💙 My money story

Hey hey, happy Monday.

I’ve started and deleted this draft more times than I can count.

But it’s about time I shared my money story.

How financial insecurity took over my life – and why I’m writing these words to you week after week.

Smash the button below to share OptimistiCallie with a friend 😊

A few months ago, I listened to a podcast episode that brought me to my knees.

One of my favorite financial voices – Katie Gatti-Tassin/Money with Katie – had a well-researched episode on money dysmorphia, or a warped perception about your finances. In the episode, Katie explains the roots of money dysmorphia – a riff on the medical diagnosis of body dysmorphia, where you see a different version of your physical appearance – and interviews a range of women who talk through their irrational insecurities about their finances.

And when I listened to each woman talk, I heard myself in them. I listened to the podcast on the run, and at certain points I found myself hunched over and sobbing. To all of you who saw that sweaty blonde girl crying in Myers Park, no you didn’t.

That’s me. I am incredibly insecure about money, and my insecurity has defined my life for as long as I can remember. And in the most twisted irony of all, I’m a market expert who makes a living off teaching people about money and investing. Essentially, how to become – and stay – rich.

I’m obsessed with money.

How people make so much of it, and why I could never get enough.

I’ve shared my money story in private for years, and I wrote a sanitized version for a work project I started in a former life.

Today, I share the ugly truth. Why I’m here, writing these words to you week after week.

I’m one of six kids, native to a small North Carolina city (Burlington) once known for its rich manufacturing. My dad was a self-employed electrician, and my mom was a homemaker with part-time gigs here and there.

Technically, we were a lower-middle-class family that went through some very tight financial times here and there. It’s funny – class is a relative thing in childhood when you have no concept of money. You just see what you have versus what other people have.

As some people grow older, they learn they had more as a kid than they thought. As I’ve grown older, I’ve learned the opposite. More like what the WIC program is, and how much of my life was shaped by the generosity of other kind people.

I grew up in a pressure cooker. Eight people in a 1,300 square foot house. There was a lot of love and pain to go around. Kickball games in the front yard. Breaking a window during said kickball game that was never fixed, leading to a drafty bathroom. Cozy meals at the dinner table. Fights that broke out over a set amount of chicken nuggets.

To make matters worse, I was also a member of a high-control evangelical Christian church. The kind of group that taught you the trappings of the world were evil, and that debt was the devil’s potion. That women never have a place outside the house, unless it’s to teach Sunday school. We worshipped Dave Ramsey and chastised liberal thinking. Any chance we had at digging out of a financial hole was neutered by holy shame.

A few weeks ago, I told the story of how I learned about Warren Buffett by reading the newspaper at that same table. I loved scouring the real estate page to gawk at the $500,000 houses for sale – with bedrooms for all of my siblings, wow! – and then hopping over to the markets page to get a whiff of high society.

The walls were thin, and the commons were close. I spent a lot of nights listening to loud, terrifying arguments that I won’t ever be able to fully erase from memory.

Money can be a highly personal subject, no matter how much we try to strip the humanity out of it. Our feelings of financial stability develop through experiences, not classes or textbooks.

There are mountains of research backing this up. A 2017 University of Michigan study found that children start developing spending and savings habits as young as five years old. There’s also a 2021 paper from Eastern Kentucky University researchers that suggests there’s a link between adverse childhood experiences (instances of abuse and neglect) and financial insecurity in adulthood. Money scripts are a popular tool used by financial advisors to help understand the unconscious bias that can push you to make otherwise irrational decisions.

All because of this insidious truth: early financial trauma can profoundly shape your relationship with money.

That's why personal finance can feel so illogical at times — why some of us may be set on paper but constantly fear losing it all.

A lot of these late-night arguments centered around money. We can’t afford this, why’d you spend this, how are we going to pay this bill? I heard the cries, but I also processed the amounts being thrown around.

We can’t afford this $100 program. Why’d you spend $20 at McDonald’s? How are we going to pay this $50 bill? The numbers stuck with me, and you better believe I started benchmarking my life off of them. I can’t afford this $20 takeout. I shouldn’t spend $100 on this outfit. Sounds crazy, but it’s not if you consider that was the reality for over half my life.

I was also the poor kid at school. The one who always needed a ride home. The kid who wore the same shirt every week. The girl who couldn’t bring friends over to her house. Your place, not mine. Always. 

Financial insecurity tore apart my self-confidence. Sure, it instilled drive and values, but pep talks don’t go far when you’re a 17-year-old with nothing to do on a Saturday night but listen to your CDs on repeat to drown out the noise around you.

The financial crisis hit us hard. At the time, my mom was a part-time bookkeeper at a residential construction company, and my dad still had his electrical business.

I always tell people I was too young to invest in the Great Recession, but I sure as hell felt it.

My mom lost her job after it came out that her company was swindling money from customers and subcontractors. The next day, the company’s owner was in the newspaper, photographed being led out of the building in handcuffs. My dad’s business suffered mightily, and I picked up on this through more intense arguments and dire circumstances. Like the Christmas Eve when my parents told us there would be no presents, and I screamed some unbelievably nasty things at them on behalf of my siblings. It was a new low for all of us.

That day, I swore to god that I’d never start a business. I had been burned by the nasty side of risk before I was even able to open a brokerage account.

And I wasn’t the only one.

I’m 33 years old, and a member of the largest – and most misunderstood – age cohort in America.

Millennials had an especially rough induction into adulthood. Many of us were in high school or college or our early working years during the global financial crisis.

We graduated into the worst job market for us versus our older counterparts in history, judging by the 8.8-percentage point gap between the unemployment rates for 20-24 year olds (17%) and those older than 25 (8.4%).

Every generation has its war stories, but not many can say they endured two earth-shattering financial crises by the time we turned 30. We were the Occupy Wall Street generation, and it shows in how skeptical we’ve been about taking risks.

I ran an analysis for a Business Insider piece last year that looked at just how risk-averse millennials have been relative to their Gen X counterparts. The results were stunning.

If you were born right in the middle of the millennial generation, you're now 36. These "median millennials" held an average of 13 percentage points more of their total financial assets in cash during their 20s than the median Gen Xer did at the same ages.

This, during one of the longest stock market rallies in history.

College was my ticket out of Burlington. Thank god for student loans and FAFSA. I studied journalism in college and waitressed during my summers. My dad didn’t pull any strings to get me into prestigious internships, which is usually the path into front-office Wall Street. The prodigy kid following in his partner daddy’s footsteps. 

That wasn’t me. My introduction to Wall Street was a Business Insider internship and the thrill of watching jobs report Fridays at the scrappiest financial publication in NYC, then going home to cheap NYU housing to eat boxed mac & cheese that I funded through leftover student loan money. BI portfolio pieces led to a summer at Bloomberg, and I eventually accepted a job on the Bloomberg News’ stocks desk. Not necessarily because I wanted it (I didn’t love NYC), but because it beat being back in that 1,300 square foot house. I needed to start making money yesterday. 

I made my fair share of “money mistakes” right out of college, but I was really just trying to get by on my own in the money suck that is NYC without any financial help. Any decision is fair game when you’re just trying to survive. I carried credit card debt consistently (yes, while writing in-depth columns about trading implied volatilities) and I took out more than one cash advance to move apartments (one on a late-night dash to a Chinatown ATM).

That was almost a decade ago. My life is in a better place now, emotionally and financially. I’m back in North Carolina, but in Charlotte. I have a thriving research career, an amazing partner, a beautiful house, and more money than I could’ve ever dreamed about. I even started an LLC to house my content.

But at times, I am mentally miserable. My brain is stuck in Burlington. Every time I get $20 of takeout, the guilt haunts me. I supposedly can’t afford this, but here I am spending the money anyway. My financial insecurity has manifested into a conservative approach to life, which is great on paper but not so great for my sanity.

I run our numbers constantly, including a FIRE spreadsheet I keep up with for all the hare-brained what-if scenarios my mind wanders into. I approach everything with a lose-it-all mentality, and wince at even moderate levels of risk. Yes, even though I know better. I ping-pong between spending nothing and everything, and then beating myself up on both ends.

The worst realization I’ve had is how entrenched my financial insecurity is in my adult life. My job is to think too much about money – to obsessively connect and re-draw the dots around complicated market and economic scenarios, just like I had to galaxy brain money stuff as a kid. Some people choose to run as far away as they can from trauma. I have chosen the opposite approach – to lean into my wounds.

I’ll admit that there are bright sides to this paranoia. I’m a hell of an analyst, and I’ve done well for myself because I can think in both numbers and colors. These uncomfortable edges have ground out a weird creativity and a healthy skepticism in me. I’ve been on Prozac and in therapy for years, and I can’t grow my fingernails beyond nubs without picking them off from anxiety. But hey, I can offer a relatable voice in all of this insane jargon that Wall Street experts dump on you day after day.

I also have empathy in spades, which I’ve found to be an incredible superpower. Those early days are never far from my heart. I can’t deal with the possibility of myself or others hitting those depths. They are real to me.

I’m pouring my heart out to you because I want you to understand this:

Money issues are insidious. The roots run deep.

You can’t study your way out of your perceptions of risk and safety. No matter how many newsletters you read or data sets you run to death.

From all backgrounds, too. Don’t think you’re immune because your family could afford the $500,000 house. Everybody has financial trauma – big T or little t. And you’d be surprised how much your past comes back to haunt your decisions.

Also, don’t worship those money experts you watch on TV. We’re all fighting battles we try to hide behind toothy smiles and snappy quotes.

I will always be fighting my past. But I am actively fighting it, and I’m proud of that.

I can only hope the same for you.

Thanks for reading!

Callie

Like what you just read? Share it with a friend, pretty please 😊