I Created a Writers Group, and It Changed My Freelancing Life

A few years ago, I decided to return to freelancing. This move followed a lengthy maternity leave and a lucrative run as a technical writer in the banking industry. As my son headed to kindergarten and adventures of his own, I was equally excited to take up this new challenge.

Once at it, though, I began to realize the nuts and bolts of freelancing had changed drastically. (The last time I’d sent out a query letter, fax machines were cutting-edge technology.) I was filled with questions like: What’s the best way to record and transcribe interviews? When should I Skype? Even when I landed assignments, I was uncertain: This contract is asking for one of my limbs—is it okay for me to sign it?

I Googled for answers. I also consulted writer friends. But then I started to worry these friends would start avoiding my calls. A writers group seemed like a natural next step. I live in a large city—Toronto—and knew there were plenty of groups scattered around. I didn’t envision having problems settling somewhere. However, after doing the rounds, I just wasn’t feeling it. Some groups were too literary; others seemed stuck complaining about dwindling gigs and this Internet thing. During one final test run, I visited a newly forming group that frightened me—these people seemed so lonely and talked openly about unrelieved days spent tapping away at keyboards. I left (okay, ran) from this meeting feeling depressed not just about the group but about freelancing in general.

Thankfully, my brain spit out another thought: Why not start a group myself? And so I did.

How did I go about it? All I had to do was invite a handful of writers to my house—fellow parents, a couple of friends from journalism school, and a friend of a friend. More than two years in, we now have a committed core that meets monthly at a pub. And the benefits have stretched far beyond the advice and support I originally hoped for. As we’ve gotten to know each other, many of us now get a fair bit of work via referrals from other group members.

If you’re in a similar spot as I was—talking to your computer screen way too much, struggling to find the support you need—you might want to consider leading your own group. Forming a group versus simply joining one involves a bit of extra work, but you get a lot more say in how things come together.

If you want to take on the initiative, I have some advice that could help you along the way:

Target talented people

My advice is to start small. Invite any freelancers you may already know (and like), and see what happens. When I tentatively emailed invites to an exploratory meeting, I was pleasantly surprised by the response. Almost everyone came out, and most have stayed on since.

If you target the right people, it can have a snowball effect. (The same can be said for targeting the wrong people.) Members grew the group by reaching out to their own connections. When considering whom to invite, I’d suggest paying close attention to diversity, specialities, and positive energy. Invite people you admire and can learn from. If you’re dying to invite someone to your group but think they might be hesitant, ask them to drop in as a guest speaker. At the very least you get a dynamic speaker, and if you’re lucky, you might end up with a valuable new group member as well.

Balance diversity and similarities

In one sense, our group is far from diverse—we’re all female, which may or may not change. Some common bond like this is a good starting point, but I think a strong group also needs diversity. For example, our group consists of editors, writers, and a creative director. And our beats cover the map—from academic editing to the automotive industry to beer. Some of us work in traditional media; others are bloggers and social media gurus. Ages range from thirties to fifties. Some work at home in yoga pants (me!), others commute to client sites and fly to conventions.

The best thing about all this diversity? We’re not all chasing after the same ball. And the differences are intriguing. Having members with different backgrounds can spark fresh ideas and new perspectives. Maybe I get some time-scheduling tips from that type-A member in the group, or we all get some new approaches to interviewing from each other. From a practical standpoint, editors and writers can seek each other out, while members can pass overflow work to each other.

Set positive vibes

I believe the energy you create will define your group. Let’s face it, freelancing is tough. But while it may be tempting to indulge at meetings—just one more piece of industry gossip or round of whining—think about it: What’s going to keep people coming back each month? Ultimately, everyone needs inspiration, encouragement, and an outlet for learning. Attracting positive people from the very beginning, setting a proactive tone, and limiting griping can help you keep things on track.

Embrace technology

It’s no secret writers need to stay current. One of the huge benefits of being in a group is the technical help and advice you can get. At about half of our meetings, our group tackles technology issues: social media tips, recommended apps and software, how to reap more benefits from a platform we already use—like LinkedIn, for example. We take turns presenting information as others take notes, which constantly reminds me how much we can learn from each other.

Additionally, groups can use technology to keep communicating between meetings. Our group has 18 members in a private Facebook group where, on a near-daily basis, we post questions, article links, industry events, and just check in. We also have a Google spreadsheet for listing rates for job-sharing purposes.

Stay flexible

Inevitably all groups face growing pains and identity crises. “Can I invite friends to the group?” “Can we change our meeting format?” “Can we meet somewhere different?”

How should you respond to feedback and difficult questions? In my view, a healthy group lets members make decisions together. Writers tend to be analytical, creative, insightful—and opinionated. As a facilitator, I’ve found it’s hard to predict our preferences. The group’s needs often evolve and change, so it’s best to collaborate and work issues out together as respectfully as you can. Talking things out can hopefully prevent stagnation or resentments from setting in. For example, our group recently debated our size. With a regular in-person attendance of between four and eight people, you might assume we’d be gunning for more members. However, our discussions revealed that most of us strongly value the intimacy and conversational style of a smaller group. Now we know.

Shared struggles

When it comes down to it, given the solitary nature of freelancing, finding support is a near necessity. For me, one of the most amazing aspects of being part of a group is you get a long view of the twists and turns of a career. Everyone takes turns going through rough patches, feeling uninspired, and taking risks. With a group, you get to share the excitement when things turn around and also review how far you’ve all come. Online groups can give you some of this, but nothing beats face time—oh, and getting out of the house to drink beer. In my experience, starting a group has been well worth the time I’ve put in, and I’d recommend it to all freelancers.