Hard Truths About Freelancing

It’s tough to beat the flexibility and freedom of freelancing. Now, a caveat: I picked up an extra gig as a substitute teacher this past year for two reasons: 1. It’s been eerily quiet on the writing front for several months; 2. It allows me to get out of the house, engage with others, and pull out the closetful of dress pants I accumulated over the years. It's been a different challenge for me, but one I'm enjoying.

The side hustle illustrates one of the hard truths about freelancing: when it’s good, it’s very, very good; when it’s quiet, it can be unsettling, nerve-wracking, and downright frustrating. But it's among the most satisfying jobs I've ever had.

Still ready for the best professional ride of your life?

I’ve accumulated a few “truths about freelancing learned the hard way” that I’d like to share:

1.      Don’t expect the work to (always) come to you. You’ve hung out your freelance writing shingle, so to speak. You have clips, testimonials, a flattering head shot, and skills to spare.

 So where are all the clients?

Don’t expect your LinkedIn profile to do all the work for you. Connect. Reach out. Build your network, yes, but then work your network. Start with LinkedIn if that’s where you’re most comfortable. Send a brief message to your contacts and explain you’re open for business. Contact fellow freelancers and discuss referring each other for projects. Next, move on to the Internet. Research markets. Put together a list of potential story ideas for each. And—where I’ve had the most success—draft a letter of introduction (LOI) to send to clients you’d like to work with. An LOI is brief—state your name, a sentence or two about why you want to work with this market, and your experience. I include some of the pubs I’ve written for (especially if they are relevant to the client you’re approaching) and a link to my website.

Sometimes work does land in your lap, but I've found that to be the exception, not the rule.

2.      Follow up. This is the way. You draft your LOI, send it out, and wait anxiously for the work to come pouring in.

Instead—crickets.

I give people the benefit of the doubt. I get that people are busy. I also get that the mortgage will not pay itself. I believe in being proactive. I give folks about a week to respond, and I send a follow up to my initial message. Sometimes it results in work, sometimes not. Sometimes you get a response—any response—and sometimes not. But I believe this shows diligence, follow through, and perseverance—the same qualities you’ll bring to your working relationship with The Client.

3.      Not every project will go smoothly. Fortunately, most will, but as in any profession, expect to encounter a few Problem Projects along the way. In my time writing features, I have a handful that were absolute nightmares. I either couldn’t find enough (or the right kind) of sources, I didn’t get enough information for a round-up article, or some kind of curveball made the whole process more challenging than necessary. It’s just the nature of the beast, as they say.

4.      Over time, you won’t accept every project you’re offered. At first, you can’t afford to be selective. As you gain confidence in your skills and build your portfolio, you’ll find the projects you like best and feel most comfortable with. Features remain dear to my heart, but I also enjoy in-depth profiles, case studies, and newsletter-type pieces.

5.      Change takes time. If you shift gears into a new niche or specialty, allow time for your clients to adjust to the change. Likewise, allow time to build a portfolio of work in your new niche. For instance, feature writers who want to add white papers to their menu of offerings have to start at Square One in many ways—contact clients who might want/need a white paper and prove to them you’re the writer to do it. As you know, it took time to build your writing career to its current state—it will take more time to take it in a new direction.

What “hard truths” have you learned about freelancing?