Keen On Retirement™

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.

Longtime Keen on Retirement listeners and friends of the firm are probably familiar with The Big Hat. Matt Wilson, our Chief Investment Officer and President, is the proud owner of an oversized Dow 100,000 cap that he wears on our show from time to time. And when folks visit our offices, such as during our annual Holiday Breakfast, they often spot Matt's hat in his office and have a bit of a chuckle about its pie-in-the-sky prediction. More than once, I've heard someone tell Matt, "Gosh, I'll never see that in my lifetime." But ... is the Dow hitting 100,000 really all that far-fetched? On our final show of 2025, we look to market history and current trends to give you a head start in your financial planning for 2026. I also share some stories from my big Hollywood red carpet debut as part of the Keen Wealth Foundation’s charitable mission.

If you want proof that money alone doesn't buy happiness, just compare these two data points: By any measure, the United States is one of the wealthiest countries in the world -- if not THE wealthiest. And, at the same time, year after year, our collective happiness continues to decline. So, if having more money doesn’t create more happiness ... then what the heck are we all doing? Why are we up at the crack of dawn for our morning commute? What are all those long hours at the office for? Why are we topping off accounts longer than we have to if the ROI isn't making us feel better about our lives and our prospects for the future? A recent poll from YouGov for MarketWatch approached the relationship between money and happiness from a slightly different perspective. I was struck by how the findings align with a core belief we have here at Keen Wealth: financial happiness isn't about accumulating more money. It's about aligning the money you have with your values, your purpose, and a sense of freedom.

"This sounds too good to be true, but you’ve got to believe in those that are looking at it for you and trusting in the people with Pacific Life email addresses that are sending you the documents." So many stories of financial fraud and mismanagement boil down to statements just like this one. All too often, the folks who are losing large sums of money are hardworking folks working 9-to-5s who don't have a team of professionals looking out for them, and whose finances may never recover. But, in this case, the quote above is from racecar driver Kyle Busch, a two-time NASCAR Cup Series champion whose net worth is estimated to be around $80 million. Earlier this month, Busch and his wife, Samantha, sued Pacific Life Insurance Company for $8.5 million, alleging that Pacific Life misrepresented how a policy worked and lost almost $10.4 million that the Buschs’ thought they were safely investing for retirement. On today's show, we draw three important lessons from the Buschs' lawsuit that could help you steer clear of a similar financial crash.

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.