If you’re five years away from retirement, the decisions you make right now can determine how secure, tax-efficient, and stress-free your retirement will be. In this comprehensive retirement planning checklist, Erin Moriarity from Erin Talks Money walks you through a step-by-step 5-year retirement countdown blueprint covering everything you need to do before you retire.
You’ll learn how to build a realistic retirement budget, set a clear retirement timeline, and position your investment portfolio for the transition from saving to spending. Erin explains smart retirement tax planning strategies, including withdrawal order, Roth conversion opportunities, managing required minimum distributions (RMDs), and avoiding Medicare IRMAA surcharges and healthcare subsidy cliffs.
This video also breaks down Social Security claiming strategies for couples and singles, longevity planning, survivor benefits, and how to protect your retirement from sequence-of-returns risk using cash buffers and retirement income layering.
Whether you’re planning to retire early, approaching Medicare age, or simply want a clear retirement planning roadmap, this video provides a practical, data-driven timeline to help you retire with confidence.
00:00 – Intro: Retirement Planning Timeline: The 5-Year Blueprint Before You Retire
00:34 – 5 Years Before Retirement: Build the Plan and Fix Structural Risks
00:56 – Set a Specific Retirement Date (Why Timing Changes Everything)
01:37 – How to Build a Realistic Retirement Budget (Not a Guess)
02:36 – Are You On Track? Check Your Savings Runway Before Retirement
03:23 – Investment Risk Before Retirement: Tolerance vs Capacity Explained
04:15 – Structural Retirement Risks Most People Ignore
06:00 – 4 Years Before Retirement: Tax Planning and Portfolio Transition
06:37 – Mapping Retirement Income Sources Before You Retire
07:09 – Retirement Withdrawal Strategy: Decide the Order Before You Stop Working
08:22 – Retirement Taxes Explained: Why Tax Brackets Matter More Than Balances
09:51 – Lifetime Retirement Tax Planning (Not Just a Snapshot)
10:31 – Roth Conversions Before Retirement: When They Help and When They Don’t
11:33 – Healthcare Planning If You Retire Before Medicare
12:32 – 3 Years Before Retirement: Social Security and Sequence Risk Defense
12:56 – Social Security Survivor Planning for Married Couples
13:51 – Retirement Longevity Planning: Why Averages Are Dangerous
15:02 – Social Security Claiming as a Household Strategy
15:44 – Sequence of Returns Risk Explained (And Why It Matters Most Early)
16:55 – Building a Cash Buffer to Protect Retirement Income
18:05 – Retirement Paycheck vs Bucket Strategy Explained
18:54 – How Flexible Spending Increases Retirement Safety
20:18 – 2 Years Before Retirement: Build Your Retirement Paycheck
20:42 – Creating the First 24 Months of Retirement Cash Flow
21:21 – Which Accounts to Use First in Retirement (Tax Strategy)
21:57 – Retirement Income Layers: Floors, Growth, and Flexibility
22:52 – What to Do With Old 401(k)s and Employer Plans Before Retirement
23:41 – Retirement Tax Withholding Setup to Avoid Surprises
24:55 – 1 Year Before Retirement: Dry Runs and Execution Checklist
25:12 – Test-Driving Retirement Income Before You Quit Working
26:23 – Automating Retirement Income and Cash Flow Systems
26:50 – Final Social Security Decisions and Backup Plans
27:19 – Healthcare Transitions: Medicare, ACA, and Coverage Timing
27:54 – Final Retirement Paperwork, Rollovers, and Separations
28:30 – First Year of Retirement: Monitoring, Adjusting, and Staying Calm
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Disclaimer: Please note that this video is made for entertainment purposes only and not to be taken as financial advice. Always make sure to do your own research.
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Excellent blueprint for the final 5 years before retirement! The point about tax planning being just as important as investment returns is so underrated. So many people focus only on growing their nest egg but forget that how they withdraw it matters just as much. Great practical advice.
Great breakdown, Erin. The IRMAA point is the one people miss: Medicare looks back two years at your tax return, so what you convert to Roth at 63 can set your premiums at 65. That’s why these five years matter so much. Thanks for laying the whole countdown out step by step.
20 months left
12 years from retirement, right now I can still be aggressive with my investments. Maybe I will rebalance after 5 years…
Looks like this AI slop stole most of your script here. https://www.youtube.com/watch?v=pMWONU01RO0
i'm 50 and got laid off a few months ago, i knew i was gonna eventually find another job but i wanted to see what a mini retirement felt like, and for me its terrible, i cant relax, i feel all antsy with nothing to do every day, cant sleep because im not tired from working. i'm used to solving problems so i get all stressed out about insignificant little problems. i'm starting a new job next week i cant wait this is hell.
good info
Im a few months away😅😂
Step number one: Get your nutrition right, workout and get rid of all that stubborn weight you are carrying around. Without your health, you are just saving/investing money for someone else! Lock in with this first step, and you can incorporate all the other suggestions in the video simultaneously. Imagine you are at your ideal weight, in the best shape you have been in, in decades, and you have followed all these suggestions and hit all of your financial goal. You can transition into retirement with ease.
Thank you!
Planning to retire at 55 and then convert the traditional part of my 401k into my roth ira during the years my income is down to stay in the lowest tax bracket then file for my SS
Spot on advice in this video. Transitioning from saving money to actually living off it is a huge psychological shift. When I retired at 51 with $800,000, my main focus was protecting that core balance. Now at 56, I’ve built a business cash flow that brings in an extra $20k monthly, keeping my retirement savings 100% intact. Staying on track requires a very specific type of early planning and pivoting. If anyone is approaching their 50s and wants to know how to set up this kind of buffer, feel free to drop a question.
Exactly 1 year for us….getting excited (will be 57)
Will be 58 next week. All of a sudden I realized I have no written Will, neither have I planned my retirement. I feel irresponsible right now.
There’s no answers here. Nothing actionable. Just a list of decisions you have to make with no tools to make them or figures of merit.
I have 7 years remaining.
401K accounts may have institutionally lower net expense ratios than Individual IRA's – fees may matter!
I’m 4 years away from full retirement God-willing. This video is informative. I still have a lot to catch up🙏
I need advice pls, I change my 401 k from aggressive to very conservative during pandemic because I lost money but now I realize I made a big mistake, 52 years old now, planning to retire at 63, want to change to moderate aggressive now and change to Vanguard 20/35 or 20/40, right now I have 100% stable investments so not earning anything, is it ok to change now even if the market is high? Pls help
If you want to make tax-free QCDs you'll need to move 401k money to a rollover IRA.
@erin..i watch your channel and otherss.. in this topic.. i see so many contradictions by all of you who say thry want to help 50-65 rrtire confidently … dont blame your knowledge. But all this production techniques using AI or otherwise. people who watch u are nervous with time in their life .. being empathetic and honest is important.. all of u contradict each other .. kevin, nick and u
I'm 5-8 years out and wanted to see what I should be doing now. I got about a third of the way through the video when I became overwhelmed and had to stop watching. I'm going to try again to make it through, but I currently need to concentrate on not having a panic attack. 😣 I'd love to see a version of this geared towards ADHD or other neurodiverse folks.
You only lose in a down market if you sell