Asking Better Questions About Money Happiness

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Please note the publish date of this blog. Financial information, market conditions, and other data mentioned in this post may no longer be accurate or relevant.

Does your own relationship with money make you feel bad, uneasy, ambivalent, or uncomfortable? Do moments when you feel happy, satisfied, or fulfilled in your relationship with money not happen nearly enough? 

If these words ring true — if you have your own secret confessions — you are not only brave for admitting your feelings, you are not alone. 

Money is one of these core relationships that can cause perpetual stress, and a relationship we don’t talk about nearly enough.

The good news? By thinking slightly differently about money — by simply asking better questions about your feelings — you can transform your relationship to money in a positive way for the rest of your life. 

And as you begin challenging feelings of perpetual anxiety and worry, ask yourself: What difference will it make in my life when those burdens are gone? 

Early Money Narratives

Where do you get your ideas about money? Who taught them to you? Why do you believe them? 

There are several smart ways to find out what your current relationship to money is (for example, by taking our Financial Archetype Quiz). 

And yet, just because you can define your relationship with money doesn’t always explain how you got there.

Most, if not all, of our earliest learning experiences come from our family of origin. So many of our beliefs are difficult to change because there is pressure from family, community, and culture at large to behave in certain ways or believe certain ideas.

For example: We’re supposed to budget, save for retirement, and not run up credit card debt. We’re supposed to not go bankrupt. But what if I’ve already done all of the “bad” things and none of the “good” things? What will people think of me? Will they be ashamed? What then?

When these questions arise, ask yourself: How are these thoughts helping me? Is thinking of myself as a person who is “bad with money” changing my behavior? If the answer is no, ask yourself: What if I’m just someone who temporarily forgot what my authentic values were around money and simply needed a gentle reminder?

The stories we tell ourselves are one of the most powerful forces in our lives. Harnessing that power to find fulfillment is one of the greatest ways to experience joy. But when that power is harnessed in negative self-talk, it robs us of exceptions to our preferred narrative. In short, it robs us of other story paths.

Systemic Money Thinking

Understanding the many systems you belong to can be helpful when trying to interpret your inner thoughts and emotions. Once you can understand how you fit into systems such as your current family,  family of origin, community, culture, or country, you can have a better idea of why you may feel the way you do.

These systems can also unfold across generations of time. So it’s not only your current family system that may be influencing your beliefs, it’s likely that family beliefs from generations past are strongly influencing your thoughts and feelings today.

What did your parents believe about money? Where did they learn their beliefs? How did that influence how you think about money today? If your grandfather or grandmother were alive today to see who you became with money, how would you feel? Guilty? Ashamed? Proud? 

These feelings that come up when you think about your family members (past or present), these stories that you’re continually telling yourself… Do they help you? Do they work for you? 

If not, what do you wish your story was instead?

Changing the Narrative & Finding Exceptions

It can be anxiety-provoking to admit the stories you’ve been telling yourself no longer work for you. What will my family think if I do something that feels like it dishonors their legacy or traditions? 

But what would your loved ones think if they knew how unhappy you were because of the adverse influence of those traditions and expectations?

The truth is, if you look hard enough, you can always find an exception to the story you’ve been telling about yourself. When you say, “I’ve always been bad with money,” you are likely overlooking the many, many times you were actually quite good with money. 

Try it now. Think about a specific moment, no matter how small it may seem, where you were better with your money than you either thought or expected to be.

Think of another specific moment. And then another. How many can you think of? If you have even a handful of exceptions, by definition you cannot honestly state, “I’ve always been bad with money.”

10 New Questions to Ask Yourself About Money 

One major American cultural narrative we all tend to embrace is “solving problems.” American culture loves self-help gurus and problem-solving. And there’s nothing inherently wrong with wanting to make positive changes. But what if focusing on your story in a problem-focused way actually holds you back from solving it?

Often, by focusing on a problem, it becomes easy to get trapped in all of that ‘problem talk.’ It’s like going in circles in a maddening cul-de-sac, always focusing on where you can’t drive instead of where you can.

Asking yourself solution-based questions can help free you from feeling trapped in old stories. Looking at problems in a solution-based way can help you break thought patterns you’ve formed. 

By asking yourself what you want and hope for (instead of talking about all the problems you have), you begin finding exceptions to the “always” story. And in that little space between always and sometimes, you can start giving yourself some much-needed relief from the pressures your problem talk has likely been causing.

Below are ten questions that can help you think of your money relationship story in new ways:

  1. Starting today (and going forward the rest of your life), what are your best hopes for your relationship with money?
  2. What will be different in your life when you achieve these hopes? How will you know you’ve achieved them?
  3. What will take the place of all the time, energy, and emotion you’ve spent worrying about your money problems?
  4. If I were to ask your partner or a loved one what you will be doing differently when you achieve your best money hopes, what would they say?
  5. When are you at your ‘money best’? What does that look like? How can you do more of what is making your best money self thrive?
  6. How have you managed to survive, to get to this moment and read this sentence, and know you needed to do something different? Suppose you were to compliment yourself on this effort, what would you say?
  7. On a scale of 10 to 0, where 10 equals “I have every hope of achieving a better relationship with money” and 0 equals “I have no hope of achieving a better relationship with money”, how hopeful are you that your problem can be solved? How come you already have that much confidence or hope?
  8. What will you already be doing differently after reading this article?
  9. What would you like your life to look like a month from now, with your same friends and family in place and your same circumstances, but when your behavior is less influenced by old money narratives?
  10. How will you celebrate and honor yourself when you have managed to change your old money stories into new and authentic stories?


Giving ourselves permission to find exceptions in our old stories helps give us the space to write new ones. 

How old are you right now? How long have you lived under the grip of the money stories you’ve told yourself? 

If you put your life on a timeline and placed an X at this moment — the moment you are making a decision to declare your independence from these stories — how many years in the future do you now get to walk a new path? 

If you don’t make any changes at all, how will the future you (who deep down knows there is always a new path to be found) feel about not changing anything? 

You are part of many systems. You know exactly what your life already looks like in these systems. You already know exactly what it will look like if you never make the changes that, deep down, you know you would like to make.

So start with one small change — even if it’s just for an hour, a day, a week — do one small experiment and see what that small change makes you feel like. Even pretend for an hour that you’ve made all the changes you’d like to make and see how that makes you feel. 

Here’s guessing it will make you feel a lot better about where you’re headed than where you’ve been.


What’s your financial archetype?

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