What Order Should I Start Withdrawing From My Investment Accounts In Retirement, #318
Retire With Ryan
When you’re moving into retirement, you’re most likely to be starting to ask yourself which investment accounts you should start drawing from first. There’s really no universal answer—retirement withdrawal strategies are deeply personal and situation-dependent. But understanding the implications of each account type and the factors that influence withdrawal order can have a massive impact on your tax burden and the longevity of your assets. You will want to hear this episode if you are interested in... [00:00] Retirement withdrawal strategy options [06:37] Roth IRA and...
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3 Ways To Make The Most of Your Restricted Stock Units, #317
Retire With Ryan
On the show this week, I answer a listener question about restricted stock units, or RSUs—what they are, how they're taxed, and the best strategies for managing them as they vest. I'll take an in-depth look at different types of vesting schedules, tax implications, and the practical choices you have when your RSUs become available. This episode is all about giving you clear guidance to help you make informed decisions about RSUs and making sure your retirement strategy is on the right financial track. You will want to hear this episode if you are interested in... 00:00 Explanation of...
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Accessing Your 401k Early With The Rule of 55, #316
Retire With Ryan
For many Americans, the idea of retiring before age 59 and a half often seems out of reach, particularly when the bulk of their savings sits in an employer-sponsored 401(k) or 403(b) plan. Traditionally, the tax code penalizes early withdrawals from these accounts. However, the Rule of 55 could open the door to a more flexible, penalty-free early retirement. On this episode, I’ll share more about this IRS provision, who qualifies, how to use it wisely, and potential hazards to avoid. You will want to hear this episode if you are interested in... [00:00] Overview of the Rule of 55 and...
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How To Avoid Taxes On The Sale Of Your Primary Residence, #315
Retire With Ryan
For many retirees, their home isn't just a place of comfort, it’s one of the largest assets on their balance sheet. However, beyond the emotional value and the years of accumulated equity, there's an often-overlooked reality: selling your primary residence can bring an unexpected tax bill. If you’re contemplating a sale or want to ensure you’re planning wisely, understanding the IRS’s primary residence capital gains exclusion is essential. On the show this week, I break down what this exclusion means, who qualifies, how to maximize its benefits, and the critical planning steps to avoid...
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Give Your Child or Grandchild A Head Start On Retirement With a Trump Account, #314
Retire With Ryan
On July 4, 2026, a groundbreaking opportunity opened for parents and guardians aiming to give their children a head start on their financial journey: Trump Accounts. Created as part of the OBBA Tax Act (“One Big Beautiful Bill” Tax Act) of 2025, these tax-advantaged investment vehicles provide a unique way to grow wealth for minors. In this episode, I break down what Trump Accounts are, who’s eligible for generous bonuses, how to get started, and how they compare to other common savings options like 529 plans. You will want to hear this episode if you are interested in... [00:00]...
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Avoid These 7 Scenarios to Keep Your Medicare Premiums Lower In Retirement, #313
Retire With Ryan
Medicare brings peace of mind to millions of retirees, but for those with higher incomes, there’s an added layer of complexity called IRMAA—the Income Related Monthly Adjustment Amount. If your modified adjusted gross income (MAGI) crosses certain thresholds, you may end up paying substantially more for your Medicare Part B and Part D coverage. In this article, we break down how IRMAA works, outline common scenarios that may unexpectedly raise your premiums, and offer actionable strategies to help you avoid unnecessary costs during your retirement years. You will want to hear this...
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Do Actively Managed Funds Perform Better Than Index Funds In Volatile Markets? #312
Retire With Ryan
When it comes to planning for retirement, one of the most commonly faced decisions is how to invest for long-term growth and stability. In turbulent times, market volatility often generates renewed debate on whether index funds, or their actively managed counterparts, offer the better path for accumulating wealth. On this episode of the show, I’m unpacking what index funds are, how they stack up against actively managed funds, and what the latest data reveals about performance during both quiet and volatile markets. You will want to hear this episode if you are interested in... ...
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Is Your Money Safe With Schwab or Fidelity? #311
Retire With Ryan
This week, I’m tackling a question that’s on the minds of many investors: How safe is your money with major brokerage firms like Fidelity and Charles Schwab? In light of recent high-profile bank collapses and widespread concerns about financial security, I discuss how banks and brokerage firms operate differently, what protections exist for your investments, and what would happen if a major brokerage firm were to collapse. Whether you’re considering how best to safeguard your assets or wondering about the real risks of brokerage failures, this episode will provide the clarity and peace...
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How To Make Your Brokerage Account Work Like A Roth IRA, #310
Retire With Ryan
When it comes to planning for retirement, Roth IRAs have gained widespread attention for their tax-advantaged status and the promise of tax-free withdrawals in retirement. Financial experts, YouTubers, and podcasters have been touting the benefits of contributing to or converting assets into Roth accounts for years. But an often-overlooked vehicle could empower you to manage your investments just as efficiently: the humble taxable brokerage account. Surprisingly, with the right strategy, you can even pay 0% capital gains tax, mirroring one of the biggest appeals of a Roth. You...
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5 Reasons To Not Invest Your Retirement Savings In Variable Annuities, #309
Retire With Ryan
Variable annuities are often promoted as a secure way to generate guaranteed income during retirement, drawing the attention of retirees seeking stability for their nest eggs. But beneath the surface, these products frequently come with complications and costs that can erode your savings and limit your financial flexibility. In this episode, I share the details of the often-overlooked downsides of variable annuities and give you some important insights every investor should consider. You will want to hear this episode if you are interested in... [03:14] What is a Variable Annuity?...
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