2026: Helmets On, Enjoy the Ride

The big are getting bigger. And not just by a little. If you own a broad U.S. index fund, nearly 40 cents of every S&P 500 dollar now sits in just ten companies; those same ten produce roughly a quarter to a third of the index’s earnings. That’s concentration we haven’t seen in decades, and it’s mostly techtilted.

When One Stock Becomes Too Big: A Practical Guide to Handling Highly Appreciated Stock

Every investor dreams of it. You buy a stock early, hold it patiently, and years later realize one position has quietly become the engine of your entire portfolio. It feels validating. It feels smart. And then, usually right after that feeling sets in, it starts to feel uncomfortable.

Be Prepared for Tax Season

Tax season has a way of sneaking up on people. One minute it’s January and everyone is easing into the year, and the next minute your inbox is full of tax forms, “important documents,” and well-meaning reminders to file early. Every year, I see smart people feel rushed, confused, or worried they’re missing something.

Medicaid Trusts: What They Are, Why People Use Them, and the Parts That Get Left Out

If you’ve spent any time around retirement conversations, caregiving discussions, or estate planning chatter, you’ve almost certainly heard some version of this sentence: “We’ll just put everything in a trust so Medicaid pays for the nursing home.” It sounds clean. It sounds decisive. And unfortunately, it’s usually missing about half the story.

Your 2026 Playbook: Enjoy the Gains, Respect the Math

New calendar. Same nerves. After a year that started with tariff drama and ended with fresh market highs, investors are stepping into January 2026 asking the only question that really matters: now what?

A 401(k) Rule Change High Earners Over 50 Should Know

If you’ve ever been named executor of someone’s estate, you know that it comes with a strange mix of emotions. On one hand, it’s an honor. Someone trusted you enough to put their financial life and final wishes in your hands. On the other hand, it can feel like someone just handed you the keys to an unfamiliar car and said, “Take it on a road trip. Also, there might be a few parts missing.”

2026 Equity Market Trends

The big are getting bigger. And not just by a little. If you own a broad U.S. index fund, nearly 40 cents of every S&P 500 dollar now sits in just ten companies; those same ten produce roughly a quarter to a third of the index’s earnings. That’s concentration we haven’t seen in decades, and it’s mostly techtilted.

So You’ve Been Named Executor. Now What?

If you’ve ever been named executor of someone’s estate, you know that it comes with a strange mix of emotions. On one hand, it’s an honor. Someone trusted you enough to put their financial life and final wishes in your hands. On the other hand, it can feel like someone just handed you the keys to an unfamiliar car and said, “Take it on a road trip. Also, there might be a few parts missing.”

What America Could Learn From Australia’s Retirement System

Every so often, the retirement world gets a jolt of attention from the headlines, and this week delivered a big one. President Trump said his administration is taking a serious look at whether the United States should adopt an Australian style retirement system. Anytime a president floats the idea of rethinking how Americans save for retirement, it deserves some unpacking. Not panic. Not celebration. Just a clear-eyed walk through what this could mean.

Home Equity: The Quiet Strength Inside a Modern Retirement Plan

Retirement today looks very different from what most people grew up imagining. Costs have risen, longevity has increased, pensions have largely disappeared, and the market cycle seems to shift temperament every few years. Through all that change, many households have stayed steady. They worked hard, saved consistently, raised families, built careers, and built lives around the homes they own.