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Luck-Making and The Art of Coincidence

Stock Photo Caption: The family ignores my screams as they hasten my doom.

Several years growing up my mom (and sometimes dad) would pack the station wagon to the gills and make the trek from Evanston, Illinois to my grandparent’s house in Melrose, Florida. Melrose is about thirty minutes drive from Gainesville, Florida. For those of you who still don’t care to know where that is, Gainesville is the home of University of Florida.

These trips growing up framed Florida with rosy glasses. My grandparents house was on a small, private property edging up to a small lake shared by maybe 50 properties total. It was an idyllic rural getaway (occasionally WITH gators).

When I went to Florida it was family: grandma’s cooking, swimming, cousins, trips to Disney.

Wait Spaceship Earth? This isn't the line for Captain EO?

One year we took a flight down. This might have been my second or third flight ever, I don’t remember the specifics. In fact, the only thing I remember about that flight was walking through the Jacksonville Florida airport (fun fact Jacksonville in square footage is the largest city in the contiguous United States excluding ANY major metropolitan area. So really, Florida HAS NOTHING).

Why was that airport so memorable? Because we ran into my grade school social studies teacher.

We hadn’t taken the same flight, we hadn’t even been in Florida for the same period of time. And remember this would have been at an age when even seeing your social studies teacher at the grocery store would be a huge deal. (I think My Teacher is An Alien had just dropped and we truly never shook the idea that maybe, just maybe, the teachers lived a the school)

no joke, this changed my life a bit.

As the years trod on these fun coincidences occurred fairly regularly. Seeing a random college classmate on a random Brooklyn train platform on my first spring break road trip. Getting free drinks at Whirlyball because the managers happened to know my uncle. Running into a super close friend on Bourbon Street in New Orleans one evening while we were both there for entirely separate reasons. This is stuff that makes life truly sublime.

Religions and believers in fatalism will tell you those coincidences have some bigger meaning. Other more pragmatic or cynical folks will just say the pure chaos of life means coincidences are a natural consequence. I’m not sure where I sit on this… Humans are great at both 1) recognizing patterns, and 2) misidentifying coincidences as related. I am not immune.

That said, I do want to talk about luck for a minute.

Coincidence and luck aren’t the same. Nor do I think people are inherently lucky or unlucky people. But I have seen people ‘make their own luck’, and there’s a lot more to luck than just being lucky.


Once she anted with the popsicle sticks I knew she was drunk off juice boxes and animal crackers....

My dad liked to gamble. But he was usually broke so he had to get creative.

He would play four-deck canasta until sunrise with his twin brother over a Crown Royal sack filled with pennies.

He would play the pick 3 any time he had an extra $3-4.

He loved foraging through casinos to find one or two-penny slots.

Back at the restaurant we’d hustle pool games for a nickel a ball.

Here’s the thing though, my dad was pretty lucky.

He usually retained a solid penny stack at the end of the card game. He won the pick three at least twice in my lifetime that I knew about.

And I never saw him spend more than $20 at a casino (including a drink) and usually he walked out with his original bill tucked smugly in his pocket. Often he’d earned a little play-around money.

I did not share his luck. Often, I’d walk out next to him, having spent the $60 or so dollars I’d saved for the trip (I didn’t have a lot of scratch either) broke and frustrated for the (sometimes hour plus long) drive home. Once or twice I’d walk out over the moon, having doubled my money or even better. Either way dad would be placid, stoic. Reassuring in the down-times. Low-key during the up-times.

Don’t get me wrong, my dad wasn’t a sociopath. He’d get excited about the big win. He’d talk a little mess if he was winning at pool. But he rarely carried that vibe out of the casino or away from the pool table.

And I romanticize all of these memories to sum up that he was lucky, but there’s a more reasonable way to look at it.

My dad wasn’t any luckier than average. He might not have been particularly lucky at all. He was good at canasta. And at pool. Betting on a game that involves combinations of strategy and skill is a little different than games of pure chance (according to legal teams over at SportsBookDuelBattleDotNet), but betting on games of pure chance has a strategy to it as well.

To say dad was good at the Lottery or at penny slots would be somewhat foolish. But he employed a method to improve his chances. He kept buying the ticket. He kept spinning the wheel.

I know of the two times he won the Pick 3, but how many years did he play the game? Was he really a ‘winner’ at all, or did he just happen to win on average about the amount of times you might win given the quantity of times you played the game? (remember I’m bad with probability, I know the chances of winning each discreet game are the same in a purely random game but with scratch-offs or finite-prize lotteries there’s definitely different math there )

Seriously, Google Joan R. Ginthner. WILD story.

With the slot machines, he said he would always “feel out” the machines. I always thought this to be nonsense. But he never really lost more than $20. The truth was he was playing a relatively small amount of money at the penny slots (although for the uninitiated, “penny slot” is a misnomer, as the typical minimum bet for many penny slots can start at $.20 and go past $1.50+ per spin) so he got a lot of spins out of that $20. No matter how long the odds in a casino, a machine might hit a fair prize out of the blue after a string of nothing. Pop would immediately cash out that prize and move along to another machine. He was pretty superstitious about slot machines too, and liked going to machines after he saw someone lose a bunch of money. Totally arbitrary, but he liked his system. That said, he didn’t always walk away with the $20.

I ignored the bite of his $20 loss while stewing on my $60 loss, but that didn’t make the $20 any less painful to his bottom line.

His attitude was always “You had fun right?” And yeah, at the end of the day, gambling is exciting even when you lose. Worth it? Maybe not always… But fun, *sigh* sure.

But you never win if you don’t play.

*** As I begin the process of networking into the next phase of my career, I’ve been thinking a lot about luck and coincidences.

I feel incredibly blessed to have such a strong network. It’s not luck that I know these people per se, but how did I end up being born to decent parents who gave me a decent life, living in a decent town, without ever knowing hunger or housing insecurity? How did I get into my dream college even when only one other student from my school got into that college? How did it happen that the love of my life would be a former coworker whose profile I happened across on OK Cupid one day?

Luck is obviously part of this equation. But recognizing coincidences is critical, and taking advantage of those coincidences is even more important.

And we rarely see the literal fuckton of work that goes behind all the luck.

A trusted colleague and career coach said to me that the hit rate on networking communications is ~20%.

That means eight out of every ten contacts, however well-meaning or well-connected those contacts may be, will yield no results.

“That feels encouraging” (I said sarcastically, fighting back tears).

But then he said “OK, sure but think about it this way. I’m one of the 20%. I’m giving you free career coaching.” shit. Good point.

“And you only ever need the one job offer. And that one will be the right one. Because it’s the one where your skill set, mission, and purpose will all align because you’ve done the work of articulating what those criteria are.”

Ah, there’s the heart of it.


I don't even like salmon but I def want to try this dish.

Luck is great, and necessary, at the end of the day. We all need that little extra bit of coincidence to pop into our day-to-day to remind us of the magic and mystery of life.

But luck is a result, not a state-of-being.

And we have to be prepared to see when we’ve gotten lucky, and especially prepared to avail yourself of that opportunity when it presents itself. And that part isn’t luck, it’s just plain old-fashioned hard work.

Take risks, be prepared, rinse, repeat.

That's life, and it's happening all around you.

Good luck everyone!

Best, Doc Wattson

Native Stranger Productions

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