We’ve all been there – You have an idea, you get people involved, you make plans, you come up with a schedule. All that’s left to do is hit the start button. Or, so you thought. Instead, something goes wrong. Or everything does. So, you cancel. Teams do it with meetings. Companies do it with products. Bands do it with tours. You make a quick calculation that moving forward under less-than-ideal circumstances would be worse than not moving at all.
Is that always the right approach?
In September 2015, my friend Robbie Chernow (he acted in a TMZ parody video I directed a few years back) flew to Chicago for a bachelor party, only to find out the whole thing was off. Turns out everyone else’s flights never made it.
Instead of giving up on the idea, Robbie decided to make the most of the his weekend and started posting on Instagram under the #ChicagoForOne hashtag. Within hours, media outlets started noticing and by the end of the weekend, his misadventures had been covered in over 100 media outlets, including E!, Mashable, Buzzfeed,, MTV, Cosmopolitan, and others.
I reached out to Robbie through IM to learn more about how this whole strange weekend took shape.
When did it occur to you that this was something you were just going to plow ahead with? After the flight with the bachelor got canceled, I was pretty bummed and wasn’t sure what to do and then literally 20 minutes later the flight with everyone else got canceled and it dawned on me that I was the sole participant and I couldn’t help but laughing. Voltaire has a quote, “G-d is a comedian playing to an audience too afraid to laugh” and when all of that happened I couldn’t help but just laugh and decide to make the most of it. It sure beat trying to find a new flight home or just sitting alone in my hotel room moping.
When did you realize this was a viral sensation? The viral aspect happened very quickly. I knew it got some buzz but didn’t think much of it. It wasn’t until I got a call from my parents saying Fox News was looking for me to chat, that I realized thing had escalated beyond just a joke.
What were the “creative moments” that occurred to you as started to realize this social media campaign could be anything you wanted it to be. I think a lot of the best creative moments came from me following what I thought was fun and being as present as possible. Everything from a sign to an open field became an opportunity for a photoshoot and if I wasn’t paying attention I would miss it all. I also think so much of the creative success came because I was doing this for no one but myself at first. My posts were all originally private before Elite Daily reached out. I was doing this creatively for myself to have fun without much pressure, so the juices could flow freely.
What stuff have you tried to do that didn’t happened? The only thing I tried to do that didn’t happen was go to the top of the Willis Tower. After spending 2 days barely seeing any people, I went to go to the observatory there and I was met by a 2-hour wait. I have a picture of me sad in front of the crazy line, but didn’t think it read well, so held off posting it.
You’ve got a background in improv, which is typically a group activity, or at least thought of that way. How did all your improv training/performing influence you through this solo experience? This trip would not have happened had I not had a background in improv. It was a complete “yes and” to the hand I had been dealt. In the back of my mind the entire trip I kept replaying a quote from my first (and best) improv teacher, Shawn Westfall. After every class he would tell us, “if you’re not having fun…(and then insert some weird thing we should do instead)”. You just have to “yes and” life. Be in the moment and always follow your own fun. That’s when your creativity will be at it’s best.
Sometimes, moving ahead in spite of the original plan is the best decision you can make. The two questions I take away from Robbie’s experience are:
How do you handle cancellation? What do you do creativity just for yourself?
Founder, The Idea Enthusiast. Speaker, Trainer, Facilitator, and writer about all things creative consulting. DC-based consultant to individuals who want to be more creative, teams who want to collaborate without fear, and anyone who wants to deliver the best pitches and presentations.