Keen On Retirement

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.

No matter how you feel about your upcoming retirement, there's no denying that letting go is a part of navigating this life transition. Your daily schedule is going to change. You won't have professional responsibilities. You probably won't see your work friends as often. And you'll lose the comfort of a monthly paycheck and your benefits, including your old health insurance. But while you might have mixed feelings about some of the things you're leaving behind, letting go in retirement can also be liberating! Retirees can cross these ten items off their to-do lists and spend more time focusing on the people and activities that they love.

In this new retirement era, where government rule changes and longevity trends are nudging many seniors to work well into their 70s, a "traditional" retirement at 65 might seem way ahead of schedule. But if you’re planning to retire at 65 or later, will you still be healthy enough to enjoy it? According to recent data from the World Health Organization, healthy 60-year-old Americans can expect an average of 15 more years of good health. Is that really what you've been working, saving, investing, and waiting for? A decade, maybe two, of being well enough to play more tennis, travel all over the world with your spouse, and give back to your community? Or should you be talking to your advisor about how to accelerate your retirement timeline so you can maximize your Golden Years while still ensuring your long-term financial security?

Why do so many people focus on "hitting their number" as they approach retirement? In part, I think it's because major life transitions can feel scary, and numbers can help us feel more secure. Boiling retirement down to a figure might, in some way, shrink your worries down to size and put your goals in black and white. Unfortunately, no "magic number" is big enough or flexible enough to encompass all the variables that life will throw at you in retirement if you don’t have an effective mindset around money. That's why, to improve your retirement readiness, I'd recommend focusing less on hitting a number and more on building up these three mindsets that can help folks take a more holistic approach to preparing for the second half of their lives.

While many of the major changes that come with retirement are personal, married couples have to navigate this life transition together. Even if it's only one spouse dealing with the end of a career, both people are going to experience a significant adjustment period that can put severe strains on finances, health, emotional well-being, and the marriage itself. That's why, at Keen Wealth, we ask married couples to be equal participants in the comprehensive planning process. And as retirement draws near, we encourage spouses to discuss five important topics that they could be overlooking, or worse, avoiding. These aren't always easy conversations to have. But if you put off talking about what retirement is going to be like, you might find yourself facing some unspoken challenges that you could have been preparing to diffuse months, if not years, ahead of time.