Keen On Retirement™

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.

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.

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:

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.

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.