Today Is My Last Day As A Freelance Writer

Consider this my resignation letter

On Monday morning, I will wake up to a 7 a.m. alarm, put on business casual attire, and make a 30-minute commute to clock in for a 9-to-5 in a downtown high-rise.

This might be a standard Monday morning for most, but for me, it marks the end of an era that I once thought would be my lifelong career.

It has been almost four years since I last worked in an office, and almost two since I’ve worked full-time for another company.

[Source: Getty Images]

Since submitting my first job application a few months back, the word “failure” has been following me around, lurking behind every missed gig and rejected application.

I spent the first few weeks applying out of necessity, secretly hoping a miracle client would swoop in at the last minute and I could stop applying. That never happened, but job interviews did start to pick up—until one day, I finally received an offer, silencing that voice saying “failure” for the first time in months.

Why I Failed

In some ways, accepting a job offer does feel like I failed at being a freelance writer, but it wasn’t for lack of trying.

Before I made the jump to full-time freelancing, I did a lot of research. I paid for courses, watched YouTube videos, reached out to mentors, and felt prepared for the ebbs and flows that would come, yet still, it was nothing like I expected.

For starters, I got my first client in January of 2023, just two months after ChatGPT launched. As much as I would love to blame all my writer woes on AI, I won’t. It’s a tool that I frequently use (read more of my thoughts here), but I will say the timing was nothing if not inconvenient.

In fact, my first client wanted me to use AI in our work together. Ten months later, our contract was terminated, but the content they posted carried on as usual—without a writer. Suspicious...

I did all the things the internet promised would lead to success: creating a portfolio, cold pitching, LinkedIn networking, persistent follow-ups, reaching out to my network, rebuilding my network, signing up for countless job boards and newsletters.

The cycle felt endless, but it never took me forward.

2024 has been a hard year for freelance writers in general. I’ve seen countless posts from once-thriving writers now accepting lower rates just to have work. I’ve competed for gigs in LinkedIn comment sections against freelancers whose how-to courses I had paid for. I’ve made it to the final round of contract negotiations with numerous clients only for them to dissolve the position due to budget cuts.

There are many factors I could blame for my lack of success in freelancing, but the reality is always in the numbers.

In my best month of freelancing, I earned $5,650.

In my worst month, I earned $75.

Lately, I’ve had a lot more $75 months than $5,000 months.

This continued instability meant my emergency fund was drained, I wasn’t able to contribute to my retirement or investment accounts, and I spent the last few months financially relying on my partner.

That all ends on Monday, and I couldn’t be happier.

[Source: Getty Images]

The idea of applying for full-time roles again was first floated by my partner, who made some valid points: It’s a chance to hone my craft. It’s an opportunity to meet new people in our new city. Earning consistent money will boost my confidence. And, benefits!

While these are things I want, I was offended by the suggestion. Applying for full-time jobs felt like admitting that I failed at freelancing.

It took a few months, but I came around to the idea. Then it took a few more months to get an actual offer.

Now, just days away from my start date, I’m genuinely excited to be reentering the workforce.

Here’s why:

1. I am a people person. Being cooped up in my home all day has stifled my social skills and skyrocketed my anxiety.

2. I have an excuse to wear nice clothes again. (And an excuse to buy new clothes.)

3. Going into an office will provide more structure and routine to my week.

4. I am getting paid a full-time salary to write, which has always been the real dream.

5. Benefits, benefits, benefits!

Everyone I’ve told so far has had the same reaction: “That’s going to be a big adjustment!”

It most definitely will be.

While I’m not disillusioned about how much my life is going to change (I’m already having a hard time figuring out how to schedule my ongoing doctor’s appointments—help!), I no longer feel like accepting this job offer means I was a failure.

I certainly did not achieve that dream of being a six-figure freelancer, but I did learn a lot about myself and my relationship with money.

Lesson 1: I have great control of my money when I am earning it. I have zero control of my money when I am not.

The first month I needed to tap into my emergency fund to supplement my disappearing income was the month I completely stopped budgeting. My routine, which once involved meticulously tracking my expenses, regularly checking my bank account, and setting monthly goals, went out the window.

Why? Avoidance.

It’s no surprise my emergency fund didn’t last nearly as long as I had planned. Despite a lot of therapy, it turns out I still have a long way to go in healing my inner wounds around money.

It’s been a harsh reality to confront just how far I am from having control of my money, especially since I had dedicated my career to writing about money.

[Source: Getty Images]

Lesson 2: You can’t simply ‘online course’ yourself into success.

I never expected to fail. That may sound silly, especially as someone with chronic anxiety, but I truly never expected that I wouldn’t reach all my goals as a freelancer. I had consumed so much content guaranteeing that as long as I followed X advice, did Y thing, and implemented Z systems, I’d be making six figures in no time!

“I was never told that I wasn’t gonna get the things I want the most.” - Chappell Roan

This was not the reality. As months passed by and I was still not hitting those goals, I began to beat myself up, believing it was because I was lazy, unmotivated, or maybe I just didn’t want it enough. It became a vicious cycle.

Lesson 3: Sometimes you end up being a statistic, and that’s okay.

When I first started freelancing, I was constantly being fed the statistic that 20% of freelancers fail within their first year, and 60% fail within the first five years. I was determined not to be on the failing end of these statistics. I wanted to make it.

Even though I was suffering—mentally, emotionally, financially—I wanted to uphold the image that I was living my dream life and pursuing my dream career, despite being chronically stressed about money and more than a little miserable.

Lesson 4: You don’t have to be perfect at something to be passionate about it.

While my bank account certainly took a hit during my stint as a freelancer, my confidence in talking about money suffered the most.

It was hard to find the motivation to wake up and write about money when I was hardly making any of my own. It was tough to coach clients on how to reach their own financial goals when I wasn’t working towards mine.

[Source: Getty Images]

My imposter syndrome was at an all-time high, despite working a job I created entirely around my own passion and interests. It took me a while to accept that my advice isn’t any less valid just because I haven’t perfected the art of personal finance.

Lesson 5: Your definition of success and failure is relative to your own happiness

Before I started freelancing, I genuinely believed I’d rather struggle financially doing what I love than earn money in a job I hate. But as time passed, walking away from something that caused me so much financial stress no longer feels like failure.

Today, I’m simply proud that I succeeded in the job application process, especially in this market.

As for this newsletter, it’s not going anywhere. In fact, I’m more excited than ever to keep posting and sharing what this next phase of my financial life will hold.

Stay tuned!