Income Over Wealth

Once You See This Number, You Stop Worrying About Running Out of Money

Dan Wilson — Sat, 24 Oct 2026 11:00:00 -0400

A bigger balance rarely quiets the worry about running out of money in retirement. Dan runs the same $1.5 million from 2000 through 2007 on real S&P 500 returns, once selling shares to pay every bill and once with the bills covered by private mortgage note income, a year of cash set aside, and the rest left in an index fund. He then runs a second test starting in 2010, the decade when selling shares came out ahead. Like any investment, a note carries risk: the money is committed for the term, and a borrower can stop paying.

What 3 straight losing years did to $1.5 million when every bill was paid by selling shares
Why you don't get to pick your decade, and what the 2010s test showed
How to work out your own number with 2 lines on a piece of paper

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=yUgvSEWgBhA

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

Retire at 50, 55, or 60? Here's Exactly How Much Income You Need

Dan Wilson — Tue, 20 Oct 2026 11:00:00 -0400

Your monthly bills are only part of the answer. This episode prices one couple's $7,000-a-month life at each target age, starting with what health coverage costs once the job stops paying most of it. KFF puts the average family premium at $26,993, with the employer covering about three quarters. Dan also covers which savings are allowed to pay you before 59 and a half, and how long the income has to keep up with prices when you plan to 95.

Why the 10% early withdrawal penalty matters more at 50 than at 55
How the Rule of 55 works, and the accounts it doesn't cover
Why stopping at 50 is mostly about where your money sits

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=c8CC41z8SmU

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

I Lived on Rental Income for 4 Years (The Brutal Truth)

Dan Wilson — Sat, 17 Oct 2026 11:00:00 -0400

Dan left the Air Force at 33 and let 6 rental properties pay every bill, including about 2 years of slow travel. This episode covers what a spreadsheet leaves out, from tenants who pay on their own schedule to the 3 months it took for the stress to wear off. The harder question turned out to be what to do with his days once work was optional. He closes with what carries over if you're 55 with bigger bills and no interest in becoming a landlord.

Why income that shows up every month made leaving possible when a savings balance wouldn't have
How $4,000 a month from 6 rentals compares to $1.2 million under the 4% rule
Why the same health plan costs almost twice as much at 55 as at 33

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=e44Ro_nu46c

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

3 Assets That Replace a Paycheck in Retirement

Dan Wilson — Tue, 13 Oct 2026 11:00:00 -0400

If most of your savings sits in the stock market, it only pays you when you sell shares. This episode prices the same $5,000 a month from dividend stocks, rental houses and private mortgage notes, and grades each one on what it asks of you and where it falls short. It also looks at what an 18% market drop does to someone whose bills are covered by notes.

Why a dividend check still moves with the market, using the 2009 cut
Where a rental fails the paycheck test, even at a 7.4% cap rate
Why a note fits inside a self-directed IRA and a rental runs into the IRS rules

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=G1VXyV4lSwQ

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

The Savings Number That Finally Lets You Stop Working

Dan Wilson — Sat, 10 Oct 2026 11:00:00 -0400

The 4% rule tells a 56-year-old with $900,000 and $6,000 a month in bills that he needs $1.8 million, which means 8 more years of work. This episode prices those same bills as monthly income using private mortgage notes and shows how the date he can stop working moves years sooner. It also covers what can go wrong with notes, including borrowers who stop paying and payments that never rise with inflation. No Social Security is counted anywhere in the plan.

Why your retirement number should come from your bills instead of your salary
What health coverage before 65 costs, with KFF putting the average benchmark plan for a 60-year-old at $15,914 a year with no subsidy
How to cover your bills in stages while you're still working, and why he keeps working 3 more years

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=s5GMqRBcPq4

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

How Much $500K, $1M, and $2M Really Give You Every Month in Retirement

Dan Wilson — Tue, 06 Oct 2026 11:00:00 -0400

This episode prices three retirement balances two ways and shows each one in dollars per month, with no Social Security in any of the numbers. The first way is the 4% rule, where everything stays invested and a little gets sold every month. The second is how Dan would set it up with his own money: private mortgage notes cover the bills with 12 months of cash behind them, and the rest stays in stock index funds that never get sold to buy groceries. It ends on a reader in his early 50s with $2.3 million and $7,000 a month of fixed bills, run both ways.

What the 4% rule pays at each balance, and what Morningstar found in nearly 70% of the plans that ran out of money
How each balance splits under the income approach, using the 8% to 12% market range for mortgage notes published by The Entrust Group, and which retirement accounts can hold a note
What can go wrong with notes, from borrowers who stop paying to a payment that never gets an inflation raise

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=-tmnBnfg4tg

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

Watch a $500K Roth Conversion Save Six Figures, Start to Finish

Dan Wilson — Sat, 03 Oct 2026 11:00:00 -0400

A couple both 62, with $1.2 million in a traditional IRA and $850,000 in a brokerage account, get one $500,000 Roth conversion priced out year by year. The same $100,000 runs about 30% at 63, about 11% at 65 through 69, and about 24% at 71, while the federal bracket at 63 and 65 is identical. What the conversion runs into is what sets the price. This episode follows the math from the first $50,000 through what the couple has left after tax at 92.

Why the first $50,000 converted at 65 costs $1,450 and the second $50,000 that same year costs about $9,900
The two ceilings that appear on no tax table: the marketplace subsidy cliff at $84,600 and the Medicare surcharge line at $218,000, which sits $28,900 below the top of the 22% bracket
Why most of the saving lands in the years after one spouse dies, and the five things that break the whole case

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=IgZvX8hERgw

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

5 Signs You're More Ready to Retire Than You Think

Dan Wilson — Tue, 29 Sep 2026 11:00:00 -0400

Whether you can retire comes down to five obligations: your housing, your kids, your health coverage, the years before your benefits start, and whether your money pays you without being sold. Your account balance is not on the list. A household at $900,000 that has cleared all five is further along than a household at $2 million that has cleared two. This episode gives the threshold for each condition and a check you can run on yourself.

Why ending a $1,600 monthly mortgage payment does the same work as saving another $480,000
What health coverage costs before and after Medicare, and why the pre-65 gap depends on your own zip code and income
The J.P. Morgan finding that households with the same wealth spend 44% more when most of it arrives as guaranteed income

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=OH-bPzLNQmU

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

Is Your Retirement Cash in the Right Place? 4 Options, Ranked

Dan Wilson — Sat, 26 Sep 2026 11:00:00 -0400

Where you keep cash in retirement comes down to what each dollar has to do. This episode ranks four places retirement cash sits for one job: the money you plan to spend. It walks through the real rates on each and what backs them, then covers how much of your money belongs in any of them.

Why the same $100,000 in cash earns about $10 a year at one big brokerage and about $3,300 at the same firm on the same day
Why the account paying the most today does not rank first, and how the answer flips inside an IRA
The sizing rule for a cash cushion, and the study where five years of withdrawals in cash took the failure rate from under 10% to over 25%

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=rItYwOprLe4

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

8 Things Retirees Wish They'd Known at 55

Dan Wilson — Tue, 22 Sep 2026 11:00:00 -0400

Workers say they will stop at 65. The people who have actually retired stopped at 62, and 46% of them went earlier than they had planned. This episode walks through the 8 decisions that come due in the years before that date and what each one costs if you meet it late. At 55, every one of them is still open.

Why rolling a 401(k) into an IRA on the way out can permanently cost you penalty-free access to it
How the tax return you file in the year you turn 63 sets your first Medicare premium
What the research says separates retirees who feel comfortable from the ones who don't

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=TEfjxxsSVCU

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

25 Retirement Withdrawal Strategies, Tested. One Keeps Winning

Dan Wilson — Sat, 19 Sep 2026 11:00:00 -0400

Nine withdrawal methods scored on six measures, and no method won all six. Stanford ran a separate comparison across 292 retirement income strategies and named a winner. Dan walks through what the higher starting rates cost you when the market falls, and what the winning approach handles before it sets any rate at all.

Why the tested methods start you anywhere from 39,000 to 57,000 a year on the same million dollars
The guardrails rule that would have cut a 2007 retiree's real spending 28%, and a 1965 retiree's 54%
What a 10% portfolio cut does when 36,000 of an 88,000 income already arrives without selling anything

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=ZmQqJFNYNQU

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

After 60, Never Keep Your Money in These 7 Places

Dan Wilson — Tue, 15 Sep 2026 11:00:00 -0400

After 60, where your money sits matters as much as how much of it you have. This episode walks through seven common spots where being careful is exactly what created the problem, from an app that says FDIC insured to a rollover that lands in cash and stays there for years. Dan covers what the FDIC actually insures, why a 5-year CD can pay less than a 1-year, and what happens to the 401(k) you left behind.

Why FDIC coverage runs per ownership category, and how a married couple reaches $1,000,000 of insurance at a single bank without moving a dollar
The one-minute check that tells an app apart from an actual bank account
Why the 60-month CD national average is currently below the 12-month, and the two words to look for on any CD term sheet

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=4GjVQRBG22g

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

Why a Will Isn't Enough to Keep Your House Out of Court

Dan Wilson — Sat, 12 Sep 2026 11:00:00 -0400

A will does not move your house. It gets filed with the probate court, usually within 10 to 30 days of a death, and the title stays in your name until a judge signs it over. In seven states the fee is calculated on what the house appraises for with the mortgage ignored, which runs about $11,700 on a $434,000 home even with $150,000 still owed. This episode covers the three documents that transfer a house without a judge, plus the shortcut that skips probate and hands your kids a much bigger tax bill.

What probate actually costs on a median-priced home, and why the mortgage does not lower the bill in 7 states
The transfer-on-death deed and the Lady Bird deed: which states allow each one, and what they cost to record
Why a trust you paid for can stop working after a refinance, and the 10-minute check on your county's website that tells you whether yours still owns the house

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=ZV-jA05D_1o

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

How Much You Actually Need for $3,000 a Month in Retirement

Dan Wilson — Tue, 08 Sep 2026 11:00:00 -0400

The average Social Security check is $2,071. The average household over 65 spends $5,119. This episode puts a real number on filling that gap, first under the 4% rule, then with a bond ladder held to maturity, then with private mortgage notes. It closes on what the same savings can do once income dollars and growth dollars stop competing for the same job.

What $3,000 a month costs under the 4% rule, and the two things $900,000 is actually buying you that a cheaper option doesn't
What the same income costs from a bond ladder at today's Treasury yields, why bond funds can't do that job, and what it means that the coupon never gets a raise
How the same savings gets split so the whole gap is covered by payments that arrive on a schedule while the rest keeps growing, with the honest catch stated plainly

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=Fadi3VgJbVE

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

What a 30% Crash Does to Your First Year of Retirement

Dan Wilson — Sat, 05 Sep 2026 11:00:00 -0400

A crash in your first year of retirement costs more than the drop itself, and this episode puts a number on it. Dan walks through what a 30% year-one drop does to a $1,000,000 portfolio even after the market fully recovers, then the harder version where the recovery never arrives. The last stretch covers where your spending comes from while you wait.

Why the damage from a first-year crash is easier to see in shares than in dollars
Why the worst year to retire in American history had no crash in it at all
How much cash to hold against a $40,000 withdrawal, and what a temporary 10% spending cut buys you

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=ygZafRwzaZU

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

The Math That Convinces People to Stop Working at 58

Dan Wilson — Tue, 01 Sep 2026 11:00:00 -0400

The example in this episode moves the portfolio about $115,000 for one more year of work, which comes out to roughly $380 a month for life. Dan shows where each input comes from so you can run the same math on your own situation. All numbers are 2026.

Why another year of work raises your Social Security check by only about $10 or $20 a month once you have 35 years of earnings, and the situation where it's worth several times that
The 17-year low-income window that opens the day your paycheck stops, and why working until 62 deletes four years of it
The 30-hour line that keeps employer health coverage in place, so you can drop the hours without giving up the benefit

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=Db-D35f2EkU

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

7 Taxes Smart Retirees Legally Stop Paying

Dan Wilson — Sat, 29 Aug 2026 11:00:00 -0400

Every one of these seven taxes goes to zero, and every one runs on a window that opens on an age or a condition and closes on another. Dan walks through all seven with 2026 numbers, including two that aren't technically taxes, which he says on camera. The order the tax code stacks your income drives most of what follows.

Why a Roth conversion you think costs 12 cents on the dollar can really cost about 27, and the ordinary move in the same year that causes it
The 2026 income line where long-term capital gains are taxed at zero, and why the wash-sale rule lets you buy the identical fund back that same afternoon
The health insurance cliff that came back for 2026, where one dollar of income takes the whole subsidy to zero

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=YL3XDeQYsP8

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

Average Net Worth by Age 55/60/65 (Where Do You Stand?)

Dan Wilson — Tue, 25 Aug 2026 11:00:00 -0400

Most benchmark numbers stop at net worth, which hides the part that matters. The typical household aged 55 to 64 holds about $364,000 in net worth but only about $64,000 in financial assets. This episode walks the Federal Reserve's own survey figures for 55, 60, and 65, then splits the number into the part that can pay you and the part that cannot.

Why the average is over $1.4 million when about 8 out of 10 households that age sit below it
Where the top 25% and top 10% lines fall, and why the climb flattens out in the early 60s
Why single and married households are two different benchmarks

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=Im6D97dMuqg

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

The Portfolio Size Where Dividends Cover Your Bills

Dan Wilson — Sat, 22 Aug 2026 11:00:00 -0400

Living off dividends sounds simple until you work out the savings it takes to pull off. This episode runs both numbers at today's yields, the bigger one for the years before Social Security starts and the smaller one after, then looks at what dividend investing has actually delivered. That includes what the major dividend funds returned over the last ten years, what the 8% and 12% funds are doing under the hood, and the tax break that comes with a catch.

Why a couple can need $400,000 less than a single person with identical bills
What every major dividend ETF returned over the last decade against a plain index fund
How to test any high-yield fund in two minutes, and what one filing showed about where 36% of a fund's payout came from

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=xP2OM0SDFU8

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

The 8 Real Retirement Income Streams (Your 401k Isn't One)

Dan Wilson — Tue, 18 Aug 2026 11:00:00 -0400

Your 401(k) balance isn't income. Pulling money out of it means selling an asset, and that hurts most when the market is down. This episode sorts through what actually pays your bills after the paycheck stops, from Social Security and dividends to bonds, rentals, and private notes, then asks you to count how many real streams you have right now.

Why a withdrawal from a 401(k) or IRA is a sale, not income, and when that timing hurts
How a married couple can collect around $99,000 in dividends and long-term gains at 0% federal tax in 2026
The eight streams sorted by whether they pay you without selling or working, and which one to build next

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=Y1GV_LiyK80

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

The Surprise Bill That Hits Two Years After You Sell Your House

Dan Wilson — Sat, 15 Aug 2026 11:00:00 -0400

Medicare sets your premium from the tax return you filed two years earlier, so the taxable profit on a home sale can follow you into your first year of coverage. That makes 63 the year that decides your premium at 65, while a sale at 62 lands on a year Medicare never charges you for. This episode covers who actually gets caught, what the surcharge costs in 2026, and what to do before you sell.

The $250,000 and $500,000 home sale exclusion, and why a cap frozen since 1997 now catches ordinary long-time owners
What the surcharge costs at each 2026 tier, and the two-year window that protects a surviving spouse
Why the SSA-44 appeal will not work for a home sale

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=uDBP5XD6Po8

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

After 60, Never Share These 6 Things With Your Adult Children

Dan Wilson — Tue, 11 Aug 2026 11:00:00 -0400

Most of the money taken from Americans over 60 is taken by someone they already know. That changes what money boundaries with your own family are actually for. This episode walks through six specific things worth keeping to yourself after 60, the mechanism behind why each one backfires, and what to do instead in every case. The point is keeping your retirement under your own control so you can help your kids from a position of strength.

Why adding your child's name to your bank account exposes that money to their creditors and their divorce, and how it can cut your other kids out
What long-term care actually runs per year, and how a few years of it can erase an inheritance you already promised out loud
The line between telling your kids a plan exists and showing them what's in it, and why announcing the split early invites the exact fight you're trying to prevent

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=URH6jRBXhFg

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

Why So Many People Die Right After They Retire

Dan Wilson — Sat, 08 Aug 2026 11:00:00 -0400

The idea that retirement starts a clock is one of the most repeated fears people carry into it. The studies built to test that idea find no spike in death risk on the day you retire, and the first year looks closer to a honeymoon. What the research does point to is a slower danger, and it shows up for people who leave a job for an empty calendar.

Where the famous "retire at 65, dead by 66" statistic actually comes from, and why the scary version sticks in your head anyway
The habits that keep you out of that group, including volunteering, phasing out of work, and having a retire-to plan
The first-year trap, and why the risk builds after the honeymoon ends

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=VRlZgX0OKQA

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

How Private Mortgage Notes Work

Dan Wilson — Wed, 05 Aug 2026 11:00:00 -0400

If you've ever paid a mortgage, you already understand half of this. Someone on the other end held a piece of paper and got paid every month, with the house standing behind it. This episode walks through how that works when the person holding the paper is an individual instead of a bank, and how to evaluate a note deal yourself before a dollar moves.

The two documents behind every note, and why the recorded one decides who gets paid first
What happens when a borrower stops paying, and why the same default takes five months in one state and over five years in another
Ten questions to run on any note deal, plus the scam pattern that should end a conversation on arrival

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=S0DFg8f--Fo

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

7 Things Wealthy Retirees Refuse to Buy (But Poor Ones Do)

Dan Wilson — Sat, 01 Aug 2026 11:00:00 -0400

The purchases that drain a retirement plan are rarely the obvious splurges. This episode walks through seven of them, from the oversized house and the new luxury car to the vacation home, the timeshare, and the remodel right before you retire. You get the real math on each one, plus the honest exceptions worth making.

Why the biggest house the bank approves is built for the bank's interest, and the smarter number to buy at
The true weekly cost of a vacation home you use only a few weeks a year, and when renting is the better deal
The one question that decides whether a purchase pays you or costs you for the rest of your life

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=C7xJ5Dp4CjU

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

Losing Your Job at 60 Can Actually Make You Richer

Dan Wilson — Tue, 28 Jul 2026 11:00:00 -0400

Losing a job before retirement can leave you better off than walking away on your own terms. Severance and unemployment only show up when the company ends it, and a single line on your exit paperwork decides whether you collect either one. This episode covers what that paperwork has to say, what to keep quiet about while the package is still in play, and how to turn a funded runway into a bigger retirement.

The difference between fired, laid off, and quitting, and what it does to your severance and unemployment
Why claiming Social Security the month you lose your job can cut your check about 30% for life
How a year without a paycheck lets you move traditional savings into a Roth at a fraction of the tax you paid while working

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=ebcET1G2gFk

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

The $300,000 Nursing Home Trap (And How to Avoid It)

Dan Wilson — Sat, 25 Jul 2026 11:00:00 -0400

Most families learn how nursing home costs work too late, usually in a hospital hallway. This episode breaks down the two parts of the trap: the Medicare coverage gap and Medicaid estate recovery. It also covers what the healthy spouse gets to keep and why one popular move, gifting the house to the kids, usually backfires.

What Medicare actually covers in a nursing home, the 100-day cliff, and why it pays nothing for daily custodial care
How Medicaid spend-down and estate recovery can put a lien on your "exempt" home after death, and what the healthy spouse keeps
Why gifting the house away usually backfires, and the trust and five-year timing that actually protect it

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=KINAVcLhNEo

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

After 59½, Your IRA Can Do Things Your Brokerage Won't Allow

Dan Wilson — Tue, 21 Jul 2026 11:00:00 -0400

This is the plain-English walkthrough of how a self-directed IRA actually works: what it can hold, what it really costs, and the prohibited-transaction rules that keep you safe. You'll see why operating a rental inside one is usually the wrong move, and why secured mortgage notes fit those same rules so well.

Why your IRA can legally hold real estate, private mortgage notes, and private loans, plus the short list of things it can't
The fee most people never see: how a "free" brokerage IRA can cost more than a self-directed custodian's flat fee
Why running a rental inside an IRA wastes depreciation, 1031 exchanges, and capital-gains rates, and what to hold instead

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=iMpuNi_MDQY

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

The Dark Side of Retiring Abroad

Dan Wilson — Sat, 18 Jul 2026 11:00:00 -0400

Retiring overseas gets sold as the move that makes a smaller nest egg work. This episode walks through the costs that don't show up on the cost-of-living blogs: healthcare, US taxes that follow you for life, currency swings, account access, visas and property, and the price of coming home, with the real numbers on each.

Why the Foreign Earned Income Exclusion shelters almost none of a retiree's income, and what you still owe the IRS every year abroad
How dropping Medicare to save money triggers a permanent penalty that can double your premium for life
The exchange-rate and account-access traps that can erase the cost-of-living savings you moved for

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=ZWd_5NDXuVw

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

12 Things That Disappear the Day You Retire (Some Are Gone Forever)

Dan Wilson — Tue, 14 Jul 2026 11:00:00 -0400

The day your earned income stops, a whole stack of things disappears at once. Some you can rebuild in a year. A few close permanently, and the only time to deal with them is while you still have a paycheck coming in. This episode sorts twelve of them into what you can rebuild and what's gone for good.

Which retirement-account and insurance doors close for good the day your earned income stops
Why a market loss you'd shrug off while working can turn permanent once you retire, and the income floor that prevents it
The 2026 ACA subsidy cliff (around $62,600 single / $84,600 for a couple) and why your bridge-year income decides which side you land on

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=frLNdk0Seu8

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

Why Smart Retirees Never Pay Cash For a Car

Dan Wilson — Sat, 11 Jul 2026 11:00:00 -0400

At a dealership, announcing cash can make you the least profitable customer in the room, which means less movement on the price. This episode breaks down where dealers actually make their money, the finance-then-prepay move that captures the discount without the debt, and the real opportunity cost of draining your capital to pay cash once you're retired.

Why the finance office, not the showroom floor, is where the dealer makes the most money
How to use dealer financing to capture a better price, then pay the loan off in week one
The simple rate spread that tells you when to pay cash and when to keep your money working

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=AlI_WCvBFkQ

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

Once Your Portfolio Hits This Number, Saving More Barely Matters

Dan Wilson — Tue, 07 Jul 2026 11:00:00 -0400

There are actually three crossovers worth knowing about. The first happens when portfolio growth exceeds your contributions. The second when it exceeds your earned income. The third, the original 1992 Vicki Robin definition, when income from your assets covers your monthly expenses. That last one is the only crossover that survives a flat market year.

Where each of the three crossovers actually sits in dollars (and the rough 20x rule of thumb)
Why the original crossover point got quietly redefined between 1992 and 2016
The four moves to make once you cross over, especially the RMD trap that hits at 73

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=zWGsGkDtu3o

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

After 55, Never Disclose These 8 Things To Anyone

Dan Wilson — Sat, 02 May 2026 11:00:00 -0400

Elder fraud cost Americans $81.5 billion in 2024, and a huge portion of it started with something someone said out loud. This episode walks through the eight disclosures that quietly expose you to financial risk after 55, from your retirement timeline to your Social Security amount to the one almost nobody talks about: your "big money" window.

Why announcing your retirement timeline at work often backfires
How your Social Security amount can make you a target for imposter scams
The "big money" window right before and after retirement that scammers know exists

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=c2MJ19oD1BY

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

The 6 Wealth Tiers in Retirement (Where Do You Rank?)

Dan Wilson — Sun, 26 Apr 2026 11:00:00 -0400

Most people think they're one tier above or below where they actually are. This episode walks through the Federal Reserve's retirement wealth breakdown and shows you what monthly income, daily stress, and real lifestyle look like from the bottom tier to the top 1%.

The net worth range for each of the 6 wealth tiers
How income structure (not just net worth) changes everything at levels 5 and 6
How to live like someone 1-2 tiers above where your savings put you

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=E9YmtNGyUu4

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

Got A Pension? Stop Following Normal Advice

Dan Wilson — Tue, 14 Apr 2026 11:00:00 -0400

If you have a pension, the usual advice on claiming Social Security, taking a lump sum, or planning survivor benefits was written for people without one. This episode walks through what changed in 2025, the 6% rule for lump sum decisions, and the inflation gap most pensions quietly carry.

How the WEP and GPO repeal changes what pension holders actually collect
The 6% rule for deciding pension vs lump sum payout
The hidden 45% pension loss from inflation and missing COLAs

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=7R95VeGFgP0

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.

9 Costly Retirement Mistakes People Make After 55 (And Regret Later)

Dan Wilson — Sat, 11 Apr 2026 11:00:00 -0400

The mid-50s are where most retirement plans start going sideways, not from a single big mistake but from a pattern of small ones. Chasing a perfect portfolio number. Staying in a job one year too long. Supporting adult children beyond what your plan can absorb. This episode walks through all nine and how to spot each one in your own plan.

Why "one more year" of working often costs more than it earns
The gift that actually hurts: supporting adult kids past the point it helps them
The one retirement decision you cannot reverse, and how to avoid it

Take the free Retirement Income Roadmap (7 questions, about 30 seconds): incomeoverwealth.com/map

Watch this episode on YouTube: https://www.youtube.com/watch?v=mwLt0AIndrg

This episode is educational and focused on strategy and math. Always consult a qualified tax or financial professional before making personal financial decisions.