The Toughest, Most Embarrassing Moment in Pursuing My Dream

My friend Michael Simmons runs the New York-based company Extreme Entrepreneurship Education. I hear from and reach out to a bunch of young entrepreneurs, and am impressed by about half of them. Michael is definitely in that category. He publishes a newsletter that goes to 4,500 young people and asked me to answer this question that he may feature in his newsletter alongside my bio:

What was your toughest, most embarrassing moment in pursuing your dream?

I thought about this for a bit of time and nothing obvious popped up. Perhaps this is because I try not to think about my life as moment-driven inasmuch as on a continuum. "Moments" are sexy. Entrepreneurs credit a breakthrough moment of insight that turned their business around. People talk about a life-changing moment when someone said something that changed the way they see the world. I don’t buy it. Moments make it easier for us to condense time and construct our life narrative.

Plus, like all good self-delusional happy people, I also think I’ve suppressed most embarrassing moments deep into the dusty dungeons of my unconscious. I don’t think I’ve lost the lessons — after all, these "truisims" I hold in my head must have come from somewhere — but I can’t easily connect the dots between specific scars and specific lessons.

But to answer the question, the "toughest" moment I’ve had in my entrepreneurial career probably was on the eve of a major executive hire in early 2003 when I was 15. Anytime a founder hires an outsider to run his or her "baby" it can be emotional. For me, it wasn’t so much reliquishing control inasmuch as the vastly greater financial and time committment that comes with hiring a full time and full salary outsider.

After a key negotiation meeting I resigned to my bedroom and collapsed on my bed. Nervous. Scared. Exhausted. At that time I wanted my world to disappear, for the stresses of my business life to fold into the seeming normalcy of freshman year high school life, which seemed so far away from my reality.

The guy we ultimately hired picked up on my body language and change of mood — a good sign — and we worked through what I was feeling. I also chose to go outside of the "inner circle" of advisors I had relied on so intensely and instead reached out to an adult friend who was familiar with the business yet far enough from the scene to offer a more dispassionate look. In the end, we pulled the trigger, with me the enthusiastic endorser of the deal, and as I write in my book (which you’ll have to read to get the rest of the story), "That day was the first day of the rest of my life."

A big lesson is that no matter how much you think you’re prepared to step over the ledge, it still is scary as hell once you tip-toe up to it.


What has been the toughest, most embarrassing moment you’ve experienced in pursuing your dream?

6 comments on “The Toughest, Most Embarrassing Moment in Pursuing My Dream
  • Although that’s a great story, I think what Simmons wanted to hear from you is a story that makes you human and relatable to all the people who read these blogs. You must have had an embarrasing moment somewhere. I agree with you that taking those embarrasing moments out of your reality, and not acknowledging them at all, is the key to learning lessons. However, how will future entrepreneurs progress in their own way if the people they look up to are too embarrassed to talk about the most embarrassing moment in pursuing their dream? I think Simmons, and we, deserve a better answer.

  • Zoli is right that this is tough but not embarrassing.

    Dude is right that you deserve a better answer. But I want to be clear: it’s not that I’m embarrassed to talk about an embarrassing moment, it’s that I truly can’t think of something so embarrassing worth mentioning. Sure, I’ve fucked up a demo, or blatantly mispronounced someone’s name, or left a terrible voicemail message, or asked what a basic acronym meant, etc etc. I’ve failed and made tons of mistakes. But I’ve never been particularly embarrassed about these. I’ll keep thinking, and if there’s a more erudite answer which can help other entrepreneurs, I’ll post it.

  • Hm, when I made my comment, I meant it as a somewhat positive obeservation: i.e. there is nothing wrong with exposing your fears and more personal side (in certain situations). So I simply wanted to state there was nothing embarrassing in the story, without demanding a “better answer”.

    Now, if you had gone Chuck Norris on *that girl*, that would have been embarrassing :-)))

  • Thanks Ben, for your sincere response. This should also be an exercise in showing what YOU considered embarrasing, so that you can also eliminate that in the future. It’s always a pleasure to learn about how others in the field have coped with those embarrasing moments, perhaps because I’ve had many 🙂 and because I believe that we all learn from them. Keep us posted on your book!

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