Lessons Learned as a Freelancer

I have been freelancing most of my life, but until April 2003 I did it as a side gig while gainfully employed. My initial attempts to freelance full-time came after job losses, and, unable to generate sufficient income as a freelancer, I soon returned to full-time employment.

I can point to many reasons for my initial failures, but key among them may be my inability to hustle. Selling—myself, my services, or my product—does not come naturally. Though I am much better now than I used to be, I dislike cold-calling, I’m not good at asking for work, and I’m not good at closing the deal when an opportunity arises.

Writing short fiction, essays, and fillers allowed me to avoid the parts of freelancing at which I was least successful. I could generate copy and allow it to sell itself when discovered in editorial slush piles. Alas, that method produces highly erratic income.

LESSON ONE

My current run as a full-time freelancer began, as before, with job loss. I did not, initially, consider freelancing as an option, and I prepared my resume intending to seek full-time employment. Within a week, though, the publisher of a monthly newspaper offered me a steady, long-term freelance editing gig that would pay approximately half what my previous employer paid for full-time work.

I took the gig—which lasted almost 15 years—and I dove into freelancing, seeking one-off gigs to make up the income difference.

Three months later, the publisher of a regional consumer magazine offered me a steady, long-term freelance editing gig. I took the gig, which, 16-plus years later, continues.

Even with steady income from two clients, I continued seeking one-off gigs, and that led me to a professional orchestra, where I began, in September 2005, a steady, long-term gig creating advertising and promotional material.

With three steady clients generating more income than I had earned from my previous full-time employment (though sans benefits), I stopped seeking one-off gigs.

I applied the concept of repeat clients providing steady income to my fiction production as well, and I concentrated on producing short stories for a small group of publications that, between them, published several of my stories each month.

LESSON TWO

Each of my income streams requires different, though related, skills, and it is this combination of skills that allows me to continue freelancing.

Writing fiction is my first love, and the ability to create publishable short stories provides my favorite income stream.

The other income streams include:

Writing essays and various forms of non-fiction.

Copywriting (creating advertising and promotional material).

Editing (selecting work for publication) and copyediting (correcting spelling, punctuation, and grammar).

Layout/design/typesetting, most often in combination with the other skills.

I trained as a typographer when I was younger, and I maintained many of those skills as printing and publishing transitioned to desktop publishing. So, not only do I copyedit the articles published in the consumer magazine, I also design and layout the pages, and prepare print-ready files for the printing company. The same with the orchestra’s advertising and promotional material. I not only write the magazine and newspaper ads, I also design them and submit print-ready files to the various publications in which they appear.

This combination of skills allows me to take on projects that I might otherwise avoid, and I’ve learned that a diverse set of skills opens up a wide range of opportunities.

LESSON THREE

Prior to my latest venture into freelancing, my experience was almost entirely with print media—newspapers, magazines, brochures, flyers, and all manner of other things that are produced on printing presses. During the past several years, my creative world has expanded. I’ve edited electronic newsletters (one of which I’ve produced every week since April 26, 2006), I’ve written or written for websites, and I’ve written radio and television commercials.

Though I didn’t actively seek out most of these opportunities, none of them would have come my way had I not been open to them.

LESSON FOUR

Throughout all of this, I have continued to write and edit fiction.

While I enjoy all that I do, my first love always has been, and likely always will be, telling stories. So, whenever I find the volume of work skewed too far from what I most love, I seek ways to bring everything back into balance.

SUMMARY

Before I wrap this all up, I must make a few observations:

Somewhere over the years, I stopped freelancing for the orchestra and became a part-time employee. Yet, because I work about 60 hours a week, I’m still a full-time freelancer—a full-time freelancer with a part-time job.

A freelancer’s life is not for everyone. Despite having a few steady clients, the income can be wildly erratic and things many people take for granted—health insurance, sick leave, vacation time—a freelancer just can’t.

So, the lessons:

1. Find and nurture repeat clients.

2. Market your entire skillset.

3. Expand your abilities in multiple directions.

4. Continue doing what you love.

I don’t think I will ever return to a full-time job. At 62, though, the likelihood of being offered a full-time position as anything other than a Walmart greeter is slim, and that’s fine with me.

The first season of Guns + Tacos is now available in two handsome paperbacks: 

Volume 1

Volume 2