The Death of a Dream

It’s a busy week. In addition to portfolio company work, such as board meetings and CEO interactions, I’m meeting with 11 entrepreneurs, all of whom are raising money or are about to.

So, I only have a few minutes right now to write about this: the death of a dream. Here’s what I mean.

I had breakfast with one of my CEOs today, and had a follow-up with my executive coach yesterday. Both discussions, while different, led me to the same topic: correcting old assumptions and looking at reality with a new lens.

With the CEO, for example, we talked about the fact that his company has a shot at going public one day. Lots can go wrong, but the market is moving towards this start-up and they have the “first, best and only” product in this particular space. So, his previous goal was to sell the company one day at a very big price.

Essentially, what we talked about was a new dream: taking a company public and what that may require. So, this CEO is now thinking about an even bigger dream.

In addition, I met with my executive coach yesterday. Underlying many of our conversations is the following theme: as athletes do, she asked me to think about “realistic success” and how I would visualize it? It could be improving your self-control in a difficult personal relationship. It could be dealing with a tough work situation. It could be unrealistic expectations that the other person with whom you have conflict “will change” (because people don’t).

What is the “correct” behavior, she asked me, that you want to have–and, can you visualize it? In other words, day-dream it.

So, these conversations have made me think about the “death of dreams.” Some dreams should die because they are unrealistic. Others should die because there is a better one around the corner.

I think that’s a key theme in entrepreneurship: the pursuit of dreams, but then adjusting them as you develop personally and as a start-up pivots. To me, it is now a critical step in authenticity and making sure that my dreams matter.

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