Oversharing at a Dinner Party

Oversharing at a Dinner Party

Entropy And Change

“You are the only one responsible for your own wants.” - Dr Susan Calvin (I, Robot)

Mike Oppenheim's avatar
Mike Oppenheim
Jun 30, 2026
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Today is my 45th birthday! And while, so far, I’ve never been upset by aging, this day does present an ominous occasion: Silly me, I vowed 20 years ago that if I didn’t achieve SAIDI (success as I define it) by this exact age, I’d quit my writing career.

However, now that I’m at my deadline and still far from my goal, I’ve discovered two awful things: 1. I’m really happy with my life, so 2. I have no desire to quit!

But I guess I should first address how this all began…

My quest for SAIDI started when I graduated from college in 2003. I was a 21-year-old singer/songwriter guitarist, hell bent on starting a band, which wasn’t a normal goal for a kid from my affluent suburb in California. But I’m weird, so while most kids were applying to Harvard, Stanford, and Yale, I was researching “How to play at CBGBs and convert a mini-van into a touring bus.”

My plan was no small feat. First I had to convince two high school friends to join me, and as if that weren’t enough, I had to talk one into learning a new instrument (drums). Then I had to get him and his fellow UC Berkeley alum to convince their parents to accept our decision to toss our diplomas in the trash so we could run full-speed ahead into the wall of failure that surrounds the entertainment industry.

Lucky me, their parents mostly respected our plan. We’d done research, scouted locations, and, I’m blessed with “parent-charisma.” But then we ran into a new obstacle: the other friend also wanted to play guitar, so we now needed a bassist.

More lucky me, that same friend fell in love with a girl on Spring Break, who just so happened to be an extremely talented bass player! Not one to waste time, I drove out to Chicago that summer to meet her and beg her to join our band, and she agreed!

But that’s where my luck ran out. After the drummer and I had moved 2,000 miles to meet her and the guitarist near Chicago, the bassist got cold feet and said she’d only start the band if we moved another 1,000 miles to where she lived in Ithaca, NY.

Emotionally stymied and on the verge of bankruptcy, the only “solutions” to the bassist’s red-flag-raising news was to A. Tell her and her boyfriend (AKA one of my closest friends) to take a hike, or, B. Give in to her demands and move to Ithaca.

There’s a popular idiom that evokes the image of hell freezing over, but I can tell you from experience that this adage is not a cliché. I say this because we did concede and move to Ithaca, and it is the text-book definition of a frozen hell. My proof? It was never warmer than 10 degrees, every day of January, both years I lived there.

I might sound bitter, so I’ll admit that I did get lots of personal growth from this experience, and despite the odds against us, our band ended up doing pretty well.

In just 18 months, we went from playing frat houses and coffee shops to gigging in every major city in New York, including a famous club in SoHo that I still name drop when I’m hanging with real musicians who may doubt my efforts to succeed.

My point is that I’ve always chased wild dreams, but with a structured approach, so I find it odd that as I turn 45, I’m no longer cocky or confident about “dream-chasing.”

Until recently, looking back on my life was a pleasure, because it’s like reading a story I wrote. But now, for the first time, I’m starting to wonder why I’m writing about a protagonist who is failing at his dream and doesn’t think he can change that.

OK, OK. I can see by the look in my mind’s eye’s vision of your face right now that your confused, or even worse, sad, so I’ll stick a pin in that sentiment and start anew:

One of the best things I learned in Ithaca was how to do the New York Times Crossword puzzle. I did this to flirt with a co-worker I’d fallen head over ankles for (with all due respect, heels, we can admit this now). I needed an excuse to hang with her, so since she always did the NYT puzzle after her shift, I asked her to teach me.

My plan worked, and we ended up dating. But what I never saw coming, was that while we only lasted a year, I still do the NYT Crossword every day. I’m not exaggerating. As of today, I have an 841 day streak on the app, and it should be around 3,500, but the streak was interrupted when my phone broke a few years ago and I couldn’t find my password to log in and upload the puzzle on time (But I did complete it on time!!!). And if you’re wondering why the streak isn’t from 2003, it’s because I did it the old fashioned way, in the daily newspaper until 2016 when I discovered the app.

So I was thinking today about why I love doing the crossword, and the answer explains why I feel like a loser when I look at where I am in relation to my SAIDI goal. The reason I love the crossword is that no matter how hard it gets, I know I’m good enough to solve it, which makes that challenge fun, even if it takes a long time to complete.

Ergo, challenges are only fun when I know, deep down, I have a good shot at success.

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