On Thursday September 25th, I set off to the airport for an amazing 2–3 week vacation with the following goals in mind:

  • explore the world of possibilities and opportunities
  • meet interesting people, learn about them, and and be inspired by them
  • reconnect with old friends

I don’t often take vacations of this duration by myself. So, in an effort to not instantly forget everything that happens right after it happens, I’ve decided to blog about it. I find that I remember very little unless I write it down or bring it into conversation. I hope to look back in a few months or a few years and reflect on how life changing this journey was.

But first, the flight

Vik Muniz, New York Postcard (Postcards from Nowhere)

Generally, I’m the kind of person that keeps to herself on flights. I strapped myself into a cramped coach class seat, tucked my laptop and a book into the seat back pocket, and looked out from my window seat at sunny SFO. I inhaled deeply to relax. I didn’t expect to make progress on my goals until landing in JFK.

That’s when I met Jess.

My most recent international trips were with Dropbox conducting user research to discover how people around the world use technology. Thus when I find myself on planes, a switch flips and I’m suddenly hyperaware of the way everyone around me is interacting with their devices. Jess had a MacBook perched on his pull out tray, creating what looked like a catalog of sculptures using some Adobe software I’ve never seen. He might’ve noticed me looking because, though I was supposedly reading a book with headphones in, he engaged me in conversation. I’m really glad he did — I learned something new.

Jess’s business card announces him as an “Art Advisor” for SFJ Art Advisory. I used to draw as a kid, had taken a few art history classes in college and, though shuttered away in tech, have generally been curious about the art world. I thought “wow what an opportunity I’d better ask some good questions.”

Jess’s job seems to consist primarily of visiting art galleries, auctions, shows, studios and clients around the world. What a life! We flipped through his printed deck of various artists and their work, including photography, sculpture and (my favorite) paintings. He’s actually quite analytical because he has a finance background. The deck explored the recent prices various works fetched on the secondary market and art investing trends. One finding was that iconic works generally appreciate in value more than other works even by the same artist.

The work above is Vik Muniz’s New York. Muniz is one of the contemporary artists Jess follows. I discovered that Muniz is actually affiliated with my alma mater MIT. He’s created some interesting work involving bacteria and sand through that collaboration (Vik Muniz + MIT).


Our conversation prompted me to reflect on things beyond our day to day.

The first is how, with technology making certain types of jobs obsolete, more and more people will be able to focus on creating art and pursuing their passions vs doing repetitive administrative tasks. Jess mentioned that he was involved in youth art in education initiatives. I can see how that sort of thing will increase with importance as art becomes the livelihood for a greater share of our population. On the demand side, we need to find ways to foster widespread art and culture appreciation so that there’s a market.

The second thought was how our society’s understanding of organizations, particularly knowledge organizations, is rapidly maturing. A few decades ago we didn’t really have knowledge organizations. Recently, we’ve experienced booms in financial services and technology. In addition to advancements in our understanding of efficient markets and computing, we innovated on corporate structure. Technology, the more recent boom, is an ideal training ground for young folk to begin their careers. When you see a company grow from 100 to 1,000 employees, you learn quite a bit about how organizations grow and develop. When my peers in tech and I “graduate,” we’ll hopefully go out in the world and disrupt other industries.

I’ll check back with Jess on these topics in a few years. Let’s see if I’m right!

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