Keen On Retirement™

Most people think that retirement begins the day that everything stops: the early morning alarm, the commute, the meetings, the deadlines, and, of course, the paycheck. But in my experience, a successful retirement begins 24 months before your last day on the job. Your final two working years are arguably the most critical period of your financial life. They determine your tax flexibility for the next decade, your confidence in your income stream, and your ability to adapt when life doesn't go according to plan. While no one can predict the future, with comprehensive financial planning, you can build a robust margin for error that will act as a safety net throughout your retirement. When you're landing a plane, you don’t just cut the engines at 30,000 feet and hope for the best. You begin a gradual, calculated descent towards the airport environment and ultimately the runway. Retirement is no different. The smoother and more intentional the glideslope, the safer the landing.

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.

For a retiree with a multimillion-dollar portfolio, minor fluctuations in the markets might move your net worth up or down tens of thousands of dollars during a typical day, week, or month. After a year or two, these fluctuations will likely look like small blips on an upward, wealth-building trajectory. But what if you earmarked that same five-figure sum for a different ROI: a return on your health? Here is why incorporating personal training into your comprehensive financial plan during the early stages of retirement could be one of the best investments you ever make.

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.

This is it! The year you've spent decades working for, saving for, investing for, and planning for. Many people enter their first year of retirement focused on preventing things that could go wrong. But with a little forethought and a positive attitude, a lot can go right this year as well. Here are five keys to thriving financially, physically, and emotionally during your first year of retirement.

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.