#79: The Cost of Success
The difficult work of uncoupling your definition of success from your paycheck.
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The Cost of Success
I’ve been promising to write about this topic of money since Q4 of last year. And, naturally, I’ve avoided it for a couple of months. But here I am, facing my fears…and tax season. As I’ve started rerouting my GPS for success and re-evaluating what success even means in this new era of my life, I’ve been reflecting on how I felt at my last job. Did I feel successful day to day? Not rreeeaaaallllly, if I’m being honest. What I felt was stress, striving, and an unwavering desire to bring creative ideas to life despite being wrapped in corporate red tape so tight it felt like a straightjacket.
But there was one thing that DID make me feel successful: my compensation.
I came up in my career under the assumption that if I wanted my work to be creative, I would likely never make a lot of money—unless I got lucky and fortune shone upon me. Let me give you some concrete numbers that will make your jaw drop. The fiscal year I was 24, I made less than $24K. I was scraping by, just trying to survive, but I didn’t have any real ambition to make more. As an aspiring actress juggling odd jobs in the notoriously low-paying theater industry, and later as a writer and editor, I knew I wasn’t playing on the this will make you rich playground. My work was never going to be valued the way, say, a lawyer’s was.
So when I found myself in a leadership position at a corporate media company, my salary far, far exceeded my financial expectations for myself. It surprised and delighted me. Of course, in NYC, unless you’re a multi-millionaire, even a “healthy” salary doesn’t ever stretch as far as you’d hope. But I wasn’t worried about my bills. I had money to buy nice things and even take a far-flung vacation every now and then. And I won’t lie—financial security did make me feel successful. I had exceeded not only my own expectations but also those of others. (There was even a member of my extended family who once referred to me as “the smartest underachiever in the family.” Thanks for the life-long complex!!)
But here’s the thing: Even though I was well-valued from a compensation perspective, I was not well-valued as a human being. And that rankled me to my core. The company wasn’t paying me a high salary because they valued my work. They were paying me that salary because they owned me. And I didn’t want to be owned anymore.
The Cost of Independence
Which brings me to my current financial reality.
I am absolutely fucking drowning in medical bills. Outrageous premiums. High deductibles. Garbage coverage. I don’t even want to talk about the absolute tragedy that is health insurance in this country.
But I do want to talk about Instagram. In 2014, back when I was earning much less, Instagram was just for heavily filtered photos of lattes and sunsets. Now, it’s a marketplace disguised as a social network, and I am susceptible to the ads. Every day, I have to talk myself out of buying things I don’t need—makeup brushes, lip stains, pillows that make your neck pain disappear. But I have to scroll! It’s part of staying current in my field! SEND HELP!
Then there’s the math of it all. I hustled my ass off last month—took on lots of clients, worked every possible hour. And yet, I barely broke even on my bills. Many months, I have to supplement my earnings from my savings account, which is in a slow but steady decline. How is this supposed to be sustainable? I have no idea. How can I earn more without selling my soul back to corporate America? Also, no idea…YET. There’s still a small part of me that has hope I will figure out a viable solution. But when? How?
Just for fun, I recently downloaded my Social Security statement. In 2024, I made less than I did in 2014—when I was still rising in the earnings department. That was the last time I was a freelancer before now. I’ve come full circle, but not necessarily in a way that feels great.
Redefining Wealth
And yet, if I ask myself the real question—do I feel successful?—the answer is more complicated than just looking at my bank account. I have more freedom now. I work on projects and with clients I like. My ideas aren’t strangled by endless meetings and approval chains. My productivity isn’t defined by weekly bullet points. My work finally feels valued, not because of what it earns a company, but because of what it contributes to the world.
But success, as it turns out, isn’t just about feeling valued. It’s also about, you know…being able to pay your damn bills.
So where does that leave me? I’m still figuring it out. Maybe money is just another GPS point in this rerouted journey. Maybe it’s a reality check, a recalibration, a necessary evil, a means to an end. Or maybe—just maybe—it’s something I can learn to redefine for myself, just like success.
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