I'm a #Girlboss Who Can't Afford New Underwear

I went into debt trying to get rich

Beneath the shiny exterior of a thriving online business owner was a girl drowning in debt and wearing underwear with holes. My Instagram bio read, “I teach women how to shapeshift 🐆 into their most magnetic selves by integrating their ✨ Human Design✨”—a word salad, desperately crafted to attract clients into a six-month cOaChiNg CoNtAiNer. Believing I was one viral TikTok away from changing my life, I continued working odd jobs and freelance gigs while ignoring calls from debt collectors.

My husband wiped away my tears during my daily 5 PM breakdown, hiding his concern over our spiraling finances. I drained my 401k, tanked my credit score, destroyed my nervous system, and created a four-year gap in my resume. My stress physically manifested as weight gain, back pain, and my teeth spreading further and further apart from clenching my jaw in my sleep.

I wanted to be successful—rich, location-independent, and free from the 9-5—so badly that I was willing to blow up my life.

If you scroll through Instagram long enough, you’ll find faceless accounts of rich white 20-year-olds driving G-Wagens and touting designer handbags. Hot girls claiming to make $100,000 per year or month while working minimal hours every week. Just comment ‘SCAMMER’ below, and for $777, they’ll teach you how to Escape The Matrix ™️.

I scrolled for approximately 30 seconds to find a post for this piece and voila.

The dictionary defines success as “the accomplishment of an aim or purpose.” But it’s 2024, bitches, and I live in America where success means having the money to buy whatever you want, based on quality and not price. Fancy job titles, social media followers, or a well-known brand. The ability to afford luxury travel and fly private, with a new wardrobe packed into designer luggage. Having the biggest home in the sexiest location.

Everyone I know assumed 2023 was the best year of my life… because I got married. I’m in one of those relationships where people go out of their way to let me know how lucky I am, how great we are together, and how happy they are for me (it’s okay, you can roll your eyes). To everyone else, getting married was the highlight of my life. My bridal shower, organized by my mother, was the boozy, sexy party brunch of my dreams. My girlfriends threw me an astrologically-themed bachelorette party #PartyLikeASag. Our fun micro-wedding was in Vegas, followed by a three-city honeymoon in Europe.

Anyone would kill for what I had, but leave it to me to find a way to feel like a failure while living the dream. My soon-to-be husband paid for all the wedding events, so I was riddled with guilt (now you see why I didn’t ask him to also buy me new undies). He didn’t bat an eyelash and was happy to do it, but the shame of being a failed #girlboss blinded me from the bliss I was living in.

In The Secrets of Success, Caroline Cala Donofrio draws parallels between “good, fast, cheap” and “love, glory, money.”

“I’ve had many conversations with friends and acquaintances who make ‘good money’ yet feel haunted that their efforts do not positively contribute to society or the world at large. Meanwhile, I love what I do but want to plunge my head in the sand whenever I am confronted with my ‘numbers.’”

I worry that my relationship is the most successful part of my life. The idea of 'having it all'—or having it all at once—feels like a myth. I wonder if there’s room for anything else. Do I truly have the thing that matters most? Should I just be grateful for what I have and stop being a brat?

When a woman leaves the workforce to raise children in the US, we assume her husband is very successful. How else would a family of three or more afford to live on one income? You do have to wonder, however, if the successful men of the world would be as successful if they didn’t have a partner behind the scenes to take care of their home and children. Maybe holding down the fort, and being exceptionally good at doing so, is a success.

There’s immense pressure to have something to show for the work we do. Being congratulated or recognized in some grand way, usually monetarily, but what about the impact that we have on other people or the world? Is a priest successful? Is a teacher successful? I wonder why we don’t refer to middle-class, average people as successful. Only the rich, famous, briefcase-holding, fancy-car-driving people are called successful.

It’s surprising how many celebrities, despite their wealth and accolades, turn to drugs or even take their own lives. It makes you wonder if billionaires ever feel satisfied, or if the goalpost just keeps moving, no matter how much they accumulate.

We’ve all heard the stories about musicians and the people in their lives who didn’t believe in them. They were told they’d never amount to anything, only to become musical sensations. Maybe we all yearn for that “I showed them” moment, romanticizing success when it might just be a trauma response.

My new fixation for being successful is becoming a best-seller and being featured by Substack. I can’t imagine what it feels like to consistently be on the leaderboard. Then the reality dawns on me that I’d feel the pressure to stay there, week after week. I’d never be satisfied. Is satisfaction the real measure of success? It does sound nice to be able to fall into bed at night feeling satisfied, despite nothing groundbreaking happening.

Realizing that I could literally drop dead tomorrow, I found steady work and put my Insta-baddie dreams to rest. I bought some new bloomers and sleep a little deeper now. I write because I enjoy the chatter inside my mind and thought you might too. I’ve declined coaching clients, and I’m re-examining what success means to me.

Why ruin years of my life chasing goalposts that refuse to stay put? I’m still a risk-taker, a big dreamer, and a rebel. I’ll still reach for that leaderboard, but I’ve learned that driving a G-Wagen means nothing if it comes with years of scammy insta-posts and dank panties.

If it’s not within your means to upgrade to a paid subscription, please consider a contribution to my panty fund buying me a coffee.

You can read my other publication, Designed for Success, where I discuss online business and a little coaching snark.

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