Yes, things are changing in life and work — and it's both scary and exhilarating

I recently had the privilege of mentoring a very intelligent 21-year-old who graduated from a prestigious university. He has skills in computers, finance, and what seemed to me to be limitless possibilities. New York hedge funds appealed to him.

I’ve come up with a few ideas, none of them revolutionary. You know the drill, options, lifestyle, where you’d like to be in five years (the probability of ending up where you think you are is about the same as winning the lottery), having a family, making money, etc.

What fascinated me was that having all the avenues open before him (and it could just as easily have been a woman) actually created anxiety. He felt like every decision built on the previous one, and if you get it wrong, it gets worse and before you know it, you’re living in a homeless shelter in Buffalo, New York.

We all know that’s not true. But my experience with young people is that even though they know that very few decisions are fatal, they are obsessed with getting every one of them right.

(Note here: you can’t know if life decisions are good until time passes. No instant feedback. This is not a simple assessment, like the chicken Parmigiano was really dry, next time I’ll order halibut.)

I told him he could probably have three or four different careers in the next 35 years. This frightened him more than it comforted him. Many of us want certainty and limited disruption to routine. If something is wrong, don’t fix it. But what if it needs to be broken?

I turn to New York Times columnist Nicholas Kristof, who recently wrote about the importance of the gap year or study abroad. In other words, it’s about deliberately leaving your comfort zone.

Part of any entrepreneurial adventure is going to places unknown. It is a tribal rite of youth to head off to Europe (or places unknown) with a backpack and no reservation at the Four Seasons, no itinerary, no set route.

Kristof has some advice on this. At a minimum, “carry your passport, credit card, and cash in a pouch that clips to your belt and tucks into your pants.”

Come on Nick, you’d think that by now the bandits, thieves and terrorists would have heard of this trick, invented by my parents in 1962 when I went cycling across England and Scotland.

Ultimately, I challenged the young graduate to think about how quickly things change. Consider the last 60 days of American politics. It’s this aspect of our world that blinds us to what’s coming (it’s easy to be a futurist if you’re only right 30% of the time) that is both frightening and exhilarating. Consider artificial intelligence.

Four years ago, I started a deep data mining company. It was a pain in the neck. Now, just ask Perplexity.

Then think about an investment that can never go wrong: owning an office building in New York. Then think about COVID-19. There are no certainties, and that’s the message I had to convey to my friend.

I would argue that this fluidity is precisely what fuels the attitudes and concerns of Generations X, Y and Z. We baby boomers have been lucky. Change has been slow by comparison, which has allowed us to make plans.

Today, the fact that the pace of change is exponential to the cube is exactly what gives everyone “their chance.” Pop-up restaurant, two years later, Michelin star. Mind your own business, a viral video and you’ve got an agent and a movie deal. Solve a simple problem (they’re never simple), the world comes rushing to your door.

No guarantees. In a sense, the democratization of opportunity is both a blessing and a curse. My college friend is gifted and privileged, but he can hear the footsteps of the poor immigrant, the hungry entrepreneur who has him in his sights. (As Satchel Paige put it — “Don’t look back. Something might catch up with you.”)

That “competitive advantage” slide every founder has in their pitch deck deserves an asterisk: “Starting today, until someone else comes along to eat our lunch.”

Rule #821: “Be afraid. Be very afraid.” — The Fly

Senturia is a serial entrepreneur who invests in startups. Please email your ideas to [email protected].