The day before my deadline, I received a text from the journalist who was going to be the subject of this week's column. It turns out they had concerns about how they would be portrayed. "Maybe we need to talk about this," they wrote to me on Thursday. I quickly realized that this was going to be an issue. The interview subject is someone I've been on friendly terms with over the years. We've shared texts about our favorite sports teams during football season and once met for lunch when I visited their city.
I usually avoid writing about people I know to some extent, but I thought this could be different. After all, this column is about emotions and attitudes toward money, and I appreciated their candid and thoughtful social media post about their current professional reality, notably the low pay. The timing seemed apt with recent news about layoffs and buyouts in the industry. I asked them if they would talk to me for a column, and they eagerly agreed, thinking our previous relationship would give them a safe space to be open.
We had a lengthy conversation, delving into intimate details about their financial struggles and the challenges of finding well-paying freelance work. Our discussion also ventured into personal issues like divorce and addiction and how they affected their life. However, when I probed for specific financial details, they became uneasy. They made it clear that they were not comfortable discussing specific amounts.
Later that evening, after discussing it with my editor, we decided to anonymize their account and remove most identifying details from the column. I learned a lot from this experience. When we launched Emotional Investment, I anticipated that soliciting stories about people's emotions regarding money and its impact on their lives would be extremely challenging. This is why my wife was hesitant for me to write about our finances in this column and why I was concerned about mentioning my parents at all.
Even if we feel fine about the objective facts of our relationship with money, we worry about how these stories and confessions will be received. It's difficult to predict how others will interpret them and how they might judge us. When we share these details, we lose control over our narrative, and that's intimidating. Will readers think we're broke, irresponsible, privileged, or elitist? The subject of the column, now anonymized, was concerned that my comparison of their current income to what they earned in the past depicted them as a "has been." I can understand wanting to maintain control of your story, even if you're a professional writer who understands the demands of journalism.
However, considering the recent challenges in the news industry, from major layoffs to the collapse of news startups, it's important to have honest conversations about the feasibility of freelance work. So here is an anonymized version of our conversation.
First, some context: This journalist was realizing that a long-term project they'd been working on wasn't going to materialize. Even after securing good print work, they knew the rates didn't make sense. The $1,500 payment for a 3,000-word feature that involved travel wouldn't translate to a reasonable hourly rate. So they were preparing for the worst by taking out zero-interest credit cards and a personal loan to tide them over.
Here are the parts of our conversation that resonated with me:
On how divorce changed their financial reality:
- They mentioned that paying divorce attorney fees took a substantial portion of the settlement, which was unexpected and became a major point of contention.
- They described the shift from a life of financial comfort to a more constrained existence, where they had to consciously consider every expense and live within their means.
On keeping up with mortgage payments:
- The journalist expressed concerns about maintaining the mortgage but saw the property as an investment and a potential retirement asset.
On how their childhood changed after their parents' divorce:
- They shared their experiences of financial instability after their parents' divorce, moving between comfort and struggle, and learning to live modestly.
On becoming a journalist:
- They reflected on their early career in journalism, initially expecting career progression to be straightforward, which they attributed in part to their privilege as a white person.
On the challenges of earning a livable wage as a freelance writer:
- They discussed the increasingly unsustainable nature of freelance journalism, citing significantly reduced pay compared to fifteen years ago.
On why they don't want to write a newsletter:
- They expressed reservations about the feasibility and market demand for regular newsletter production, particularly highlighting the confidence of some writers in this endeavor.
Their experiences and reflections reveal a broader issue in the journalism industry regarding financial stability and the challenges faced by freelance writers.
I've long believed that op-ed writers should have a system of rotation for their own well-being. Writing op-eds continuously for more than six months can lead to running out of fresh opinions. That's why I've been reluctant to start a newsletter. Substack approached me early on, during the days when I was making six figures, and maybe I should have considered it then.
I believe they're in trouble. When my friends started losing their jobs, I began subscribing to newsletters, and the costs quickly added up to around $50 a month or more. This is more than a digital New York Times subscription, which offers a wealth of content from numerous writers.
Regarding the prospect of never again earning a livable wage as a writer, I've learned to be self-reliant. However, deep down, I always hoped that someone would eventually take care of me. The goal was to work hard early in life so that I wouldn't have to work as hard all the time. It feels like I've always secretly wished for a future where I won't have to work as hard without consciously planning to take care of myself.