Seven Essential Tips to Maximize Your Lifetime Social Security Benefits, #274
Release Date: 10/07/2025
Should You Add a Transfer on Death Beneficiary to Your Assets? #298
Retire With Ryan
On the show this week, I’m talking all about the topic of probate and how adding a Transfer on Death (TOD) or Payable on Death (POD) beneficiary designation to certain assets can help you avoid your estate being tied up in the probate process. You’ll learn which types of accounts allow for TOD or POD beneficiaries, why these designations might be preferable to joint tenancy, and the pros and cons of setting them up. I break down step-ups in cost basis, the impact on estate taxes, and touch on differences across states—plus considerations to make sure your estate plan actually fits your...
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Tax Extension Mistakes to Avoid This Filing Season, #297
Retire With Ryan
In the last episode, I discussed seven mistakes to avoid when filing your 2025 taxes. So in this episode, I'm going to discuss the tax-filing mistakes people can make when filing an extension. Here are the four most common extension errors that could cost you money, including misconceptions about payment deadlines, underestimating taxes, and the importance of understanding state-specific extension rules. You will want to hear this episode if you are interested in... [00:00] Mistakes that people can make if they're filing an extension [01:41] Importance of filing for an extension by...
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7 Tax Mistakes to Avoid When Filing Your 2025 Taxes, Ep#296
Retire With Ryan
Tax season is here, and if you’re just now gathering your documents to file your return—or preparing them for your CPA—this is the time to slow down and make sure you’re not making costly mistakes. In this episode, I walk through seven tax mistakes I frequently see both tax preparers and self-filers make when filing their returns. Some of these errors seem simple on the surface, but they can lead to penalties, missed deductions, delayed refunds, or paying more taxes than necessary. My goal in this episode is to help you avoid these pitfalls so you can file confidently and keep more of...
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What We Still Don’t Know About Trump Accounts, Ep#295
Retire With Ryan
If you watched President Trump’s recent State of the Union address, you probably heard about the new Trump accounts, also known as 530A accounts. In this episode, I break down how these tax-advantaged investment accounts are designed to work, who qualifies, and—just as importantly, what we still don’t know. There’s been a lot of excitement, especially around the $1,000 seed money for eligible children. But before you rush to open one, there are several unanswered questions that deserve your attention. What Are Trump Accounts—and Who Qualifies? Trump accounts were introduced...
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Is It Wise to Gift My Children Money While I’m Alive? Ep#294
Retire With Ryan
If you have children and you’ve been thinking, “Why wait until I’m gone to help them financially?”—this episode is for you. In Episode 294, I walk through the biggest things to consider before making gifts to your kids while you’re still alive, and I break down some of the smartest ways to do it without triggering unnecessary taxes. I’m seeing this trend more and more with my clients, and it makes sense. Financial markets have performed well, real estate has surged, and many retirees are in a stronger position than generations before them. But just because you can gift money...
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Learn the ABCs of Medicare, Ep293
Retire With Ryan
If you’re approaching age 65, Medicare can feel overwhelming fast. Between Parts A, B, C, and D and the timing rules tied to each—it’s easy to make a costly mistake if you don’t understand how the pieces fit together. In this episode, I walk through the Medicare “alphabet,” explaining what each part does, when enrollment matters most, and how your decisions interact with the rest of your retirement plan. We also cover common questions that come up when clients transition from employer-sponsored coverage to Medicare for the first time. Whether retirement is right around the corner...
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6 Changes To Social Security Happening in 2026, #292
Retire With Ryan
The landscape of Social Security is changing yet again. As we enter 2026, six big changes will impact both current and future retirees. I break down everything from the new cost of living adjustment (COLA), increases in the earnings test limit, and updated eligibility requirements, all the way to shifts in the full retirement age and the solvency projections for the Social Security Trust Fund. You’ll also hear practical tips on maximizing your Social Security benefits, how to prepare for what’s ahead, and why it’s more important than ever to have a solid retirement plan in place. ...
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Protecting Your Schwab Accounts From A RAT Attack, #291
Retire With Ryan
Have you ever fallen victim to a RAT attack? No, not the furry kind, a Remote Access Trojan attack. I’m discussing how cybercriminals use social engineering to target victims, and the real-world impact these threats can have on your investment accounts and personal information. I reveal the latest tactics scammers use, and, most importantly, offer practical tips to help you recognize warning signs, safeguard your accounts, and minimize your risk, whether you’re an individual managing your retirement nest egg or a business owner overseeing company assets. You will want to hear...
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Can I Contribute to My 401(k) and a Traditional IRA in the Same Tax Year?, #290
Retire With Ryan
A listener recently wrote in with a common and important retirement planning question: If I’m already maxing out my 401(k), can I also contribute to a traditional IRA in the same year? The short answer is yes—but whether it makes sense, and how much benefit you receive, depends on your income, tax situation, and long-term goals. In this episode, I break down how traditional IRA contributions work alongside employer-sponsored retirement plans, when those contributions are deductible, and what options are available if your income is too high for a deduction. We also explore alternative...
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Top 5 Growth ETFs to Own For 2026 and Beyond, #289
Retire With Ryan
Last week, we covered the best investments to preserve your money, but this week we are shifting gears to focus on growth. For retirees, the goal is to have an income that outpaces inflation, and historically, the best way to achieve that is by having 50% to 70% of your portfolio invested in stock funds. In this episode, I break down five specific Exchange Traded Funds (ETFs) that can help you grow your wealth in 2026. I discuss why I prefer ETFs over mutual funds, specifically focusing on cost, transparency, and liquidity, and provide the exact ticker symbols and expense ratios for the funds...
info_outlineYou might have seen those viral articles promising a mysterious multi-thousand-dollar Social Security “bonus,” but are they actually legit? On the show this week, I separate fact from fiction, debunking the myths and sharing seven actionable strategies to help you get the most out of your Social Security over your lifetime.
Whether you’re curious about how working longer, delaying your benefits, checking your earnings record, or understanding tax implications can impact your retirement paycheck, this episode is packed with valuable tips to help you make sure you’re not leaving money on the table.
You will want to hear this episode if you are interested in...
- [00:00] Retirement Planning Misconceptions Explained.
- [03:25] Filling in or replacing "zero" or low-earning years boosts benefits.
- [04:26] Reasons for and against early collection.
- [06:48] Repay benefits within one year of starting to “reset” your claim.
- [08:15] Eligibility requirements for spousal benefits.
- [12:28] How to check your Social Security earnings.
- [13:00] Strategies to delay taxable distributions and reduce Social Security taxation.
Debunking the Social Security "Bonus" Myth
Many retirees have seen headlines promising a massive Social Security “bonus" that most people don’t collect. Let’s be real, this so-called "bonus" isn’t some sort of secret benefit; it’s a reference to the cumulative value you could gain over your lifetime by paying a little attention to your Social Security strategy and reducing your tax liability. In other words, there’s no one-time check or hidden program, just savvy planning that can add up to tens of thousands more in your pocket.
1. Work Longer, Maximize 35 Years of Earnings
The Social Security Administration calculates your benefit using the highest 35 years of your working life. If you retire with fewer than 35 years of work, the missing years count as zero, lowering your benefit. Even for those with a full 35-year history, additional years of higher earnings (often later in your career) can replace lower-earning years, bumping up your monthly check. Working a little longer not only increases your benefit but may also put you in a better position for retirement overall.
2. Delay Claiming Benefits
While you are eligible to start at age 62, waiting until your full retirement age (typically 66 or 67), or even delaying to age 70, can significantly increase your monthly benefit. For every year you wait past full retirement age (up to age 70), you receive an 8% credit, on top of any cost-of-living adjustments. There are some exceptions where it may make sense to claim early, such as serious health issues or unique family situations.
3. Unwind an Early Claim with Repayment
If you’ve already claimed Social Security but then realize you made a mistake, there is a potential do-over option. If you started benefits within the past year, you can repay the benefits received (without interest) and reset your claiming strategy to earn a higher benefit later. This is a once-in-a-lifetime opportunity and includes repayment of any Medicare premiums withheld, so be sure this move fits your broader financial plan.
4. Don’t Miss Out on Spousal and Survivor Benefits
If you’re married, you can claim a spousal benefit up to 50% of your spouse’s benefit at your full retirement age. This strategy can be a huge game-changer for non-working or lower-earning spouses. When a spouse passes away, the survivor can step up to the higher of the two benefits, which is why it’s important to maximize the higher earner’s benefit for long-term security.
5. Check Your Social Security Earnings Statement Regularly
Mistakes happen, even with Social Security’s generally high record-keeping accuracy. Reviewing your annual earnings statement ensures all your income is being counted, and thus, your benefit is maximized. Errors not caught early can seriously reduce your benefit down the road.
6. Be Tax-Smart About Social Security Benefits
By smartly timing IRA distributions, capital gains, and part-time work, you can potentially reduce or even eliminate the tax owed on your benefits for several years. For couples with a combined income under $32,000, none of the benefit is taxable, while at higher incomes, up to 85% can be taxed. Knowing these thresholds is key to tax-efficient retirement income planning.
7. Get Advice When Needed
Social Security may be just one piece of your retirement puzzle, but it’s a critical one. Consulting with a financial advisor can help you coordinate claiming strategies, minimize taxes, and make the right decisions for your unique situation.
While there’s no hidden "Social Security bonus" waiting to be claimed, a thoughtful approach to your Social Security strategy can result in thousands, even tens of thousands, of dollars more in your retirement years.
Resources Mentioned
- Retirement Readiness Review
- Subscribe to the Retire with Ryan YouTube Channel
- Download my entire book for FREE
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