Preparing for Retirement? This Checklist Helps You Avoid Costly Mistakes
You’ve put in the years. You’ve done the work, saved consistently, maybe even knocked out the mortgage. Now comes the part that looks easy on paper: retirement. But this is exactly where things can fall apart fast.
Here’s the reality: 83% of American workers admit they’ve made mistakes with retirement planning. Most didn’t get it all right, and many are finding out the hard way that growing the nest egg was only half the battle. Protecting it takes just as much strategy.
This checklist breaks down what actually matters: spending plans, income strategy, taxes, and more. This isn’t theory. It’s the kind of planning that keeps your money working while you stop.
Every situation is different, so adjust as needed. But the goal stays the same. Read this, use it, and retire on your terms.
Table of Contents
Why Listen To Dad is FIRE?
Before we get into the retirement checklist, let’s talk about why you should listen to Dad is FIRE. I am a Chartered Financial Analyst. I have more than 20 years experience in Financial Services.
Many of my roles have been around building tools, systems, and policies around reaching financial goals. I’ve had titles like First Vice President at two of the larger Financial Services firms.
I also retired young. So I’m not just guessing here. I’ve used this retirement checklist.
Retirement Checklist Step 1: Know Your Spending Number
Retirement success doesn’t come down to some magic portfolio balance. It comes down to one number: what you spend. If you don’t know that, everything else is just guesswork.
To do this, look at your trailing 24 month expenses. Divide that by 24. That is your normal monthly spend. Then factor in major purchases you will make in the future. Things like replacing HVAC, cars, etc.
Inflation needs to be part of the picture too, it won’t hit every category the same, but it’ll hit. Once you’ve got a handle on the real number you need to cover each year, you can build everything else around it.
That number is your foundation. Without it, your plan is built on sand.
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Retirement Checklist Step 2: Map Out Income Sources
Knowing where your money will come from is just as important as knowing where it’s going. Social Security is a piece of the puzzle, but don’t stop there. Add in any pensions, IRA or 401(k) withdrawals, dividends from brokerage accounts, and annuity income if you’ve got it.
If you’ve got rental properties or part-time work lined up, count those too. Once you’ve mapped everything out, the next move is to build a tax-efficient plan around it.
Some sources are taxed differently than others, and pulling from the wrong bucket at the wrong time can cost you thousands. Line it up right and you’re not just funding retirement, you’re preserving it.
Retirement Checklist Step 3: Build a Smart Withdrawal Strategy
You’ve got the accounts. Now the question is, which one do you tap first? There’s no one-size-fits-all answer, but there is a smart way to approach it.
Typically, you want to draw down taxable accounts first, then tax-deferred, then tax-free, but that depends on your income, tax bracket, and goals. The goal is simple: minimize taxes over time, not just this year.
A good withdrawal strategy can stretch your savings, protect against sequence of return risk, and even lower your Medicare premiums. Don’t wait until you’re already pulling funds to figure it out. Build a plan that works now and adapts later.
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Retirement Checklist Step 4: Prepare for RMDs Before They Hit
Required Minimum Distributions (RMDs) start at age 73 for most, or 75 if you were born in 1960 or later. And they don’t care if you need the money, they’re mandatory, and the IRS is watching.
Miss one or mess it up, and you’re looking at a hefty penalty. But the real damage is what it does to your taxes. Big RMDs can spike your income, push you into a higher bracket, and increase Medicare premiums.
That’s why smart retirees think ahead. Roth conversions in the early years of retirement, when income is lower, can help smooth out those later tax hits. This isn’t just about compliance, it’s about control. Plan now so future-you isn’t cornered later.
Related Video: The Top Mistakes People Make with Their 401ks and How to Avoid Them
Retirement Checklist Step 5: Manage Sequence of Return Risk
This is the silent killer of retirement plans, the kind no one warns you about until it’s too late. Sequence of return risk means the order of your investment returns matters, especially once you start withdrawing.
A major market drop early in retirement can do way more damage than the same drop later on. Why? Because you’re taking money out while your portfolio’s trying to recover, which locks in losses and shrinks future growth.
The fix isn’t complicated, but it takes discipline. Keep one to two years of expenses in cash or short-term assets. Set withdrawal rules that adjust during down years. And keep your portfolio diversified enough to handle storms without capsizing.
You’re not just aiming for growth, you’re building resilience.
Retirement Checklist Step 6: Plan for Healthcare and Long-Term Care
Too many retirees assume Medicare will handle most of the costs. It won’t. It covers a lot, but not everything, and the gaps get expensive fast. Think hospital stays, prescriptions, dental, vision, and long-term care.
Those aren’t just side expenses, they can wreck a retirement budget if you’re not ready. You need a clear understanding of Medicare Parts A, B, and D, and then decide if a Medigap or Advantage plan fits better.
Don’t forget the wildcard, long-term care. Be it for home assistance or a facility, it adds up quickly. Get coverage, set aside funds, or build it into your budget.
You’re not just protecting yourself, you’re protecting your spouse and kids from scrambling later.
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Retirement Checklist Step 7: Lock In Estate and Legacy Plans
A lot of people think estate planning is just about having a will. It’s not. It’s about making sure your wishes hold up legally and practically when you’re not around to explain them.
That means reviewing and updating your will, setting up a durable power of attorney, confirming healthcare proxies, and making sure every single account has the right beneficiary listed. If a trust makes sense for your situation, set it up and fund it properly.
These aren’t just documents, they’re instructions for your family during the most stressful time they’ll face. Do it now, so they don’t have to deal with courts, delays, or guesswork. Peace of mind is part of the legacy too.
Retirement Checklist Step 8: Keep Taxes Under Control
Retirement doesn’t mean you stop thinking about taxes, it means you start thinking about them differently. You now have more flexibility, and if you use it right, that means real savings.
Take advantage of low-income years to do Roth conversions while your tax bracket is friendly. Use Qualified Charitable Distributions (QCDs) to give directly from an IRA if you’re over 70½. Sell appreciated investments when they fall into the 0% capital gains zone.
And keep an eye on IRMAA thresholds, because a higher income can mean higher Medicare premiums. Every tax dollar you keep is another dollar working for you. Don’t give the IRS more than you owe, legally avoid, don’t blindly pay.
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Retirement Checklist Step 9: Know When to Hire a Pro
You only get one shot at retirement. You don’t need to figure out every detail on your own. A good financial planner, ideally fee-only and a fiduciary, can help you craft a withdrawal plan, keep your tax strategy sharp, adjust your investments, and plan ahead for big expenses.
The right one doesn’t sell products, they build strategies that fit your goals. Life changes, markets shift, laws update. Having a pro in your corner means your plan doesn’t sit still while the world moves.
It’s not about complexity, it’s about peace of mind. You worked hard to build this life. A planner helps you protect it.
Retirement Planning That Lasts
You don’t always get a second shot at retirement. You either plan well, or you leave your future up to chance. Every step on this checklist helps you stay in control of your money, your time, and your peace of mind.
Retirement shouldn’t feel like a gamble, and it won’t if you treat it like a real plan, not just a payout phase. The hard part’s already done: you earned it, saved it, and showed up.
Now it’s time to make sure it actually lasts.
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