The money habits I learned as a kid left me bankrupt at 29, but losing everything turned out to be the best thing for me and my money

  • My mother taught me to spend money but hide it as a kid, and I did that for years into my 20s.
  • Living above my means caught up to me eventually, and I filed for bankruptcy at 29.
  • Losing everything in bankruptcy finally showed me I don’t have to connect spending with shame.

“Take these bags and go straight to your bedroom. Don’t let your dad see.” 

My mother had just bought me two shirts, Maybelline mascara in brownish-black, and a new push-up bra at Target. At 13, I had learned that there was a certain magic to wearing a new shirt, a confidence born of fabric, one that guaranteed a good day, and maybe a compliment or two. 

Sneaking rustling shopping bags of new clothes, of potential, past my dad on the couch was the first rush of adrenaline I associated with spending. Growing up, we didn’t have much, but we had each other, and the chaos and intimacy that accompanied four siblings in a small house was enough to distract from what we didn’t have.

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When I became a teenager, the desire to look like everyone else, to have “cool clothes” and “cool things,” crept into my psyche. I remember being determined to turn my scientific calculator into a Tamagotchi, and I was sure I could do it. What I mean to say is that my childhood was one of deep longing.

My teenage spending habits carried over into my adult life

On Fridays, at the toy store where I worked at 16, I’d cash my check on my 30-minute break and go straight to Abercrombie & Fitch, where I’d spend it all. I didn’t mind giving up dinner or lunch to buy clothes — these physical representations of confidence, of “enough,” meant more to me than a meal. 

The habits you form in your teens don’t vanish in your 20s. My spending habits lurked; they sprouted from the seeds planted in childhood. My parents planted them, yes, but I watered them, sunned them over the years and they flourished. Thrived, even.

After graduation, I moved to San Francisco, a city with old homes and bay windows that protruded into the sidewalks like pregnant bellies. And it was romantic at first, to be 24 and scrounging for quarters for the bus every morning. To have $11 in my bank account until I got paid at the end of the week. To only go to free events, to walk, everywhere. 

It’s not that I didn’t want a savings account, or a nice apartment with a shower that drained efficiently, it was that no one had ever taught me to want it, or how to strive for it. I took out credit cards to keep up with my more privileged friends. To stay on the same level as them was just as important to me as paying rent — to have “enough” was the feeling that drove these decisions.

The idea that my curiosity had to be limited by money — for adventure, for travel, to seek and see the world — was crushing. I failed to see that money is often a boundary in which the confines of our care, physical and mental, can reside. To live above my means for so long meant that both of these would eventually decline, too.

My overspending eventually caught up with me

For years I’d wake up every morning with a suffocating weight on my chest. I’d defer scheduled payments, cancel them, overdraw my account, once, twice, thrice — all in a week, telling no one, keeping the secret between myself and my shame. After years of trying to pay off my credit card debt, I met with a financial advisor who recommended I file for bankruptcy.

I had said yes to vacations when I couldn’t afford them, gone on writing retreats, bought new shoes, expensive sweaters, fancy dinners, festival tickets, attended bachelorette parties, and now it was time to pay. After almost 10 years of applying the logic I learned as a child, spend, but hide it, I was ready to face it. 

There was shame in this, too. To me, filing for bankruptcy was the biggest indicator of financial failure that existed. I was 29, and even though the friends I tried so hard to keep up with were buying houses and starting their lives, I realized I’d never be able to get on with mine unless I did this. At almost 30, I’d have to begin. 

Even though I grew up in a low-income home, we always had enough to eat, I was always taken care of, I was privileged. And yet, there was that deep longing in me, rooted in not belonging, that caused me to spend money with shame.

But without shame, spending can be powerful. It can be intentional. I can have student loans and still buy $11 olives and I don’t have to feel guilty about it. And I really love fancy olives. I can skip bachelorette parties to Europe and I can still have “enough.” I can still be “enough.”

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