The money monster in my mind

Unraveling my financial insecurities

My first money memory was when I was ten years old. My family had just moved to the US after a comfortable middle-class life in India, Saudi Arabia, and New Zealand. My father was doing his residency, which meant living off a $45,000 paycheck in New York City while supporting a family of four. My mom had paused her medical career to help our family through this transition. 

I quickly learned how expensive it was to exist in the US. For example, my dad received a $250 fine for parking next to a fire hydrant, a rule that didn’t exist in India. This surprise bill jolted my parents, even if they didn’t directly tell me. I could see the signs: Mom double-checked grocery prices at the store, Dad bought a car secondhand, Mom filled out applications for free and reduced lunches, and no talks of vacation or travel. Money was the tightest it had ever been, despite my parent’s insistence that we were okay. 

To ease my family's financial strain, I minimized my expenses. I borrowed books and CDs from the library, helped with household chores, and scoured the internet for deals and coupons. Though I occasionally longed for trendy toys like Furbies, I reserved such requests for special occasions, constantly feeling guilty about asking.

Our financial situation improved during my high school and college years as my parents re-established their medical careers. However, the anxiety lingered. Even as my parents reassured me of our stability, a part of me - that responsible 10-year-old - remained skeptical, preferring to stay cautious.

Making my own money

When I started my first full-time job at Google, suddenly flush with a signing bonus and regular paychecks, I experienced the freedom of having more than enough money. I could indulge in fancy restaurants and nice things without jeopardizing my or my parents' financial future. Plus, the perks at Google made me feel like I deserved them—business class on corporate travel, free meals, and a generous expense policy. I experienced the freedom of having enough money, and I liked it. 

Me with a stack of rupees, my reward from winning the joota chupai competition at my cousin’s wedding.

This newfound abundance led to a relaxed approach to money management. I spent freely and stashed the rest into savings and investments, avoiding a detailed examination of my finances. I didn’t know if it was the most financially responsible way to manage my finances, but it shielded me from the perceived stress of looking at them. I didn’t want to confront the 10-year-old me, panicking about whether a Furby purchase would ruin her parents' economic future. 

As I grew older, I questioned this avoidance strategy. After I left Google and worked at startups, a Google friend told me he had finally hit $1M in net worth. Despite my happiness for him, I immediately questioned why I hadn't hit this milestone. Was leaving Google a mistake? Was the learning and impact worth the pay cut? I went from feeling free to feeling behind with money. 

The financial discomfort of the sabbatical

For years, this “behind” feeling made me believe that I wasn’t “ready” for a sabbatical. But I struggled to answer what dollar amount would make me comfortable taking that leap, because there was always more money in staying. This is why I hired a financial advisor, so they could give me the permission to quit that I couldn’t give myself. 

Even though I had prepared a budget and methodically tracked my expenses leading up to the sabbatical, I was not prepared for the sheer financial anxiety and pressure. Day-to-day activities like eating out suddenly felt like navigating a series of neverending landmines. Should I get the avocado on my salad? Is the $8 matcha latte worth it? Is it a good idea to eat at a $$$ place? 

As time went on, I found myself settling into a rhythm. Through inner work and spreadsheet math, I developed better intuition about which “splurges” add value without jeopardizing my financial future (a la Ramit Sethi’s rich life). When my anxiety spiked, I used my IFS tools to identify, listen, and validate 10-year-old me to understand the emotion. 

But this was a fleeting feeling. 

Prenup: the fear is back

Three months into my sabbatical, my husband and I began the prenuptial process. I was aware of our net worth disparity, which my husband modestly attributed to his longer career. In truth, his financial success stemmed from his rigorous discipline and rigorous portfolio management. However, as we navigated the complex legal terrain with New York lawyers, my admiration for his financial acumen gave way to feelings of fear and shame.

I wondered if the lawyers thought I was “leeching” off my high-earning partner. Was I a gold digger? Or maybe because I’m a woman, it’s socially acceptable gold-digging? I wondered if I was anti-feminist for not contributing the same, or even more, than my husband. 

The complicated feelings about my worth and identity left me all over the place. At my best, it was an opportunity for reflection and expressing vulnerability to my husband. At my worst, it turned into lashing out and getting into fights over petty disagreements. But more than anything, this experience made me realize that my financial insecurities are back. 

Why am I so financially insecure?

I am insecure because I feel my net worth should be higher, given my pedigree and career path. 

I am insecure because I simultaneously want and don’t want a financial safety net. I want the safety of having a resource with the pride of never using it. 

I am insecure because I feel like I’m falling into traditional gender roles, with the man making more money than the woman, and I don’t know if I’m okay with that. 

When I confront these insecurities, I often ask myself: Do I care? Making money so I can have lots of money has never motivated me. But I feel this constant tension between who I am and my environment, especially in tech and NYC cultures, which subtly emphasize chasing the highest total compensation. 

However, as I reflect further, I see that this sabbatical has been both the catalyst and the remedy for my financial insecurity. Through this journey, I’ve learned to accept my unique career trajectory and reconcile conflicting parts of my identity. That healing has helped me accept that I’ll probably not have a similar life or career trajectory as my peers, and that’s okay. 

All we can do is stay true to our current experience. The rest is noise. 

Thanks for Reading! 

I’m on a journey to share the messiness of my career transition into a creative & entrepreneurial career while also reflecting on the hard-won lessons from my product career. This is my 30th post, so I appreciate those of you who have been here since the beginning. You know who you are <3 

If you want to see more content like this, heart the post or leave a comment about any parts of the reflection that stood out to you. Better yet, share it with a friend!

• I would love feedback on this post. 

  • If you want to see more content like this, heart the post. 

  • Hearing from readers also gives me a ton of energy. Drop a comment if you have any money stories that have influenced your relationship with it. 

• If you’re figuring out your own career transition or looking for more support in your product career, consider working with me as a coach. Here’s my calendly if you want to get the ball rolling.