The Question to Ask Your Money

I have a bit of a love-hate relationship with my industry.

I love what good financial planning can do for people. I hate how hard it can be for someone to know what to ask, who to trust, and how to evaluate advice. It shouldn’t feel this confusing.

Part of the problem is how easy — even natural — it is to focus on the wrong questions.

It seems perfectly sensible to ask a prospective advisor what kind of returns they think they can get. After all, if you’re hiring someone to help with your money, performance sounds like the point.

In reality, if you’re looking for personalized advice, that’s a terrible place to start.

You don’t start with numbers. You back into them[i].

Ask not what I can do for your money, but what your money can do for you.

Before we talk about returns, we need context. What are you trying to accomplish? When do you want to accomplish it? What does success actually look like in your life?

Different goals, with different timelines, require different strategies. Money needed in the near term should be treated differently than money meant to support a life decades from now. Time changes what’s appropriate. It changes how much uncertainty you can tolerate. It changes how patient you’re allowed to be.

Risk tolerance isn’t just a personality quiz — it’s closely tied to timing and purpose.

Taxes matter too. Over time, building flexibility across different types of accounts can create options. Laws change. Circumstances change. Having multiple “levers” to pull when it comes time to distribute income can make a meaningful difference. The goal isn’t to predict the future perfectly — it’s to avoid cornering yourself.

But none of that matters until there’s clarity.

What do you want your money to do?

Do you want it to buy back your time? Create stability for your family? Fund experiences? Support causes you care about? Provide the confidence to make a career change? Leave something behind?

And when do you want those things to happen?

Those answers shape everything else.

Only after that do the numbers start to mean something. Asset allocation, tax strategy, withdrawal planning — they’re tools. Useful tools. But tools are only as good as the blueprint they’re built around.

Gaining clarity on what you want from your money — and when — is the real starting point.

Then you build the math around it.

And you build in margin[ii].

Because no matter how good the plan is, life won’t unfold exactly as projected. Flexibility isn’t a luxury. It’s a requirement.

This is exactly how we approach planning with clients. We start with purpose, not performance. We define the life first, then design the strategy to support it.

If you’re not sure where to begin, start with this: write down what you want your money to make possible over the next five, ten, and twenty years. Not numbers — outcomes. Then bring those to the conversation.

Better advice starts with better questions.

And the first one is yours to answer.