Articles by Oakleigh Wealth
Doing Everything Right and Still Feeling Behind
Most of the people I work with are not living through the economic story of the moment. But they are watching it happen to their adult children.
You (the parent) did the things in roughly the order you were told to do them. School, work, a house, 2.1 children, a long stretch of saving, and the math worked out the way it was supposed to. So, when your son or daughter (the one with the good degree and the real job and the title that sounds impressive at Thanksgiving) feels permanently behind, it can be hard to make sense of it. The numbers on their pay stub are larger than yours were at that age. And yet the life those numbers are supposed to buy keeps receding from them in a way it did not for you.
There is a gap between a generation that found the ladder roughly where it expected it and a generation that keeps reaching for a rung that has moved, and it’s worth exploring. Not so you can tell your kids that they are imagining it, because they are not. And not so you can hand them a budgeting lecture, because they have heard it.
What To Do With a Concentrated Stock Position
My co-host, Taylor Stewart, told a story on our podcast recently that gets right to the heart of what makes concentrated positions so tricky. A client came to him with essentially all of his net worth in a single stock. Taylor gave what most advisors would consider sound advice: sell at least half and diversify. The client didn't follow that advice. The stock went up eight times.
What’s worth measuring
I've been thinking about the role that metrics play in life, prompted by a recent Derek Thompson interview with the philosopher C. Thi Nguyen, whose new book is called The Score: How to Stop Playing Somebody Else's Game. Nguyen has a useful term for what happens when a simplified measure quietly takes over a richer set of values: value capture. It happens, he writes, when your values are "rich, subtle, or developing," and then an institution or technology hands you a simplified, quantified measure, and that version takes over. We start with something meaningful, like giving our child a good education, eating healthy food, getting in shape, or having a stable financial life, and somewhere along the way, we slap a number on it. Sooner or later, the number starts setting the agenda. The metric becomes the thing.
What Is a Fulfilling Life?
The Masters is this week. I'm not much of a golfer, but I've always loved the tournament. There's something about the first full week of April, the azaleas, the quiet tension of Amen Corner. It draws you in even if you've never picked up a club.
But this year, the tournament has me thinking again about an interview Scottie Scheffler gave last summer. Scheffler is the best golfer in the world right now, and a favorite to win again in Augusta. At 29, he's won four majors, twenty career tournaments, and by any measure is living out the dream he's worked toward his entire life.
And yet, he said plainly that winning is not a fulfilling life.
Financial Planning and AI: What It Can Do, and What It Can't Do... Yet
A few weeks ago, a post by AI entrepreneur Matt Shumer started circulating in business and finance circles under the title “Something Big Is Happening.” It’s written for people outside the technology industry, and it makes an unsettling argument: that AI is improving faster than most people realize, that the people building it are more alarmed than they publicly admit, and that the disruption already underway in software engineering is coming for nearly every field that involves cognitive work. If you haven’t read it, I’d recommend it. Shumer is neither a doom-monger nor a utopian. He’s someone who watched his own job change dramatically in the span of only a few months.
Around the same time, the Atlantic ran a cover story on what AI may do to the labor market, and the New Yorker published a long profile of Anthropic — the company that builds Claude, one of the leading AI models — that grappled with some genuinely strange questions about what these systems actually are.
What none of those pieces can offer is the view from inside a financial planning practice. I’ve been using AI tools in my work for a few years now. The experience has been instructive, sometimes frustrating, and more recently, a little startling. So in addition to pointing you toward other people’s writing, I want to tell you what I’ve actually seen.
A Smarter Way to Think About Retirement Income
The 4% rule gave retirees a research-backed starting point. But it's static — it doesn't care what the market is doing, how old you are, or whether your income picture has changed. Here's a better framework.
When Your Child Turns 18: Financial and Planning Considerations for Parents
A college freshman is injured in a car accident. Her parents, who pay her tuition and insurance, drive three hours to the hospital—only to learn they have no legal right to her medical information.
Turning 18 is one of those milestones that feels symbolic more than practical. There’s no graduation ceremony, no obvious lifestyle change, and for many families, daily life looks exactly the same as it did the day before. But from a legal and financial standpoint, something significant happens overnight: your child becomes a legal adult.
What I Learned Rewatching Toy Story 1-4
We spent last week's snow days rewatching the Toy Story films. Like most Pixar movies, they work on multiple levels; what appears to be a story about friendship and childhood transitions also addresses parenting, purpose, legacy, and the feelings of obsolescence many of us experience as we age. The children who relied on us have grown up. We're replaced by younger colleagues at work. These questions can simmer for years, but they tend to come to a head as retirement approaches.
Portfolio Reviews Are (Mostly) a Waste of Time
A few weeks ago, Taylor (financial advisor, friend, and podcast cohost) was at the OU–Texas football game, catching up with college buddies before kickoff. As tends to happen when people know you’re a financial advisor, the conversation turned to the markets. It had been a rough day on Wall Street — the market was down about 2% — and someone asked, “What did you think about yesterday’s drop?”
He laughed and admitted I hadn’t really looked. He knew roughly what the market had done, but between family and work, he hadn’t followed the play-by-play. That answer got a few puzzled looks.
“What do you mean you didn’t check?” one asked.
Taylor told me later that if it weren’t for those conversations, he probably wouldn’t check the markets as often. Because in the grand scheme, those day-to-day moves don’t really matter.
That exchange got us thinking: how often should you actually review your portfolio — and what should you be looking for when you do?
A Big Change to 401(k) Catch-Up Contributions Is Coming in 2026
Thanks to changes enacted under the SECURE 2.0 Act, starting in 2026, many catch-up contributions will be required to be made as Roth contributions, meaning after-tax rather than pre-tax. This is a meaningful shift, and one that deserves some advance planning.
Let’s walk through what’s changing, who it applies to, and how to think about it.
Wherever You Go, There You Are
Over Thanksgiving, our family spent a week in Sicily, where we rented a home with close friends and their four children. It was one of those trips that checks all the obvious boxes: beautiful scenery, unforgettable food, layered history, and the kind of slow evenings and deep conversations that only happen when you’re far from normal routines. It was a week filled with laughter and adventure, but also chaotic mornings, tired kids, and all the familiar dynamics that come with traveling as families who know each other well.
In other words, it was wonderful. And it was real.
Using Your HSA in Retirement
For many retirees, healthcare is the biggest wild card in the plan. In retirement, Health Savings Accounts (HSAs) give you a lot of flexibility and tax advantages that other accounts do not.
HSAs have a rare triple tax advantage: contributions are deductible, growth is tax-free, and withdrawals are tax-free when used for qualified medical expenses.
Below is a simple guide to what is and is not allowed, how to use the popular “shoebox” strategy, and how HSAs can support long-term care needs
Spear Phishing Scams: A Growing Threat for Seniors
Fraud targeting older adults is reaching crisis levels—and the numbers are staggering. According to the latest FTC Data Spotlight (August 2025), Americans over 60 lost a record $700 million to imposter and phishing scams in 2024 alone—more than five times the amount reported just four years earlier. The FBI’s 2024 Internet Crime Report paints an even grimmer picture: seniors lost a total of $4.9 billion to scams last year, a shocking 43% increase over 2023. Not only are older adults reporting the most complaints of any age group, but their average losses—at $83,000 per victim—far exceed those of younger generations.
What’s driving this alarming surge? Scammers are leveraging sophisticated spear phishing tactics, often powered by artificial intelligence, to craft convincing messages that prey on life transitions, emotional vulnerability, and social isolation. These attacks are meticulously researched, highly personalized, and increasingly difficult to detect—even for the tech-savvy.
In this post, we’ll break down how spear phishing scams work, why retirees are prime targets, the emotional and financial toll these crimes inflict, and—most importantly—how you and your loved ones can recognize the red flags and stay protected.
Open Enrollment: Don’t Just Click “Repeat” This Year
Every fall, millions of employees (and retirees) face the same task: reviewing their benefits during open enrollment. And if you’re like most people, you might be tempted to simply check “same as last year” and move on.
I get it—benefits paperwork isn’t anyone’s idea of fun. But the truth is, these choices can have a meaningful impact on your finances and your peace of mind for the year ahead. Spending even an hour thinking them through can pay off in real dollars.
Here’s how to approach open enrollment with a clear framework so you can make smart, confident choices.
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.