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.