The Money (and Style) Message Pit: Do Childhood Money and Style Messages Rob Us of Agency?

By Randy Kaufman and Andrea Greenspan

Reprinted with permission from Randy Kaufman. Randykaufman.com© with research assistance from Dustin Lowman, Guitar & Pen

Are you walking the dog, ‘cause that dog isn’t new
Are you out of control, is that dog walking you
Haven’t you had enough, now your time is up
Baby, show me your hand

Voices start to ring in your head
Tell me, what do they say
Distant echoes from another time
Start to creep in your brain
So you’re playing ‘round, like it’s on rewind
You blew it so often that you start to believe it
You have demons so nobody can blame you
But who is the master and who is the slave?

– Madonna, “Voices”

In an image- and status-obsessed world, how we look and what we spend are at the root of identity issues and are deeply intertwined. Their sensitivity also means they’re rarely discussed in a constructive way — leaving us vulnerable to old messages that don’t always have our best interests at heart.

In this article, Andrea and Randy review some of the most common — and destructive — messages in their respective fields and put forth some tips on how to take back control.

Huddled in a loud Orlando bar, we winked at each other, then practically tumbled into a corner table, where we spent the rest of the evening avoiding the sea of ear-splitting, inebriated lawyers and accountants. Two hours later, we realized how much we had in common: our backgrounds, a passion for helping people, a healthy love of fashion, a willingness (eagerness) to stand out in a crowd, and an interest in what lies beneath.

A dollar isn’t just a dollar; it’s fraught with hidden meaning that goes back to our childhoods. Is discussing money the last, absolute taboo? Are all wealthy people bad?

A designer gown isn’t merely a garment; it, too, is fraught with hidden meanings. Must you always sport designer clothing? What would the neighbors think if you bought a dress at TJ Maxx? If you wore red? If you walked the dogs without wearing your signature Charlotte Tilbury pillow talk lipstick?

One of the main insights we’ve unearthed – internalized messages eclipse our natural decision-making processes. Voices echo in our heads, telling us to act a certain way, look a certain way, value certain things — Jimmy Choo shoes, Gucci bags, Mercedes-Benz cars, for instance. We inadvertently become slaves to messages — told to us either explicitly or implicitly, from the people we know or the worlds we inhabit — about what’s desirable, what’s valuable, what’s “good.”

Dancing In High Heels

Randy has often said that in a world in which we freely discuss sex, drugs, and rock and roll, money is the last taboo. Far too often, money is the elephant in the room. With elephants and with messages, turning your back and hoping they’ll go away is a plan to fail. As Bari Tessler writes in her fascinating book, The Art Of Money: A Life-Changing Guide To Financial Happiness, “Money isn’t just about the numbers. It’s also our relationship with ourselves. In order to shift our relationship with money, then, we must untangle old patterns and challenge our assumptions about ourselves.”

So, let’s begin at the beginning. How did these messages infiltrate our heads?

Women are often afraid — petrified even — of money. We’re told that money is the domain of men, and we internalize the message that we’re not “good” with money.

Same with fashion, where we internalize all manner of messages – we can’t rock long hair, we can’t wear “big” jewelry, we can’t wear loud colors.

Not only are these deep-seated beliefs fictitious, but they also don’t serve anyone well. The very women who tell themselves they “can’t do money” run households, take care of their children and husbands, obtain medical degrees, earn Ph.Ds., often while working full-time. Let’s not forget: “Fred Astaire was great, but Ginger Rogers did everything he did, backwards and in high heels.”

The genesis of these beliefs has little to do with intelligence and much to do with messages learned in our childhoods. Try googling “Fairy tales popular for girls.” “Cinderella” still pops up. Prince Charming rides in on a white horse, saves you, and gives you a “happily-ever-after” ending.

Analyzing fairy tales, Dr. Lauren Rosewarne, a social studies expert at the University of Melbourne, identified the following sexist tropes:

  • Women being saved by men
  • Women’s value being attached to their beauty
  • Old women being witches

According to studies, “The most famous fairy tales were propagated as the desired model of a woman: weak, subject, dependent, passive, enslaved, silent, and self-sacrificing, while the men they portray are powerful, active, and dominant.”[i]

These fairy tales, told to girls as soon as they can understand stories, start the tapes that play in many women’s heads. “We aren’t good with finances or math, and we should leave those tasks to the men in our lives. We should do our jobs — raising wonderful families, keeping gorgeous houses, be fit and slim, stay gorgeous.”

After fairy tales come family “values.” Most people’s first and strongest influence is their family. Every family has a set of values — for better and worse — and these values formulate our identity messages.

Were you told there is no such thing as enough money, or that you can never have enough shoes? That diamonds are a girl’s best friend? Were you told to make it, save it, spend it, and share it? Or that good girls don’t wear short skirts? Mature women must cut their hair short? That before you leave the house each day, take off one piece of jewelry, lest you come across as a “fast girl”?

Our social network also plays a role in this. We go into the world – to school, on sports teams, to non-familial places that all have their own sets of values that subconsciously influence our thinking.

Finally, the media — never in human history have we interacted as much with media and images as we do today. And never has it had such a profound effect on our self-conceptions. As we all know, “life” always looks great on Instagram and Facebook.

Freedom Rings: Let That Elephant Go

Let’s unpack some of these specific messages so we can identify the elephant in the room — and perhaps set it free.

Style Messages

  • “You must look ‘conventionally attractive.’” This is probably the clearest message we get from all kinds of sources. Consciously and unconsciously, societies shape our idea of what attractiveness looks like. Without examining these conventional ideas with a critical eye, we lose our self-image and style to convention.
  • “Nice girls blend into the background.” This is a variation on the idea of “taking up space,” i.e., men are entitled to take up space, and women are not. This message constricts our style and quiets our presentation of ourselves — our brand.
  • “Wearing impressive logos = looking good.” In a capitalist world, money is seen as the ultimate source of value. Therefore, clothing that costs a lot of money is seen as the most valuable and desirable — regardless of whether it looks good on you, or whether it connects to your personal values.

What’s the result of these messages? Confusion, desperation, and bad decision-making. Not that we are against a little retail therapy but beware of buying too much when there is a sale, or you’re furious at a colleague or partner. The end result can be a big dose of guilt, plus a large credit card bill.

Money Messages

There are similar themes across fashion and money messages, but money, unlike style, tends to be under-discussed — leaving us to make inferences based on limited information.

  • “Spending money is bad — you should save as much as possible.” This message is particularly loud for anyone who grew up in economically trying times — the Great Depression was a strong one for people of my parents’ generation. Trauma from financial hardship leads many to fear spending.
  • “Saving money is bad — you should spend as much as possible.” The opposite message is just as much of an issue. Many people view money as something to spend as fast as possible, often in pursuit of having enough stuff to impress their peers. Which leads to…
  • “More stuff will make me happier.” Expensive clothing is just one of the things people erroneously conflate with value. Cars, paintings, jewelry, real estate — the list of things people think will make them happy goes on and on. But more and more never brings happiness — when you seek more, there is always more, and you’ll never find enough.
  • The Cinderella story: “I’ll be saved by a knight in shining armor.” This one is specifically one I sadly observe in women. Conventional gender roles cast men as breadwinners and women as kind, sweet, sexy homemakers. There’s nothing inherently wrong with this configuration, but when it causes a passive approach to money and wealth, it becomes problematic.

Write Your Own Messages

Messages are not inherently evil — there are a lot of constructive ones that help us be more of who we are. But whatever your messages, you want to be sure that you’re controlling them, not the other way around. If they don’t serve you, you might want to push those messages right out of your head. Here are some steps towards controlling your own personal narrative.

1. Identify the demons.

Ask yourself the following questions:

  • What messages did you receive about money and/or style as a child? Think about things your mother, your father, your grandparents, and/or anyone else important to you told you. Remember to include verbal and non-verbal messages, like emotions and behaviors.
  • What money/style messages did you receive from larger, cultural sources? Think about your family lineage, bedtime stories, ethnic background, religious/spiritual upbringing, and cultural milieu.
  • As a child, did you think of yourself as rich, poor, middle class, or something else? How did that feel?
  • Have you had any pivotal money/style moments in your life? Big successes, painful events, struggles, or breakthroughs?

2. Connect the dots between past and present.

How does your money history impact you here and now?

  • Review the people and stories that influenced your money/style relationships as a child. Are you repeating any of these stories or patterns today? Are you rebelling against them?
  • Are there some aspects of money and style history that you’re ready to let go of? What might that look like for you? How would it feel?
  • Think about declarative statements in which you believe. Some examples:
    • “We never talk about money.”
    • “Money is embarrassing.”
    • “Never take on debt.”
    • Never spend “principal.”
    • “Good girls wear designer clothes.”
    • “I’ll be saved by a knight in shining armor.”

3. Define your values.

Your values are what you believe in, and they form the coordinates for how you live a good life. Kindness, generosity, ambition, integrity — all these and more could be core to who you are and directly impact the decisions you make with money, style, and more.

4. Plan accordingly.

Once you know your values, you can assess whether the choices you’re making reflect them. If family stewardship is one of your values, does it really make sense to spend another $80,000 on a luxury car? Does it really make sense to buy a new $3,000 gown for every outing? Let your values dictate your decisions, not vice versa.

5. Seek help.

It’s not easy — maybe impossible — to do these exercises alone. Often, we benefit from input on who we are and whether our decisions reflect it. Plus, we may not realize the consequences of our decisions the way an expert would.

On the surface, our work is about money and style, but our real work is helping people understand their values, make decisions about money and style that reflect them, and sustain good habits over time.

Please reach out to either one of us if you have any questions. You can find Andrea’s website here, and you can contact Randy here.


Wealthspire Advisors is the common brand and trade name used by Wealthspire Advisors LLC, Private Ocean, LLC, and ACG Advisory Services, LLC, separately registered investment advisers and subsidiary companies of NFP Corp.
Guitar & Pen and Wealthspire Advisors are not affiliated companies. Neither Wealthspire Advisors nor Guitar & Pen received direct or indirect compensation from the other party for their involvement in the production of this podcast episode, and such involvement should not be construed as a current or past endorsement of Guitar & Pen by Wealthspire Advisors.
© 2024 Wealthspire Advisors

[i] Kuykendal & Sturm 2007; Slany 2011; Śmiałowicz 2013
Randy Kaufman

About Randy Kaufman

Randy is an advisor based in our NYC office.

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