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  • The Real Cost of Divorce After 50 (And How to Not Pay It)

    The Real Cost of Divorce After 50 (And How to Not Pay It)
    2026/06/15

    Divorce is never easy. But divorce after 50? That's a completely different animal.

    We're talking about decades of accumulated assets, retirement accounts, Social Security decisions, healthcare coverage, and tax consequences that can follow you for the rest of your life — and one wrong move can cost you far more than just the marriage.

    In this episode, we're breaking down the real financial damage of what's called "Gray Divorce"; the mistakes I see people make in practice, and exactly what you need to do to protect yourself.

    More specifically, I discuss:

    • Gray Divorce Study – What Divorcees are saying about retirement and finances post-divorce
    • The difference between divorce after 50 versus divorce in your 30s and 40s
    • The differing realities of men vs. women post-divorce
    • Mistakes during and after the divorce process regarding retirement savings
    • Social Security and healthcare decisions post-divorce
    • Making key financial decisions under pressure and common regrets

    Key moments:

    (03:04) Uncertainty in Retirement Planning for Divorcees

    (06:38) Retirement Savings Mistakes

    (11:11) Financial Blind Spots and Costly Decisions in Divorce

    (14:27) Social Security Claiming Risks Post-Divorce

    (21:11) Health Insurance Decisions Post-Divorce

    (24:40) Seeking Professional Financial Guidance During & After Divorce

    Resources From The Episode:

    • Retired-ish Newsletter Sign-Up
    • Get Show Notes Here
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    31 分
  • Prices Keep Rising - Make Sure Your Money Rises With Them

    Prices Keep Rising - Make Sure Your Money Rises With Them
    2026/06/01

    You wake up everyday, check your bank account on your phone, and you see all your money sitting there, just as it was the day before. How do you feel? Pretty good, right? That number hasn't moved. It's exactly where you left it. Safe.

    Here's the problem: that money is slowly disappearing even though you can't tell by looking at your bank app. This is because every single day, the purchasing power of that money is quietly shrinking. The things you will actually buy one day with those dollars — groceries, gas, insurance, healthcare — are getting more expensive. But your balance stays the same, so it feels fine. However, it's not fine.

    That is inflation. And most people will go their entire lives without sitting down and doing the math on what it actually does to their money over 20 or 30 years and take it seriously because we're too busy watching Netflix and wasting time wondering how our neighbor could afford that nice new car.

    In this episode, we're explaining the two best — and in my opinion, the most effortless — ways to fight back against inflation to make sure that your money keeps up with rising prices, because let's be honest, they're never going to start trending backwards.

    More specifically, I discuss:

    • Why is inflation for so important and how can it damage a retirees' financial life?
    • What is the rate of inflation?
    • Different types of inflation
    • How does inflation affect retirement accounts? What about cash in the bank?
    • Effortless inflation hedge #1: fixed-rate debt + home ownership
    • Effortless inflation hedge #2: the primarily equity investment portfolio

    Resources From The Episode:

    • Retired-ish Newsletter Sign-Up
    • Get Show Notes Here

    Key moments:

    (03:26) Understanding Inflation's Impact

    (07:09) The Illusion of Cash Safety

    (09:42) Fixed-Rate Debt as an Inflation Hedge

    (14:48) Addressing Homeownership Objections

    (20:28) Equity Portfolio: The Best Hedge

    (23:08) The Power of Compounding Equities

    (25:16) Equity Liquidity and Flexibility

    (29:20) Long-Term Investing Discipline

    (33:37) Combining Strategies for Resilience

    (35:00) Final Takeaways
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    40 分
  • Encore - Retirement Income & Thoughts on Dividend Investing

    Encore - Retirement Income & Thoughts on Dividend Investing
    2026/05/04

    My firm, Planable Wealth, is currently very busy in the midst of our Spring Strategy Meetings with clients where we help people just like you create and retool their financial and tax plans for 2026 and beyond. That said I wanted to bring you an encore episode this week, which I think, is one of the core episodes we've done so far

    Back in episode 70, I discussed the importance of retirement income and the realities of your cash flow in retirement. I also share my thoughts on dividend investing especially when trying to utilize dividends as an income stream in retirement.

    Income planning will make or break your retirement years - This is because your income in retirement will be what controls your lifestyle, not your net worth.

    When doing your pre-retirement planning - hopefully several years before your desired retirement - you'll want to match your lifestyle wants, needs, and goals with the income you are able to generate from your various financial assets and resources – but, depending on where you generate income from, you may run into certain hurdles along the way.

    In this episode we break down the important pillars of retirement income planning, matching your income sources to your retirement goals, and why a dividend income strategy may not be the best choice.

    Thanks for being a loyal listener and we'll be back with new episodes soon.

    More specifically, I discuss:

    • Defining retirement income planning
    • The 2 major pitfalls you need top watch out for when creating your retirement plan
    • Investment returns or income?
    • Potential cons of a "probability-based" retirement plan
    • Wade Pfau's Four L's of Retirement
    • Matching your various retirement income sources with your goals
    • Potential issues when relying on only one income source such as real estate or dividends
    • The importance of dividends
    • A pure dividend spending strategy isn't a great retirement income strategy

    The Key Moments In This Episode Are:

    (02:43) The Error of Relying Solely on 1 Retirement Income Source

    (03:39) Challenges of Basic Income Planning

    (06:03) Retirement Income is More Important Than Investment Returns

    (09:15) The Four L's of Retirement Planning

    (11:57) Funding Your Desired Lifestyle

    (13:09) Rental Real Estate May Not Be The Most Efficient Retirement Income Plan

    (15:35) Planning for Legacy, or Not

    (16:46) The Importance of Liquidity in Retirement

    (18:42) The "Live Off Of Dividends" Strategy Debate

    (25:25) The Risks of High-Dividend Paying Stocks

    (30:36) Total Return Investing as an Alternative

    Resources:

    • Retired-ish Newsletter Sign-Up
    • Get Show Notes Here
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    36 分
  • How to Fight Back Against Your Medicare IRMAA Surcharge

    How to Fight Back Against Your Medicare IRMAA Surcharge
    2026/04/20

    You worked hard your whole career, you saved, you did everything right — and now you're on Medicare and you get a letter from Social Security telling you that you owe hundreds of dollars extra every single month in premiums just because you made too much money!

    No warning. No opt-out. Just, what looks like punishment for doing a good job and setting yourself up for retirement.

    That's IRMAA. And what most people don't know is that in certain situations, you can fight back — and win.

    Today we're breaking all of it down. The real numbers, the real rules, and exactly how to use the appeal process strategically if you qualify.

    More specifically, we discuss:

    • What is Income Related Adjustment Amount (IRMAA)?
    • How to calculate what your potential Medicare premium surcharges will be
    • Common situations that cause Medicare enrollees to be subject to IRMAA surcharges
    • When and how can you appeal IRMAA surcharges on your Medicare premiums?
    • Practical tips when appealing IRMAA surcharges
    • Strategies to avoid IRMAA surcharges

    Resources:

    • Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
    • Ask Cameron A Question!

    Key moments:

    (02:56) IRMAA Medicare Premium Surcharges: How it Works

    (05:50) Calculating Your MAGI (Income) for IRMAA

    (09:27) IRMAA Brackets and Cliff System

    (17:37) Common IRMAA Medicare Premium Surcharge Triggers

    (23:07) Appealing IRMAA with Form SSA-44

    (26:52) IRMAA Appeal Example Scenarios

    (31:37) Non-Qualifying Events for IRMAA Appeal

    (40:02) Practical Tips for Filing an IRMAA Appeal

    (41:00) Strategies to Avoid IRMAA

    (46:51) Listener Question: IRMAA appeal for deferred compensation
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    55 分
  • How Are Restricted Stock Units (RSUs) Treated in a Divorce?

    How Are Restricted Stock Units (RSUs) Treated in a Divorce?
    2026/04/06

    Your spouse works at a major publicly traded company. You're going through a divorce. And somewhere in their compensation package are restricted stock units or RSUs — awards of shares of company stock that haven't even vested yet.

    Are you supposed to receive stock? Are the RSUs considered income? Are they both? How much are we actually talking about here?

    By the end of this episode, you're going to understand Restricted Stock Units (RSU) and how they are commonly handled in a divorce so you can be better prepared!

    More specifically, we discuss:

    • What are Restricted Stock Units (RSUs)?
    • Dividing RSUs in a Divorce
    • Characterizing RSUs as Income or Assets
    • Determining RSU Community Property and Separate Property
    • Commonly Used Formulas for Splitting RSUs in California

    Key moments:

    (00:00) Introduction

    (00:59) What are Restricted Stock Units (RSUs)?

    (04:37) RSUs vs. Stock Options

    (07:02) Understanding Vesting Schedules

    (09:14) Companies that Offer RSUs

    (11:45) Dividing RSUs in a Divorce

    (13:15) Characterizing RSUs as Income or Assets in Divorce

    (16:11) Unvested RSUs at Date of Separation (DoS)

    (17:36) Determining Community Property and Separate Property for RSUs

    (20:32) Commonly Utilized Formulas for RSUs in California Divorces

    (27:48) Practical Example: Jim and Rachel Johnson

    (33:52) Important Information to Gather Regarding RSUs In The Divorce Process

    Resources:

    • Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
    • Ask Cameron A Question!
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    42 分
  • Invest All at Once Or Gradually Over Time?

    Invest All at Once Or Gradually Over Time?
    2026/03/23

    You just came into a large sum of money. Could be an inheritance, a business sale, a 401(k) rollover. And now you're paralyzed trying to figure out when to invest it.

    Do you invest it all today? Spread it out over six months? A year? Wait for the markets to drop or the perfect opportunity to cruise by?

    In this episode, Cameron summarizes what the research actually says, and more importantly—when the math matters and when it doesn't.

    More specifically, we discuss:

    • What is Dollar Cost Averaging (DCA)?
    • The Problem With Dollar Cost Averaging
    • Vanguard's Research on DCA vs. Lump Sum Investing
    • What If You End Up Investing "At All Time Highs"?
    • How To Decide Whether or Not To Invest The Lump Sum or DCA Over Time

    Resources:

    • Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
    • Ask Cameron A Question!
    • 2012 Vanguard: "Dollar-cost averaging just means taking risk later" https://static.twentyoverten.com/5980d16bbfb1c93238ad9c24/rJpQmY8o7/Dollar-Cost-Averaging-Just-Means-Taking-Risk-Later-Vanguard.pdf
    • 2023 Vanguard: "Cost averaging: Invest now or temporarily hold your cash?" https://corporate.vanguard.com/content/dam/corp/research/pdf/cost_averaging_invest_now_or_temporarily_hold_your_cash.pdf
    • Vanguard Summary Article: https://investor.vanguard.com/investor-resources-education/news/lump-sum-investing-versus-cost-averaging-which-is-better
    • Kitces Article: "Dollar Cost Averaging Manages Risk But Reduces Returns" https://www.kitces.com/blog/dollar-cost-averaging-versus-lump-sum-how-dca-investing-can-manage-risk-but-on-average-reduces-returns/

    Key moments:

    (00:00) Invest All at Once Or Gradually Over Time?

    (01:16) What is Lump Sum Investing vs Dollar Cost Averaging?

    (05:18) The Math Problem with Dollar Cost Averaging

    (07:35) Vanguard's Research on Lump Sum Investing vs Dollar Cost Averaging

    (11:27) The All-Time Highs Myth

    (16:07) The Impossibility of Being Right Twice

    (18:44) Three Questions to Ask Before Investing a Lump Sum

    (23:02) A Hybrid Approach to Investing a Lump Sum

    (27:03) A Hierarchy for Investing a Lump Sum

    (28:38) Get More Useful Information
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    31 分
  • What To Do With The House?: A Tax Planning Case Study for Families Looking to Fund Long-Term Care

    What To Do With The House?: A Tax Planning Case Study for Families Looking to Fund Long-Term Care
    2026/03/09

    If your aging parent owns a home and they are reaching the point in life where their physical and or mental health is rapidly declining and they need additional care, there is a clock ticking on decisions that most families don't even know they need to make.

    And those decisions — specifically, what to do with their house and how to fund their care— carry tax consequences that can either preserve tens of thousands of dollars for the next generation or quietly hand it to the IRS. Typically, the responsibility of figuring all this stuff out lands on your shoulders.

    In this episode, Cameron walks you through a real-world case study, step by step, so you can see exactly how this can play out while minimizing taxes as much as possible and funding their care.

    More specifically, we discuss:

    • What are the tax ramifications of selling the home to fund long-term care?
    • What are the tax ramifications of renting the home to help pay for care?
    • What are the tax consequences of staying in the home and paying for care?
    • Utilizing a Multiple Support Agreement to obtain tax deductions for the adult child caregiver
    • The Section 121 gain exclusion on a personal residence
    • A detailed walkthrough of tax saving strategies in all scenarios

    Resources:

    • Access Episode Show Notes and Sign Up for the Retired·ish Newsletter
    • Ask Cameron A Question!
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    45 分
  • Encore: Betting the Farm

    Encore: Betting the Farm
    2026/02/23
    This episode is actually a replay of a previous episode we had done - Episode 63 - about the danger of picking individual stocks. This time we wanted to rename it "Betting the Farm" because we feel like that title is more representative of what we're seeing today in 2026. In January of 2026, the S&P 500 had crossed the 7,000 mark and the Dow Jones had passed the 50,000 mark. These are both tremendous milestones in the United States stock market. Not to mention, countries other than the United States, which have struggled over the past decade plus, have significantly outperformed most companies in the United States over the past year or so, and history has shown us that this trend can continue for quite a long time. Another reason I wanted to bring this episode back is because it's easy to look like you know what you're doing and feel good about picking stocks when the overall market is doing well. It isn't until you experience a significant drawdown that your thoughts, confidence, and emotions start to change. And this isn't just about stocks either. This can be really any asset class. It could be owning real estate while it's going up substantially. It could be buying gold before it takes off like it has throughout 2025 and 2026 so far, or even cryptocurrency. Simply as a product of human nature, investors are extremely overconfident in their abilities and they're not realistic with themselves. Many times, in practice, we often see portfolios full of risky positions that have very little to no rational rhyme or reason for owning – and the reasons are many. Many times, investors get into these positions simply because it was recently going up in value and so they didn't want to miss out. Or someone they know, who, by the way, is not a professional investor, shared with them their recent experience in the position. It also happens by reading some article on the internet or watching some show on financial television that all seem to be in consensus that a particular company or investment should be a good investment moving forward. Another common one we see in practice is that positions start to build substantially and become overly concentrated in a portfolio when investors are afraid of taxation. Everyone hates paying taxes, including myself, and when people purchase an investment and it appreciates substantially and now has embedded capital gains, if they were to sell some or all of it, oftentimes people do not want to pay the tax that comes with it. That causes them to hold the position for far too long and add additional risk to the portfolio by being over concentrated in that position. While this is understandable, you cannot let the tax tail wag the dog. Would you rather pay preferred capital gains rates and rip the band aid off to diversify, or would you rather take the risk that your position falls 70 or 80% or worse, slowly drags on with little return over the next decade? People hate paying taxes but I'd say losing 70 to 80% is worse than paying 15 to 20% in tax. It also commonly happens when you work for a company that offers employer stock awards, such as RSU's, stock options, or stock in the 401k plan. Because as you work, you just continue to accumulate this stock and, while it's going up, you feel like you should just continue accumulating it without a need to diversify at any point in time, since it seems like it's always going to make you money, and you have a natural bias towards the great company that you work for. But the vast majority of the time, it's purely a hunch or a guess. You're purchasing an investment just hoping and thinking that it will succeed over the long run. I want this episode to serve as a reminder about risk taking and diversification. While times are good we feel good and we often lose sight of the ultimate goal for our investments and what we need them to do for our financial plan. Sometimes when things do extraordinarily well, we continue to ride the wave, thinking we'll make more and more money, and don't think about the potential ramifications of when the tide goes out. And I have a feeling that the next time the tide goes out, many people are going to be caught swimming naked and get burned in a lot of the positions we're seeing people accumulate today. Whether that's stocks particularly in companies in the US, large positions in AI-related stocks, your employer stock awards at work, cryptocurrencies, or even commodities like gold. If you're one of those investors that has been riding the wave on a certain position and you feel like you've made a lot of money and that the trend could continue, you may want to rethink your overall goal and strategy and consider proper diversification. Especially if you are trying to grow a portfolio that you will need to live on throughout a potential 20 to 30-year retirement. That being said, enjoy this week's replay of why picking stocks can be dangerous. More specifically, we discuss: The most important question for DIY ...
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    30 分