Events, conferences, and retreats: How to make the most of them

Freelance Writing Coach

Events, conferences, and retreats offer freelance writers a break from the average day-to-day grind in front of the computer. They claim to help you learn from experienced speakers and grow your network, but…do they?

Emma and I chat about our experiences with events and conferences and how we look at them moving forward. Fun Fact: We met at a conference for the first time after knowing each other online for a long time.

Our experiences with conferences as freelance writers

Kaleigh’s stance has been negative on conferences and events most of the time. Primarily because she finds it stressful to travel, and going to an event requires her to break from her normal routine. Post-pandemic, she’s been trying to challenge herself and try speaking at events and conferences to see if her views change.

Earlier in 2022, Emma attended a conference or an event every month, sometimes even two. Even though giving keynotes and moderating panels were great experiences, her stance on events as a freelance writer has mostly stayed the same. Travel is still exhausting. She still doesn’t think conferences and events bring enough value to go to all that trouble.

At the beginning of Emma’s freelance writing career, she found conferences to be much more helpful in gaining insights and connecting with people she could work with. But as she has grown her freelance writing business, her reason for going to conferences shifted from learning to meeting friends in the trade.

Shortcomings of events

There are two broad categories of events: one is the hustle-centric category with “go for it” events. The sessions have titles such as “how to 10x your revenue” and often boast a male-dominated speaker panel.

The other category is “follow your dream” events—usually branded as hyper-feminine and very “woo-woo.” Sessions can be helpful if there’s a middle ground between these two extremes, but often, there isn’t.

“When it comes to conferences, I don’t care about the branding of the event. I think: Just teach me something without the special packaging.”

Then there’s the matter of the content. Some conferences are great for beginner writers, but not many cater to experienced freelance writers. The ones that do can be extremely expensive: At a couple of thousand dollars for the tickets, then a couple more for your travel and stays, it can be a substantial investment.

Other issues

What does a typical conference look like? You wear a badge, listen to people speak—the learning part—and try to meet other attendees. But is “sit in a 30-minute session and listen” the best format for learning in today’s world? Eh, maybe not. We both would prefer to go to dinner with the people who were at the conference, skip the actual sessions in the conference, and just hop in during a happy hour.

“I’m so bad at sitting in a chair and listening to somebody talk for any extended period.”

What about virtual events, you say? Virtual events seem nice for the sessions initially, but it’s hard to stare at a screen and fully pay attention when you’ve already been doing that in your job. Moreover, they also lack the in-person connection between attendees.

When we met at a conference, we realized that the best part of the conference was meeting each other IN PERSON. Several years ago, Emma and I hosted a retreat for female freelancers. It stemmed from our dissatisfaction with big marketing conferences and wanting to deliver something different. And guess what? It was great. The in-person aspect is huge.

Conferences: Your call as a freelance writer

We’re not saying don't go to conferences. We just want to highlight that it’s more of an investment than just the money it costs. If you decide to make that investment, our advice is to be mentally prepared to introduce yourself and put yourself out there. The connections you make are often more valuable than the session content.

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