Shows / How to Retire on Time
How to Retire on Time
Welcome to How to Retire on Time, a show that answers your retirement questions. Say goodbye to the oversimplified advice you've heard hundreds of times. This show is about getting into the nitty-gritty so you can make better decisions as you prepare for retirement. Text your questions to 913-363-1234 and we'll feature them on the show. Don't forget to grab a copy of the book, How to Retire on Time, or check out our resources by going to www.retireontime.com.
Episodes
- How to Retire on Time
When Roth Conversions Might Not Be the Right Move
When online advice treats Roth conversions as a must, Michael Decker, NSSA® explains how the standard deduction and lower brackets can change the math for some…
- How to Retire on Time
When a MYGA Ladder Meets a Bond Ladder
When money is needed within five years, Michael Decker, NSSA® explains how a MYGA ladder, a bond ladder, and a buffered ETF can differ, and why defining the…
- How to Retire on Time
When a Note Can Offer Principal Protection
When a product promises protection and upside, Michael Decker, NSSA® walks through how structured notes work, where the risks sit, and how TIPS compare. The…
- How to Retire on Time
When Do Alternatives Belong in Your Portfolio?
When stocks and bonds are not the whole picture, Michael Decker, NSSA® explains where alternatives like real estate, private equity, and gold can fit, and what…
- How to Retire on Time
When Can a Medigap Plan Deny You?
When a plan looks cheaper now and switching later sounds simple, Michael Decker, NSSA® explains how the Medigap enrollment window at 65 can change what happens…
- How to Retire on Time
Why Healthcare Costs Keep Rising
When healthcare premiums keep climbing, Michael Decker, NSSA® explains why he treats healthcare as a cost to plan for, not an investment, and why a…
- How to Retire on Time
Is Long-Term Care Insurance Worth It?
When long-term care insurance is sold on fear, Michael Decker, NSSA® explains how a break-even view and peace of mind can each be a fair reason to decide. The…
- How to Retire on Time
How Do Survivor Benefits Work?
When a spouse passes, Michael Decker, NSSA® explains how a survivor benefit and a person’s own retirement benefit can be treated as two separate choices. The…
- How to Retire on Time
Can You Plan for the Widow Tax?
When one spouse passes and the household becomes a single filer, Michael Decker, NSSA® explains how a plan can account for it years ahead. The following is…
- How to Retire on Time
Is Two Years of Reserves Enough?
When a portfolio is all in stocks with two years of income set aside, Michael Decker, NSSA® explains how a timeline view of fixed, index, and variable money…
- How to Retire on Time
When Tax Law Is Written in Pencil
When tax brackets can change with new legislation, Michael Decker, NSSA® explains why he benchmarks the effective tax rate instead of chasing the lowest bill…
- How to Retire on Time
What Does Social Security Insolvency Mean?
When headlines say Social Security is insolvent, Michael Decker, NSSA® explains what the word means, which fixes have been floated, and where filing decisions…
- How to Retire on Time
When Your CDs Mature and Inflation Lingers
When your CDs mature and inflation is still a concern, Michael Decker, NSSA® explains how your timeline can shape the choice between fixed and indexed options…
- How to Retire on Time
Where Does Social Security Belong in Your Plan?
When maximizing Social Security and maximizing quality of life are not the same goal, Michael Decker, NSSA® explains where filing fits in a plan. The following…
- How to Retire on Time
When Inflation Risk and Market Risk Collide
When lowering market risk can raise inflation risk, Michael Decker, NSSA® explains where reserves fit, including for a viewer around age 50. The following is…
- How to Retire on Time
When Maxing Out a Bracket Misses the Point
When moving income at a higher bracket looks like the better deal, Michael Decker, NSSA® explains how the effective tax rate can tell a different story. The…
- How to Retire on Time
How to Actually Balance Risk and Protection in Retirement
Michael Decker, NSSA® answers a viewer question on balancing risk and protection using a food-storage analogy, splitting a portfolio into smaller pieces that…
- How to Retire on Time
Why Just Buying the S&P 500 Does Not Solve Retirement Math
Michael Decker, NSSA® responds to a viewer who says the math only works with stocks and the S&P 500, and the risk that gets left out when withdrawals start…
- How to Retire on Time
What to Do With Your Money Five Years Before Retirement
Michael Decker, NSSA® answers a viewer question on repositioning savings five years from retirement, and why shopping around matters here as much as anywhere…
- How to Retire on Time
A Way to Decide Whether You Actually Need an Annuity
Michael Decker, NSSA® walks through how to decide if an annuity fits your plan before shopping for one, then answers a follow-up question on timing IRA to Roth…
- How to Retire on Time
How to Plan Retirement Around an Inheritance You Might Not Get
Michael Decker, NSSA® answers a viewer question on planning retirement income around a future inheritance, and why treating it as a backup plan works better…
- How to Retire on Time
The Bond Market Warning Sign Behind This Year's Market Jitters
Michael Decker, NSSA® walks through a widening gap between short-term and long-term interest rates that echoes the run-up to 2008. Plus two "would you rather"…
- How to Retire on Time
Why Some People Don't Need to Do Roth Conversions
Michael Decker, NSSA® answers a viewer question on why some people don't need IRA to Roth conversions even as taxes go up, and the one number he says actually…
- How to Retire on Time
How You can Exit a Concentrated Company Stock Position
Michael Decker, NSSA® answers a viewer question on selling company stock that makes up over half their savings, and three ways to manage the tax bill along the…
- How to Retire on Time
How to Schedule Withdrawals From a $750,000 401(k)
Michael Decker, NSSA® answers a viewer question on withdrawing from a $750,000 401(k) at 65, and tells a CVS receipt story he uses to explain wasted tax…
- How to Retire on Time
A Way to Think About a 403(b) Rollover
Michael Decker, NSSA® answers a viewer question on an in-service 403(b) rollover, an index annuity, and withdrawal order, and why the real first question isn't…
- How to Retire on Time
How A Few Stocks Can Prop Up the Whole Market
Michael Decker, NSSA® walks through how much of the market's growth is riding on a handful of AI-related companies, and shares the story of the day he learned…
- How to Retire on Time
How the Widow Tax Changes a Retirement Plan
Michael Decker, NSSA® answers a viewer question on the widow tax, and why a surviving spouse can end up taxed at close to double the rate on roughly the same…
- How to Retire on Time
What a Financial Advisor Can Offer That You Can't Get Yourself
Michael Decker, NSSA® answers a viewer question on what a financial advisor can actually offer that you can't get on your own, and where that access matters…
- How to Retire on Time
How Your Social Security Timing Can Affects Everything Else
Michael Decker, NSSA® answers a viewer question on how Social Security timing can affects the rest of a retirement plan, well beyond just maximizing the…
- How to Retire on Time
Tax Planning for Retirement Accounts Under $1 Million
Michael Decker, NSSA® answers a viewer question on tax planning for retirement savings under $1 million, and why the right approach is more subtle than it…
- How to Retire on Time
Is the Stock Market in another Bubble Right Now?
Michael Decker, NSSA® answers a viewer question on whether he's concerned about the markets right now, and explains why a flat market worries him more than a…
- How to Retire on Time
Three Common Leaks in a Retirement Plan
Michael Decker, NSSA® answers a viewer question on the most common leaks he sees in a retirement plan, and the first one is tied to how much AI exposure people…
- How to Retire on Time
A Retirement Plan That Ran Out of Money Doing Everything "Right"
Michael Decker, NSSA® runs the same million-dollar IRA forward in two different ways, one converting aggressively to a Roth and one does not. Only one of them…
- How to Retire on Time
How to Plan for a Big Expense in Retirement
How do you fit the large bills in your retirement plan? New roof? New car? Michael Decker, NSSA® answers a viewer question on planning around a big one-time…
- How to Retire on Time
What's Changing with Medicare This Year
Don’t let yourself auto-renew your current plan. Big changes could cause you to want to shop this season before you commit. Michael Decker, NSSA® covers what's…
- How to Retire on Time
Can Anyone Time the AI Bubble?
Is there an AI bubble and if so, can you time your exit? Michael Decker, NSSA® answers a viewer's question on whether he believes AI stocks are a bubble, and…
- How to Retire on Time
Why Tax Planning Starts with Where to Put Your Savings
Where your money goes and when you want to pull it out shapes the planning on where you should place it in the first place. The 401(k) is only one place to…
- How to Retire on Time
Which is better, lifetime income from an annuity or a bond?
There is no such thing as a perfect investment, product, or strategy, which is why the comparison between a 30-year treasury vs an indexed annuity is so…
- How to Retire on Time
Why the Surviving Spouse Carries More Risk
Michael Decker, NSSA® walks through the tax risk, longevity risk, healthcare risk, and other risks unique to the spouse who lives longer, and what many people…
- How to Retire on Time
What If It Takes Year To Recover From a Market Crash
Michael Decker, NSSA® takes on a market-crash reserves question and a Roth conversion sizing question back-to-back, and why the right answer to each one…
- How to Retire on Time
How Retirees Plan for Healthcare Before Medicare Kicks In
Michael Decker, NSSA® answers a viewer question on retiring before 65, and how the options for covering healthcare before Medicare actually compare. The…
- How to Retire on Time
Why Complicated Doesn’t Mean Better
Michael Decker, NSSA® breaks down complicated investments like non-traded REITs, private credit, structured notes, and gold and crypto pitches, and the risk…
- How to Retire on Time
How to Retire on Time, 9/1/26
Michael Decker, NSSA® walks through annuities, options trading, and "be your own bank" life insurance, what that word "guaranteed" does and doesn't actually…
- How to Retire on Time
What Happens to Your IRA After You're Gone
Two viewers ask about protecting their money after death, one from Medicaid and one from the IRS. The answers are more restrictive than either expected. The…
- How to Retire on Time
When Roth Conversions Might Not Be the Right Move
A high income earner asks about all the Roth conversion hype, and Michael Decker, NSSA® explains why her situation is when that advice falls apart. The…
- How to Retire on Time
When Your Advisor Fees Are More Than Your Tax Bill
Michael Decker, NSSA® runs the numbers on a million-dollar retirement account and shows how the advisor fee is twice as expensive as what the government…
- How to Retire on Time
Tax Brackets Matter Less Than People Realize
There’s more to tax planning than looking at your income tax brackets Discover the different ways to take income and how to get the most out of your money…
- How to Retire on Time
When Roth Conversion Don’t Apply in Retirement
Many advisors talk about converting to a Roth before taxes go up. Michael Decker, NSSA® says most retirees with a million dollars or less should be doing…
- How to Retire on Time
The Tax Bill Landlords Don't See Until They Sell
Selling a rental property can trigger a bigger tax bill than most landlords expect, and Mike Decker walks through two lesser known ways to exit instead. The…
- How to Retire on Time
Why Income Order Matters More Than the Amount
One line on your tax return could be quietly costing you thousands a year, and Mike Decker ties it straight into the biggest Social Security filing mistake he…
- How to Retire on Time
Two Risks Retirement Calculators Don't Warn You About
A question about retiring in your fifties and a question about hyperinflation turn out to have the exact same answer. The following is from Mike’s weekly…
- How to Retire on Time
Why "I'm Comfortable With Risk" Is the Wrong Answer
Every retiree says the same four words about risk tolerance, and Mike Decker says all four of them miss the point. The following is from Mike’s weekly webinar…
- How to Retire on Time
Planning For When One Spouse Passes First
There's a retirement conversation almost no one wants to have. Skipping it is exactly how a surviving spouse ends up blindsided by taxes and decisions they…
- How to Retire on Time
Why There's No Flowchart For Your Annuity Taxes
There's a version of the answer that would let you pay the least possible tax on your retirement money. The following is from Mike’s weekly webinar. Ready to…
- How to Retire on Time
We Asked AI About Long-Term Care Insurance
Live on the show, we asked an AI chatbot whether you should buy long-term care insurance. Its answer says a lot about why this decision trips up almost…
- How to Retire on Time
The Retirement-Income Ad That's Actually Two Red Flags
There's a specific kind of retirement-income ad that sounds like a great deal, and once you see why it isn't, you'll spot it everywhere. The following is from…
- How to Retire on Time
The Biggest Retirement Mistake Isn't About Money
The single biggest factor in whether a retirement plan actually holds up has almost nothing to do with the portfolio inside it. The following is from Mike’s…
- How to Retire on Time
Is There Really A Safe Retirement Withdrawal Rate?
The withdrawal number most retirees have memorized might be based on market conditions that no longer exist. The following is from Mike’s weekly webinar. Ready…
- How to Retire on Time
The Long-Term Care Decision Most People Get Wrong
There are at least four different ways to plan for long-term care costs, and the one most people assume is the "safe choice" usually isn't the best fit. The…