Keen On Retirement™

Two of the saddest words a retiree can say are "If only ..." No one makes it through their entire life without a few missteps. But your Golden Years are supposed to be about enjoying the freedom, relationships, and, yes, money that you've spent decades cultivating. The good news for pre-retirees is that regret isn't inevitable. If you learn from the experiences of seniors who've gone through some ups and downs already, you can plan ahead so you're not spending your retirement dwelling on do-overs. Let’s explore ten of the most common "If onlys" I've heard in my 30-plus years as an advisor and how you can prepare to face them with clarity and confidence.

"Risk" and "uncertainty" are similar concepts. But your financial plan has to be prepared to cope with both. I think that mix is what’s making some folks a little uneasy right now. In addition to the typical risks that all investors accept, we're also dealing with uncertainty around the government shutdown and what the effects on the economy will be until our leaders get back to the negotiating table. And, despite strong market returns this year, some observers are uncertain about the outsized impact that big tech companies might be having on portfolios. On today's show, we try to clear away some of the fog around the shutdown and the latest market data so that folks can start clarifying their plans for 2026.

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.

Change is in the air every fall – not just in the leaves and weather, but in your financial planning. At this time of year, the federal government announces some important rate adjustments that affect tax planning and retirement benefits for the year ahead. And complicating matters this fall is a government shutdown that has many seniors worried about the benefits and services that they’ve earned, and that they rely on. On today’s show, we answer questions from some very astute listeners in the Keen on Retirement audience who are already looking ahead and wondering what they need to prepare for as we move towards the end of the year.

Way back in February 2019 I wrote a blog post titled "Are You in the Top 1%, 5%, or 10% of Income Earners?" While digging into the numbers, I also cautioned folks about worrying too much about how their finances stack up against those of other people, especially if they're looking at life through the lens of social media. Almost six years, one pandemic, and a couple of technological leaps later, both the numbers around wealth and the influence of the media have gone up. The financial trends aren't surprising. High earners tend to be good investors. Good investors tend to have the discipline to stick to their plans through regular ups and downs. And despite those ups and downs, the markets continue to grow wealth for investors. But as we're living more and more of our lives online, I think our view of what "wealth" really means and the true value of money is becoming more and more distorted. Let's take a look at the latest data on affluence and try to gain a little clarity on how these trends might affect your thinking about financial planning and living your best life in retirement.

In 1988, William Post won $16.2 million in the Pennsylvania lottery. A year later, he was $1 million in debt. First, he splurged: houses, cars, a plane. Then a former girlfriend sued him for a third of his winnings. His brother was arrested and convicted for hiring a hitman to kill Post and his then-wife in hopes that he'd inherit a share. And after sinking money into a failing family business, Post spent time in jail for firing a gun over the head of a bill collector. In the end, Post said he was happier living quietly on $450 a month and food stamps than he was when he was rich. Post's story is an extreme example of the bad decisions and bad luck that leave so many lotto winners wishing they'd never won at all. But while you're more likely to be struck by lightning than hit the winning numbers, an inheritance, a promotion, a legal settlement, selling a business, and reaching retirement can all create significant windfall scenarios as well. On today's show, we offer some tips on how to manage life-changing money, including tax planning, dealing with friends and family, and the kind of team that can help you protect your assets.