Longtime Keen on Retirement listeners and friends of the firm are probably familiar with The Big Hat.

Matt Wilson, our Chief Investment Officer and President, is the proud owner of an oversized Dow 100,000 cap that he wears on our show from time to time. And when folks visit our offices, such as during our annual Holiday Breakfast, they often spot Matt's hat in his office and have a bit of a chuckle about its pie-in-the-sky prediction. More than once, I've heard someone tell Matt, "Gosh, I'll never see that in my lifetime."

But ... is the Dow hitting 100,000 really all that far-fetched?

On our final show of 2025, we look to market history and current trends to give you a head start in your financial planning for 2026.

I also share some stories from my big Hollywood red carpet debut as part of the Keen Wealth Foundation's charitable mission.

"How am I doing?"

"Am I falling behind my peers?"

"Do I have enough money?"

"How does my nest egg measure up?"

My team at Keen Wealth spends a lot of time talking folks through these kinds of questions. And, as the years go by and folks enter their 50s, 60s and beyond, that conversation evolves and begins to coalesce around another question: "Can I retire?"

You might try to answer these questions on your own by comparing your account balances to benchmarks or rules of thumb you've seen on social media. But are "averages" really the best way to assess where you are on your financial journey, especially as you get closer to retirement?

On today's show, we dig into some recent data on retirement savings and discuss why achieving your financial goals is about more than dollars and decimal points.

Does your financial team provide you with comprehensive tax planning, or just annual tax reporting?

When you file your 2025 taxes next April, you're essentially just reporting your financial data from the previous year.

At Keen Wealth, tax planning is a proactive, year-round process we use to put your annual report in the best shape possible before the ink dries and windows close.

And when it comes to your 2025 tax return, some important windows are closing right now.

Today, on our 250th episode, we explore some recent changes to tax law and potential moves that you need to discuss with your financial advisor before the end of the year.