The Power of Better Questions
“Every financial decision is a life decision. Make sure you’re asking the right questions.”
"These are dark times, John...not that dark."
Q: What's Going On In the Market?
If you tune into market headlines, you've probably stumbled across at least one of these questions lately:
Is this the bottom (of the market) for now?
Should I invest more?
Should I hold onto more cash right now?
Is this a good time to buy a house?
Is the price of [something] going to go up?
And here's the thing. Most of our money moves are initiated by trying to solve for whether or not we are going to be okay...which is the question behind every single one of the questions above, and importantly - a fine and reasonable question to be asking.
The harsh reality, though, is that never before have we ever truly been able to determine whether *now* is...(relative to some time in the future)...a good time to execute a money move, without considering other -- more personal -- variables.
So in that way, at least, current times and circumstances aren't any different. It just feels different. (More on that another day.)
A: I don't know. And neither does anyone else.
Regarding the questions above, I could certainly give you my best educated guess. I could cite economic reports, historical trends, and expert opinions.
But would it matter to you and your ability to fund a life of meaning and purpose?
Because that's what matters to me (and many other financial planners that I love and respect).
What I've found to be significantly more helpful than seeking out answers to generic-type financial headliners, is is to solve for what matters for you and your specific situation.
To not just answer what/where/when...but WHY.
So What Should I Do?
With just a few slight adjustments, the questions that could have led to false security above, become questions that can be used create a meaningful and purposeful plan, even (and especially) in the midst of uncertainty:
Does it matter for me and my financial goals...if this is the bottom (of the market) for now?
Given that I have some money ready to be put to use…should I invest more...in my 401(k)?
Should I hold onto more cash…than I currently have in my emergency fund…right now?
Is this a good time…for me…to buy a house?
Is the price of [something...important to me...] going to go up?
See the difference?
When you reframe the question to hone in on what matters specifically to you, to your financial goals, to your priorities...you shift from seeking predictions to seeking clarity.
You stop looking for certainty in an uncertain world and start focusing on what truly matters: your own financial reality, and how you can (or cannot) use your current financial reality to fund what matters to you.
Better Questions, Better Answers
PS - Those headlines aren’t designed to give you better financial guidance. They’re designed to generate clicks. Those questions—the ones that drive fear, urgency, and speculation—help the media stay in business.
Better money questions for YOU aren’t the ones that fuel news cycles. They’re the ones that lead to better decisions for your specific life.
Instead of asking: "Is the market going to crash?"
Ask: "Am I comfortable with the level of risk in my portfolio? If the market drops tomorrow, will I still be able to meet my goals?"
Instead of asking: "Is now a good time to buy a house?"
Ask: "Does buying a home right now align with my financial goals, my lifestyle, and my long-term stability?"
Instead of asking: "Should I hold onto more cash?"
Ask: "Do I have enough liquidity (emergency savings) to cover unexpected expenses, opportunities, or peace of mind for my personal situation?"
Why We Crave Certainty
The reason we chase definitive answers is simple: uncertainty is uncomfortable.
Our brains are wired to seek patterns, predict outcomes, and create a sense of stability. This instinct kept our ancestors alive—if you weren’t certain about whether that rustling in the bushes was the wind or a predator, you wouldn’t last long. Today, this same mechanism plays out in different ways.
That sound in the middle of the night? Our brain rushes to explain it.
That shadow lurking around the corner? Our mind demands clarity—is it a threat or just a trick of the light?
The ambiguity itself is stressful. Uncertainty requires energy—it keeps our brain on high alert, forcing it to assess possibilities, weigh risks, and prepare for action. And because our brains love efficiency, it pushes us toward quick conclusions.
But here’s the problem: quick conclusions aren’t always good conclusions.
The Hidden Cost of Chasing Certainty
When we demand certainty in situations that don’t offer it, we often end up paying for that false sense of security.
We hesitate too long. A fear of making the "wrong" decision can lead to indecision—paralysis by analysis—leaving us stuck while opportunities pass us by.
We act too quickly. Seeking instant certainty can push us to react impulsively to short-term events instead of thinking long-term.
We trust the wrong sources. In a world where everyone claims to have answers, we may fall for advice that feels certain but isn’t sound.
Embracing Smart Uncertainty
The best investors, business leaders, and financially secure individuals don’t eliminate uncertainty—they learn how to navigate it.
Instead of searching for absolute answers, they ask better questions:
Not “Is now a good time to invest?” but “Does this investment align with my long-term strategy?”
Not “Will the market crash?” but “Do I have a plan in place for market downturns?”
Not “Will I regret this decision?” but “Have I considered the risks and rewards thoroughly?”
The Right Questions Put You in Control
The more you embrace the fact that some things can’t be predicted, the more control you actually gain—because you’ll stop reacting out of fear and start making decisions that serve you in the long run.
And when we focus on asking better questions—the ones that center our personal circumstances instead of market predictions—we step into a position of power.
We may not control the markets, interest rates, or inflation. But we do control how we prepare, how we respond, and how we make decisions that align with our financial well-being.
So the next time you find yourself searching for answers, start by asking: "Is this even the right question for me?"
Because better questions lead to better decisions. And better decisions? They build the kind of financial plan that’s not dependent on guessing what’s next—but on knowing what truly matters to you.
Warmly,
Jess
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