Keen On Retirement™

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.

As we head into the final stretch of Tax Season 2026, I imagine many folks are organizing statements and spreadsheets, receipts and reports, all the data that represents the last year of your financial life. Many seniors might also be looking at all those charts and numbers for some help with one of life's most complicated decisions: Is it finally time to retire? But in my experience, the most consequential choices folks make around retirement aren't mathematical. And many don't have one "right" or "wrong" answer. A successful retirement transition often comes down to making judgment calls that weigh tradeoffs, unavoidable uncertainty, and what matters the most to each individual. Here's how Keen Wealth can help you look beyond your numbers and make four decisions that could have a lasting impact on your Golden Years.

Many financial conversations around retirement focus on projections, simulations, probability of success scores, and average annual returns. And, since the long-term history of market investing continues to be positive, many folks see graphs trending up and to the right and think, “Okay, the math works. I’ve hit my number. It’s time to retire.” But what seniors often overlook, especially if they’re planning solo, are all the things that don’t show up in a typical financial projection. A slip-and-fall that changes your health care spending. A hurricane that drives up inflation. A once-in-a-generation global pandemic. No one can predict the future – not even my team at Keen Wealth. But I can tell you that the durability of a retirement plan isn’t just about your net worth or maintaining averages. It’s about sequencing how you use your assets and maintaining flexibility to deal with surprises. And as you get closer to retirement, the question you and your advisor should be answering isn’t, "Will it work if everything goes right?" It’s, "What happens if something goes wrong early?" Here are five stress tests your financial plan should be able to pass in the early stages of retirement:

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.

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.