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.

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 that having a professional financial team in your corner is more important than ever.

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.

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.