How I Failed At Freelancing—And Why I’m Glad I Did

By Kaitlin Stevens August 9th, 2019

Ever since I landed my first position at McDonald’s at sixteen, I knew I’d never enjoy working a “real job.” I’ve always preferred having my freedom: no one to tell me I can’t go on vacation when I want, the ability to work from bed and take a Netflix break when I feel like it, the option to finish all my work past midnight when I’m less distracted.

When I was nineteen, I landed my dream gig—an internship writing for The Source. I loved writing, especially about music, but until that big break, I didn’t think it was something I could get paid for. I kept taking on internships, telling myself the perks were enough to sustain me. But, despite getting VIP access to Drake shows and shaking hands with Jay-Z, I was living off student loan money, and it quickly ran out. By then, I had been writing for a few music blogs and trying to make a name for myself in the underground music scene, juggling freelance blogging with a day job. I was left with precious little time for sleep and a social life.

One day, I got an email from the manager of an artist I’d written a feature about. The manager asked if I could craft a press release for the single his artist had just dropped. He wanted me to pitch the single to my network and he offered me $300. I wrote up a quick bio for the artist, a blurb about his single, and I whipped up an eye-catching email with links to his work and an ask to feature it on recipients’ sites. My network was pretty receptive, and I managed to land the artist’s single on nearly every blog I pitched. I felt exhilarated.

Word spread about my services and suddenly, my inbox was full of requests for PR work. I’d actually found a way to sustain myself while writing about music and really, I’d just stumbled into it.

How freelancing became hard

Within a month of freelancing as a PR rep, I decided I could confidently quit my day job. Another two months of PR work, I had saved enough to move out on my own. For the next five years, I didn’t just survive. I thrived on my freelance income: paying rent, going on trips to Europe, and even managing to save. But after five years of steady work, gigs started to dry up, and I had to pick up odd jobs here and there just to make rent. Music promotion was changing. Blogs were no longer the primary source for music discovery. Streaming services and playlist curators had become the new gatekeepers—seemingly overnight.

Before I noticed it was too late. I realize now that I’d made a big mistake by failing to adapt. I didn’t expand my approach to incorporate this new playing field, and in time, I lost clients who needed new services I just couldn’t offer.

The mistakes I made as a freelancer

There were other areas where I went wrong. Though I had worked extensively as a writer, contributing to a number of sites and helping build brands up from nothing, I didn’t have much to show for it—at least, not tangibly. All my clips at The Source were erased in a merge to a different site host. Two other publications I wrote for went under as well, hundreds of my posts disappearing with them.

I never thought to save HTML files or screenshots of my work, because I figured they would always be there as links. The effect was a near-total annihilation of any proof that I could write original content. Worse, I never thought to save the hundreds of press releases I wrote, which could have gone a long way in selling my copywriting and email marketing skills.

Looking back, I think my biggest mistake was not taking freelancing seriously enough. I naively believed that business would always be plentiful, and I took for granted the freedom to make money on my own terms. If I had treated freelancing like a “real job,” I would have been more focused on maintaining a sustainable business for myself.

What I did right in my freelance career

Luckily, I did get some things right in my freelance journey, like carefully managing my money. Whenever I landed a project that paid well, I would put the whole check in savings (which eased the blow at tax time). And since I made most of my money through PayPal, I used my PayPal debit card for purchases. Every month, I could download my statement and compare my spending to what I had made that month.

Another thing I got right was the honest approach I brought to my work. Candor is an important aspect of self-employment—for you and for clients. I never lied to my clients or oversold them on projects, and I know that set me apart from some of my competitors. For example, I always told musicians exactly how I could help them and outlined without exaggeration what they could expect to gain from my services. I didn’t pretend I could make them famous overnight or guarantee an inflated number of views or streams.

My steady clients appreciated my integrity, and a handful of new clients came to me after being burned by other freelance publicists who looked flashy on social media and made big promises they couldn’t keep.

I was honest with myself, too. I would carefully plan my calendar and the number of clients I took on so that I could really focus. I avoided multitasking and drowning myself in work. I figured it was never worth the risk of leaving a client unsatisfied and possibly losing business.

As I navigate the writing world with the specific goal of making freelance work my sole source of income, I’m actually grateful for the mistakes I once made. Informed by my prior missteps, I’ve made a strong second attempt at freelancing, prioritizing my portfolio and opening myself up to all avenues of writing so I never again find myself stuck in a place where I can’t adapt.

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