Why Now? What Changed That Made Your Financial Life Feel More Important?

The Questions Investors Should Be Asking Themselves — Part 1

By Brett Carleton, CFP®, ChFC® President & Founder, Heritage Wealth Management

One of the first questions I like to ask when I meet with someone new is remarkably simple:

Why now?

Why are you thinking about your financial life today?

Most people have been saving, investing, paying taxes, making financial decisions, and thinking about the future for decades. So, when someone decides now is the time to take a closer look at their finances—or to find a new financial advisor—there is usually a reason.

Sometimes the answer is obvious.

Other times, that simple question leads to a much bigger conversation.

And in my experience, that conversation can tell us far more about what someone needs than starting with a discussion about their investment portfolio.

Something Usually Changes

People rarely wake up one morning and suddenly decide they need a comprehensive financial plan.

Usually, something has changed.

Maybe you're getting closer to the next phase of life and beginning to wonder whether you've accumulated enough.

Maybe your company has offered an early exit package, or you're considering leaving a career that has defined much of your adult life.

Maybe you've sold a business.

Perhaps you've received an inheritance or lost a parent.

Your children may be starting families of their own, and you're beginning to think differently about helping your grandchildren.

Or maybe nothing dramatic has happened at all.

You may simply have reached a point where your financial life has become more complicated than you want to manage on your own.

Whatever the reason, understanding why now is important because it often reveals the real financial question underneath the surface.

The Question Behind the Question

Someone may come to us asking: “Can I afford to stop working?”

That's an important financial question. We can run projections, evaluate income sources, look at taxes, review investments, and determine whether the numbers support the decision.

But there may be another question underneath it:

“What am I going to do when I don't go to work every day?”

That's a very different conversation.

Someone else might ask whether they should give money to their children now or leave it to them later.

The financial analysis may involve estate planning, gifting strategies, taxes, and cash flow.

But the deeper question might be:

“How can I help my children without taking away their motivation or independence?”

Another family might come to us concerned about market volatility.

We can talk about diversification, risk, and historical market behavior. But after enough conversation, we may discover that their real concern isn't the stock market at all.

It's: “If something happens to me, will my spouse be okay?”

Those are the conversations where financial planning becomes much more meaningful.

Financial Planning Should Begin with Listening

I've been doing this for a long time, and one thing I've learned is that you can't build the right financial plan until you understand the people the plan is supposed to serve.

Before we talk about solutions, I want to understand what's happening in someone's life.

• Who is important to you?
• What are you worried about?
• What are you looking forward to?
• What would you like the next ten or twenty years to look like?
• Are there children or grandchildren you'd like to help?
• Are you concerned about aging parents?
• Are there charitable organizations or causes that matter to you?
• Is there something you've always wanted to do but haven't given yourself permission to do yet?

Those answers provide context that a balance sheet never can.

Sometimes “Why Now?” Is About Complexity

For many successful families, there isn't one major event that triggers the conversation.

Instead, financial complexity gradually accumulates. You may have multiple investment accounts, retirement plans, real estate, company stock, insurance policies, estate documents, charitable interests, and different tax considerations.

At some point, the issue isn't whether you're capable of managing each individual piece.

The question becomes whether all those pieces are working together.

Your investment strategy can affect your taxes.

Your estate plan can affect your family.

Your charitable giving can affect your tax strategy.

Your decision about when to stop working can affect Social Security, Medicare, portfolio withdrawals, and how much risk you need to take.

Financial decisions rarely exist in isolation.

Sometimes “why now?” simply means you've reached the point where you want someone helping you see the whole picture.

Other Times, “Why Now?” Is About Time

There is another reason this question becomes increasingly important as we get older.

Time begins to feel different.

When we're younger, many financial goals seem far away. There's always another year to save, another year to work, another year to take that trip.

Eventually, we begin to recognize that money is only one of the resources we're managing.

Time is another.

That realization can change the financial conversation.

Instead of asking only:

“How much more can I accumulate?”

You may begin by asking:

“What do I want to do with what I've accumulated?”

That might mean traveling more.

Spending more time with children and grandchildren.

Helping family while you're here to see the impact.

Giving more generously.

Working less.

Starting something new.

Or simply having greater confidence that you don't have to keep chasing the next financial milestone.

You Don't Need to Have All the Answers

One reason I like the question “Why now?” is that you don't need a perfectly formulated answer. Sometimes people know exactly what has changed. Sometimes they don't. That's okay.

A good financial planning conversation should help uncover the answer. The goal isn't to walk into an advisor's office already knowing exactly what you need. The advisor's job should be to listen, ask good questions, understand what's important to you, and help turn those conversations into financial decisions.

Start With One Question

So, before looking at your investment returns or wondering whether you need to change something in your portfolio, ask yourself:

Why am I thinking about my financial life more seriously right now?

Did something change?

Is something worrying you?

Is there an opportunity you don't want to miss?

Are you approaching a transition?

Or have you simply reached a point where you want greater clarity about what comes next?

Your answer may reveal that the financial question you've been asking isn't actually the question you need answered. And that can be a very good place to begin.

Coming Next: What Does Money Mean to You?

In the next installment of The Questions Investors Should Be Asking Themselves, we'll explore a question that sounds simple but can be surprisingly difficult to answer:

Why is money important to you?

For most of us, the answer isn't the money itself. It's what money allows us to do for ourselves, our families, and the people and causes we care about.

About This Series

The Questions Investors Should Be Asking Themselves is an ongoing Heritage Wealth Management series exploring some of the questions that can lead to more meaningful financial planning conversations. Because sometimes improving your financial life doesn't begin with finding a better answer. It begins with asking a better question.

Disclosure: This material is for informational purposes only and should not be considered investment, tax, or legal advice. Investment strategies involve risk, including possible loss of principal. The questions and concepts discussed in this article were inspired in part by the work and perspectives of David Booth, founder of Dimensional Fund Advisors and author of Stay Calm. Heritage Wealth Management is not affiliated with or endorsed by David Booth or Dimensional Fund Advisors.