Articles by Oakleigh Wealth
How to Evaluate Your Medicare Part D Drug Coverage
When it comes to Medicare, one area that deserves an annual check-up is your prescription drug coverage. Many retirees don’t realize that while Medicare Supplement (Medigap) policies generally lock you into your original carrier and plan, Medicare Part D drug plans are different. You can review and change your Part D plan every year during the Annual Enrollment Period (October 15 – December 7). Any changes you make will take effect on January 1. That flexibility is valuable — but only if you take the time to compare your options.
Beyond Resilience: Building an Antifragile Retirement
If there’s one thing I’ve learned working with families in retirement, it’s this: life rarely unfolds according to the spreadsheet. Markets move, health changes, families grow, opportunities arise. Some surprises are wonderful, others are extremely difficult.
The families who thrive are the ones who can adapt. Flexibility in retirement doesn’t mean giving up control. It means creating a plan that can bend without breaking. It’s about leaving room for change, so that when life doesn’t go according to plan, you still have choices.
This idea lines up beautifully with the work of Nassim Nicholas Taleb, whose book Antifragile explores how certain systems don’t just survive stress but actually grow stronger from it.
How Much Do You Need to Carry With You?
Packing light isn't just about luggage—it’s a metaphor. We carry more than we realize: fears, regrets, habits, busyness, expectations. Some of that “stuff” once served a purpose. But over time, it can become a burden.
Introducing Wealth.com: DIY Estate Planning with Advisor Support
Estate planning doesn’t have to be overwhelming. With Wealth.com, you can create a legally valid will or trust from the comfort of your home—no attorney required (unless you want one). This modern platform walks you through each step, and while Oakleigh Wealth doesn’t provide legal advice, we’re here to help you understand the key terms and decisions along the way.
Beauty is in the Eye of the Beholder: What the OBBBA Means for Your Taxes and Planning
On July 4, 2025, the “One Big Beautiful Bill Act” (OBBBA) was signed into law. While the name might sound like a joke, the changes it introduces to the tax code are very real, and they’ll affect nearly every household in some way, especially retirees and those approaching retirement.
Why Financial Projections Are Both Helpful—and Misleading
We humans like to know what’s coming. That’s why weather forecasts exist. And financial forecasts. And why so many people think of projections as the heart of financial planning.
And there’s some truth to that. Seeing your financial life mapped out over time—how your savings might grow, how your expenses will evolve—can be incredibly clarifying. But if we’re not careful, those projections can give us a false sense of certainty. They can feel like a crystal ball when they’re really just a spreadsheet.
This month, I recorded a podcast episode exploring the pros and cons of financial projections: when they’re useful, how they can go wrong, and what to focus on instead. Below are a few key takeaways.
Why Reviewing Your Beneficiaries Should Be Part of Your Regular Financial Checkup
When it comes to estate planning, one of the most overlooked—but most important—steps is reviewing your beneficiary designations. These designations can override the instructions in your will or trust, which is why they warrant regular attention.
A Closer Look at Hybrid or “Asset-Based” Long-Term Care Insurance
In a recent episode of the Make the Most of Your Money podcast, we spoke with insurance specialist Roger Cantu about how to protect your family and finances from the emotional and financial strain of a long-term care event. One solution is a hybrid or asset-based long term care insurance policy, which overcomes some key issues with traditional LTC insurance plans. This type of LTC policy is worth a closer look.
What to Do When the Market Drops: Bear Market Action Plan
It’s never easy to watch the market decline. While we know intellectually that staying disciplined is the right move, removing emotion from financial decisions is hard—especially when there’s always a real and unsettling reason behind the drop. Whether it’s a pandemic, financial panic, or global instability, downturns never feel like just numbers on a screen; they come with headlines that make it tempting to act. The highly charged 24/7 media cycle that follows you everywhere in your pocket doesn’t help either.
But history has shown that staying strategic, not emotional, leads to better long-term results. Still, there are things you can do to take advantage of market downturns instead of reacting emotionally.
Here’s a simple action plan based on how much the market has declined:
How to pay your taxes online
Whether you need to make estimated tax payments throughout the year, pay a balance due when filing your return, or submit a payment with your tax extension, making an electronic payment from your bank account is the fastest and most secure way. Below are step-by-step instructions to guide you through making these payments to the IRS.
Buffet has the highest cash balances of all time; should I sell everything?
A family member texted me after seeing headlines following Warren Buffett's annual letter to Berkshire Hathaway's shareholders (read the full letter here). A smattering of headlines read: "Warren Buffett amasses more cash and sells more stock" and "Why Warren Buffett's cash pile is growing, and what it means for markets."
In other words, "Is it time to get out of the market?"
The Backdoor Roth IRA
Roth IRA accounts are one of the most tax efficient retirement savings vehicles. But if your income is over the phase-out limits, you will not be able to contribute directly to your Roth IRA. Enter the so-called “backdoor Roth,” a loophole which allows you to add to your Roth IRA when your income is otherwise over the limit. BUT… it doesn’t come without risk.
John D’earth’s Retirement
Two weeks ago, The Daily Progress, Charlottesville’s local newspaper, featured one of the most inspiring retirement announcements I’ve ever read. John D’earth—the legendary jazz trumpeter, bandleader, and director of jazz performance at UVa—officially “retired” this past December.
Rolling funds from a 529 acocunt to a Roth IRA
A 529 plan is traditionally known for its role in helping families save for education expenses. However, recent legislative changes have introduced an exciting new possibility: the ability to roll over unused funds from a 529 account into a Roth IRA for the beneficiary. This feature can be a powerful tool for jump-starting retirement savings, but it comes with specific rules and limitations. Here’s what you need to know.
Should I take My Pension as a Lump Sum?
For many, employer pensions are a key part of retirement planning. While these plans are increasingly rare, they often represent a significant portion of anticipated retirement income. If you're nearing retirement or already receiving pension payments, you may face an important decision: Should you opt for a lump sum distribution or continue receiving a lifetime stream of payments?
How to Employ Your Children (and Why)
My oldest son always asks how he can earn money, so this year, I employed him to help pack and ship holiday gifts to all of my clients. He actually made my life easier during this busy time of year, but the best part was seeing his pride and satisfaction.
A Proclamation of Thanksgiving
This past Sunday, I heard this excerpt from Abraham Lincoln’s Thanksgiving Proclamation of 1863. It was penned mere months after Gettysburg, the bloodiest battle of the American Civil War. It was a year of perilous uncertainty when our nation was on the brink of moral and political collapse, and families were bitterly divided and grieving. And yet, even amidst strife and humbling loss, Lincoln extolled his hopeful thanksgiving for the nation’s many blessings.
529 Plan Hack: Maximizing state tax benefits by routing education expenses through a 529 plan.
529 plans are a powerful tools for funding education in the United States, offering tax-free growth and withdrawals for qualified expenses. In some states, they also come with an attractive bonus: state income tax deductions or credits for contributions.
While these incentives are designed to encourage long-term saving for education, savvy families may be able to utilize 529 plans to receive an immediate tax deduction for qualifying education expenses they are paying for now.
Fooled by Certainty: Embracing Uncertainty in a Random and Noisy World
We live in a world governed by random events, yet humans are terrible at thinking probabilistically. We vastly prefer certainty over probability, narratives of skill and design over luck, and we find all manner of patterns within noise.
We listen to the “experts” who talk confidently about the future and make concrete projections about what’s coming next. Can you imagine an economist who states, “There is a 60% chance of a recession next year” getting any air time? We much prefer the certainty of the broken clock, even if it’s only right twice a day.