Keen On Retirement™

When I think about the start of spring, I think about spending the Easter holiday with my family, the colors returning to our green spaces, a little more sunshine, and maybe a shower or two. Hail the size of baseballs? Not a part of my vision! But that’s what a massive storm brought to Kansas City a few weeks ago. Like so many folks, I'm still fixing broken windshields and dents on my family's cars and having my roof checked out. Of course, none of us can control the weather. But we can prepare for the unexpected by buying insurance, keeping some emergency cash in our savings, and making home upgrades that protect our most valuable assets. And, as we discuss on today's show while answering three timely listener questions, the same principle applies to financial planning. We can't control what's happening in the world or how the markets react to the news of the day. But we can be proactive about how we weather the storms of inflation and volatility.

The most critical decisions you'll make about retirement are never just about accounts, amounts, and calculations. And if you do try to create a "perfect" plan just by optimizing your numbers, you'll probably sacrifice the flexibility most seniors need to succeed in retirement. So ... If there are no “perfect” mathematical answers to major life and money decisions ... And over-optimization can backfire ... How does anyone actually make these important choices? Unfortunately, many folks don't. The multiple branching pathways we all face at major life transitions can look so daunting that the choices and implications might paralyze your thinking. Rather than game out those options and, potentially, make the "wrong" choice, too many seniors head into retirement with a back-of-the-napkin retirement plan and hope for the best. Of course, as we often discuss in our blog posts and podcasts, retirement planning is never as binary as "right" or "wrong." It's about analyzing competing trade-offs and choosing the ones that move you toward your retirement goals. And to make those choices, you need a framework.

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.

As I discussed in a recent blog post, many of the most important retirement decisions you’ll make aren't about your accounts and amounts. They're emotional choices that involve personal judgment, weighing trade-offs, and your most deeply held personal values. However, refocusing your retirement planning on the things that matter as much or more than money might spark a new concern: perfection. If hitting a number is your main retirement concern, you can always work longer, save and invest more, and keep topping off your accounts. But once you start thinking about your money as a tool that you'll use to support bucket list travel, philanthropy, lifelong learning, and your grandkid's education, the pressure to get every detail right on paper might feel overwhelming, even paralyzing. These three examples of financial planning "perfection" all start from a place that seems logical and proactive. But they all come with downsides that could sacrifice the flexibility and resilience most seniors need to succeed throughout 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.