Keen On 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.

One of the joys – and challenges – of every holiday season is the hustle and bustle. All that planning, shopping, baking, wrapping, mailing, travelling, and celebrating fills our calendars with unique things to do, all centered around spending time with our loved ones and showing each other how much we care. But once the leftovers are gone and the wrapping paper is recycled, there's a quiet that settles over many of us. You might still be enjoying some time off work. The rest of your regular routine is probably still on pause. Your grown kids may have headed back to college, or back home with their own families. And any pending plans, meetings, projects, or decisions have been bumped to “after the first of the year." In this quiet week between the end of the year and the beginning of a new one, you might find yourself alone a little bit more than usual, enjoying a walk through your neighborhood or a cup of coffee near the fireplace. And that's when some of life's biggest questions often come to the surface, especially if you're nearing retirement.

"How am I doing?" "Am I falling behind my peers?" "Do I have enough money?" "How does my nest egg measure up?" My team at Keen Wealth spends a lot of time talking folks through these kinds of questions. And, as the years go by and folks enter their 50s, 60s and beyond, that conversation evolves and begins to coalesce around another question: "Can I retire?" You might try to answer these questions on your own by comparing your account balances to benchmarks or rules of thumb you've seen on social media. But are "averages" really the best way to assess where you are on your financial journey, especially as you get closer to retirement? On today's show, we dig into some recent data on retirement savings and discuss why achieving your financial goals is about more than dollars and decimal points.

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.

Does your financial team provide you with comprehensive tax planning, or just annual tax reporting? When you file your 2025 taxes next April, you're essentially just reporting your financial data from the previous year. At Keen Wealth, tax planning is a proactive, year-round process we use to put your annual report in the best shape possible before the ink dries and windows close. And when it comes to your 2025 tax return, some important windows are closing right now. Today, on our 250th episode, we explore some recent changes to tax law and potential moves that you need to discuss with your financial advisor before the end of the year.

Sometimes we have to let go in order to move forward, add on, and grow. That's certainly one of the challenges of retirement. From bucket list travel to grandbabies, most seniors have a lot to look forward to during the Golden Years. But to make the most of this precious time, you also have to leave behind the career that no longer determines your schedule, habits that no longer serve your wellbeing, and even some relationships that might be holding you back. I've noticed that many of the seniors I've worked with over the years don't truly embrace retirement until they let go of these five things: