The Fun Box - Entrepreneurship & Decision Making

This weekend I was a facilitator for a local Cincinnati non-profit InOneWeekend. It’s a concept improving upon the existing: StartUpWeekend. I was honored to be brought in on the development team last year when it launched its first program.

The concept of InOneWeekend is: 100 people get together and launch a company in one weekend. We start on Friday night and go until Sunday late afternoon. By the time we get to Sunday afternoon, we give birth to a company – or at least a fleshed out concept and feasibility plan.

One of the dangers of this type of event is what I like to call the “runaway conversation” (AKA: shiny ball syndrome). Basically, it’s an inability to focus on the end goal because other distractions are allowed to detour the conversation. I am sure each of you have had this happen in more than one conversation.

Well, as you can probably guess, this happened a LOT this past weekend. It was painful to watch at times. As a facilitator, I was not supposed to intrude too deeply in the conversations. So, without giving an actual example, here’s taste of how the dialogue typically went. To give you a bit of background, this group is trying to decide on a target market for a website. The website connects users with discounted event tickets in the local area. (These aren't real names.)

Brian: We should focus our sales toward single people in the high-income brackets locally.
Jill: I don’t know, my husband and I are always looking for things to do. I mean I would use the website, and I’m married.
Maggie: Yeah, exactly. I mean the single people here all go the same places anyway – they already know where to go.
Brian: Yeah, but do they really know where to go or are they just sticking with what they know? They might be afraid to go to new places because they might not know anyone there.
Chris: Well, we could add a dating and matchmaking piece to the event listing.
Tim: Yeah, we could have people enter information into a profile and then you could see who was going and if you wanted to meet up.
Jill: Well, we have to have a married section then – we could do a couples section for couples looking for other couples.
Maggie: Yeah, you know I’m always looking for cool couples to hang out with.
Jill: Maybe instead of discounted tickets, we offer tickets designed for people to meet up with each other. We would be a dating/event website! Then we could change the name of the website to…

Within two minutes of the conversation – the sales team has reinvented the website. This conversation will go around and around imagining new features and fancy ideas for the website. Typically, they last about 30 minutes. The group gets WAY off track, then realizes they only have 15 minutes left to decide their target market. Frustration kicks in, emotions start to take over, arguments ensue, and the group might make a half-ass decision. Sound familiar? This is a classic case of a “runaway conversation.”

A runaway conversation is like a pinball in a pinball machine – every idea sparks the next. Decisions are NEVER made when a conversation gets in this mode. To give my visual thinkers an idea here, I’d like to refer to the OODA (for Observe, Orient, Decide and Act) loop designed by military strategist and USAF Colonel John Boyd. Basically the framework walks us through the decision making process.

Image Credit: Wikimedia Commons

You see that pretty blue box with all the pretty lines and circles? (BTW :the words there are Cultural Traditions, Genetic Heritage, Analysis & Synthesis, New Information, and Previous Experiences). That pretty blue box is the FUN box. It is fun and EASY to play in the box. This is the box where we get to use our individuality to pose all kinds of what-if scenarios. We get to talk about our likes, our dislikes, our experiences, our culture, and play around with all of them. Everybody get’s to be a critic. We get to dream, imagine, and create all kinds of wonderful scenarios.

But very few people actually ever get out of that box. Why? Well, it’s EASIER to stay in the fun box. It is much easier to talk about what a picture should look like, than it is to actually draw it. It takes COURAGE to leave the fun box.

Notice though, the one thing is that gets you out of the box. A DECISION. And that decision inevitably leads you to an action. So why is that scary? Why does that take courage? The simple answer is that we are all afraid of being wrong. If we make a decision and act upon it, we might be wrong. No one likes being wrong.

See, the best thing about the pretty blue box isn’t that its fun – it’s that YOU ARE NEVER WRONG IN THE BOX.

Well, personally, I get freakin’ bored in the box. I like to make decisions. I like to learn. So, in many ways – while I hate to be wrong – I need to be wrong sometimes in order to be better.

We’ve all met some guy who says – “That was my idea. It got stolen!” Well that guy probably never left the pretty blue box. He never made the decision to take any action on the idea. Ideas are worthless –the decision to implement them makes them valuable.

This past weekend that I spent with 100 people trying to create a company reminded me that difference between a mediocre entrepreneur and a great entrepreneur is the ability to make a friggin’ decision!

So, don’t just think outside the box – actually GET outside of the box.