Retired-ish

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

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  

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!

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  

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!  

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 investors picking stocks and funds What does the research say about stock picking and market speculation? A surprisingly small percentage of stocks generate an overwhelming majority of shareholder wealth Investor emotions serve as a significant roadblock in making investment decisions Your Family Risk Profile Resources: Access Episode Show Notes and Sign Up for the Retired·ish Newsletter Ask Cameron A Question!   Key Moments: (00:00) Introduction to Betting the Farm (08:43) DIY Investing: Picking Individual Stocks (10:43) Stock Pickers Typically Underperform Market. What Does The Research Say? (16:41) Very Few Stocks Drive All of The Market's Growth Over Time (23:34) Emotions Make Investing Extremely Difficult (26:03) The #1 Question You Should Ask Yourself When Picking Stocks or Timing The Markets  

If you're doing your own taxes or working with a tax preparer who doesn't specialize in wealth accumulation, financial planning and retirement, there's a good chance you're leaving thousands of dollars on the table every single year. We're talking four and five-figure mistakes that happen because nobody's looking at the details. In this episode, Cameron walks you through six of the most expensive tax blunders he sees wealth accumulators and retirees make - from losing track of IRA basis to triggering Medicare surcharges you didn't see coming. These aren't theoretical problems. These are real mistakes costing real people real money. Learn about these potential issues before they arise so you don't make the same mistakes! More specifically, Cameron discusses: 1. Losing Track of Form 8606 and Non-Deductible IRA Basis 2. Estimated Tax Payment Disasters 3. The IRMAA Time Bomb & Medicare Premium Surcharges 4. QCD Mistakes 5. Missing Cost Basis on Old Stock Positions & Paying More Taxes Than Necessary 6. State Tax Exempt Interest and Dividend Mistakes Resources: Get Show Notes Here Retired-ish Newsletter Sign-Up See if you're a good fit for our Free Tax-Optimized Retirement Playbook™ Key moments: (00:00) Tax Season Blunders to Learn From and Avoid (05:33) 1. Losing Track of Form 8606 and Non-Deductible IRA Basis (12:28) 2. Estimated Tax Payment Disasters (18:10) 3. The IRMAA Time Bomb (22:56) 4. QCD Mistakes (28:16) 5. Missing Cost Basis on Old Stock Positions (32:30) 6. State Tax Exempt Interest and Dividend Mistakes

If you think estate taxes are only a problem for billionaires and celebrities, I've got news for you: A couple in their 50s with a combined few million in retirement accounts, a paid-off home, maybe a rental property, and 20 + years of compounding ahead of them? Their beneficiaries could easily be looking at a 40% + federal estate tax bill when they die. However, there are legitimate, legal strategies to dramatically reduce or even eliminate these taxes. Some of them are as simple as how you spend your money today. Others involve sophisticated trust structures that can save your family hundreds of thousands, if not millions in taxes. In this episode of Retired-ish, Cameron pulls back the curtain on estate tax reduction strategies that high-net-worth retirees utilize to preserve their wealth and pass it on efficiently. More specifically, Cameron discusses: What are gift and estate taxes? And how much are they? Who is subject to gift and estate taxes? Should you try and avoid gift and estate taxes or capital gains taxes? Stocks and real estate in irrevocable trusts Power of Substitution to swap assets between irrevocable trusts and your estate Retirement accounts and estate taxes Other strategies to reduce gift and estate taxes Resources: Get Show Notes Here Retired-ish Newsletter Sign-Up See if you're a good fit for our Free Tax-Optimized Retirement Playbook™ Chapters: (00:00) Understanding Estate Taxes (04:00) Who Needs Estate Planning? (08:19) Gift & Estate Taxes vs. Capital Gains Taxes (10:41) Irrevocable Trusts: Real Estate & Stocks (17:00) Advanced Asset "Substitution" or "Swap" Strategy (20:29) Retirement Accounts & Estate Tax (25:00) The Smart Spending Strategy (30:42) Sophisticated Estate Planning Tools to Reduce Estate Tax Exposure

If you're going through a divorce or thinking about one, I've got news for you: your divorce decree doesn't override federal tax law, no matter what it says. That rental property buyout you negotiated.  You could be getting screwed on the tax basis. And that division of your ex's 401(k)? There's a one-time penalty-free distribution opportunity that most people miss because nobody tells them about it. In this episode, I'm covering the frequently asked tax questions I get from clients and prospective clients going through divorce—from filing status rules that actually matter, to rental property tax nightmares, to who gets to claim the student in college. Some of this is basic and applies to everyone, while some of it's rather nuanced, but all of it can cost you real money if you don't understand. More specifically, Cameron discusses: How do I file my taxes in the year I get divorced? Is Alimony or Spousal Support taxed? Can I deduct legal fees paid during a divorce? What happens to a retirement account like a 401(k) or IRA in a divorce? Do those get taxed if transferred to my ex? What happens with Health Savings Accounts (HSAs) during divorce? After a divorce, who gets any capital losses we have that we have been carrying forward to offset our capital gains and income? What are the tax implications of buying out your ex's share in an investment property? Who gets to claim our student in college? Key Moments: (00:00) Introduction to Divorce Tax Questions (02:47) Filing Status and Suspended Divorce (07:27) Married, Filing Separate, or Head of Household? (09:19) Alimony and Legal Fees (11:34) Retirement Account Transfers (15:10) Health Savings Accounts and Capital Losses (17:36) Rental Property Buyouts & Basis (24:24) Claiming Dependents and Tax Credits  Resources: Get Show Notes Here Retired-ish Newsletter Sign-Up See if you're a good fit for our Free Tax-Optimized Retirement Playbook™  

If you're planning to retire in the next year or two and you have a 401(k) loan, this episode could save you thousands of dollars in taxes. I've seen too many people walk into retirement with an outstanding loan balance and get blindsided by a massive tax bill they could have easily avoided with a little planning. Then we're going to tackle one of the biggest myths in the retirement world - the idea that 401(k) loans are double taxed. Spoiler alert: they're not, and even very influential financial gurus get this wrong. More specifically, Cameron discusses: The requirements for a tax-free loan from an employer plan such as a 401(k) The tax ramifications of a "Deemed Distribution" The tax ramifications of a "Qualified Plan Loan Offset" or QPLO Potential tax pitfalls when retiring with an outstanding plan loan balance Are 401(k) loans double taxed? Key moments: (00:00) 401(k) Loans and Retirement (02:12) Requirements for Tax-Free 401(k) Loans (06:33) "Deemed Distributions" Explained (11:03) "Qualified Plan Loan Offsets" and Rollovers (15:43) Retirement Tax Planning & ACA Subsidies (19:28) Case Study: ACA Subsidies at Risk with Outstanding 401(k) Loan Balance (27:01) Alternatives for 401(k) Loan Repayment (30:20) Debunking the Double Taxation Myth of 401(k) Loans (39:51) True Costs of 401(k) Loans Resources: Get Show Notes Here Retired-ish Newsletter Sign-Up See if you're a good fit for our Free Tax-Optimized Retirement Playbook™      

If you are turning 65 soon, you are closer to becoming eligible for potentially thousands of dollars in tax deductions and savings opportunities that many people never take advantage of. And if you're helping with your elderly parent's finances, there's a good chance they're entitled to tax breaks they don't even know exist. The tax code is full of opportunities specifically designed for retirees—but here's the problem: Social Security isn't going to call and tell you about them. The IRS certainly won't. And unfortunately, most tax preparers are so focused on compliance and filing deadlines that they miss most of these strategies entirely. I'm about to walk you through the most valuable tax-saving opportunities available once you reach your retirement years — some you've probably never heard of, and some that could literally save you tens of thousands of dollars over your retirement. More specifically, Cameron discusses: Changes in the Standard Deduction and the new Enhanced Senior Deduction for those over age 65 Tax impacts when a spouse or parent passes away When and what medical expenses can be deductible Using suspended rental real estate losses from previous years to offset other taxable income Funding Roth IRAs from otherwise taxable money and inheritances How an elderly parent can become a dependent of yours for tax purposes and the potential tax advantages Tax strategies when receiving lump sum payouts from Social Security now that the WEP & GPO provisions have been eliminated Qualified Charitable Distributions from IRAs   Key Moments: (03:11) Increased Standard Deductions & New Deduction for Seniors (05:32) Tax Opportunities After Spouse or Parent Passing (08:31) Deductible Medical Expenses (15:59) Utilizing Rental Real Estate Losses (19:54) Taxable Wealth to Tax-Free Wealth (26:12) Claiming Elderly Parents as Dependents for Tax Purposes (29:58) Taxation Options for Social Security Lump Sum Payments (34:50) Qualified Charitable Distributions (QCDs) (41:39) Conclusion and Disclaimer   Resources: Get Show Notes Here Retired-ish Newsletter Sign-Up Cameron's book for Divorcées and Widows: Finding Financial Clarity & Confidence When Starting Over See if you're a good fit for our Free Tax-Optimized Retirement Playbook™

Most women become widows at just 60 years old—right when they're finalizing retirement plans and making critical Social Security decisions. And here's what nobody tells you: after the death of your spouse, your brain literally doesn't work the same way while you're grieving, yet people around you are pushing you to make life-altering financial decisions. In this episode, Cameron gives you a timeline of what needs to happen soon, what can wait six months, and what absolutely should not be decided on within your first year. Because the decisions you make in the next 6 to 18 months will determine your financial security for the next 20-30 years—and many widows are making at least two or three major mistakes that cost them hundreds of thousands of dollars over their lifetime. Whether you've recently lost your spouse, you're preparing for the inevitable, or you want to help someone who's going through this right now—this episode could be the difference between financial clarity and decades of financial struggle. More specifically, Cameron discusses: How your decision-making changes after the loss of a spouse The importance of creating a written timeline of to-do's to help gain financial clarity in widowhood What actions to take shortly after entering widowhood What actions can wait 6 months or more after entering widowhood Considerations and financial implications when it comes time to make big financial decisions When to consider making changes to your investment strategy and financial plan Resources: Get Show Notes Here Retired-ish Newsletter Sign-Up Cameron's book for Divorcées and Widows: Finding Financial Clarity & Confidence When Starting Over See if you're a good fit for our Free Tax-Optimized Retirement Playbook™ Key moments: (00:00) Widowhood: A Financial Guide (03:26) Grief and Financial Decisions (06:18) Immediate Financial Organization (07:22) Urgent Financial Actions (09:39) Accessing Emergency Funds (10:41) One-Month Financial Priorities (12:09) Contacting Institutions & Asset Identification (14:37) Six-Month Review and Updates (16:17) Longer-Term Decisions: Housing (19:21) Housing: Financial and Tax Implications (21:02) Investment Strategy Overhauls (22:45) Key Takeaways for Widows  

Our firm is currently hard at work conducting our second semi-annual strategy meetings with clients, serving real people just like you, and doing important planning for their retirement for income, taxes, investing, estate planning, and making important decisions such as Medicare enrollment and Social Security claiming. Therefore, we're bringing you another encore episode today in honor of Medicare Open Enrollment, which kicks off every year on October 15th and runs through December 7th. During this time you can make certain changes to various types of additional Medicare coverage such as a Medicare Advantage plan or Prescription Drug plan (Part D). Then, Cameron breaks down the different components of Medicare and additional coverage options in layman's terms. More specifically, Cameron discusses: Medicare Open Enrollment What is Medicare, and what are the main components What does Medicare pay for? What types of additional coverage are available? What are the costs? The difference between Medicare Advantage Plans (Part C) and Medicare Supplement Plans (Medigap), and some of the pros and cons of each. What factors should you consider when making coverage decisions? Resources: Get Show Notes Here Retired-ish Newsletter Sign-Up See if you're a good fit for our Free Tax-Optimized Retirement Playbook™  Key moments: (00:00) Medicare Open Enrollment 2025 (05:16) Medicare Basics and Misconceptions (07:45) Original Medicare (Parts A, B, and D) (09:13) Medicare Advantage Plans (Part C) (14:30) Costs of Medicare Advantage Plans (17:03) Medicare Supplement Plans (Medigap) (22:31) Costs and Benefits of Medigap Plans (28:27) MA vs. Medigap: Key Comparisons

This is an encore episode of one of our favorites! Retirement income planning is vital to the sustainability of your lifestyle in retirement, so don't neglect it! Plain and simple, your retirement income plan will make or break you in retirement. In this episode, we discuss the importance of creating an actual plan that focuses solely on how you will get your income in retirement, and the greatest risks your income will face. An appropriately structured income plan is crucial so that you can avoid entering retirement being uncertain about how much you can spend each month, vulnerable to the big retirement risks, and unstructured with your nest egg – meaning that you really have no idea how to arrange your affairs, what accounts to have, what investments to select, and what accounts they should go in. Your retirement income will drive your lifestyle, not necessarily the amount of money you have. The more confidence you have in your retirement income plan, the more likely you will live a happy and fulfilling lifestyle that allows you to focus on the more important things in life. More specifically, I discuss: How to Determine of You Are a Constrained Investor The Dangers of "The 4% Rule" Retirement Timing Risk (Sequence of Returns Risk) Explained Inflation and Longevity Risk Advantages of Segmenting or Bucketing Your Nest Egg Our Free Tax-Optimized Retirement Playbook™ Resources: Get Show Notes Here Retired-ish Newsletter Sign-Up See if you're a good fit for our Free Tax-Optimized Retirement Playbook™  

This one free action could save you thousands in an identity theft or fraud situation - yet 90% of affluent Americans never do it. In today's world of AI-powered scams and relentless fraudsters, protecting your identity isn't just optional, it's essential. Whether you're safeguarding substantial assets, retirement funds, or helping an elderly parent navigate their financial vulnerability, the threats are real and growing. While some asset protection strategies require complex planning for those with intricate financial situations, there's one powerful tool that's available to everyone: the credit freeze. In this episode, we dive into how this simple step can become your first line of defense against identity theft and fraud. More specifically, Cameron discusses: What is a credit freeze or security freeze? Who is a credit freeze a good strategy for? How do you freeze your credit? What happens if you need to apply for a loan or new credit when you have a credit freeze in place? How do you remove or lift a credit freeze? Can you help your elderly parents freeze their credit to better prevent fraud?   LISTENER Q & A:  Question: "I am about to start the process of creating a revocable living trust for my spouse and I. We own our home, but we also own three rental properties out of state, two located in the same state and one located in another state. From what I understand so far, this trust is going to be specific to the state in which I live. What are the implications here for my home and my other properties? Any tips you can provide on what to do so I can make sure I understand the situation better when I consult the attorney?" Resources: Get Show Notes Here Retired-ish Newsletter Sign-Up See if you're a good fit for our Free Tax-Optimized Retirement Playbook™ Key moments: (03:17) Credit Freeze: How It Works (06:12) Implementing and Managing Credit Freezes (08:17) Lifting and Removing a Freeze and Other Tips (11:18) Credit Freezes for Elderly Parents (13:39) Listener Question: Funding a Revocable Living Trust with Real Estate (16:25) Multi-State Properties and Insurance When Dealing with Trusts (18:47) Estate Planning Guidance & Additional Resources  

Attention retirement savers! If you don't expect to accumulate tens of millions in your retirement account, you may want to stop contributing to a Roth. That's right, I said tens of millions. Roth accounts can be a fantastic wealth accumulation for some, and an expensive mistake for others. In this episode, we discuss what many people, including many professionals often miss when it comes to deciding whether or not to contribute on a pre-tax basis, or after-tax basis to a Roth. More specifically, Cameron discusses: The common errors people make when trying to determine whether or not to go Roth. 3 major factors that contribute to your future tax situation The impacts of taxation at marginal vs. effective tax rates An example case study of a high earning married couple A shocking reality for some making the case for Roth contributions An alternative example for our case study that reflects most people's reality   Key moments: (01:05) The Critical Math Most People Miss (02:30) The Real Decision Factor: Your Personal Future Tax Situation (04:12) Three Key Questions to Ask Yourself (05:15) Understanding Marginal vs Effective Tax Rates (06:28) High Earner Example: $500K Income Analysis (08:36) The Shocking Reality: $40 Million Required to pay 32% in Fed Taxes (09:55) Realistic Retirement Scenario: $240K Annual Spending (12:25) The 32% Tax Rate Scenario Breakdown (14:54) Why You Need a Financial Plan Resources: Get Show Notes Here Retired-ish Newsletter Sign-Up See if you're a good fit for our Free Tax-Optimized Retirement Playbook™  

If you've ever wondered why seasoned investors tell you to "stay the course," it's because history has taught us something simple but profound: time in the market beats timing the market. But let's rewind a bit. Investing isn't just about stocks going up and down on a chart — it's about preserving your purchasing power, compounding your money, and building resilience against life's financial curveballs. So today, I'm going to take you on a journey: from the magic of compound interest, to the harsh reality of inflation, to how the stock market has historically rewarded patience — even through wars, recessions, and crises. More specifically, Cameron discusses: A powerful example of how compound interest and inflation will affect you over time Historical statistics of the U.S. stock market that will shock you Bull markets vs. Bear markets and what to expect The difference between volatility and risk when investing for your financial goals How to manage risk with asset allocation and diversification The overconcentration problem of the S&P 500 as it stands today   Definitions: The S&P 500 tracks the performance of 500 large-cap U.S. companies, serving as a benchmark for the U.S. stock market. The index is weighted by market capitalization. Compound Interest: Compound interest is the interest earned on both the original amount and the accumulated interest. Bear Markets are defined as periods when the S&P 500 experiences a price loss of 20% or more following a gain of 20% or more from its previous trough. Bull Markets are defined as periods when the S&P 500 experiences a price gain of 20% or more following a decline of 20% or more from its previous peak.   Resources: Get Show Notes Here Retired-ish Newsletter Sign-Up See if you're a good fit for our Free Tax-Optimized Retirement Playbook™   Key moments: (03:24) Compound Interest and Inflation Explained (06:48) Rethink What You Think You Know About Investing (09:55) Historical U.S. Stock Market Performance (14:27) Understanding Market Cycles (17:49) Market Volatility vs. Investment Risk (21:11) Asset Allocation and Diversification (26:20) Key Takeaways  

You've saved diligently in your IRA, built a comfortable retirement nest egg, and set up a family trust to avoid probate and streamline your estate. And then—because it feels like the safe, responsible thing to do—you name your trust as the beneficiary of your IRA. But here's the problem... In the post–SECURE Act world, naming a revocable living trust as the beneficiary of a Traditional IRA can unintentionally trigger a tax disaster for your heirs. Instead of a steady stream of income over a lifetime, they may be forced to drain the account—and pay taxes on the entire balance over just several years at the highest marginal tax brackets. We're talking about six- or even seven-figure IRAs being distributed in ways that not only defeat your estate planning goals but also crush your heirs with avoidable taxes. This isn't theoretical, it's happening now. And with compressed trust tax brackets, a badly structured trust can push your retirement dollars into the 37% federal tax bracket, sometimes with just $16,000 of income.   More specifically, Cameron discusses: When should you consider naming your family living trust/revocable living trust as a beneficiary of your retirement account? What are the potential consequences of naming a trust as the beneficiary of your retirement account? How should my trust be structured in order to pass retirement assets to my beneficiaries in the most tax-efficient manner? What if my one of my trust beneficiaries is a charity? What if I name my trust as a beneficiary of my Roth IRA?   Resources: Get Show Notes Here Retired-ish Newsletter Sign-Up See if you're a good fit for our Free Tax-Optimized Retirement Playbook™   Key moments: (04:41) When Naming a Trust as the Beneficiary of Your IRA Makes Sense (10:22) Potential Issues with Trusts as Beneficiaries of a Retirement Account (17:55) Why Trusts Fail to Qualify as a "See-Through" Trust (21:52) Tax Implications of Trusts as Beneficiaries (27:42) Charities as Beneficiaries of Your Retirement Accounts and Trusts (31:44) Roth IRAs: A Potential Solution  

Social Security can be a maze of rules and decisions to make if you're widowed or divorced, which makes claiming a daunting task. Most claiming decisions are permanent and can make a difference of tens if not hundreds of thousands of dollars over the rest of your lifetime, so you want to get it right. In this episode, Cameron Valadez, CERTIFIED FINANCIAL PLANNER™ and Enrolled Agent shows you how to navigate these important decisions faced on your own. More specifically, Cameron discusses: The current state of Social Security and why early filing may not be in your best interest What divorcées need to know about benefit eligibility, what they may be entitled to, and future changes in life circumstances Questions Cameron has received in the past from divorcées What widows need to know about survivor benefit eligibility, what they may be entitled to, and future changes in life circumstances Differences between widow and divorced widow benefit eligibility Coordinating survivor benefits with your own potential retirement benefits Questions Cameron has received in the past from widows Tax withholding implications on Social Security benefits Resources From The Episode: Retired-ish Newsletter Sign-Up Access Show Notes Here  Schedule a 20-Minute Discovery Call & Get Your Copy of "Finding Financial Clarity & Confidence When Starting Over": 10 Blind Spots You Should Know To Help Mitigate Financial Uncertainties In Your New Life Key Moments: (01:11) The Social Security Crossroads (02:09) Debunking the Bankruptcy Myth (08:19) Understanding Divorcee Benefits (12:04) The 10-Year Rule and Its Impact (17:03) Real Questions from Real Divorcees (22:06) Survivor Benefits: What You Need to Know (27:06) Strategic Options for Survivor Benefits (29:22) Understanding Survivor Benefits and Earnings Limits (32:20) Navigating Remarriage and Survivor Benefits (35:03) Full Retirement Age Confusion: Survivor vs. Retirement Benefits (36:00) Strategic Switching: Survivor to Retirement Benefits (37:20) Tax Considerations for Social Security Recipients (40:33) Final Thoughts and Key Takeaways  

Can Artificial Intelligence really give you solid financial advice—or just a generic roadmap that ignores the potholes? In this episode of Retired·ish, we explore the growing trend of people turning to AI tools like ChatGPT for help with retirement planning, tax questions, and investment strategies. Sure, AI can be fast, cheap, and eerily accurate… sometimes. But when life gets complicated—and it always does—there's no substitute for personalized advice from someone who understands the human side of money. Join Cameron Valadez, CFP® and Enrolled Agent, as he breaks down where AI shines, where it falls flat, and when it's time to stop asking the chatbot and consult a pro. More specifically, I discuss: The use of AI chatbots for advice CFP® Board consumer survey on where Americans are getting financial advice Limitations and drawbacks of financial advice from AI chatbots vs professional advice from humans Generative AI vs Predictive AI AI financial scams and how to protect yourself Resources From The Episode: Retired-ish Newsletter Sign-Up Get Show Notes Here    

Here we go again, discussing hot takes on permanent life insurance and its use as an investment vehicle. In this episode, I tackle one of the best questions I have received in a long time regarding the cash value and hidden costs associated with permanent life insurance that I think is critical to understand. Before considering a permanent life insurance policy as an investment option, make sure you are utilizing the more transparent, low cost, and tax efficient investment vehicles on a regular basis. More specifically, I discuss: The biggest hidden cost in many permanent life insurance policies Where your premiums go when funding permanent life insurance What is the cash value component of a permanent life insurance policy? How does the death benefit payout work in permanent life insurance policies? What can happen if you take a loan from your permanent life policy? Why permanent life insurance policies make for poor "investment vehicles" Resources From The Episode: Retired-ish Newsletter Sign-Up Get Show Notes Here   Key Moments: (02:05) The Controversial Question About Permanent Life Insurance Nobody is Asking (05:18) The Answer (06:23) Understanding Permanent Life Insurance Premiums (10:33) Taking A Loan From Your Permanent Life Insurance Policy  

With the growing US federal deficit, tariffs, fears of recession, and upcoming tax breaks, inflation is a top concern in the minds of many retirees and soon-to-be-retirees. Investing in TIPS, or Treasury Inflation-Protected Securities, is one of the most commonly touted strategies that can help stave off unexpected inflation, however there are still important risks to understand.  Can TIPS really preserve your purchasing power in a meaningful way and kill off inflation no matter what happens in the markets or economy? Or are they just another government bond with a fancy name and a built-in marketing hook? More specifically, I discuss: What are Treasury Inflation Protected Securities (TIPS)? How do TIPS work? How are they different from traditional (nominal) bonds? Important things to know when purchasing TIPS Individual TIPS vs. mutual funds and ETFs that invest in TIPS Potential risks of investing in TIPS Tax ramifications of TIPS Why would a pre-retiree or retiree consider adding TIPS to their portfolio? Resources From The Episode: Retired-ish Newsletter Sign-Up Get Show Notes Here Key moments: (02:35) Understanding TIPS: The Basics (08:55) Important Things to Know When Buying TIPS and/or TIPS Fund (15:09) Some Risks With TIPS (19:03) Tax Implications of TIPS (23:32) Should You Consider Investing in TIPS?

The "One Big Beautiful Bill" recently passed through the House of Representatives by a narrow margin and is now in the Senate's hands. This bill consists of extremely important tax legislation that aims to continue on and add to the current tax provisions we have grown accustomed to for the last several years under the Tax Cuts and Jobs Act. As a pre-retiree or retiree, many of the federal tax proposals in the current bill are highly relevant and could warrant adjustments to your retirement planning if passed. In this episode, Cameron provides a breakdown of the most impactful changes and how they may affect you. More specifically, I discuss: Proposed changes to current Tax Cuts & Jobs Act legislation State & local tax deduction (SALT) cap proposed changes Deduction updates for business owners and landlord (bonus depreciation, QBI) Current tax provisions to be repealed under the One Big Beautiful Bill Brand new provisions in the One Big Beautiful Bill relevant to pre-retirees and retirees Proposed changes to Health Savings Accounts (HSA) Resources From The Episode: Retired-ish Newsletter Sign-Up Get Show Notes Here Key moments: (00:00) Introduction to the One Big Beautiful Bill (02:05) Key Provisions of the Proposed Bill (03:56) Proposed Changes to Current Tax Law (08:52) Proposed Changes to SALT Deduction (11:01) Proposed Changes in Small Business Owner Tax Breaks (14:10) Proposed Tax Provisions Set to be Repealed (15:43) Proposed Brand New Tax Provisions  

Income planning will make or break your retirement years - This is because your income throughout 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. However, depending on where and how you plan to generate income from, you may run into problems along the way. Many times, we see issues arise with those who primarily focus on a dividend spending strategy from their investment portfolios to supplement their other retirement income sources.   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   Resources From The Episode: Retired-ish Newsletter Sign-Up Get Show Notes Here   Key moments: (02:02) The Error of Relying Solely on 1 Retirement Income Source (02:57) Challenges of Basic Income Planning (04:58) Retirement Income is More Important Than Investment Returns (08:33) The Four L's of Retirement Planning (11:15) Funding Your Desired Lifestyle (12:30) Rental Real Estate May Not Be The Most Efficient Retirement Income Plan (14:53) Planning for Legacy, or Not (16:04) The Importance of Liquidity in Retirement (18:06) The "Live Off Of Dividends" Strategy Debate (24:44) The Risks of High-Dividend Paying Stocks (29:52) Total Return Investing as an Alternative

This is a must-listen episode that could save your family's financial future… Seriously. Estate planning is important, we know that, but what happens when things go wrong, very wrong? In this episode, we delve into true stories of oversight and missed opportunities, each one a powerful lesson in what not to do. Learn how simple mistakes today can cause chaos tomorrow and discover the steps you can take to avoid these pitfalls. Don't let your hard-earned legacy become a cautionary tale. More specifically, I discuss: When multiple executors/trustees disagree Who has the power to make decisions when you're gone? Corporate trustee failures tie up significant family wealth Digital recordkeeping in the 21st century put beneficiaries at a stand still Outdated estate plans can create tax time bombs Resources: Retired-ish Newsletter Sign-Up Get a 2nd Opinion on Your Estate Planning Strategy Get Show Notes Here   Key moments: (02:00) Sibling Disagreements and Executor Conflicts (08:22) Who Holds the Power After You're Gone? Decision-Making in Trusts (13:04) Corporate Trustee Mishaps (20:25) Digital Recordkeeping Issues (24:32) Retirement Accounts and Trusts (29:57) The Expensive Dangers of Outdated Estate Planning Strategies

Long-term care insurance typically becomes a consideration for people in their 50s and 60s after they experience helping out with their aging parent's care and realizing the substantial hit it can make on their life savings. But one of the most overlooked aspects of long-term care insurance is the potential tax benefits that can be had. When considering long-term care insurance, understanding the potential tax benefits and how they pertain to your own financial situation can help you make a more informed decision. More specifically, I discuss: How does the potential deduction for long-term care insurance work? What are the limitations when trying to deduct qualified long-term care insurance premiums? How might changes in tax law allow for or increase your long-term care premium deduction? What types of long-term care insurance are considered "qualified"? Can you deduct premiums paid for hybrid or asset based long-term care insurance? Can business owners get a deduction for long-term care insurance premiums paid? When can't you deduct premiums paid for long-term care insurance? Resources From The Episode: Retired-ish Newsletter Sign-Up Get Show Notes Here   Key moments: (03:02) Are Long-Term Care Insurance Premiums Deductible? (05:33) Deducting Medical Expenses Above 7.5% Adjusted Gross Income (06:14) Long-Term Care Premium Deduction Limits By Age (10:53) Issues With Itemizing Deductions & The SALT Cap (13:24) What Constitutes a "Qualified" Long-Term Care Policy (15:31) Deducting Hybrid or Asset Based LTC vs. Traditional Long-Term Care Insurance (19:19) Deducting Long-Term Care Premiums for Business Owners (22:19) When Can't You Deduct Your Long-Term Care Premiums?

Since President Trump took office for the second time in 2025, tariff talks are all the rage and markets have entered a new phase of extreme volatility. Since tariffs can be a good and a bad thing, we think it's necessary to have some additional context beyond what the mainstream media seems to be focused on specifically - which is higher prices and inflation. To understand the potential economic impacts moving forward and how these tariffs might affect markets and your investment portfolio, we need to zoom out and take a look at more than just the current headlines. More specifically, I discuss: What are tariffs in layman's terms, and why do they exist? What are the potential impacts of tariffs? What has happened historically with tariffs in the U.S. and how did the stock market react? What happened to inflation and the stock market during President Trump's first term and his "America First" trade policies? What can happen with inflation and volatility in the stock market when tariffs are increased? LISTENER QUESTION: Collecting Social Security Benefits while working and when benefit payments adjust for additional years of earnings. Resources From The Episode: Retired-ish Newsletter Sign-up Get Show Notes Here Key moments: (02:01) What are tariffs and why do they exist? (03:14) Potential impact of tariffs (04:19) Historical facts about U.S. tariffs (06:53) Potential impacts of tariffs on your investment portfolio (07:36) What happened the last time President Trump's Administration increased tariffs? (14:42) Listener question: Collecting Social Security while working and benefit adjustments

Due to the increasing political and market uncertainty, and recent stock market correction, we felt it was more important than ever to reintroduce this episode of the Retired·ish Podcast throwing it back to episode #8! In this episode we defined the downside of what is called Sequence of Returns Risk - which is in my opinion can be the greatest threat to your retirement savings and income. This risk can present itself when markets happen to be volatile to the downside at nearly the same time that you enter retirement when you go from saving to spending your retirement nest-egg – which can be a very nerve-wracking experience to go through. We explained why it is crucial to understand that saving for retirement is actually the easy part, and how spending what you've saved up in your investment portfolio can quickly become a risky endeavor, especially if you have no strategy to mitigate the downside of Sequence of Returns Risk. More specifically, I discuss: What is the greatest threat to your retirement savings? Examples of sequence of returns risk in the savings phase of your life Examples of sequence of returns risk in the spending phase of your life The difference between monitoring account balances vs. average investment returns What types of strategies can you implement to try and reduce sequence of returns risk Resources From The Episode: Retired-ish Newsletter Sign-Up Get Show Notes Here   Key moments: (05:23) "Sequence of Returns Risk": Retirement's Hidden Threat (08:06) When The Sequence of Returns is Irrelevant (10:34) Impact of Return Sequence When Spending in Retirement (20:51) Emotion-Free Investment Strategy (23:09) Short-Term Retirement Fund Strategy (26:11) Investment Growth and Legacy Strategy

When the stock market produces double digit returns over multiple years in a row, investors and retirement savers naturally begin to get nervous and anticipate some sort of inevitable financial bubble.  This fear often stems from two things, from living and investing through recent historic market crashes such as the dot-com bubble and the great financial crisis, as well as the mere thought about how the recent and exuberant growth of your financial nest egg can sharply and suddenly be given back – and ultimately the thought of how that hit to your investments might impact your livelihood in retirement. In this episode, we take a historical look at financial bubbles and what a "bubble" entails. More specifically, we discuss: Insights from Howard Marks' memo: "On Bubble Watch" and defining a financial "bubble" What causes financial or asset bubbles? How bubbles and market crashes can negatively affect investor behavior Media headlines and stock market bubbles Understanding the cycle of investment fads: My "Asset Bubble Circular Calculation" How an investment plan can guide you through market turmoil Resources: Access Episode Show Notes and Sign Up for the Retired·ish Newsletter Ask Cameron A Question! "On Bubble Watch" – Howard Marks https://www.oaktreecapital.com/insights/memo/on-bubble-watch Key moments: (03:36) Exploring Stock Market Bubbles and What They Really Are (04:15) What Actually Causes Stock Market & Other Asset "Bubbles" (09:55) Bubbles Can Cause Negative Changes To Your Investing Behaviors (12:49) The Impact of Media Headlines (15:17) "The Asset Bubble Circular Calculation"

If you're a diligent retirement saver, you've likely heard of - and maybe even explored - executing a Roth conversion of some of your pre-tax retirement savings. Executing the Roth conversion itself is the easy part, but trying to figure out whether or not it makes sense and will benefit your particular financial situation is the hard part - since you will voluntarily pay taxes when you convert and the conversion can't be undone. Rather than start converting to Roth on a whim, a thorough analysis should be done before making any decisions since a Roth conversion has risk and could end up being a very expensive mistake, but when done opportunistically, can save tens of thousands or more in taxes. More specifically, we discuss: What has to happen for a Roth conversion to make sense? What is a Roth conversion and why do people and their professional advisors typically do them? What are the potential benefits that can come from a Roth conversion? Understanding Net Present Value (NPV) when determining whether or not a conversion makes sense When might a Roth conversion hurt you? Resources: Access Episode Show Notes and Sign Up for the Retired·ish Newsletter Ask Cameron A Question! Blog Article: Roth 5 Year Rule Previous Podcast Episode: What is a Roth Conversion and Should I Consider It? Decision Chart: Should I Consider Doing a Roth Conversion?   Key moments: (05:01) What is a Roth Conversion? (07:50) When Does It Make Sense to Consider a Roth Conversion? (12:30) "Net Present Value" and Why It's Important to Understand (15:55) Recouping The Costs of a Roth Conversion Depends on Multiple Factors (19:25) Roth Conversions with The Fastest Pay-Off (20:25) When a Roth Conversion Might Hurt You (25:40) Roth Conversions Carry Risks

Investing in the stock market by selecting a handful of individual stocks is tempting for many investors who dream of making substantial gains by picking the "next big thing." But despite the allure, there are many compelling reasons why investors should think twice before diving into individual stock picking and market speculation… More specifically, we discuss: The most important question for DIY investors picking stocks and funds What does the research say about stock picking and market speculation? A surprisingly small percentage of stocks generate an overwhelming majority of shareholder wealth Investor emotions serve as a significant roadblock in making investment decisions Your Family Risk Profile Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Ask Cameron A Question!   Key Moments: (02:15) DIY Investing: Picking Individual Stocks (04:15) Stock Pickers Typically Underperform Market. What Does The Research Say? (10:12) Very Few Stocks Drive All of The Market's Growth Over Time (17:04) Emotions Make Investing Extremely Difficult (19:33) The #1 Question You Should Ask Yourself When Picking Stocks or Timing The Markets

Retirement is often imagined as a permanent vacation that's been earned over many years of sacrifice. You envision yourself traveling the world on cruises, playing endless rounds of golf or pickleball, or telling yourself that you will finally spend more of your time with family and start exercising more. While these dreams can certainly be part of your retirement, it's essential to understand that this is just one side of the coin. More specifically, we discuss: How retirement has changed over the past few decades What it means to be Retired·ish Your dream retirement vs. the realities of day-to-day life in retirement Emotional aspects of retirement and sense of self-worth Changes to your social network in retirement The importance of financial and retirement planning before retiring. Resources: Access Episode Show Notes and Sign Up for the Retired·ish Newsletter Ask Cameron A Question!   Key moments: (00:00) Redefining Retirement: A Lifestyle Choice (06:17) Plan Retirement Activities Early (10:00) Reconnecting with Social Circles in Retirement (11:14) Dynamic Retirement and Financial Planning Essentials

Two of the most prominent provisions – the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO) - that can substantially reduce Social Security benefits for some federal, many public sector and civil service employees were just eliminated after being in effect for the last 40 years! Teacher, police officers, firemen, and some federal workers are some of the most common groups affected by these provisions, and as of December 31st, 2023, they may see a bump in benefits or expected benefits they're eligible to receive. More specifically, we discuss: President Biden passes the Social Security Fairness Act on January 5th, 2025 What are the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO) and how do they work? How were some public sector and federal employees and retirees affected by these Social Security provisions? What are the potential benefits now that these provisions have gone away? Retroactive 2024 lump-sum payments Tax implications now that the WEP and GPO have been eliminated What you need to do to receive potential additional Social Security benefits Resources: Access Episode Show Notes and Sign Up for the Retired·ish Newsletter Ask Cameron A Question!   Key moments: (00:00) WEP & GPO provisions reduce Social Security benefits for public servants. (07:00) How do the WEP and GPO provisions work? (08:51) GPO reduces public pension spouse's Social Security w/ examples. (13:25) How might your benefits change moving forward in 2025 and beyond? (14:19) Lump sum back-pay of Social Security benefits for 2024. (14:55) Tax implications of lump sum payments and increased benefits.

There's no question about it, that when it comes to saving for retirement, the financial mass media pounds the table with all things retirement accounts like IRAs and 401(k)s, but there's a vastly underutilized investment vehicle that can help retirees enjoy a potential 6-figure retirement income, entirely tax-free. We are referring to the good olé brokerage account. A brokerage account is simply an investment account you open where you deposit money from your own bank account and then you can use that cash to invest in various investments held inside that brokerage account. Most commonly, people will invest in things like stocks, bonds, mutual funds, ETFs, things of that nature. In this episode, I teach you how you might utilize a brokerage account for a 6-figure retirement income, tax-free. More specifically, we discuss: The difference between a brokerage account and a retirement account such as an IRA or 401(k) How a pre-retiree might accumulate funds inside of a brokerage account How taxes work when it comes to brokerage accounts and the investments held inside them How exactly you can end up paying no federal taxes on over 6-figures of income Hypothetical scenarios (basic concept and real-world) The importance of a retirement income plan and investment strategy Resources: Access Episode Show Notes and Sign Up for the Retired·ish Newsletter Ask Cameron A Question! Key moments: (03:44) Build brokerage account for retirement income flexibility (07:35) Pre-Tax IRA/401(k) assets taxed as ordinary income, brokerage assets can be subject to lower long-term capital gains rates (10:08) 0% capital gains tax up to $96,700 for married filing joint in 2025 (12:07) Conceptual Scenario: high 6-figure income in retirement, zero taxes (15:24) Real-World Scenario: high 6-figure income in retirement, zero taxes (23:02) Key points when using brokerage accounts as part of your retirement income strategy

Building up a substantial amount of savings in your 401(k) or IRA may serve as an indicator for a job well done in saving for retirement. But what soon-to-be retirees need to realize is that if the majority of your retirement savings is in pre-tax dollars, taxes will eventually be owed while in retirement and taking distributions. Depending on your tax situation in retirement and the tax laws in place at that time, these large account balances may cause a tornado of taxation that you weren't expecting - which can cause you to have to rethink your retirement strategy altogether. In this episode, Cameron discusses why pre-retirees should reconsider building up their pre-tax retirement account balances, and what to do instead. More specifically, we discuss: The potential tax problem Cameron has seen recently when talking with those age 50+ The "shadow taxes" that await you in retirement The potential tax ramifications of building up large pre-tax IRA and 401(k) balances Alternatives to saving money on a pre-tax basis Why tax rates are likely to be higher in the future Roth conversions How to mitigate or avoid estimated tax penalties when implementing Roth conversions Resources: Access Episode Show Notes and Sign Up for the Retired·ish Newsletter Ask Cameron A Question!   A Roth IRA offers tax deferral on any earnings in the account. Qualified withdrawals of earnings from the account are tax-free. Withdrawals of earnings prior to age 59 ½ or prior to the account being opened for 5 years, whichever is later, may result in a 10% IRS penalty tax. Limitations and restrictions may apply.   (01:58) Those age 50 and over should slow down building up pre-tax 401(k) and IRA. (06:01) Roth 401(k) employer match/profit sharing is taxable; 401(k) plan document dependent. (07:48) Tax deduction today, or in retirement? Time Value of Money concept isn't always what it seems. (10:13) Consider choosing Roth IRA/401K over traditional savings moving forward. (15:09) Optimize tax strategies with underutilized brackets. (16:22) Potential tax changes could affect inheritance complexities. (18:27) How to pay for taxes due from a Roth conversion and avoid underpayment penalties.

The landscape of taxes, retirement savings and Medicare are ever changing. Every year we see changes to the laws and limitations such as tax rates, brackets, and deductions, limitations on retirement plan contributions, and premium changes to Medicare to name a few. 2025 brings us some run of the mill changes sprinkled with substantial changes that can largely benefit retirees and soon to be retirees. In this episode, we discuss some of the most important changes and how they may affect you. More specifically, I discuss: Important adjustments to common tax deductions and tax rates Changes in the gift and estate tax landscape New retirement savings laws and updates for those still working in 2025 Important changes for Medicare and prescription drug plans Social Security related updates for 2025 Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Ask Cameron A Question!   Key moments are: (00:00) 2025 standard deduction amounts increased for inflation. (05:32) Estate tax exemption may significantly decrease post-2025. (09:40) Those ages 60-63 can now put more into their employer sponsored retirement plan in 2025 (12:29) Employers can now contribute Roth, impacting taxes. (17:41) High out-of-pocket costs for Medicare prescriptions. (20:07) Out-of-pocket drug costs capped at $2,000. (22:59) 2.5% COLA for Social Security in 2025. Wage limit increases 4.5%.

If you've built or inherited an investment portfolio alongside the savings in your retirement accounts, you are likely to face some taxation every year on things like interest, dividends, and capital gains generated from the investments. These might be investments such as stocks, bonds, mutual funds, or ETFs held in a brokerage account to name a few. While these investments can serve as a fantastic compliment to your other retirement savings, you'll want to be sure to manage this money in the most tax-efficient manner each year to allow your money to last as long as possible. In this episode we discuss 6 year-end strategies to help you reduce the annual tax bill from your portfolio. More specifically, I discuss: 7 basic tax rules you need to know when it comes to non-retirement investment portfolios Properly offsetting gains and losses Properly use long-term losses Avoiding the wash-sale rule Make use of lower tax brackets Donating appreciated stock to charity Do not donate depreciated stock to charity Resources: Access Episode Show Notes and Sign Up for the Retired·ish Newsletter Ask Cameron A Question!   Key moments: 00:00 Non-retirement accounts have annual tax implications 05:29 Capital gains can be taxed between 0% to 40.8% based on income and nature of gain 09:02 Properly offset short and long-term gains with losses to defer taxes and optimize savings 10:22 Consider strategic tax planning for mutual funds held in non-retirement accounts 15:04 Transfer appreciated stock to family in lower tax brackets 17:22 Donate appreciated stocks if itemizing deductions and charitably inclined

In a recent study published by the investment research company Morningstar, they estimate that the average dollar invested in funds by individual investors over the 10 years ending December 31st, 2023 earned a 1.1% lower rate of return per year than the actual investments they were invested in. This resulted in individual investors out on nearly 16% of the investment's actual returns each year, even without consideration of any investment fees. Morningstar updates this data annually as part of their "Mind The Gap" study, and in this episode I break down why this is happening and what this means for investors. More specifically, I discuss: What investing insights does this research show us? The difference in investor return "gaps" per asset classes invested in. Investors miss out on 50% of taxable bond fund returns! Why are many individual investors earning lower average rates of return than their investments themselves? The difference in investor return "gaps" based on the volatility of a particular asset class. Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Ask Cameron A Question!   Key moments are: 00:00 Difference between investment and investor returns. 05:07 Investor behaviors remain consistent over the years despite political and economic uncertainty. 06:37 Return gap varies widely depending on asset class. 12:55 Investors tend to receive about 50% of bond fund returns. 16:33 The more volatile the fund, the more likely investor's poorly time investment activity.

Kamala Harris and Donald Trump present starkly different tax proposals for the 2024 election reflecting their contrasting economic priorities. And while the exact outcomes of future tax policy are unknowable, you can be better prepared by having a good understanding of the potential changes. In this episode, I address some of the major tax policies at play if either candidate takes office, and how they might affect your situation. More specifically, I discuss: A basic review of the current tax laws in place under the Tax Cuts and Jobs Act (TCJA) What will happen if the TCJA sunsets (expires) in 2026 without intervention from either candidate? How might you be affected by the sunsetting of the TCJA. Brief overview of Harris's main tax proposals and what it means for you. Brief overview of Trump's main tax proposals and what it means for you. Will the State and Local Tax deduction (SALT) limits be removed before 2026? Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis  Ask Cameron A Question! 00:00 Political uncertainty surrounds future tax provision changes 04:15 Middle-class tax burden increasing significantly by 2026 08:01 Harris aims to raise taxes on the wealthy, but Trump's cuts may be too expensive 11:12 Higher corporate taxes could mean higher prices 16:39 $10,000 SALT cap limits state tax deductions significantly 21:05 Existing small businesses may face tax increases in 2026 24:50 Tax proposals may influence voters significantly come November 2024

In today's challenging and expensive economic environment, many young adults in their 20's and 30's are struggling to find stable footing when it comes to their finances. Whether that's struggling to find that perfect career that can help them pay off their student debt, saving enough for a downpayment on a first home, or having extra cash each month to pay for childcare.  These common issues are causing many parents in retirement to rethink their own situation by contemplating whether or not they should step in to help, and if so, how?   More specifically, I discuss: How to go about making the decision to help your children out financially from your own retirement resources Gifting and seeing your kids benefit from financial help while you're alive, or let them inherit your wealth at death Potential financial and tax ramifications of gifting your children money or assets vs. inheriting Important things to consider before making the decision to help your children out financially Real-life case study of a retired couple with 4 children Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis  Ask Cameron A Question!    Key moments are: 02:37 Case Study of retired couple wanting to help children financially 04:55 Capital gains implications and cost basis 07:45 Child daycare for grandchildren, downpayment for a bigger home 10:50 What to consider when deciding whether or not to gift children money 15:01 Consider family dynamics, fair inheritance, and taxes 18:50 Assessing your children's "wants" vs. their actual "needs" and strategies to preserve wealth

When approaching a retirement from a long and successful career, you'll likely have a list of big decisions to make in a relatively short time. One of those decisions will be whether or not you should manage your retirement account(s) on your own after retiring - when you begin to convert them into an income stream to support your lifestyle. This is opposed to looking for outside help from a professional such as a financial advisor or planner, and it's a decision that comes with both pros and cons. However, before you decide, I think it's important to understand what you may be getting yourself into since spending and distributing your retirement savings is much different than saving for retirement. More specifically, I discuss: What does it mean to manage your own retirement savings? What common tasks and expertise does managing your own retirement account(s) entail? What are some of the pros and cons to the "do it yourself (DIY)" approach to investing? Common examples of costly retirement mistakes, even when it feels like you're making money Should you take on the responsibilities of investment management and retirement planning or seek help? Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Start Your Complimentary "Jump-Start" Retirement Analysis Here Ask Cameron A Question!   Chapters: 00:00 Managing your own retirement accounts: what's involved. 05:21 DIY investing can save direct costs but may have larger indirect costs. 09:55 Having accountability from a 3rd party may yield better outcomes. 13:57 Market drops can cause panic, lifestyle, and strategy concerns. 16:24 Have a plan to mitigate potential retirement risks and changes throughout life. 20:45 Examples of costly investment mistakes that feel like wins. 27:09 Managing your investments in retirement is not what you expect it to be.

When you have assets such as rental property that are going to need to provide you with cash flow throughout your retirement years, you'll want to look into some level of asset protection at some point. When it comes to rental real estate, the Limited Liability Company or LLC might be worth considering. However, the methods and strategies you use will depend on what you have at risk and certain risks that you might be creating yourself. More specifically, I discuss: Setting up an LLC prematurely What is asset protection? Determining what assets to protect and how with examples Basic asset protection techniques What is a Limited Liability Company (LLC)? Benefits when used for rental property What does an LLC not do? How is an LLC commonly used for rental property? How can an LLC provide asset protection? - "Inside" & "Outside" liability When might you consider putting rental property in an LLC? Having your Revocable Living Trust own an LLC used for rental property Asset protection techniques to explore before creating an LLC Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis  Ask Cameron A Question!   Key moments are: 00:00 Asset protection, LLCs, benefits, drawbacks. 04:00 You may not need an LLC for your rental property 05:38 There are no silver bullet asset protection strategies, even LLCs 07:37 Potential benefits of an LLC for rental properties 09:25 Tax return ramifications with an LLC 10:45 Potential drawbacks of an LLC and what they don't do for you as a landlord 13:46 How can an LLC actually give you asset protection (inside and outside liability) 19:17 When might you consider putting your rental property in an LLC? 22:29 Series LLCs 23:30 Consider having your Revocable Living Trust own your LLC

Having too much of your net worth tied up in one or a couple individual stocks can be a dangerous game to play. It's one that relies heavily on luck and can present a significant risk to your life savings. Things can either turn out really well, or very poorly. Sadly, many people often let their emotions and the potential tax ramifications dictate their next move, but should they? In this episode, we discuss the risk of relying on one or two companies' success to dictate your financial future, and how you can begin to mitigate that risk while saving taxes. More specifically, I discuss: Why are large, concentrated stock positions a potential problem? What types of investors might have highly concentrated stock positions? What if the majority of my compensation is via employer stock? The dangers of relying on one company and overconfidence How to diversify your concentrated stock position Examples of methods you can use to divest of shares Tax efficient example of reducing concentrated stock positions, diversifying, and saving taxes A little-known strategy to consider if you have appreciated company stock positions inside your 401(k) Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis  Ask Cameron A Question!   Key moments: 00:00 Diversify investments to minimize risk and avoid emotional biases 05:34 Active management and stock picking often fails to outperform benchmarks. 07:59 Timing markets is risky; consider long-term goals. 10:31 Diversification benefits 16:44 Expect intra-year stock market declines 18:54 Strategy for controlling taxes and staying diversified in the market with concentrated stock position

Implementing important estate planning documents is critical to leaving your ideal legacy upon your death. Among the critical estate planning documents are wills and trusts. Often times, many people confuse the differences between the two, the benefits they can provide, and whether or not they need them at all! More specifically, I discuss: Why getting the appropriate estate planning documents in place is so important What is a Will? What can it do? What is a Trust? What can it do? What is the difference between a Revocable Living Trust and an Irrevocable Trust? Common uses for Revocable Living Trusts Common uses for Irrevocable Trusts What Revocable Living Trusts and Irrevocable Trusts don't do How the titling of assets can work in your estate plan The importance of naming beneficiaries Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis Ask Cameron A Question!   Key moments are: 00:00 Estate planning: wills, trusts, assets, and advice. 05:09 What does a will do? 08:26 Title of property and beneficiary designations. 10:24 What can a trust do? 14:16 Revocable trusts does not offer tax benefits. 20:20 Irrevocable trusts can have significant tax implications, good or bad. 22:18 The importance of naming beneficiaries and titling assets appropriately. 26:35 Estate planning can save your family money.  

Retirees and pre-retirees often struggle when it comes to spending down their nest-egg in retirement because of the fear of the unknown. No one wants to run out of money too early, yet most people would also like to enjoy what they've worked so hard for. So how do you find that balance? How can you know what you can spend, and for how long?  Living off of your wealth is entirely different than building your wealth. Without a retirement spending strategy, most people are going to either end up really worried about running out too early throughout their retirement, but end up leaving a pile of money on the table when they die, or running out of money too early in retirement – which for some, can be scarier than death itself More specifically, I discuss: Why are retirement withdrawal strategies important? The main types of retirement withdrawal strategies Systematic Withdrawal Plan/Constant Dollar Time-Based Segmentation or "Buckets" Floor and Upside Dynamic Spending Strategy Variations and examples of real-world withdrawal strategies Strengths and weaknesses of the different retirement income strategies LISTENER QUESTION: Excess IRA/Roth IRA Contributions Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis  Ask Cameron A Question! Key moments: 00:00 Decades of work for retirement, learning to spend. 05:09 Customized retirement planning requires personalized, flexible strategies. 07:15 Customize retirement income strategy to meet financial goals. 13:57 Constant Dollar Strategy / 4% rule 16:36 Time Segmenting and Bucket Strategy 22:28 Floor and Upside Strategy 27:20 Dynamic Withdrawal Strategy 34:47 Listener Question: Excess IRA/Roth IRA Contributions

Life insurance has become an increasingly controversial topic in recent years due to the opinions of financial gurus on YouTube, insurance salesmen, and media giants especially when it comes to using it as a vehicle to build wealth. When considering life insurance as a wealth building vehicle, it really comes down to who is using it and how they are using it. Ultimately, when it comes to building wealth, permanent life insurance is a potential option, but only in very unique circumstances. More specifically, I discuss: The two main types of life insurance The main types of permanent life insurance The structure of permanent life insurance The different variations of universal life insurance Benefits and downsides to permanent life insurance How permanent life insurance can be used to build wealth How to structure permanent life insurance policies for wealth building purposes Who should consider using life insurance to build wealth, and who shouldn't Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis  Ask Cameron A Question!   Key moments: 00:00 Understanding when life insurance can build wealth. 05:58 Permanent insurance costs more than term insurance. 10:05 Universal life insurance allows tax-free loans. 13:35 Insurance policies allow redepositing, not like retirement. 14:58 Limited control over investments, potential for higher returns. 21:17 Evaluate costs and fit for wealth building. 23:11 Future episode will cover life insurance info.

Investing in real estate historically has been a tried-and-true method of building wealth over the long-run, if you have the right wherewithal and mentality to do it – Let's face it, it takes work. However, as with any type of investment, investing in real estate has its own set of risks. Without proper analysis, you can lose a lot of money even if you accept what looked like a great deal. Or, you might be generating minimal cash flow that could have been a lot more cash flow if you were better prepared when analyzing your real estate deals. In this episode, we show you how to analyze a real estate deal and compare it with other investment opportunities. More specifically, I discuss: Real estate is a numbers game Some of the risks involved with real estate investing The "4 Return Components of Rental Real Estate" The potential tax benefits of investing in real estate Analyzing a real estate deal Using your analysis to help you make decisions Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis  Ask Cameron A Question!   Key moments are: 00:00 Real estate investing has inherent uncontrollable risks 04:07 Critical components of real estate investment analysis 07:25 Hypothetical 20% return on property investment 11:26 Consult a tax advisor for potential write-offs 14:17 Avoid negative cash flow with proper monitoring 18:27 Using analysis for hypothetical $650,000 inherited property 21:36 Low rate of return, mortgage doesn't matter 23:14 Conservative 4% annual appreciation yields $26,000 27:26 LPL Financial offers advisory services, consult professional 28:57 Municipal bonds tax free, consult advisor, no guarantees

2024 is an election year, and not just any election year, but what could be one of the most controversial election years in our Nation's history. Given the constant influx of media hype around everything such as: geopolitical tension, political dispersion within the US, inequality, inflation, government spending and the nation's screaming debt levels, the collapse of the US dollar, student debt, the uncertainty of Social Security, all while the stock market has continued to new make new highs - Investors and everyday people saving for retirement are left to wonder, what's going to happen to my investments? More specifically, I discuss: Does the US president influence US stock market returns in an election year? Have markets fared better during election years with a Republican or Democratic President? Does the political make up of Congress influence market returns in an election year? What should I do with my investment strategy during an election year? Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis Ask Cameron A Question! Key moments are: 00:00 Presidents have limited impact on the economy. 03:48 Economy and stock market are driven by many factors. 09:59 Investing not tied to political party affiliations. 12:16 Worrying about market uncertainty can be counterproductive. 14:54 Invest carefully for long-term success in companies. 18:11 Investment strategy should match long-term goals.

Whether you're self-employed or an employee, a Health Savings Account or HSA can provide you with a triple tax benefit! Therefore, if you're serious about saving taxes and building wealth, it's critical to understand the benefits and rules of the Health Savings Account. If an HSA makes sense for your situation, you can benefit by receiving tax deductions based on money contributed into the account, tax-deferred growth on any interest or gains earned on the investments inside the account, and potentially tax-free distributions from the account that you take for medical expenses. The HSA is the only tax-advantaged account that has the ability to give you both a tax deduction for the money you put in, and tax-free withdrawals on the way out. Even better than the Roth IRA! You can also invest the money inside an HSA in a wide variety of investments! In some people's opinion, it is seen as the ultimate retirement savings vehicle, so don't let the name fool you! More specifically, I discuss: What is a Health Savings Account (HSA)? The triple tax benefits of an HSA The rules and eligibility requirements when utilizing an HSA Who should consider an HSA? The "13-month" or "last month" rule when contributing to an HSA The 3 methods of using an HSA Other unique strategies and other opportunities unique to HSAs BONUS: HSA strategy for adult children under age 26 with high earnings such as professional and college athletes, entertainers, business owners, and young professionals LISTENER QUESTION: HSA contributions and Medicare!   Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis Ask Cameron A Question!   Key moments: 00:00 HSA for healthcare savings provides a triple-tax advantage. 03:38 HSA offers triple tax benefits for saving. 09:02 Eligibility for HSA: high deductible health plan. 11:04 Consider plan's deductible, out-of-pocket expenses. HSA criteria. 16:41 HSA contributions and potential penalties explained. 18:08 At 65, take money out - no penalty. 23:00 Be careful of double dipping with taxes. 28:42 Maximize HSA contributions for long-term tax benefits. 30:20 Listener Question from Diane

Are you tired of handing over too much of your money to the tax authorities every year? Or wondering if there's a better way to go about managing your cash flow when it comes to paying your taxes? If so, it's time to take control of your finances and maximize your wealth building machine. In this episode, I will show you how to adjust your tax withholding to keep more money in your pocket throughout the year so you can create a plan to make more of your money work for you, and not the IRS. More specifically, I discuss: Understanding tax withholding Why adjusting tax withholding is important Major factors to consider when adjusting tax withholding How to determine the appropriate tax withholding or estimated payment amounts Steps to adjust tax withholding or making estimated payments Exemption from tax withholding Resources: Access Show Notes and Sign Up for the Retired·ish Newsletter HERE Free Retirement Jump-Start Analysis  Ask Cameron A Question!   The key moments in this episode are: 00:00:00 - Tax Withholding Challenges  00:03:17 - Importance of Adjusting Tax Withholdings  00:06:11 - Avoiding Underpaying Taxes  00:11:56 - Factors to Consider When Adjusting Withholdings  00:15:36 - Understanding Withholdings and Tax Advice  00:16:13 - Tax Implications of Inheritance and Investments  00:17:32 - Tax Considerations for Starting a Business  00:18:57 - Navigating IRS Withholding Calculator  00:25:32 - Options for Adjusting Tax Withholdings  00:31:51 - Qualifying for Tax Exemption  00:32:26 - IRS Lock-In Letter  00:33:04 - Updating Form w Four  00:34:11 - Maximizing Financial Growth