We caught up with the brilliant and insightful Dianna Gunn a few weeks ago and have shared our conversation below.

Dianna, thanks for taking the time to share your stories with us today Alright, so you had your idea and then what happened? Can you walk us through the story of how you went from just an idea to executing on the idea

In 2018 I started a Twitter chat using the hashtag #WeeknightWriters. This was a space where writers could gather every Thursday to talk about writing-related subjects, with each week based on a different theme. I eventually created a Discord server where writers could have accountability check-ins and discuss writing all week long, but I wasn’t thinking about it as a business yet. It was simply a community space where writers could support each other, and everything was free.

In 2020, the world changed and virtual events became the norm. I saw an opportunity to host a virtual conference under the Weeknight Writers umbrella and brought on a co-organizer, Jade Benjamin, to help me make it happen. This conference was an experiment and, again, was 100% free.

What I learned from that first conference was that a) I loved hosting conferences and b) it was a hell of a lot of work. So in 2021 I switched to one-day conferences instead of full-weekend conferences and also began thinking about it as a business, looking for ways to monetize it.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’ve wanted to be a writer since I was eight years old, and I’ve been actively pursuing that dream in one way or another since I wrote my first novel at 11. Writing is still my first love, and it is actually what pays the bills: I’m a freelance writer by day, which gives me the flexibility I need to pursue writing and community-building.

Despite being rather introverted (and becoming more so every year), I’ve always naturally flourished in artistic community spaces. Supporting, organizing, and encouraging writers and artists comes easily to me. I also love public speaking – there’s something about speaking to an audience that, for me, is somehow easier than maintaining a one-on-one conversation.

My passions for writing and community-building came together with my passion for learning when I created the Weeknight Writers Group. We create safe spaces for writers to discuss difficult topics, to share knowledge with each other, and to encourage each other. And we’re committed to making those spaces accessible, both by keeping them virtual and by keeping them affordable. In fact, our flagship event series, Storycrafting Sessions, are free to participate in (with an option to contribute financially if you have the means) and we plan to keep it that way forever.

What sets us apart from other writing community spaces is our commitment to creating high-quality, safe spaces where people from all walks of life feel welcome. We work hard to make sure Black people, Indigenous people, people of color, queer people, disabled people, neurodivergent people, and all other marginalized people are represented on our panels and feel comfortable both attending and speaking at our events. This isn’t always done in the writing space, as publishing is still a massively white space and many white people still aren’t thinking about representation or accommodations.

I want all fiction writers, especially marginalized writers, to know that the Weeknight Writers Group is here to support them and create spaces where they can learn and create. And I hope we always will be.

We’d love to hear a story of resilience from your journey.

My entire story is about resilience if I’m being honest. I grew up in poverty, I lost my dad when I was 12, and I lived through enormous amounts of bullying and other traumas growing up. I can’t think of a single thing in my life that I haven’t struggled for.

I think, though, that the biggest demonstration of resilience is my continued commitment to writing fiction and supporting other fiction writers. Books take an enormous amount of time and energy to write, and I’ve pushed through a lot of trauma and health struggles to keep working on them. Publishing, too, takes an enormous amount of energy and, for most people, comes with very little material reward. But I stick with it, and I support others who are trying to stick with it, because there’s nothing I love more in this world than books.

How’d you build such a strong reputation within your market?

The reputation of the Weeknight Writers Group comes from the quality of our events. We’ve worked incredibly hard to create safe, educational, and supportive spaces, and judging by how much our guests say they love every one of our events, we’ve succeeded.

And how do we succeed? We succeed by listening. I spent years on Twitter and in other spaces listening to marginalized folks about what made them comfortable (or uncomfortable) at writing events. Every time I create an event, I think about what the community has said about similar events and how we can recreate the good and eliminate the bad.

I listen after our events, too. I’m always happy to receive feedback from both panelists and participants and I work hard to make sure that feedback is considered during our planning process when we move on to the next thing. This is doubly important since so much of our community has been ignored in mainstream writing and publishing spaces, often making them wary of participating in these spaces and doubly wary of giving feedback or criticism. I and my co-organizer work hard to make sure these people feel listened to, and that listening is what builds trust with our community.

Contact Info:

• Website: https://ko-fi.com/weeknightwriters
• Instagram: https://www.instagram.com/weeknightwriters/
• Twitter: https://twitter.com/WknightWriters
• Youtube: https://www.youtube.com/@weeknightwritersvirtualeve8181

Image Credits
Photo credit – Sandy Kennedy Image credits – Carmilla Mayes