Financial Articles - Hobart Wealth

How Money Scripts Influence the Choices We Make – Part Two

July 28, 2026 | in Financial Planning, Retirement Planning

At the end of the first article in this series, I suggested that the first step in understanding your money script is simply noticing when it appears. That idea sounds straightforward on the surface, but in practice, money scripts rarely announce themselves in a clear or obvious way.

Nobody walks into my office and says, “My tendency toward money vigilance is creating an emotional barrier to retirement spending.” That would definitely make the meeting efficient and frankly, a little unsettling, but it is not usually how these conversations begin. Instead, someone says they need to keep another $500,000 in cash, or that they want to work one more year, or that the family vacation feels too expensive even though the financial plan comfortably supports it. They may explain that they cannot sell a concentrated investment because it has always done well, or that they need to help an adult child one more time.

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Why Smart People Make Complicated Decisions About Money – Part One

July 21, 2026 | in Financial Planning, Retirement Planning

A few years ago, I started with a couple who had done almost everything right.

They had built successful careers, saved consistently, avoided unnecessary debt, and accumulated a portfolio that most people would consider more than enough for a comfortable retirement. When we reviewed their financial plan, the numbers were clear: they could retire whenever they wanted.

One spouse leaned back in their chair and said, “So… we’re done? We can actually do this?”

We would have loved to stay where we were. It was familiar, comfortable, and already felt like home. But once we started looking honestly at the space, the layout, and everything that comes with adding a child to the equation, it became pretty clear that making it work long term was going to be difficult. Babies may be small, but they come with an impressive amount of furniture, equipment, laundry, and general logistical chaos.

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Perspective at Mid-Year

July 14, 2026 | in Financial Planning, Investment Planning

My wife and our two boys spent last week in Southport, North Carolina, celebrating the Fourth of July with our family. It’s become one of those traditions we genuinely look forward to every summer, and it’s become even more meaningful now with a three-year-old and one- year-old.
The streets are draped in red, white, and blue, American flags sway from nearly every storefront, boats fill the waterfront, and the smell of sunscreen, salt air, and backyard cookouts seems to linger everywhere you go. The parade is still one of my favorite parts of the week. Watching veterans, first responders, scout troops, local businesses, and families make their way through downtown is a simple reminder that, despite everything happening in the world, there are still plenty of reasons to be optimistic about our future.
This year felt especially meaningful as our country celebrated its 250th anniversary. I couldn’t help but reflect on where we’ve been as a nation, the sacrifices that made those celebrations possible, and the resilience that has carried America through generations of uncertainty. Our history has never been a straight line, yet time and again we’ve found ways to innovate, adapt, and move forward.

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America’s Two Housing Markets, and What Congress Is Trying to Do About Them

July 8, 2026 | in Financial Planning

About a year and a half ago, after we found out we were expecting, Lizy and I began a journey almost everyone is familiar with: trying to figure out where, exactly, we were going to raise a growing family.

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The 5 Numbers Pre-Retirees Need Before Giving Notice

June 30, 2026 | in Financial Planning, Retirement Planning

There is a point in nearly every retirement planning conversation when someone reaches an inflection point.

For years, the questions are comfortably theoretical. Am I saving enough? Should I contribute more to my 401(k)? At what age could I reasonably retire? Retirement sits somewhere in the distance, safely tucked behind several more performance reviews, tax returns, and company holiday parties.

Then one day, the question bubbles up because something at work happens, our health changes, or we’re just flat out ready for a change.

“Could I actually give notice?”

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The Difference Between Trust and Preparedness

June 23, 2026 | in Estate Planning, Financial Planning

When people think about financial risk, they often picture stock market declines, recessions, inflation, or changes in tax law. Those are certainly real risks, and they deserve attention. Yet after years of sitting across the table from families, I’ve become convinced that the events that create the most stress are usually far more personal. The moments that truly test a financial plan rarely begin with a headline on CNBC. More often, they begin with a phone call from a doctor, an unexpected diagnosis, the loss of a spouse, a cognitive decline that unfolds gradually over time, or a life transition that nobody anticipated when the plan was originally built.

In other words, the greatest challenges are often not financial events at all. They’re human events that happen to carry financial consequences.

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Beyond the IPO

June 16, 2026 | in Financial Planning, Investment Planning

Last week, I attended a wealth symposium in Washington, D.C. and one of the more
interesting takeaways had little to do with stock prices, interest rates, or election
forecasts.

During discussions featuring former Federal Reserve Chair and Treasury Secretary
Janet Yellen, Democratic strategist James Carville, and Republican strategist Karl Rove,
a common theme kept emerging. Despite their different backgrounds and perspectives,
all three spoke about the resilience of the American people, the strength of our
economy, and the unique ability of this country to innovate and create opportunity.

As I listened, I could not help but think about one of the biggest investment stories
capturing headlines today: the growing space economy.

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Supercharging Roth Conversions with Charitable Giving

June 10, 2026 | in Estate Planning, Financial Planning, Legacy Planning

What I’ve learned is that backpacking isn’t about adding comfortable, luxurious items to my pack. It’s about figuring out what you can remove without sacrificing the experience. Nobody reaches mile 15 wishing they had packed more stuff. The biggest gains usually come from eliminating the things that were weighing me down in the first place.
Financial planning tends to work the same way. When we’re building wealth, most of our focus is on accumulation. We spend decades adding. More savings, more investments, and more retirement accounts. And at some point, we’ve added so much that we’re not quite sure what’s in our “pack.”

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Don’t Let IRMAA Drive Your Retirement Plan

June 3, 2026 | in Financial Planning, Investment Planning

Most retirees have never heard the term IRMAA until they enroll in Medicare or begin discussing retirement income planning. Once it enters the conversation, however, it often becomes a major focus. Questions about Roth conversions, capital gains, retirement account withdrawals, and other income decisions suddenly take on added importance because of their potential impact on Medicare premiums.

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Beach Tents and Restricted Stock

May 27, 2026 | in Financial Planning, Investment Planning

Growing up, my family always went to Oak Island, North Carolina, a tradition that still stands to this day. If you’ve never been, it’s not the polished, energetic, high-rise version of a bustling beach town. Oak Island is different. It’s quieter, more lived-in, and unapologetically real in a way that feels harder and harder to find along the Carolina coast.

It’s the kind of place where faded beach cottages sit on stilts beside newer homes with wide porches and rocking chairs, where golf carts drift down side streets carrying sunburned kids with sandy feet and melting ice cream cones, and where seafood restaurants still write their specials by hand out front while seasoned fishermen crowd the piers swapping stories about tides and bait like they’re discussing the stock market.