The Loser Who Won

M.G. Siegler
Published in
3 min readNov 10, 2016

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When I was a kid I used to have bad nightmares. Worse, the nightmares were recurring. Every night I would go to bed knowing my mind was about to come under assault. It seemed like the worse affliction possible. But eventually, because I knew the dreams were coming, I was able to use this to my advantage. I was able to force myself to realize that I was simply dreaming during my nightmares and I could actually wake myself up.

The trick didn’t work last night.

Today was absolutely surreal. I had to wake up especially early to get down south for a board meeting and my grogginess just added to the dream-like state of reality. I kept having to remind myself that yesterday actually happened. That it wasn’t just a bad nightmare.

This was especially hard because outside of my house, life seemed to be going on as it had the day before. I got an Uber. I got coffee. Businesses were open, people were working. But something seemed off about nearly every person I encountered today. Most seemed unusually quiet, though plenty were just overtly sad. Nearly everyone I interacted with asked if I could believe that yesterday had happened. I could not, of course.

As I get ready to go to sleep tonight, I keep coming back to the notion of today being the most dream-like day ever. Maybe it’s just wishful thinking. Maybe it’s because the world didn’t end. But today just didn’t feel real.

In fact, the only time it started to feel real is when I would load up Twitter. I kept doing it, as it’s so ingrained into my daily habit. But almost immediately, I felt this weird urge: to close the app. It was making reality too real. I just wanted to believe I was in the dream and I would soon wake.

So that’s my takeaway from today. It was just surreal. I eventually forced myself to think about what had happened and I kept coming back to the tweet I sent this morning (before my Twitter hiatus) of the JFK quote:

Now, it turns out, this quote may actually be factually inaccurate. But it really doesn’t matter. What matters is the point. While JFK may have made this speech leading up to the Cuban Missile Crisis, I think it applies to nearly any crisis. And it feels particularly apt during our current crisis.

There’s a real feeling of danger amongst many of us. Not so much physical danger — though that threat is certainly not off the table! — but more so the danger of not knowing where things are going to go from here.

But I do think it’s important to think about the flipside. The optimistic side. In all times of great change there is always opportunity. To me, in this case, it’s a matter of figuring out what those opportunities are and turning a weakness into a strength. Turning the fact that you’re having continuous nightmares into the ability to wake up from them.

That’s what I keep coming back to. I honestly do believe there’s opportunity in this situation. Maybe even for Donald Trump himself, to surprise people by not ruining our country with the enormous responsibility he’s been given. I don’t have a lot of hope, but I do have some hope. Maybe I’m dreaming.

Sometimes it sure feels like I am…

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Writer turned investor turned investor who writes. General Partner at GV. I blog to think.