Keen On Retirement

As we discussed on a recent podcast, converting money from a traditional IRA into a Roth IRA could be a beneficial move this year due to ongoing market volatility. But that's not an automatic decision. Everyone's retirement plan and goals are different. Everyone's situation in life is different. And while a well-timed Roth conversion can help folks save money now and build wealth in the future, you shouldn't be thinking about a conversion as a lifesaver that's going to support you through some turbulence all by itself. In fact, here are several scenarios where a Roth conversion could hurt your retirement plan more than it helps.

According to recent data, 62 has become the new 65. This generation of healthier, more active, more connected seniors wants to start enjoying their Golden Years as soon as possible. But there's one reason why age 65 is still a major marker on a retirement timeline: Medicare eligibility. Early retirement can also trigger some critical decisions about the best time to start claiming Social Security benefits. Let's look at five items on Keen Wealth's early retirement checklist that we use to help seniors bridge the gap to Medicare and Social Security.

Figuring out "the perfect time" to retire is only partially a financial decision. After all, if the second half of your life was just about money, then no one would ever stop working and earning. But when your retirement timeline intersects with major economic uncertainty, it's understandable that the money side of the equation might start to feel a little more important. News headlines blaring words like DOWNTURN, INFLATION, and RECESSION can overwhelm plans you've been making for years, and the goals you've been dreaming about for decades. It's at these uneasy moments that the true value of a comprehensive financial plan shines through. Right now, most folks who are willing to stick with their plan and work closely with a trusted advisor should be able navigate some turbulence and stay on course for a secure retirement.

For the eighth year in a row, the happiest country in the world is ... Finland! An annual collaboration between Gallup polling, the University of Oxford, and the United Nations, the 2025 World Happiness Report asked respondents from more than 130 countries to rate their lives on a scale from zero (the worst) to 10 (the best). Researchers also factored in questions about kindness and generosity, as well as how people perceive the benevolence of their neighbors. Not only did Finland claim the top spot, but fellow Nordic countries Denmark, Iceland, Sweden, and the Netherlands rounded out the top five. And the United States? We actually dropped from 23 last year down to 24, due in part to younger people feeling more pessimistic about the future. So, where would you rate yourself on that scale? Is there anything we can do to experience more happiness in our lives? And how does money fit into this equation? Let's look at the three main conclusions that the WHR drew from its data and think about how we can apply those lessons to comprehensive financial planning.

At the 2025 Barron’s Advisor Independent Summit last month, my Keen on Retirement cohosts and I attended an inspiring keynote address from Chip Conley, author and former Head of Global Hospitality for Airbnb. Chip's talk was called "Why Your Best Years Are Ahead of You," a topic that certainly aligns with how Keen Wealth approaches its financial planning mission, especially as folks prepare for retirement. Today I want to share eight specific aspects of healthy aging Chip discussed that are also important parts of Keen Wealth’s comprehensive financial planning process.

If you receive most of your financial advice from cable news and social media, you might feel like we're perpetually on the brink of a recession. The prospect of a major downturn can feel especially unsettling for those whose short-term financial goals include retirement. Even aspiring retirees who do understand the inevitable ups and downs of investing might worry that now isn't "the right time" to retire. One of the benefits of the Keen Wealth Advantage is that we don't just react to external economic events, we proactively plan for a wide variety of contingencies -- including recessions. And while retiring during a downturn might sound like bad timing, with proper planning it's possible to retire on your terms, and on your timeline, no matter what's happening on Wall Street. In some cases, following your retirement plan right through market volatility can even be advantageous.