How drinking cost me $20M

It can be tempting to add up what I’m saving by not buying cocktails, beer and wine—and I used to have cases and cases of wine in the garage—but if you really want to know what drinking cost me, and what not drinking is worth, I have to go back to my late twenties.

In those years I was working for HotWired, the digital media sister company of WIRED magazine. It was a pretty great place to work, as those things go. WIRED was cool before anything else on the internet was cool, and I had the good fortune to work with a lot of smart people. I even enjoyed the work, for a time. As a someone who had grown up writing code from the age of eight or nine, building search engines and big (for the time) web sites was interesting work.

As I got deeper into the emerging field of online media, I started to meet people starting other companies. While I remained wary of becoming a techie (simply the latest form of what we called yuppies when I was a kid), it sure was nice to be offered a even-cooler sounding and even better-paying job, and I was starting to get offers.

At one point, I got the offer I wanted. I’d been talking with two guys that I had come to know, and they’d offered me the job that I’d designed for myself. I said yes. And then I fell deeper into depression.

The thing is, I didn’t know whether I actually wanted the take the job, and I had no way of knowing how I would come to know. When I asked myself, “do you want to do this?”, the answer I got back was a big shrug. Nothing. You know how people say “go with your gut feeling”? I had no gut feeling, no reassuring voice, no feeling at all. I had plenty of good reasons to accept the offer, and also some good ones not to—and I had no way to weigh the decision.

It wasn’t a question of analysis. There was no right and wrong answer. I was free to decide, and I had no idea what decision to make. I became frustrated and angry with myself for being unable to proceed or to make any sense of my situation. In fact, the very positive situation that I had created for myself quickly became a negative situation for me, because I was unable to do anything with the options that I had conjured.

What I didn’t know then was that I couldn’t decide because my decider was broken. I didn’t have any feeling about whether to take the job because I wasn’t feeling anything. I didn’t have a sense of which direction I wanted to go in, because my sense of intuition wasn’t working. I couldn’t see the answer—because I had no second sight.

In the end, I said no. “No” is the default answer of the unready, the unwilling and the unable. I said no because I couldn’t decide, and so I made the choice to not change, to do nothing, to pass. I had some justification: I already hated advertising, and the strange little world that I found myself working in was all about advertising. That’s another story—and I told myself for years that was the reason that I didn’t take the job, but that’s not the truth.

The truth is that I didn’t know what was right for me because my intuition wasn’t working, and my intuition wasn’t working because I had been drinking since I was eleven years old.

Lacking any internal sense of what to do, I might have gone to friends or peers for counsel, but I had no friends—at least no friends that I trusted, no friends that knew me well enough to speak with relevance to my situation. I had no friends for the same reason: I had been drinking all my life, and all of my friendships were fairly superficial. Most people knew me as the guy who traveled all the time, and just about the only question people had for me about my life was “where are you going next?

I said no, and the two guys that offered me the job went on to build a very successful company, and then another, and another. The classic sequence, leading to larger and larger “exits” along the way as the companies were sold or went public. If I had chosen to work with them, my stock would certainly have been worth at least $20M.

I couldn’t agree more with Nassim Taleb‘s assertion that “many things we think are derived from skill come largely from options”, but I would add that, along with options, we need our second sight to be able to choose the right option at the critical moment.

Without our intuition, all of the work we’ve done to create options for ourselves is worthless. Or, in my case, it was worth twenty million dollars.

That’s how much drinking cost me, and how much not drinking is worth—and how much my intuition is worth. Not that I would be happier now if I had made a different choice; there’s no way to know that, and I don’t wish that was the case. I was an expensive lesson though, and I’m glad that I have come to appreciate the value of my second sight.