We've run Underdog Con 5 times...

And each time, including the last, I felt like canceling the event 20 days before DDay.

Because the truth is I had less than 20 sign-ups, 20 days before the conference.

Here's a snapshot from our WooCommerce dashboard:

20 days. Put yourself in my shoes. That's about 2 weeks left/2 weekends left, before the conference. Where would I get at least another 130 paying participants?

I complained, cursed, and beat myself up to it. Why do this to me?

It sucked. But it taught me lessons:

  • Set deadlines. Deadlines suck. It creates pressure. As dates edge closer, the more uncomfortable you'll feel. But if we didn't set a deadline and told ourselves it was do - or die, we would never have run the conference.
  • Trust the process. Once you set a plan, trust the process and carry on. I could stop everything we were doing and cancel the event. However, having some sponsors (Saltycustoms, OtomateMe, EasyStore) meant we can't just drop the event. Trust the process.
  • The process is never pretty. Marketing is tough work. People romanticize the ease of being a marketer. Just press a few buttons on your laptop. In reality, it takes lots of content creation, work, partnerships, and sleepless nights.
  • People need a reason to act. I never liked putting countdowns and salesy "Click funnel-Ish" landing pages. Big brands don't do that. The weird thing is the Click funnel-Ish landing pages work! But why? Because people need a reason to take action. We had to give them a reason to – join early, save on tickets, etc. in an elegant way.

From organizing Underdog Con, I learned a lot about marketing and more importantly learned to stomach the fear of failure. (It never gets easier)

Marketers got to learn to set deadlines and stomach the suck.

But I didn't expect it'll reveal my biggest weakness.

I wanted to do everything myself throughout the entire process. It ended up causing me lots of stress – and to make matters worse, affected my work for clients.

But after doing this, I learned that delegation is a learnable skill. (I hired an assistant).

Will share more lessons from organizing Underdog E-Commerce Con in the next emails.

For now, I wanted to let you know that Underdog E-Commerce Con is now available as a recording, for people who want to relive the lessons from the conference – and join the conversations with everyone involved in the event.

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