Building Your Business

What I’ve Learned From Starting a Business for Freelancers—While Freelancing

By Sonia Weiser October 24th, 2019

There’s nothing particularly obvious about the inner workings of the freelance writing industry. Magazine editors don’t post calls for pitches on traditional job boards, so unless you know where to look, you won’t be getting published anytime soon. And even if you do know where to look, it’s a time suck and often yields little reward.

In June 2018, after years cultivating a nearly perfect job-hunting practice, I turned my nightly anxiety-fueled ritual into a public service. Along with retweeting all of the freelance writing opportunities editors post on Twitter, I collect them, stick them in Mailchimp, and fire them out in a newsletter called Opportunities of the Week.

One year and a few pricing adjustments later, it’s a successful business, and I learned a thing or two in the process.

Whether you’re launching a new creative project while juggling freelance work or venturing into contract work for the first time, here are my tips to head off problems at the start.

Prepare for a Business, Not a Hobby

Don’t wait to set up a professional-grade organizational system—you never know when your tiny venture will take off, demanding careful bookkeeping and streamlined customer service.

I encourage you to be overzealous with your use of spreadsheets, labels, and notes as you grow. Keep track of your income, your deadlines, who’s paying you and when that money is going to roll in, and whatever terms you and your client agreed upon. A laissez-faire approach may work when you can still rattle off the names of your clients from memory, but once your business grows, it’ll be chaos.

Set Client Expectations and Manage Your Boundaries

When I started the newsletter, I made it clear that subscribers could always email me with career questions or for life advice. They did. A lot. I found they were frequently asking me for “favors” that roughly translated into me doing their work for them.

At first, I obliged. You want me to find someone’s contact information for you? No problem. Don’t know which publications take personal essays? Here are some options. I’m a people pleaser by default, so I was willing to help, and I didn’t want to earn a negative reputation with my burgeoning subscriber base.

Trouble is, as a freelancer myself, the more time I spent doing other people’s work, the less I time I had to do my own.

After a few months of Googling things on subscribers’ behalves, I began enforcing a “do your research before you talk to me” caveat to my previously open-ended offer for guidance. From the jump, give your clients or users a clear picture of what you will and won’t do for them, how you prefer to be contacted, the services you charge for versus the ones you’ll do for free, and what you absolutely won’t tolerate. Not sure how to handle an unpaid invoice? Sure, contact me. Don’t know the name of a magazine’s editor? I’ve heard wonderful things about the internet, you should try it sometime

Consider Your Own Needs Before Monetizing

A fundamental part of freelancing is creating a sustainable business model, and in order to do that, you must take into account not only what your clients or users want, but what you need. When I launched the newsletter, subscriptions were free and I promised that they would remain free forever. I believed this was a demonstration of my commitment to making freelance writing opportunities accessible to everyone, regardless of whether they have time to look for them or not.

However, the 5-10 hours per week I spent enabling others’ success started eating into my own time for paid freelance work. It got to the point where I had to decide whether to take on a new part-time job to be able to afford to run my free newsletter or ask for a small monthly fee from my subscribers as compensation for my labor.

With an overwhelming sense of guilt and quite a few tears, I began charging my subscribers $1/month, soon raising the price to $3/month at the start of 2019. In continuation of my mission to democratize freelancing, I abide by a “pay what you can” system and I don’t turn anyone away due to lack of funds. While I did eventually step away from my original plan, I had to make compromises in order to keep the newsletter going long term.

Welcome Constructive Feedback and Act On It

When providing a paid service, it’s worth checking in with your customers regularly to see if they’re satisfied. Offer them the opportunity to share their thoughts about how you could improve your product.

Some of your audience’s requests may be unreasonable, but others may prove useful and ultimately enhance the value of your product. Creating a multiple choice survey with Google Forms or SurveyMonkey is a fairly painless way to collate data.

You may also find that your clients don’t need—or haven’t even noticed—some of the special sauce you’ve been adding, which means you can cut out a step or two and save yourself time.

Keep Experimenting

Nothing is ever exactly right from day one, and sometimes this means you’ll have to modify something you thought was already perfect. Don’t be afraid to tinker as you go, whether it’s as simple and seemingly insignificant as adjusting the font size, or as monumental as switching from a free to paid model. Some adjustments will work, some will backfire. Some may garner praise, some may drive clients away.

Prior to making my newsletter a once-a-week event, I would send it out every few days depending on the quantity of calls for pitches posted on Twitter. After cutting back, complaints rolled in from subscribers who felt that I was doing them a disservice–they wanted to be first in line to submit their ideas and that wouldn’t be possible if I didn’t send them editors’ tweets immediately.

Which leads me to my favorite piece of advice:

Pick Your Battles

It’s much easier to respond to non-constructive feedback from readers and followers with “thanks for your input,” or “I’ll consider it” than it is to justify your decisions or argue with them about why they’re wrong. It takes discipline and self control to be gracious, but it’ll eliminate so much unnecessary aggravation.

These lessons didn’t come easy—no sudden realizations or aha! moments. They are the product of an endless stream of emails, lengthy diatribes against humanity, crying in public, and the acknowledgement that what was once a little experiment could actually be something worthwhile. And even after more than a year, I’m still learning.

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Sonia Weiser is a freelance writer and the creator of Opportunities of the Week. She’s previously written for The New York Times, The Boston Globe, TIME, among others. You can view her published clips here, her Contently portfolio here, and sign up for her newsletter here.