Day 57: Host An Unusual Meetup

For day 57, I hosted a meetup of my own unique design for the Chicago Active/Lucid Dreaming meetup.

Back on day 27, I wrote about my ideas for the meetup:

I want the meetup to be a hybrid of:

– stoicism
– comfort zone challenges
– pranks
– lucid dreaming
– self development
– maybe even entrepreneurship

In other words, a bunch of stuff I like.

My Discomfort

It felt risky. I had no map. In the past, my meetups were all basic; mostly lucid dream book clubs. But I wanted something different.

I’d actually been nervous since I first asked to host the meetup, over a month ago. Was I really fit to do this? Would people get it? Am I just a loon?

Gaining Perspective

Inspired by the book Getting Things Done, I wrote out why I wanted to host this meetup in the first place. It reinvigorated my purpose and took the focus off of me.

By clarifying my purpose, I realized meetup is about helping others. It has nothing to do with me or my worth. So I need to put my ego aside and do a good job.

But doing a good job doesn’t mean never failing. I should fail. At least, in the micro. I should test, try, iterate. Which means some level of failing.

Therefore, before the meetup, I set up my failure bingo list.

From my notebook:

To Fail:

•scare people

•confuse people


•get nervous

Think for one minute before talking

Cover ideas that people don’t care for

Self conscious

Bore or make members uncomfortable in what I deem is a bad way

Be too focused on what I want

Lose control of the group

Anger Someone

Not be curious enough

Of course, many of these failures are subjective. But labeling my mistakes as “goals” reduced my anxiety about them.

I achieved many of my failure goals during the meetup. And had a successful meet up. People wanted to come back, and even stayed late.

Next time, I’d like to get written feedback.


The night before the meetup, I was trying to finalize the meetup itinerary. But the number of possible activities overwhelmed me. I journaled that night.

Journal Entry:

You can prepare until you perfect your plan. Or you can jump in unprepared, learning as you go. 

As a perfectionist I gravitate towards the first. But I’m slowly learning the advantages of the second.

When it comes to new skills, too much preparation can be presumptuous. If you have no baseline, how can you judge what will be good? Sometimes you only need a little bit of preparation plus some room to experiment.

If I obsessive over every detail of the meetup, never having run this format before, I might overplan details that end up being irrelevant. First, I must let my audience taste what’s to come and see how they respond. Then I can focus on the details for the next iteration.

The Meetup Itinerary

  • Introductions
  • Discussion: What does it mean think like a lucid dreamer?
  • Prank News Article
  • Reality Check Hunt
  • Lucidity Awards

My No-Speaking Experiment

Amongst my list of fears, one was not knowing what to say. Sometimes, when I’m trying to speak I’ll get debilitatingly self-aware. My thoughts go something like this:

Am I explaining this right? Oh man I don’t know what I’m saying. Oh no, now I can’t focus on what I’m trying to say because I’m distracted by thinking about all of this stuff. What was I even saying? Everyone must dislike me now. How am I ever going to get back from this? I can’t think of what I need to say, I’m too nervous now!

Usually, I conceal this mental script by saying “umm”, “I lost my train of thought”, or anything outside of what I originally wanted to say.

Instead, this time I decided to stay quiet until I got my brain under control. Even if that meant remaining silent for a full minute while the group stared at me.

I leaned into the discomfort! Amazingly, my nerves dissipated because I was intentional. My brain and I weren’t fighting. I was quiet for so long, that a member in the group tried to help by guessing what I meant to say. That could be a cool tactic to get the group to pay attention and participate.

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