3 Entrepreneurial Lessons Learned From Speaking in the Dark

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Professional Speaker
5 min read
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As entrepreneurs, we’re learning when we fail. I personally have learned as much from past failures as successes.

Even before my speaking career, I was learning about failing during my time in stand-up comedy. My first time on the stage was shortly after attending a stand-up comedy workshop. Sadly, during the first two weeks, all I “really” learned was how to adjust the mic stand. 

During week three we showed up at a night club to watch comics perform, and study the craft of stand-up comedy. We discovered five minutes to show-time that we were the entertainers. Some of the would-be comics exited through the front door while I disappeared into the bathroom to find an exit window. There were no windows.

Minutes past show-time everyone was debating who would be the sacrificial lamb, as no one had any (comedy) material prepared. I was terrified, and couldn't focus on any one thing. I had learned in the past though that it’s always best to go first.

Related: 10 Tips to Beat Your Fear of Public Speaking

Without hesitation, I jumped on the stage, grabbed the mic and told what I felt was my best joke. If there was a cricket in the club, everyone heard it.

The sweat started dripping down my face but I proceeded with my next joke.

Seconds later, the workshop facilitator that got us into this whole mess called me over and hit me in the back of the head. "you idiot." he said, shaking his head. "The mic isn’t even on yet."

Turns out, my jokes “actually” fell on deaf ears, and that was the beginning of my speaking career, and learning while failing.

Fifteen years later I have spoken on stages across North America, conquered my fears, and faced every possible situation -- or so I thought.

Recently, I had a chance to apply what I had learned during past failures.

While on a speaking tour I arrived to deliver my keynote at a large conference. I immediately learned from my understandably frazzled client that the power was out and I might be presenting in the dark.

This was a first.

I had another challenge though. I had invited two prospective clients to see me present. I thought it was a great chance for us to meet face to face. Hopefully it was them I met.

One thing I do know is that my prospective client smirked as he said “I wouldn’t want to be you” and disappeared to one of the tables in the dark.

I watched the stage while the speaker before me presented in the dark. I thought about how much I would have loved if my audience couldn’t see me and I couldn’t see them, that first night on the comedy club stage.

Finally, I was called to present. Had this been early in my speaking career, I would have been an absolute mess.

Related: The 2 Unbreakable Laws of Public Speaking

The difference was I had learned many lessons from my early failures that could be applied to this situation; lessons any Entrepreneur can apply to their business structure.

Here are three:

1. Have a back-up plan for your back-up plan.

As someone wisely said, “It’s better to measure twice and cut once than measure once and cut twice.” The power was out so I couldn't use my laptop to project my slides. I always carry my presentation on a USB stick to run my slides from a different computer when necessary. That option was useless on this day.

Here is where my back-up to my back-up plan came into play. I had emailed a copy of my presentation to myself, and viewing the emailed slide-show from my phone allowed me (in the dark) to deliver my talk with confidence.

2. Communicating effectively with your customer.

My customer was uncertain as to how I would present to an audience that was sitting in the dark. I took the time to fully explain my approach; easing her that I would be able to deliver as promised.

3. Focusing on the solution.

In the past, I didn’t allow myself to take time to think of possible solutions. In this case, I was able to take a breath and consider options. More than one solution came to the surface whereas in the past only problems would have appeared.

Related: 4 Strategies to Navigate the Fear of Public Speaking

As entrepreneurs, it’s okay that we fail. The important thing is that we use those lessons to help us take better action going forward.

Oh, and here’s the proof that my past failures indeed helped me through this new, difficult, situation: First off, the prospective client hired me for their event and second, the feedback on my talk was so positive that I'm actually debating if we should turn the lights off for future presentations.

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