The Flamboyant Optimist


I used to say that pessimists were actually closet-optimists: why point out the bad if you didn’t secretly believe that by pointing it out, you could make something better happen.

In the past few years I’ve realized that’s not the case; pessimists are cowards. It’s easier to prepare yourself for the worst and then be surprised by the best, than expect the best of the world and adjust when everything inevitably falls short.

I made a point when moving to New York two years ago to come out of the closet and try to live life from an optimistic perspective. This was new for me; prior to that I’d been an avowed pessimist.

Yet here I am, about to leave New York for San Francisco, and I find it harder than ever to maintain my new optimist lifestyle.

Why? Because I’ve been so lucky over the past two years… how can it possibly continue?


I was optimistic about my move to New York, but even so I’m surprised. The world did not fall short of my expectations: instead, it exceeded them. As those who’ve read this blog (I know, I’ve been intermittent of late), I’ve been trying to do a lot of things with my time here, and looking back on it now, I’m quite happy with where I got.

In leaving though, I realize it’s not because of my effort alone, but because of the help of others, that I had such a great two years. So, in no particular order, here are some of what I was involved with in New York (at least the things that really mattered to me), and some shout-outs to those responsible:

  • Raised over $15,000 for care of cancer patients: Thank you to everyone who donated. (Including over $3,600 with the stupidest online competition ever: Thanks Jonathan, Sanjeev, Matt, Gary, Will, and James.)
  • Met some amazing students, and fantastic volunteers at the New Song Learning Partnership: Thank you Stephanie, Grace, Roger, Robert, Neil (for introductions) and others, and a big thank you to all the kids!
  • Met some great International students learning English in the US who taught me a lot about Korea: Thanks Woolee and Hyung
  • Trained for and completed the Jack Brown Charity Ride from New York, NY to Providence, RI: Thanks to everyone who participated, but especially Mark for pulling it all together.
  • Trained for (but alas, did not complete) the New York City marathon: Thanks to Team Continuum, and especially Paul for being the driving force behind that.
  • Learned how to swim (sort-of) and then trained for and completed my first Triathlon (the Philadelphia Olympic-Distance Triathlon): Thanks to Grant, Mike, Erica, Jay, but especially to Gustavo for convincing me to sign-up and helping me learn to swim.
  • Helped start Stolen Bases, and learnt a lot about what do when you’re trying to start a company: Thanks Mike, Rick and Cliff.
  • Started my own company Vlideshow, and learnt a lot more about what to do (and not do) in the process: Thanks especially to Eric for introducing me to Robert.
  • Made a lot of new friends in NYC (who I hope will visit in SF), and deepened my friendship with several old friends who also moved to New York: Thanks to new friends Gustavo, Mariella, Diego, Jocelyn, Tony, Alyssa, Zahra, Kim, Lisa, Eve, and Zohn, and old friends Kathleen, Regan, Abbie, John, David, Ryan, Gisela, Kevin and Nolan.
  • And for the first time in our life together, my wife and I discovered we actually had weekends and evening available to spend together, and despite living in a 380-square-foot apartment, still found we liked each other. Thanks to J for putting up with me.
  • (…and yes, I lost 30 pounds and then gained 7-10 back. The true thanks for that goes to everyone mentioned so far, along with Microsoft Excel.)

(My apologies if I missed anyone.)

Given all that, I worry a little about how the next phase of my life can possibly measure up.

And the answer is it can’t… I can’t expect to compare and measure the past phase of my life to the next.

To remain an optimist, heck to become a Flamboyant-Optimist, I need to think about it differently.

The Worst Day of the Rest of my Life

Which brings me to Li and Eric’s wedding. Two weekends ago I was in California at a college-friend’s wedding. It was a beautiful wedding, and the entire crowd seemed a natural extension of Li and Eric’s relationship (which for me is the mark of a great wedding).

The bride and groom wrote their own vows, and something from Eric’s stuck with me. He said (I paraphrase):

“I believe today is the happiest day of my life so far, and also the worst day of the rest of my life.”

That, in many ways, is the creed of the Flamboyant Optimist.

Eric had faith, that despite the ups and downs of life, each day his relationship with Li would deepen in some way compared to the day before.

Now, Eric’s not stupid; he doesn’t expect each day will, when compared via all metrics, be better than the last; he only pledged that he would look for the way in which his relationship with Li deepened and became stronger in that day.

I need to now do the same. I am nervous in many ways about my return to San Francisco: will I be able to keep up the same philosophies? Will I find the right programs to give back to? Will my company succeed? Will my hair magically stop receding and getting grey (hmm…)? These are all questions that only time will answer.

But, as with my trip to New York, I am taking the following approach: I have faith that my life will be richer and deeper tomorrow, next week, five years (and further) from now than it is today. I don’t quite know how, but I leave here convinced that today is in fact the worst day of the rest of my life, and I go forth as an out and proud Flamboyant Optimist.

Thank you New York and good night.

– Art

p.s. As folks may have noticed, I’ve seriously decreased my postings to this blog. I expect that trend to continue for a while as I resettle in CA. I do hope to resume the “Naked Numbers” posts in August, and may post other things as time permits. The transparency the blog forced on me has been quite useful, and I may resume it again as a framework to help me push through other difficult changes I want to make. Feel free to keep an RSS reader pointed at the link.

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