I've Been Meaning to Ask...

After nearly twenty years as a financial advisor, one lesson keeps proving itself over and over again: people rarely ask the question they're trying to ask.

"Can I retire?" usually means, "Am I going to be okay? 

“Will I run out of money?" usually means “Can I stop worrying?"

"Why did my account buy $43 worth of an ETF?" usually means “What’s changing, and why?”

Here are the questions we hear most often and some that we wish you’d ask.

TLDR: If you're short on time, feel free to skip the middle paragraphs and just read the bold questions and the last sentence of each answer. I've been told I can be a little long-winded, the evidence is below. 

Q. Why don't we react to every scary headline?

A. Because there's always another one. Over the last decade we’ve had Brexit, inflation, trade wars, bank failures, international conflicts, elections, and more scary headlines than I can remember. 

Every one dominated the news. Every one felt different. Every one eventually became yesterday’s headline. We pay attention to what's happening in the world. We just don't believe your retirement plan should change every time someone on television raises their voice.

We pay attention to the headlines. We just don't let them write your retirement plan.

Q. My brother-in-law just bought (insert magical investment). Why didn’t we?

 A. Because there’s always another one. Dot-Coms, housing, cannabis stocks, NFTs, SPACs, cryptocurrencies, and now AI are just a few things that created FOMO with investors. 

 Some of those innovations changed the world. Some disappeared almost as quickly as they arrived. History is full of great businesses that became terrible investments simply because investors paid too much after everyone else had already fallen in love with them.

 Finding a great company is only half the equation. The price you pay still matters.

 If you'd like to read more, check out our article, SpaceX Could Change the World: That Doesn't Mean It's Cheap.

 Our job isn’t to make sure you own every winner. It’s to make sure that you don’t have to. 

Q. My brother-in-law’s portfolio is invested this way. Why isn’t mine? 

A. Your retirement probably doesn't look like his either. Different income. Different tax brackets. Different pensions. Different Social Security benefits. Different spending goals. Different families. Different comfort with risk.

Comparing portfolios without understanding the people behind them is like comparing prescriptions without knowing the patients. The goal isn't to own the same investments as someone else. The goal is to own the investments that give you the highest probability of achieving your goals.

The best portfolio isn't the one that made the most money. It's the one most likely to get you where you want to go.

Q. Why do you sometimes sell investments that are doing well?

A. Because good performance changes risk. Rebalancing simply brings your portfolio back to the level of risk you originally intended. It naturally encourages us to trim investments after they've done exceptionally well and add to areas that have lagged. It’s one of the few investing disciplines that quietly encourages us to sell high and buy lower.

Rebalancing is wonderfully boring. That's exactly why it works.

Q. What am I paying you for?

A. Managing investments is important but helping you make good financial decisions for decades is even more important.

When to retire. When to claim Social Security. How much you can safely spend. Which accounts to withdraw from first. How to reduce taxes. How to prepare for healthcare costs. How to protect your family. How to avoid making a six-figure emotional mistake during the next bear market.

Investments build wealth. Planning helps you keep it.

Those decisions create far more value than trying to outperform the market by a fraction of a percent. Investments are simply one of the tools we use to help you achieve your goals. The real value comes from helping you make better financial decisions year after year.

Information has never been cheaper. Knowing what matters has never been more valuable. 

Q. Why do you keep asking for my tax return?

A. Because some of the biggest financial opportunities never appear on an investment statement. It helps us identify Roth conversion opportunities, charitable giving strategies, Medicare planning, capital gain planning, and ways to potentially reduce your lifetime tax bill—not just this year's.

Your tax return tells us a story.

Sometimes we review a tax return and discover an opportunity that saves a client thousands of dollars, and other times we simply confirm they're already doing everything right. Either outcome is valuable. Our goal isn't to prepare your taxes. It’s to make sure your tax return and your financial plan are working together.

Sometimes the biggest investment opportunity is hiding on your tax return.

Q. Why do our meetings sometimes have very little to do with investments?

A. Because investments are just tools to achieve your goals, our most valuable conversations have nothing to do with the stock market.

They're about retirement. Taxes. Estate planning. Building a legacy. Selling a business. Helping kiddos and grandkiddos without jeopardizing your own retirement. Taking care of aging parents. How to sleep well at night. 

Those decisions often have a much bigger impact on your financial future than whether one mutual fund outperformed another. Investments matter. They're just not the whole plan.

 A portfolio is a collection of investments. A financial plan is a strategy for your life.

Q. What happens if something happens to me—or my spouse?

A. I believe this is the most important reason to work with us.  Unfortunately, over the years we've had clients pass away, and no amount of planning makes those conversations easy. Good planning just makes them less overwhelming. Because we've spent years organizing your financial life, your surviving spouse or family doesn't have to start from scratch trying to figure everything out. 

They only need to make one phone call. To us. 

We already know the accounts. We know the beneficiaries. We know the professionals you've worked with. We know where the important documents are—or at least where to begin looking.

We can't take away the grief. But we can take away much of the uncertainty that comes with it. That's one of the most meaningful parts of our job.

Money is complicated and losing someone you love is hard. Your family shouldn't have to figure both out on the same day.

Q. What happens if something happens to you?

A. It's a fair question—and one I think every client should ask their financial advisor. While I certainly don't plan on going anywhere anytime soon, we've intentionally built our firm so that no client relationship depends on one person. 

Your financial plan doesn't live only in my head. It involves detailed planning notes, documented processes, and a team of experienced advisors and support staff who already know you and understand your goals.

If something ever happened to me, your family wouldn't be handed off to a stranger. They'd continue working with people who understand your financial life and are committed to helping you achieve your goals. Good planning should outlast any one advisor, and that’s exactly how we've built our firm.

The goal was never to build a plan that depends on me. The goal is to build one your family can depend on. 

Q. Why do you recommend estate planning so often?

A. Because we've never met a family that wished Mom and Dad had made things more complicated, and because predators, creditors, outlaws, and in-laws exist. Estate planning isn’t really about money. It’s about making one of life’s hardest days easier for the people you love. 

Estate planning documents don’t just protect assets, they protect families from confusion, delays, unnecessary expenses, and disagreements during an already difficult time. One of the last gifts you can leave your family is making sure they know exactly what to do when you're no longer here to tell them.

The most valuable part of a financial plan is often the part you hope your family never needs.

Q. What's one financial question you wish every client would ask?

A. "What could derail my plan?"

Most retirements aren't derailed by one bad investment. They're derailed by a series of avoidable decisions.

Unexpected taxes. Healthcare costs. Claiming Social Security too early without understanding the tradeoffs. Helping adult children a little more than you can comfortably afford. Failing to update an estate plan. Having insufficient insurance. Making emotional decisions during difficult markets.

Good financial planning isn't about predicting the future, it's about preparing for it. The best plans aren't built on perfect forecasts, they're built to adapt when life doesn't go according to plan.

A good financial plan shouldn't depend on predicting the future. It should be strong enough to survive it.

One Last Thought

After nearly twenty years, I can honestly say we've never heard a dumb question. We've heard questions people were embarrassed to ask, questions they thought they should already know, and questions they put off asking for years because they didn't want to sound uninformed.

But never a dumb one.

If you've ever thought, "I've been meaning to ask you about something..." Please ask.

Sometimes the answer is simple. Sometimes it uncovers an opportunity, and sometimes it prevents a mistake. Occasionally, it changes the course of a family’s future. That's why we encourage questions. Not because we have all the answers—but because the right answer, at the right time, can make a remarkable difference. 

If someone came to mind while you were reading this, feel free to forward it to them. They might have been meaning to ask the same questions.

Thank you for trusting us to be part of your family’s journey, for your business, and your friendship. 

Money is complicated. Life is unpredictable. 

Good financial planning isn't about predicting the future, it's about helping you feel confident no matter what it brings.