After a six week hiatus I am resuming Uncertainty Wednesday. Much as I have done at varying points with my prior Tech Tuesday series, I have decided to head off in a different direction, at least for some time. Instead of the theoretical approach so far, I will focus more on the philosophy of living in a world full of uncertainty. How should we live our lives, make business and personal decisions, judge performance, etc. given pervasive uncertainty?

My plan is roughly as follows, but I am open to suggestions. First, I intend to write a bit about just how much of our lives is impacted by uncertainty (hint: all of it) despite us largely not acknowledging this reality. Then I plan to look at examples that illustrate how poor our intuitions are when it comes to dealing with uncertainty. With that in place, I will share the answers I have arrived at for myself for how to live with uncertainty.

An interesting exercise is to look back at one’s life and think about how events that had a big impact came about. Here are three examples from my life: the first was my father mentioning rather off-handedly when I was young that a year abroad might be a good idea. Without his comment I might not have applied for a 1-year stay in the United States – none of my childhood friends did anything remotely similar. Yet living with a wonderful host family in Rochester Minnesota when I was sixteen years old was a crucial formative experience in my life.

The second example is meeting Susan, my now wife of 21 years and mother of our three children (and co-founder and CEO of Ziggeo and so much more). I was sitting in a cafe in Paris in the Carrefour Odeon when I heard two non-native French speakers conversing diagonally behind me. As I was in Paris to practice French myself, I decided to turn around and say hello. That’s how I met Susan, who herself was there by chance having abandoned a trip to Belgium to visit a relative of hers in Paris!

My third example is how I wound up at Union Square Ventures. My now partner Brad had been an investor in and board member of an accelerator I had co-founded in 1999. Following the implosion of the dotcom bubble, Brad and I tried to raise a fund (together with another friend) but nobody wanted to invest in Venture Capital in the “nuclear winter” that ensued. I went off to work on another project, which also failed about two years later. By that time Brad and Fred had raised the first Union Square Ventures fund. They asked me to take a look at del.icio.us with them and after the purchase of that company I wound up joining USV as a venture partner.

All three of these events had a massive impact on my life. And yet in each case it is quite clear that there was a huge amount of uncertainty involved, meaning each of these events might also not have happened and my life would be quite different today.