Embrace the Uncertainty: On the Benefits of Upside Surprises

I’m generally a risk-averse person. I don’t drive motorcycles. I don’t own individual stocks. I don’t deadlift anything heavier than my bodyweight. When analyzing a new situation I tend to focus on what can go wrong before thinking about what could go right.

As former Intel CEO Andy Grove once said, “Only the paranoid survive.” This has been my operating manual for most of my life. I’ve been paranoid of failure. I’ve been afraid of uncertainty.

However, as I’ve gotten older I’ve started to appreciate the other side of uncertainty. The side where things go right. Where they go more right than you could ever expect. These are known as “upside surprises” and they can be absolutely delightful.

The most recent upside surprise I’ve had came last week at FutureProof, the financial conference my firm co-hosts in Huntington Beach, California.

When I first heard the idea for FutureProof many years ago, I was a bit skeptical. It’s going to be outside? What about the weather? People will be wearing casual attire? Who will take it seriously? I had more questions than answers.

But after my first time attending it in 2022, I got it. It turned the traditional conference experience completely on its head. No more stuffy ballrooms with suits and boring catering. It was shorts, sunshine, and food trucks. Now that I’ve attended for the last three years, it’s hard to imagine doing a conference any other way.

But a cool conference is just the beginning of the upside surprise. The growth of that conference has been even better. Don’t quote me on these numbers, but in the first year FutureProof had 1,300 attendees, something like 2,200 in its second year, and over 4,200 this year.

Yes, FutureProof doubled in a year after basically doubling the year before that. And

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Nick Maggiulli: