Keen On Retirement™

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.

"How am I doing?" "Am I falling behind my peers?" "Do I have enough money?" "How does my nest egg measure up?" My team at Keen Wealth spends a lot of time talking folks through these kinds of questions. And, as the years go by and folks enter their 50s, 60s and beyond, that conversation evolves and begins to coalesce around another question: "Can I retire?" You might try to answer these questions on your own by comparing your account balances to benchmarks or rules of thumb you've seen on social media. But are "averages" really the best way to assess where you are on your financial journey, especially as you get closer to retirement? On today's show, we dig into some recent data on retirement savings and discuss why achieving your financial goals is about more than dollars and decimal points.

If you want proof that money alone doesn't buy happiness, just compare these two data points: By any measure, the United States is one of the wealthiest countries in the world -- if not THE wealthiest. And, at the same time, year after year, our collective happiness continues to decline. So, if having more money doesn’t create more happiness ... then what the heck are we all doing? Why are we up at the crack of dawn for our morning commute? What are all those long hours at the office for? Why are we topping off accounts longer than we have to if the ROI isn't making us feel better about our lives and our prospects for the future? A recent poll from YouGov for MarketWatch approached the relationship between money and happiness from a slightly different perspective. I was struck by how the findings align with a core belief we have here at Keen Wealth: financial happiness isn't about accumulating more money. It's about aligning the money you have with your values, your purpose, and a sense of freedom.

Does your financial team provide you with comprehensive tax planning, or just annual tax reporting? When you file your 2025 taxes next April, you're essentially just reporting your financial data from the previous year. At Keen Wealth, tax planning is a proactive, year-round process we use to put your annual report in the best shape possible before the ink dries and windows close. And when it comes to your 2025 tax return, some important windows are closing right now. Today, on our 250th episode, we explore some recent changes to tax law and potential moves that you need to discuss with your financial advisor before the end of the year.

As they're nearing retirement and finalizing their withdrawal, spending, and healthcare plans, many seniors aren't aware that there's a trap waiting on the other side of the finish line. IRMAA, the Income-Related Monthly Adjustment Amount, is a surcharge that can drive up Medicare Part B and D premiums for high-earning seniors. The catch? IRMAA is based on your modified adjusted gross income (MAGI) from two years prior. That means the Medicare premiums you pay at age 65 are determined by the income you earned at age 63. If you’re approaching retirement, it’s important to think ahead about what your retirement income will look like and how it could affect your Medicare premiums down the road. Proactive tax and withdrawal planning in the years leading up to retirement, and throughout retirement, can help reduce future IRMAA surcharges and keep your healthcare costs in check.