The Ultimate Retirement Checklist (Don’t Skip #3!)

Planning for retirement isn’t just about saving money—it’s about making smart, intentional choices that shape the life you want to live. Yet, with so many moving parts—finances, healthcare, housing, relationships—it’s easy to overlook a few critical steps.

That’s why we created this ultimate retirement checklist.

Whether you’re five years out or five months away, this list will guide you through everything you need to retire with confidence.

And yes—#3 is one most people forget, but it could make or break your retirement. Don’t skip it.

Let’s walk through what really matters—and how to make sure nothing important slips through the cracks.

✅ 1. Define Your Retirement Vision

Before you dive into numbers and documents, take a moment to imagine what you actually want retirement to look like. This isn’t fluff—it’s the foundation for every decision you’ll make.

✨ Ask Yourself:

• What does a great day in retirement look like?

• Do I want to travel, stay close to home, or relocate entirely?

• Will I work part-time, volunteer, or focus on hobbies?

• How do I want to spend time—with family, friends, solo?

“I thought I just wanted to relax—but it turns out, I thrive on having structure. Planning my lifestyle first helped me figure out what I actually needed to budget for.”
– Susan R., retired at 64

When you define your vision, you’re not just creating goals—you’re shaping a retirement that fits your values, pace, and personality.

✅ 2. Calculate Your Monthly Budget

Once you know what kind of lifestyle you want, it’s time to figure out what that lifestyle will cost. A solid monthly budget is key to making sure your savings and income can support your retirement goals.

📊 Break It Down Into Two Categories:

🧾 Don’t Forget:

• Inflation (costs will rise over time)

• Unexpected expenses (car repairs, dental work, etc.)

• Long-term care or help around the home

“Knowing our monthly ‘magic number’ helped us stop guessing. We could confidently say yes to things that brought us joy.”
– Mike & Trisha, retired in North Carolina

A realistic budget helps you retire with peace of mind—not financial anxiety.

✅ 3. Review Your Healthcare Coverage (Don’t Skip This!)

Healthcare can be one of the biggest and most overlooked expenses in retirement—and failing to plan for it can derail even the most carefully built retirement strategy.

🏥 Here’s What You Need to Do:

• Understand Medicare Basics

  • Medicare Part A (hospital), Part B (medical), and Part D (prescriptions)

  • Supplemental (Medigap) vs. Medicare Advantage plans

  • Know when and how to enroll—missing deadlines can mean penalties

• Estimate Out-of-Pocket Costs

  • Premiums, co-pays, prescriptions, dental/vision (not always covered)

  • Set aside funds for yearly costs and emergencies

• Consider Long-Term Care

  • Assisted living or nursing care isn’t covered by Medicare

  • Explore long-term care insurance or set up a designated fund

“We had saved diligently for retirement—but didn’t realize how much healthcare would cost. Getting educated early helped us avoid some big surprises.”
– Theresa M., 68

Don’t treat healthcare as an afterthought. Planning now can save you thousands—and give you confidence to enjoy the years ahead.

✅ 4. Create an Income Strategy

You’ve saved and budgeted—now it’s time to figure out how you’ll turn those savings into steady income. A thoughtful withdrawal strategy can mean the difference between stress and security in retirement.

💸 Key Components to Plan:

• Social Security Timing

  • Claim early (62) and get smaller checks for longer

  • Wait until full retirement age—or 70—for bigger monthly benefits

  • Use tools or meet with a planner to determine your optimal timing

• Withdrawals From Retirement Accounts

  • Plan your strategy for 401(k), IRA, and other investment accounts

  • Be mindful of Required Minimum Distributions (RMDs) starting at age 73

  • Use the “4% rule” as a rough guide—but be flexible

• Other Income Streams

  • Part-time work, rental income, annuities, or side hustles

  • Passive income from dividends or royalties

📊 Simple Example: Monthly Income Plan

“Once I created my income roadmap, I stopped worrying and started living. The peace of mind was priceless.”
– Glenn W., retired engineer

✅ 5. Eliminate or Reduce Debt

One of the smartest moves you can make before retirement? Get rid of as much debt as possible. The fewer monthly obligations you carry, the more freedom—and peace of mind—you’ll have.

🧾 Target These First:

• Credit cards: Pay off high-interest balances to free up cash flow

• Auto loans: Consider downsizing to a reliable, paid-off vehicle

• Personal loans: Reevaluate any installment loans eating into your monthly budget

• Mortgages: If possible, pay off your home—or refinance while you still have steady income

💡 Pro Tip:

If you can’t pay off a loan completely before retiring, aim to lock in lower rates or consolidate to reduce payments.

“We entered retirement mortgage-free and debt-free. That alone shaved $1,300 off our monthly expenses—it changed everything.”
– Paula & Rich T., retired at 65

Retiring without debt isn’t always easy, but it gives you flexibility and security—two things money can’t always buy.

✅ 6. Review Your Investments

As you approach retirement—or settle into it—your investing strategy should shift from growth to preservation and income. Now’s the time to ensure your portfolio is aligned with your goals, timeline, and risk tolerance.

📉 What to Look For:

• Reduce high-risk investments: Consider dialing back exposure to volatile stocks

• Increase income-generating assets: Bonds, dividend-paying stocks, and annuities can provide predictable cash flow

• Diversify wisely: A mix of assets helps protect against market swings

📋 Rebalance Your Portfolio

• Adjust your allocation annually

• Consider a 60/40 or 50/50 mix of stocks to bonds as a retirement-friendly strategy

• Use a target-date fund or consult with a financial advisor

“We shifted to a more conservative mix and added some dividend-paying ETFs. Now, we’re getting monthly income without constantly watching the market.”
– Leonard J., 70

Your investments don’t need to be aggressive anymore—they need to be reliable, steady, and aligned with your retirement income plan.

✅ 7. Secure Legal Documents

No retirement checklist is complete without ensuring your legal affairs are in order. It’s not just about preparing for the unexpected—it’s about protecting your wishes, your family, and your peace of mind.

📄 Essential Documents to Review and Update:

• Will or Living Trust

  • Outlines how your assets will be distributed

  • Avoids family disputes and legal confusion

• Power of Attorney (POA)

  • Appoints someone to handle financial matters if you become unable

• Healthcare Proxy & Advance Directive

  • Designates someone to make medical decisions on your behalf

  • Lays out your preferences for treatment in critical situations

• Beneficiary Designations

  • Review who’s listed on your retirement accounts, life insurance, and bank accounts

  • These override your will—so they must be up-to-date

“We had wills, but our beneficiaries hadn’t been updated in 12 years. Fixing that avoided what could’ve been a big mess down the road.”
– Denise & Tom R., 66 and 68

Getting your paperwork in order ensures your loved ones are protected—and your legacy is preserved.

✅ 8. Downsize and Declutter

Downsizing isn’t just about saving money—it’s about simplifying your life for the next chapter. Whether it’s moving to a smaller home or just clearing out unused space, this step can bring surprising clarity and freedom.

🧹 Where to Start:

• Go room by room and ask: Do I still use this? Does it bring me joy?

• Donate or sell furniture, clothing, and household items you no longer need

• Digitize paperwork and photos to reduce clutter

🏠 Consider a Smaller or Smarter Living Space

• One-story homes, condos, or 55+ communities can offer easier living

• Lower maintenance = more time for what you love

• Selling your home could unlock extra cash for retirement goals

“We moved from a 4-bedroom to a 2-bedroom townhouse and haven’t looked back. Life is simpler, cleaner, and we have money left over each month.”
– Maria & Allen S., 67

Decluttering isn’t just about your space—it’s about your state of mind. It’s a powerful step toward a lighter, more intentional retirement.

✅ 9. Plan Your Daily Routine

You’ve planned the money, the healthcare, and the paperwork—but what will you actually do each day? A meaningful retirement isn’t just about freedom—it’s about having a purposeful rhythm to your life.

🗓️ Why a Routine Matters:

• Provides structure after years of scheduled workdays

• Helps combat boredom, isolation, or low motivation

• Keeps you physically active, mentally engaged, and socially connected

🔄 Ideas to Build Your Routine Around:

• Morning walks or fitness classes

• Weekly volunteer work or social groups

• Hobbies like gardening, writing, or music

• Grandparent time or caregiving

• Learning something new—languages, painting, local history

“I was worried retirement would feel aimless. But once I built a weekly rhythm of volunteering and hobby time, I felt more energized than ever.”
– Clara N., 65

Creating a routine isn’t about being busy—it’s about waking up with purpose.

✅ 10. Talk With Your Partner or Family

Retirement may feel like a personal milestone—but it affects the people closest to you, too. Having open conversations now can help align expectations, reduce stress, and build stronger support systems for the future.

🗣️ What to Discuss:

• Retirement goals: Are you and your spouse or partner on the same page about lifestyle, location, and spending?

• Financial expectations: Will you help support kids or grandkids? How will you handle big expenses?

• Caregiving responsibilities: Who will take care of you—or a loved one—if the need arises?

• Legacy and inheritance: Ensure your family knows your wishes and how to access important documents

💬 Pro Tip:

Start small. You don’t need to cover everything in one conversation. The goal is communication, not perfection.

“Talking through our plans helped us uncover things we hadn’t thought about—like when we wanted to travel and how often we’d see family. Now, we’re working as a team.”
– Jerome & Faith P., retired couple in Georgia

Retirement is more rewarding when it’s shared, supported, and understood by those around you.

Final Thoughts

Retirement isn’t just a financial milestone—it’s a life transition. And like any transition, it’s smoother (and less stressful) when you have a clear roadmap.

This checklist isn’t just a to-do list—it’s your toolkit for creating a retirement that’s secure, joyful, and uniquely yours.

Whether you’re months away from retiring or still years out, now is the time to act. Start conversations. Get organized. And revisit this list regularly to make sure your plans stay aligned with your goals.

For more personalized support and tools to guide your next steps, visit RetiredLifeTips.com—your trusted source for Retirement Planning support and everyday wisdom for building a better retired life.