For the last several weeks, I’ve been writing about the value and power of questions, albeit from different angles. If you’ve missed any of those missives, you can click here, here, and here

Honestly, I thought I said all I wanted to say on the subject for the time being, anyway. But then, Twitter…

I’m an avid NPR listener and am a big fan of Audie Cornish. She posted her frustration about “financial advice,” a sentiment with which I wholeheartedly agree. Because it drives me crazy how much my industry can be tone deaf, especially in times like these. I truly wish some of my peers would stop prioritizing information over insight.

But it got to me thinking about what we haven’t covered in this series: The questions that aren’t asked enough in my opinion. This is what I want to shift your attention to today.

If you’ve been in my world for awhile, you know I’ve mentioned these before. But, I think it’s worth sharing them again. For many reasons, not the least of which is this: 

The questions below can deepen your relationship with money. 

In other words, the nature of these questions help you to go several layers beneath the surface. By doing so, you end up delving into “better” questions — ones that go a long way in helping you to strengthen your relationship with money. Ones that center insight.

They are “better” in that they:

  • Help you better understand your situation, and often, in the process, help you expand your range of vision and possibilities;
  • Tend not to elicit a binary response;
  • Create the space for discovery and contemplation;
  • Challenge existing assumptions; 
  • Increase your discernment; and
  • Prompt you to confront your comfort level and (hopefully) encourage you to dance with discomfort and embrace uncertainty.

The words that make up these questions isn’t what makes them powerful. What makes them powerful is what you end up learning about yourself vis-a-vis the process of answering them!

Questions = Self Discovery

These questions are listed in no particular order. Though I’ve endeavored to cluster together questions of a similar nature:

Am I spending my money on things and experiences that truly matter to me? 

At first blush, your initial answer to this may be, “Of course I am!” But when you examine your banking and credit card statements by merchant and category, how closely is what you are actually doing with your money aligned with what you say is important to you. What’s the symmetry between where your money is going and your values and beliefs?

Am I spending my money with vendors that are in alignment with my values?

Think of this as voting with your dollars. For example, I’m preparing to leave a current vendor because of their stance on Black Lives Matter – they are not supporters.

How can I be less transactional and passive with my money and more intentional and strategic?

People are accustomed to me suggesting they track their money so that they can identify their pattern of behavior with it. What’s also useful: tracking if you tend to only really give money your attention when you are stressed about it, or when you’re about to make a big-ticket purchase or a consequential decision or choice. If this is your tendency, you’re being transactional about money and missing out on some useful data and insight that would actually help you to be more intentional and strategic.

Like much in life, this is not either/or; it’s both/and.

How should my financial team work together?

Most of the folks with whom I work in my coaching practice have a CPA. Some also have a financial advisor who manages their investments. I’m always astonished, though, by how often they don’t have financial team meetings to ensure that everyone is on the same page, making complementary moves and decisions. Instead of siloed ones.

Similarly, it surprises me that people who, otherwise, wouldn’t abdicate responsibility of other areas in their life to someone else, willingly (or maybe unwittingly) do so when it comes to money. Sometimes this is due to disinterest; other times, it’s due to a lack of knowledge or confidence.

One of the things I always remind people of is this: Hire professionals, but never, ever abdicate your responsibility. It’s your money!

When it comes to money, are my beliefs about and behavior with it really that different from my family’s?

What’s interesting about this question is that some people who swear they are not like their parents (or whomever raised them) when it comes to money are frequently exactly like them! They just don’t notice the similarities in beliefs, behavior, and expectations because the results and consequences manifest differently.

This is one of my favorite questions because of all the territory you can end up covering with a seemingly binary question.

Do I have a spending or earnings problem — or both?

Again, another seemingly binary question that really isn’t. And, it is a question anyone feeling overwhelmed with their debt should ask themselves.

Because far too often people look to tackle their debt solely by cutting expenses. That may be needed, but once you reach the point where there’s nothing else to cut, what do you do?

Realizing you need to earn more may upend emotions and matters of confidence and courage that you’d never have to address if all you needed to do was cut expenses.

How are the five people I spend the most time with affecting my relationship with money?

More specifically, how are these people affecting your beliefs about money; your behavior with it; and what you believe is possible when it comes to your earning potential, how much you can save, how much wealth you can create, what kind of lifestyle you can have and support?

Sure, we may no longer be in middle- or high-school. But that doesn’t mean we aren’t still influenced by our peeps.

For example, let’s say one of your metrics for professional success is how much you earn or how much revenue your business is generating or how much wealth you’ve accumulated. But the people you care a lot about eschew the pursuit of wealth, how do you reconcile the internal tension this may cause for you? And, how does this tension affect the decisions and choices you make?


Questions like these herein can help you deepen your relationship with money from all sides. It can help you understand the relationship you’ve had with it; the one you currently have with it; and what you can do to shape your future relationship with it. All questions serve a purpose. So technically no question is “bad.” It’s just that some are “better” than others. These are the ones that invite you to go deep and learn more about yourself – and those around you.

Ask more of these types of questions. Because, you’ll end up having an even better relationship with money as a result thereof. The benefit: better, smarter and more relevant decisions and choices.

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