An AAR of the Freelancer’s Conference (inspired by the Fyre Festival documentary)

In 2016, I launched a conference for freelancers that would be held the following year, in April 2017. In late February 2017, I cancelled that conference and refunded all of the tickets.

After watching the Fyre Festival documentary on Netflix this afternoon, I decided to write a bit about my own failure launching an event, and what I learned from it.

Reviewing the mission, and some background.

For seven years, I organized a local conference for users and developers of WordPress. Every year, that conference included a Business track, dedicated to discussing the BUSINESS of WordPress. This track was mostly filled with freelancers and small agencies who sold design and development services.

And every year, without fail, dozens of people would tell me the Business track was their favorite part of the conference, and that they wished I’d do a whole conference just for that. So after seven years of asking, I finally did it and laid the groundwork for The Freelancers’ Conference.

The purpose of the conference was to provide freelancers encouragement and accountability for building a stable and scalable business.

The conference was setup in a unique fashion compared to most conferences I’ve been to. After each speaker’s session, there would be a 45 minute, small group work session.

These small groups were designed to let guests ask questions specific to their own business, and to begin immediately implementing what was learned. A seasoned freelancer would lead discussion between each small group of guests.

The general admission ticket ($399) covered entrance to this part of the conference, including meals, and an after-party.

To reinforce that freelancers can further together, another ticket ($599) was offered that provided access to a private, 12-week mastermind, as well as a private brunch with the speakers the morning after the conference.

There were eight speakers scheduled to attend the two day conference, each an expert in their own right and niche. They were also coming to the conference at their own expense, as a favor to me, their love for seeing freelancers succeed and potentially, to earn business. Though to that last point, not all of them even offered services or products to freelancers, so I want to be certain to say I think they were coming more for #1 and #2, than #3.

Had we reached particular sales goals, the speakers were my first priority to compensate by covering their travel costs and providing an honorarium. It was an honor that they would even consider coming to the conference in the first place, and I didn’t take that lightly.

Our family/my business footed the bill for the hard costs associated with launching the conference, like booking the venue seating up to 150 guests, and catering deposits.

How things ended up

We opened ticket sales in October 2016. By February 2017, we had sold fewer than 20 tickets. Most what we did sell included the mastermind. I made the decision to cancel the conference a month prior to the event.

To be clear, we didn’t cancel because we didn’t have the money to cover the conference. I cancelled because I didn’t think that our speakers’ time and money invested would be honored by only 20 guests, when my goal and promise to them was 100-150. More on this later.

I emailed every guest to tell them that we were cancelling, and that refunds would be processed by the date the conference would have happened (a month later). We had to wait to get deposits back from all of our vendors before I could refund everyone, so I refunded in order of purchase. As soon as a deposit was returned, I’d process another batch of refunds. And I was upfront about this being the reason for the delay.

Not every deposit was refundable, though, and we ended up losing the $2,000 we had personally invested.

If losing $2K felt bad, it felt 1000X worse to tell guests that they would have to wait for their refunds. Even though I knew with 100% certainty their money would be returned, it made me feel like a fraud to tell them they’d have to wait.

I imagine there were some conversations around their dinner tables about whether or not they’d ever see their money again.

The guests were all perfectly kind and understanding. Some even expressed great disappointment at the cancellation, saying how much they were looking forward to those exact speakers, and the specific content we’d laid out, and how much they needed it to exist at that point in time.

What went well?

That’s a great question, Angie. Even now, it feels like not much actually went well, to be really honest.

I think the content of the conference, the speakers, the unique flow of it – I think those were right. Not just a little bit, but I still think they were spot on. If the conference had gone on as planned, and you were a freelancer in attendance, I have no doubt you would have left there a changed business, equipped with the tools and network to make huge leaps forward.

What could be done better next time?

I should not have even considered the conference without a strategy and team in place to help promote it. Not just “promoters” but owners.

You know how in business people always say, “NO! It’s NOT ‘If you build it, they will come.”

I know that – and yet, for some reason I assumed that because people had ASKED me to build it, that they would just come if I DID build it.

That’s a poor assumption. There is a BIG difference between, “I wish this thing existed,” and “Here is my credit card, thank you for building it.”

The gaps between those two statements – that’s business, right? I took it for granted not because I don’t KNOW that you have to move someone from one to the other, but because I assumed I already had.

In reality, I needed a much larger, deeper audience than the one I had built personally to fill the conference.

A few people even asked how they could help, but by that point, it all felt so far gone, I didn’t have a way for anyone else to step in.

Had I started with a team in place to help, it’s very possible we could have produced both the time for organic growth and the money for paid growth.

But taking a step back even, in the weeks that I was deciding what to do (cancel or go on), I had a conversation with Syed about the conference. By that point, I’d been working for OptinMonster for a few months, and Syed was familiar with the conference and how it was going.

I told him some of the options I’d been presented with. They included selling the whole conference to another company, giving the conference to another company to execute online (rather than in person) in exchange for an opp to salvage a personal gain by selling the mastermind to their list, or cancelling the conference altogether.

I told him how most of the speakers said they would still come, even for twenty people.

I also told him how one of the speakers told me that if I cancelled the conference, no one would ever trust me again.

Syed didn’t tell me what to do, for sure. He just asked me to think about what I personally wanted to get out of it, and why I did it in the first place.

When he asked me why I was doing the conference in the first place, what I wanted the conference to become after this year… I didn’t really have an answer. My WHY for the conference wasn’t strong enough to have even thought past that year.

I think it’s at least possible that because my WHY was not deep enough, I never fully committed the energy or resources needed to make it happen.

And that by itself, was reason enough to let it go.

Looking back, I think the gift he gave me in that conversation was that it was ok to not get this right, and to admit the correction by letting it go. There was no judgement for having tried, and failed.

It was as if the trying was the intention in the first place.

Maybe that’s not what he meant to say, but that’s what I heard.

It has taken me a few years to crawl out from under the disappointment of cancelling the conference. For a long time I thought that if I ever tried anything again, people would think, “Oh, she’s the one who cancelled that conference…” but now I don’t care if they think that.

I tried something. I learned from it. I know what not to do again. And I wouldn’t know those things if I hadn’t tried in the first place.

The end.