t overlook the non-financial side of retirement.

Plan for purpose: Volunteering, hobbies, part-time work, or travel.
Set a new routine: Fill the 40+ hours you’ll regain each week.
Discuss lifestyle expectations with your spouse or family.
Build a social plan: Stay connected to community and avoid isolation.

Pro tip: Retirement isn’t just a finish line — it’s a new beginning.

8. Set Up Automation & Monitoring Tools

Make your retirement plan work with as little friction as possible.

Automate withdrawals from retirement accounts
Enable automatic bill pay and account alerts
Consolidate financial accounts for easier management
Track net worth and spending using free dashboards like Empower

Extra layer: Hire a fiduciary financial advisor or robo-advisor for ongoing oversight.

9. Review Legal and Financial Safeguards

Avoid nasty surprises and ensure your retirement is protected.

Check for identity theft protection
Freeze your credit reports if not applying for new credit
Review umbrella insurance coverage
Reconfirm access to important accounts and passwords (use a secure manager)

Reminder: Digital estate planning is now a thing make a plan for online logins and digital assets.

10. Take a Final Full-Plan Walkthrough

Before you retire, run your full plan by:

A trusted financial planner
A tax advisor or CPA
Your partner or family

This “retirement rehearsal” ensures you’ve checked all the boxes and helps uncover blind spots before they become costly.

You’re Ready. Now What?

You’ve earned your financial freedom. By completing this pre-retirement checklist, you’ve put yourself in control and given yourself permission to enjoy what’s next.