Retire With Ryan
In this episode, I’m helping you kick off 2026 by reflecting on financial habits that pave the way for a successful retirement. As we set our goals for the year ahead, I share the four key traits I’ve observed in successful retirees, drawn from years of experience working with people from all walks of life. You’ll hear practical advice on how to work hard and invest consistently, the importance of living within your means, and ways to avoid common investment pitfalls that can derail your progress. Whether you’re just starting your retirement planning or fine-tuning your financial...
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As we turn the calendar to 2026, I reveal my forecasts for the stock market, interest rates, and top asset classes, and take a look back at how my 2025 predictions stacked up against reality. From the S&P 500’s rollercoaster performance to the ongoing rivalry between growth and value stocks, and even a showdown between bitcoin and gold, I break down what the numbers were, where I hit the mark, and where I missed. You’ll also hear my insights on international versus U.S. stocks, the outlook for small caps, and what the Federal Reserve might do with interest rates in the year ahead. Get...
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2025 has been a year of significant highs and lows, a bittersweet time marked by personal loss but also tremendous growth in our community of listeners and clients. As we wrap up the year, I wanted to take a moment to reflect and, more importantly, to give back by answering the most pressing questions on your minds. In this episode, I’m tackling the top 10 most asked financial questions I received in 2025 from both clients and listeners. From the future solvency of Social Security and the reality of rising inflation to the specifics of Bitcoin and long-term care, we are covering the topics...
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529 college savings plans are a favorite tool for families looking to fund education, but recent updates have made them even more compelling. With the passing of the One Big Beautiful Tax Act in 2025, there have been some exciting changes to what you can use 529 funds for, including expanded coverage for K-12 tuition, test fees, vocational programs, and support for learning differences. I also discuss the various tax advantages of contributing to a 529 plan, like state tax deductions, tax-deferred growth, and even the ability to roll leftover funds into a Roth IRA for your child. He offers...
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In the season of giving, we’re discussing making charitable contributions in 2025 and 2026. Americans are known for their generous donations to worthy causes, but understanding the best ways to give and maximize your tax benefits is key. This episode covers four effective strategies for making charitable contributions, from utilizing Qualified Charitable Distributions (QCDs) from your retirement accounts to cash donations, gifting highly appreciated stock or real estate, and using donor-advised funds. I also break down recent and upcoming tax law changes that impact your ability to itemize...
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Healthcare planning is a huge part of getting ready for your retirement. In this episode, I tackle one of the most pressing updates for retirees: the latest changes to Medicare premiums for 2026, including important surcharges, deductibles, and strategies to help you manage your healthcare expenses. I’m helping you understand the significant increases in Medicare Part B premiums and deductibles, the impact these changes will have on your Social Security benefits, and why waiting to claim Social Security might pay off. Listen in to get helpful strategies for appealing IRMAA surcharges...
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As 2025 comes to a close, we’re here to help you make the most of year-end tax planning. I’m explaining seven actionable strategies to help you minimize your tax liability and optimize your retirement savings before the New Year. From maximizing retirement plan contributions and exploring Roth conversion opportunities to using donor-advised funds for charitable giving and getting the most from your health savings accounts, this episode is packed with practical advice. The insights I’m sharing in this episode will guide you through the essential moves you need to consider before...
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There are important changes coming to 401 (k), 403 (b), and 457 retirement plans in 2026, so I’m focusing on how these updates may impact catch-up contributions for individuals over age 50. With the Secure Act 2.0 on the horizon, higher earners will soon have to make their catch-up contributions as Roth (post-tax) rather than pre-tax contributions, potentially affecting their take-home pay and tax strategies. Tune in as I walk you through what you need to know, how to prepare for these new rules, and actionable steps to make the most of your retirement savings. You will want to hear...
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If you’ve spent any time on social media or read personal finance blogs, you’ve likely encountered a buzz around Roth IRAs and, specifically, Roth conversions. This week I’m discussing the details of Roth conversions, what they are, how they work, and why they’re crucial for those looking to optimize their retirement finances. Roth IRAs hold a special appeal: the promise of tax-free income in retirement. And most people would agree that having tax free income in retirement is preferable over having taxable income. Yet, for many people, especially those in their 50s and older, most of...
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Retirement planning is an ever-evolving process, and staying informed about changes to Social Security, Medicare, and tax limits is crucial to making the most of your golden years. On this episode of Retire with Ryan, I’m sharing important updates on the 2026 Social Security cost of living adjustment (COLA), projected changes to Medicare Part B premiums, and strategies for managing income in retirement. The newly announced cost-of-living adjustment (COLA) for 2026 will see benefit checks rise by 2.8%. I break down how the yearly adjustments are calculated, why they matter for seniors,...
info_outlineIn this episode, I’m helping you kick off 2026 by reflecting on financial habits that pave the way for a successful retirement. As we set our goals for the year ahead, I share the four key traits I’ve observed in successful retirees, drawn from years of experience working with people from all walks of life. You’ll hear practical advice on how to work hard and invest consistently, the importance of living within your means, and ways to avoid common investment pitfalls that can derail your progress.
Whether you’re just starting your retirement planning or fine-tuning your financial strategy, this episode is full of actionable tips to help you improve your financial life in 2026. If you’re ready to take charge of your future and put a solid plan in place, this episode is a must-listen.
You will want to hear this episode if you are interested in...
- 00:00 Retirement success traits revealed.
- 05:29 Budgeting for financial growth.
- 07:49 Invest simply and consistently.
- 10:36 Improve and grow net worth.
- 13:38 Keep an eye on your net worth.
Four Habits of Highly Successful Retirees
There’s no magic bullet to achieving a comfortable retirement. Many successful retirees weren’t born into wealth; in fact, about 80% of millionaires started with little and built their nest eggs from scratch. The through-line is diligence and perseverance.
A powerful habit among this group is paying themselves first. Rather than saving what’s left at the end of the month, successful retirees set aside a portion of their income before budgeting for other expenses. Many automate investments into employer-sponsored retirement accounts or other savings vehicles. This intentionality ensures that the priority remains on building wealth, not just sustaining a lifestyle.
Budgeting plays an essential role here. I recommend reviewing your annual spending, categorizing transactions, and identifying excesses. Small changes can help you free up cash for investments and debt reduction. If you struggle with credit card overspending, consider switching to cash or debit cards, which make it easier to visualize your available funds and stay disciplined.
There’s also a growing temptation to “keep up with the Joneses,” especially when social media showcases other people’s amazing vacations! Appearances can be deceiving, you never know whether your neighbours are deeply in debt despite flashy photos. The key is to focus on your own financial journey, not someone else’s highlight reel.
Keep Your Investments Simple
Despite the barrage of complex investment themes and “get rich quick” schemes circulating online, the most effective investors stick to the basics. Avoid speculative strategies like day trading, option contracts, and penny stocks for the bulk of your portfolio. These approaches can lead to significant losses, or even financial ruin.
Successful retirees typically lean on a diversified, straightforward mix of investments: blue-chip stocks, index funds, bonds, and some real estate. A simple, repeatable investment plan not only reduces stress but also reduces the chance of costly errors. If an investment sounds complicated or “too good to be true,” it likely isn’t the right tool for you.
Track Your Net Worth, Every Year
A great habit to get into is consistently tracking your net worth. For example, every year, I take inventory and value all of my assets, subtract any liabilities, and calculate my own net worth. This exercise isn’t just about patting myself on the back, it’s an important annual check-in on financial progress which helps me course-correct if I’m getting off track.
If you discover stagnant or shrinking net worth, it’s a signal to look at spending, debt, or investment choices. For those carrying high-interest debt (over 6–7%), prioritizing repayment can yield safer and higher “returns” than most investments. Even in retirement, monitoring net worth is vital. Spending down savings is natural, but keeping an eye on the pace ensures your money lasts as long as you need it to.
Take Action Today
Successful retirees don’t wait for luck or windfalls, they put in the work, invest with discipline, stay clear of fads, and track their progress. Start by reviewing your own budget and net worth, and set realistic, meaningful goals for the year ahead. Your future self will thank you.
Resources Mentioned
- Retirement Readiness Review
- Subscribe to the Retire with Ryan YouTube Channel
- Download my entire book for FREE
- Budget Worksheet
- Net Worth Spreadsheet
Connect With Morrissey Wealth Management
www.MorrisseyWealthManagement.com/contact