Retirement planning perspectives

Investing is as much an art as it is a science. Over the last 30 years of personal finance education—both formal and informal—and real-world experience, these are the lessons I've gathered that have helped me navigate the often turbulent world of investing. I believe these principles stand the test of time, and when applied consistently, they can significantly improve your financial outcomes. Let's dive into some key insights, backed by data where possible.

Social Security benefits play a crucial role in retirement planning, but deciding when to start taking them can be challenging. Should you claim early at age 62, wait until your full retirement age (FRA) of 67, or hold out until age 70 to maximize your benefits? The best choice depends on a mix of financial needs, life expectancy, and other income sources. Let’s break down the numbers and considerations.

When most people think of estate planning, they picture something reserved for the ultra-wealthy. The reality is that everyone—regardless of age, health, or financial status—can benefit from having a solid estate plan in place. Whether you're protecting your home, providing for your family, or simply making sure your wishes are honored, a well-thought-out estate plan brings peace of mind and clarity when it matters most.

When it comes to saving for retirement, it’s not just about how much you save—it’s also about where you save it. Choosing between a Traditional IRA or 401(k) and a Roth IRA or 401(k) can have a big impact on your taxes, both now and in retirement. On top of that, there’s a powerful tool called a Roth conversion that can shift your savings strategy and potentially reduce your lifetime tax bill. But it’s not right for everyone.

Here’s what you need to know to make informed decisions about your retirement accounts and how to evaluate whether a Roth conversion is right for you.

When you start learning about investing, one of the first forks in the road is this: do you try to beat the market, or just ride along with it?

That question leads us to two big strategies—active management and index investing—and over the years, the debate between them has sparked more than a few strong opinions. But today, we want to step back from opinions and look at what the data actually says. This is the kind of information I wish had been handed down to me when I was starting out, and it's something we’re making sure to pass on to our kids.

Let’s break it down.

Managing your money and planning for your family’s future are two of the most important responsibilities in life—but it’s not always clear whether you should handle it on your own or partner with a professional. The DIY (do-it-yourself) approach can work well for some, while others find immense value in delegating this responsibility to a trusted financial advisor. So, how do you know which path is right for you?

Let’s explore together.

If you’ve found yourself staring at your investment portfolio lately with a sense of unease, you’re far from alone. With ongoing volatility across global markets, heightened geopolitical tension, renewed tariff battles, government fiscal issues, and the ever-evolving stance of central banks on interest rates, it feels like uncertainty has become the norm.

And in that uncertainty, a very human impulse kicks in—the desire to act. Maybe you're thinking, Should I just step aside for now? Sit in cash until things feel more stable?

It’s a perfectly reasonable question. But let’s pause before taking that leap. Because if history and data teach us anything, it’s this: acting on that impulse rarely ends well.

If you’re a homeowner in California over the age of 55 — or someone planning to pass down property to your children — Proposition 19 could significantly impact your future. Whether you're thinking about moving or navigating estate planning, understanding how this law works is crucial.

Let’s break down what Prop 19 changed, how it benefits certain homeowners, and why it might affect your family’s plans.

It seems like a great plan. The technology sector has absolutely crushed it over the past decade. The names are familiar: Apple, Microsoft, Amazon, Alphabet, Meta, Nvidia. Their products are everywhere, their profits are astronomical, and their stock charts look like ski slopes turned upside down. Why not just invest in these giants and call it a day? What could possibly go wrong?

Well, history has a few cautionary tales for us.

For many investors, especially U.S. investors, the United States seems like the only stock market that matters. The U.S. has been a global leader in technology, finance, and innovation for decades, and this dominance has translated into strong stock market returns. But relying solely on U.S. stocks, despite their stellar history, could be a poor long-term strategy — especially when examined through the lens of historical data, valuation, and benefits of geographic diversification.

Charles D. Ellis is a world-renowned investor, writer, and former chair of Yale’s investment committee. He worked closely with David Swensen, Yale’s legendary Chief Investment Officer, and is one of only twelve people recognized by the CFA Institute for lifetime contributions to the investment profession. Nearly four decades ago, Mr. Ellis published Winning the Loser’s Game: Timeless Strategies for Successful Investing, and in it, he sounded the alarm on the futility of trying to beat the market through individual stock selection.

The wisdom in that book has only grown more relevant over time. And after my own missteps early on in my investing life, and seeing what many friends and peers have gone through over time, I’ve come to believe deeply in its central message: individual stock picking is, for nearly all of us, a loser’s game.

Let me explain why.