Keen On 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.

During my recent trip to Australia, I learned that navigating a foreign country can feel normal but different all at the same time. On the one hand, my family and I enjoyed the familiar experiences of being on vacation, such as unplugging from our daily routines, relaxing on a long flight, seeing the sights, and spending time with loved ones. But once we arrived in Brisbane, we had to get used to a new landscape and a new set of rules. The huge time zone difference. Driving a "ute" (utility vehicle) on the left side of the road and overtaking (passing) on the right. Calling "French fries" chips and our friends “mate.” Keeping an eye out for wild kangaroos. Retirees may feel like they're facing a similar "familiar but different" financial landscape this tax season. While many of the strategies my team at Keen Wealth are discussing with folks are tried-and-true, some rules and details are changing due to new legislation that's going into effect. Your financial plan, and your financial team, need to be ready to adapt to these new rules so that you don’t miss a key deduction and pay more in taxes than you really owe. On today's show, we discuss the One Big Beautiful Bill Act's changes to the tax code and some specific provisions that require thorough proactive planning before you file your taxes in April.

This is it! The year you've spent decades working for, saving for, investing for, and planning for. Many people enter their first year of retirement focused on preventing things that could go wrong. But with a little forethought and a positive attitude, a lot can go right this year as well. Here are five keys to thriving financially, physically, and emotionally during your first year of 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.