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.

Tariffs are nothing new. They've been implemented at several points in U.S. history, including as recently as 2018. But there are a confluence of factors surrounding President Trump's current round of tariffs that make it worth discussing. On today's show, we round up questions we've been receiving at Keen Wealth about tariffs to provide a comprehensive rundown of why Wall Street is interested and what you should discuss with your financial advisor.

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.

With about a month until Tax Day on Tuesday, April 15th, you should, ideally, have all your financial documents collected. It might be a good idea to check in one last time with your financial advisor before you send your 2024 data to your CPA or start plugging away on your favorite tax software. But as you put a bow on last year, it's important to keep an eye on the future, especially for retirees. Cracking open your nest egg and sequencing how and when you use your assets and benefits is a complex process. Decisions you make today can affect your lifetime tax liability, the lifestyle you can enjoy during your Golden Years, and your legacy planning. On today's show, we use this combination of short-term and long-term perspective to tackle some listener tax questions and explain how the Keen Wealth Advantage can help you feel more confident about how taxes fit into your comprehensive planning.

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.

The words “fun” and “taxes” probably don’t go together in your mind. But, as I mention on today’s episode, they do at Keen Wealth! Helping folks be good stewards of their money so that they can enjoy life to the fullest is one of the most rewarding parts of being a financial advisor. And as Tax Day approaches, I love seeing my team in action, working through our checklist-driven process to make sure folks aren’t overlooking any details or making any mistakes that might not be fixable. Whether you’re working with professionals or preparing your taxes solo, make sure these four common filing errors are on your radar.