"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.

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.

"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 Busches thought they were safely investing for retirement.

On today's show, we draw three important lessons from the Busches' lawsuit that could help you steer clear of a similar financial crash.

"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.

Change is in the air every fall – not just in the leaves and weather, but in your financial planning.

At this time of year, the federal government announces some important rate adjustments that affect tax planning and retirement benefits for the year ahead.

And complicating matters this fall is a government shutdown that has many seniors worried about the benefits and services that they've earned, and that they rely on.

On today's show, we answer questions from some very astute listeners in the Keen on Retirement audience who are already looking ahead and wondering what they need to prepare for as we move towards the end of the year.

In 1988, William Post won $16.2 million in the Pennsylvania lottery.

A year later, he was $1 million in debt.

First, he splurged: houses, cars, a plane. Then a former girlfriend sued him for a third of his winnings. His brother was arrested and convicted for hiring a hitman to kill Post and his then-wife in hopes that he'd inherit a share. And after sinking money into a failing family business, Post spent time in jail for firing a gun over the head of a bill collector.

In the end, Post said he was happier living quietly on $450 a month and food stamps than he was when he was rich.

Post's story is an extreme example of the bad decisions and bad luck that leave so many lotto winners wishing they'd never won at all. But while you're more likely to be struck by lightning than hit the winning numbers, an inheritance, a promotion, a legal settlement, selling a business, and reaching retirement can all create significant windfall scenarios as well.

On today's show, we offer some tips on how to manage life-changing money, including tax planning, dealing with friends and family, and the kind of team that can help you protect your assets.

Charitable giving is a cornerstone of many comprehensive retirement plans.

It's also a cornerstone of our mission at Keen Wealth Advisors.

Our whole team takes great pride in serving as active members of our community, whether we're making monetary grants or lending a hand to projects around the greater Kansas City area. And through the efforts of the Keen Wealth Foundation, we're able to identify causes where we can have a high impact and share what we've learned about effective giving with friends and clients of the firm.

On today's show, I'm honored to welcome the director of the Keen Wealth Foundation, my wife Carissa Keen, to discuss our philanthropic mission. Carissa also shares some best practices and a checklist that can help you feel more confident as you evaluate and consider which charitable causes and organizations you may want to support.

Married couple "Mark" (62) and "Lisa" (60) want to retire together in the next year. They shared their financial plan and their goals with two financial advisors.

One advisor said they could retire.

The other said that they should keep working.

So ... Who's right?

On today's show, we try to split the tie and help Mark and Lisa set the best course for a successful retirement.

If you're only judging based on what's happening in the world and the financial markets, there's never a "perfect" time to retire. But 2025 is throwing a bunch of extra variables at seniors that are adding more complexity to an already complicated decision. Businesses are changing. The rules around investing are changing. And, most importantly, your life is changing. Your financial plan has to be flexible enough to keep pace while also maintaining focus on the best path towards your personal long-term retirement goals.

On today's show, we discuss two listener questions that touch on alternative investments and how to think about portfolio management at various stages of your life.

Last week, I discussed how Keen Wealth's comprehensive planning process might assess a multi-million-dollar nest egg. I think these hypotheticals, including some back-of-the-napkin math, are useful in illustrating how retirement planning can work, and also the limits of focusing exclusively on your numbers.

However, in the Keen Wealth offices, we don't work with hypotheticals. We work with real people, their real savings, their hopes, dreams, worries, and goals for the future. Every day, we help hardworking folks navigate complex financial issues that touch every part of their lives. We're honored that our clients have entrusted us with the responsibility of managing assets they've spent decades earning, and we want them to feel confident about their path to retirement.

On today's show, we explore the Keen Wealth Advantage in action as we help a couple answer one of life's most important questions: Can we retire?