Sometimes Life Lessons Come When You Least Expect Them

A few years ago I was participating in a “hackathon” of sorts where I worked with a diverse team of individuals from different industries and companies. For our project, we had to identify a solution for a problem of our choosing. From there, we had to present our pitch to a panel of judges and the winning group would be given money to pursue their project. The big difference between this event and your traditional hackathon was that it was over the course of a few months and included training to help guide your team through the process.

Things were going well – we had a problem and a solution. The team worked well together despite being made up of six very busy professionals. Overall, our idea was good, not great, but hey, it was something. We we learning a lot about entrepreneurship process, which was better than our idea itself. Towards the end of the project we had to decide how we were going to pitch it. The leaders of the hackathon recommended that only one or two people make the pitch because those tended to be presented better due to having less hand-offs between speakers. Given I was comfortable with public speaking and because we didn’t have much time to prepare, I was the chosen one. I was used to improvisation in my job because I always needed to be ready to present to leadership about various topics at the drop of a hat. So this seemed like a no-brainier to me.

What was about to happen, however, was one of the most humbling and eye-opening experiences of my career. We had to video tape a practice pitch about a week before the final pitch. It was then going to be reviewed by the hackathon leaders and the other groups to critique the presentation. I told my group I would show up to the recording studio alone and that everyone didn’t have to worry about coming since we all worked full time. It was not supposed to be a big deal.

I showed up to the studio and this is how it started:

A/V Guy: Hi, where do you want to record today?

Me: Umm, wherever you want

A/V Guy: No, this is your pitch, you tell me

Me: Umm, where have other people been recording?

A/V Guy: Pretty much everywhere

Me: Umm…up stairs in the conference room?

OK…so as you can see, not off to a good start here. The funny thing was, I knew this A/V Guy and he was not usually like this…he always had a vision but yet he was looking to me for my vision. I was totally thrown off at this point. It was not supposed to be a big deal.

So we went up stairs to get setup…I had no monitors to display my slides behind the camera, which for some reason I assumed we would have. Generally this would not be a problem for me because I can improvise, but this time was different…I was freezing. I needed those slides because the content was not something I was familiar with and I wasn’t honestly excited about our topic so I couldn’t even find the words to wing it.

The A/V Guy just watched me fumble for what seemed like forever. I kept stalling as he reassured me, “take your time, you want to get it right.” I then asked him about how many takes we get, to which he responded “only one.” At this point, I was totally off my game. I built up all the courage I had and asked him: “I know you just set up all your equipment, but can I come back and do this again? I am clearly not ready.” He responded, “Usually I am not allowed to do this, but I will let you because we have known each other for a long time. Sometimes it is all about who you know. Let’s have a seat and chat.” The chat was long and got very deep and even personal talking about how he found his father at home after he had been murdered – not what I was expecting for a quick chat. He started to explain to me why he was being difficult with me from the beginning: When you have something to pitch/sell, you need to be ready…always. You never know when you are going to be at an event or in the hallway with the exact person you need to pitch to, so you need to be ready. He preached to me that life throws you curve balls, such as death, and you never know how you are going to be able to respond. You need to be adaptive and ready for anything while also cherishing the moment. Also, he reminded me that when pitching an idea, you need to have a vision and the details matter, such as what backdrop you have when recording a video.

As you can imagine, I was a little shocked. I came in expecting to just thrown down a presentation like it was no big deal. Instead, I ended up getting a powerful life and business lesson and not even from the “leaders” of the program.

There are many articles out there about improvisation and the valuable skills you can gain from it. Additionally, in his book Messy: The Power of Disorder to Change Our Lives, Harford talks about how being “messy” can make you more creative. In my situation, the mess was too much that my improvisation could not overcome the disorder to create a rational pitch. Although I think improvisation and the ability to create order out of disorder are critical, this moment taught me that for those things to happen, you have to have some fundamental understandings first:

  1. Be ready. Always.
  2. You can’t sell something if you don’t believe in it
  3. Speak from the heart, not the slides
  4. Relationships can make or break you when you need them most

After this chat, which lasted about an hour, I headed back to my office. I didn’t have any meetings that afternoon which worked out well because I found myself just staring off thinking about our conversation and not being overly motivated to do any work. Some of my thoughts were about his father’s death and the details about the situation he shared with me, but much of it was about what I learned about myself. Needless to say, the next time around for my video recorded pitch, I was ready. To this day I still reflect on the fact that sometimes life’s best lessons come when you least expect them.


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