The 2026 news cycle is spinning at a dizzying pace. Technology is rapidly upending how we work and live. With midterm elections on the horizon, our leaders in Washington are sharpening their visions for the future and policy proposals. And geopolitical tensions across the globe are giving investors something new to react to -- and worry about -- on a daily basis.

On today's show, we unpack some of the major stories we're monitoring and give you a clear-eyed perspective on the current economic outlook.

Matt Wilson, Keen Wealth's Chief Investment Officer and President, recently hosted an excellent webinar on Tax Planning Through the Four Stages of Retirement. In addition to providing a thorough overview of the tax issues that seniors should be prepared for, Matt also wanted to remind folks that the best time to ask questions about retirement is before you retire.

And I'm glad that several of our webinar attendees took Matt up on that offer!

On today's show, we discuss three follow-up questions to Matt's webinar that touch on not just taxes but also the value of working with a financial advisor on a holistic plan for retirement.

According to the most recent available data, the IRS collected $5.1 trillion in taxes in 2024. Just ten years earlier, it collected $3.1 trillion.

We all grumble about paying the government this time of year. And gathering all our forms and statements while we're in the middle of a partial shutdown isn't going to make Tax Day 2026 any more pleasant. But those trillions are also signs of a healthy economy that continues to grow and generate wealth, which is good for your long-term financial planning.

Still, just because the government needs our tax dollars to provide essential services doesn't mean you should pay one dollar more than you're legally obligated to pay -- this year, next year, or over the course of your lifetime.

On today's show, we discuss some trends and best practices for both tax planning and tax prepping and why I believe

When was the last time you checked your penny jar?

If it's looking a little emptier than usual, that might be because we're in the middle of a penny shortage!

The U.S. Mint has ceased production of the penny because the cost of making one ($0.0369) is now almost four times what it's worth as legal tender.

While this is yet another step towards a more digital, cashless economy, you might want to take a look at that jar before you bring it down to the bank. Having fewer pennies in circulation could drive up the value of some rare pennies, like the $2.4 million 1943-D Lincoln Wheat Cent!

With more and more of our financial lives moving online, it's becoming more and more important to stay vigilant against potential scams and stay current on the rules.

As we discuss on today's show, one wrong click could share valuable information with a crook or trigger some unintended tax consequences – especially if you're managing your money solo.

During my recent trip to Australia, I learned that navigating a foreign country can feel normal but different all at the same time.

On the one hand, my family and I enjoyed the familiar experiences of being on vacation, such as unplugging from our daily routines, relaxing on a long flight, seeing the sights, and spending time with loved ones.

But once we arrived in Brisbane, we had to get used to a new landscape and a new set of rules. The huge time zone difference. Driving a "ute" (utility vehicle) on the left side of the road and overtaking (passing) on the right. Calling "French fries" chips and our friends "mate." Keeping an eye out for wild kangaroos.

Retirees may feel like they're facing a similar "familiar but different" financial landscape this tax season. While many of the strategies my team at Keen Wealth are discussing with folks are tried-and-true, some rules and details are changing due to new legislation that's going into effect. Your financial plan, and your financial team, need to be ready to adapt to these new rules so that you don't miss a key deduction and pay more in taxes than you really owe.

On today's show, we discuss the One Big Beautiful Bill Act's changes to the tax code and some specific provisions that require thorough proactive planning before you file your taxes in April.

The freshness of the New Year can also help us gain a fresh perspective on what's really important and what we want to accomplish.

From a comprehensive financial planning perspective, that might mean looking beyond your numbers and thinking about what your money is really for.

On today's show, my Keen on Retirement co-hosts and I share a few words of wisdom that I hope will help you maintain balance during the inevitable ups and downs of the markets, the news, and your life in the year ahead.

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.

"This sounds too good to be true, but you've got to believe in those that are looking at it for you and trusting in the people with Pacific Life email addresses that are sending you the documents."

So many stories of financial fraud and mismanagement boil down to statements just like this one. All too often, the folks who are losing large sums of money are hardworking folks working 9-to-5s who don't have a team of professionals looking out for them, and whose finances may never recover.

But, in this case, the quote above is from racecar driver Kyle Busch, a two-time NASCAR Cup Series champion whose net worth is estimated to be around $80 million. Earlier this month, Busch and his wife Samantha sued Pacific Life insurance company for $8.5 million, alleging that Pacific Life misrepresented how a policy worked and lost almost $10.4 million that the Busches thought they were safely investing for retirement.

On today's show, we draw three important lessons from the Busches' lawsuit that could help you steer clear of a similar financial crash.