Do Ya Feel Lucky?

Saturday, 2:21pm
Reno, NV
Well, do ya, punk?” (Clint Eastwood, “Dirty Harry”)


What’s Lady Luck done for you lately?

Humans have a strange relationship with Luck. Rome conquered the known world, yet firmly believed in a goddess named Fortuna who ruled over their fates. More modern successful folks than you can count consider luck to be a con-game. “I make my own luck,” is a common refrain… and yet these same smug studs often indulge in stark superstitious behavior.

I imagine more than a few folks have earned a PhD or two going deep into the concept of luck. Is it a random thing in the universe (like snake-eyes rolling exactly when you call it)…

… or part of a pre-determined script you’re just playing out (so of course the dice came up ones — it was part of your life’s plot-line)?

Or is it something much more mysterious and powerful?

You’re really got to settle this for yourself, I learned… because it’s in your wiring, and can affect the trajectory of your life.

However, if you look for advice from others about luck, or research it in any direction… it’s just a bottomless pit. You’ll find hard-core physicists talking about luckily stumbling upon some discovery they could easily have overlooked…

… and starry-eyed romantics believing that Fate brought them love when, actually, it was all part of a well-planned seduction. (Richard Feynman, Nobel Prize winning fizzy, had a beatnik’s appreciation of the mystical side of life… and I think it was Cary Grant who notoriously won the swooning love of a major — and majorly reluctant — actress by staging a mugging, so he could “save” her… which triggered her “White Knight” adoration pump. And he never told her it was all a set-up.)

It’s a very dangerous concept, too. I’ve seen obsessions with Luck ruin people, who believed they were swamped with the “bad” version of it and just gave up. And I’ve seen the positive side of it propel others to riches and fame, because they believed they were Lucky and had the confidence to match.

This is on my mind, because I’ve been ruminating lately on the turning points in my long career. Deconstructing how the big breaks happened, and how I ended up where I am. I’m tempted to say I’ve been a very, very lucky boy…

… except that, once you break it down and examine the details, every single big break happened through proactive movement on my part.

It may have looked like Luck from the outside, but there was a shitload of preparation, skill-building, and high-alert observation that preceded every level-jump I enjoyed.

And yet, I’m also very aware that things could have easily turned out completely differently. A second thought on a decision here, a hesitation there, an overlooked opportunity or frozen-by-fear moment of inaction there…

… and I have a hard time imagining what kind of life I’m leading now. I might be a warehouse manager in San Berdoo, or a dirt-poor wannabe writer in Sacramento pouring cappuccino at a dive coffee bar, or struggling cartoonist in Portland, or…

… I shudder to think about just how bad it could have been. Especially since the multiple game-changing events that started when I was sleeping on friends’ couches, broke and hopeless…

… were all fragile moments of fleeting decision-points.

I remember a story some guy once told me: In a big city, he hailed a taxi… but before he climbed in, a beautiful woman asked him if she could take it instead. Gallantly, he let her have the cab.  She hesitated, settling in the back seat, and asked him if he wanted to share the ride uptown. “No,” he said. “I’m headed downtown.” The cab took off… then stopped, as she rolled down the window to say one more thing: “You know, you will never know what might have happened if you’d taken me up on that offer.”

And the cab pulled away, leaving him with a Big Damn Question that would haunt him for the rest of his days.

I also had a friend who skipped going to a Jimi Hendrix concert, even though he had a ticket, because something important came up. To this day, he cannot remember what was so damned important… but he very much remembers missing seeing Jimi play live, because the great man died soon after. Perhaps this is a trivial example, but it touches on the larger point.

These stories remain swimming in my mind, after so many others fade away, because they remind me of the constant possibility for adventure and plot changes in our lives.

I’m appalled when I meet folks who are bored with life. Are you fucking kidding me? Bored? We’re a race of brainy, built-to-endure loonies on a spinning orb in the middle of a vast universe…

… with absolutely nothing or no one holding the power to control what you do next. Sure, there are laws, steel bars, fences and scowling mates (plus your own sense of decency and fear) abounding everywhere…

… and for most, the decisions to survive, to go along to get along, to take the easier path, to avoid rocking the boat… all makes perfect sense. And if you succeed too much at this, yeah, you can find yourself bored and wondering what the hell happened to your life. You’re too nice and safe and warm and free of dangerous excitement.

No shame in living that way, of course. Unless it eats at you. (That would be the first clue that you have entrepreneurial blood in your veins, you know.)

The folks who seem to exert actual control over their lives can be scary. I’m reading Steve Jobs biography, and the dude was worth $100mil in his twenties, and almost blew it all with his half-crazed need to keep pushing the envelope. He was driven. He took risks… big ones, that often ended in disaster. He eventually nailed down his place as a Hall of Fame super-success story… but it wasn’t a smooth ride.

This is why I urge all entrepreneurs to read lots and lots of biographies. You need to understand the process that great people put to use in their lives of adventure… grabbing opportunity, losing many times over, always having Achilles heel-type deficiencies that creates chaos in personal relationships, and never, ever, ever arriving at their moments of glory by an easy route. Some seek out greatness, others have it thrust on them…

… and most just seem to have been guided by something akin to Luck, being in the right place at the right time, and succeeding where others had failed just a short time before or after.

The thing is… you’ve got to come to terms with how you perceive your ability to spot opportunity, to deal with the thin air in the higher levels of adventure swirling just out of reach right now, and to understand exactly why your “Luck” is either going in a good direction or a bad one.

The tales below may or may not help you out. As trivial as they seem, they represent major shifts in the way I confronted the possibilities of life and career. This is personal shit here. I wouldn’t be sharing it, if I didn’t think it might help some dude out there struggling with the same issues (or missing some big break because of a twitchy, unnecessary fear).

Here’re the 3 turning points I experienced that helped me come to terms with Lady Luck:

Feelin’ Lucky Point #1: I played organized baseball until I was 16. Superstition is rife among athletes… as it tends to be in any group where competition is brutal, and losers suffer humiliation while winners enjoy endorphin dumps and wild euphoria.

And you’re faced with constant challenges to your physical skills, your mental state, even your notion of who you are and what worth you provide to the planet.

It’s even worse when you’re a shortstop. I clutched at the barest minimal skills required for the position, holding the job on my Colt League team by my fingernails. The majority of infield grounders and line drives came my way, and I was often the first guy to get dirty each game by diving for balls just out of easy range.

In the sandlot, baseball is fun. (My favorite game of all-time is over-the-line, two on two. I played this well into my twenties, after work, with games that went on until the darkness forced us to quit.)

Under the lights of a real ball park, in full uniform, with announcers and crowded stands and a real scoreboard…

… not so much fun.

I felt out of control… and became convinced that Luck played a huge role for me in every game. And I developed the most bizarre superstitious behavior imaginable.

It went far beyond not stepping on the lime chalk lines heading on and off the field. I had my rabbit’s foot, I had my belt clasp very precise on the left side, I pounded my glove exactly three times as I settled into my spot before each pitch…

… which was all fine. The catcher pounded his cup, the first baseman spat on the bag, and the center fielder shook himself like a wet dog… all before the next pitch. Routines. We all needed a little Luck on our side, with so much chaos impending with each swing of the bat. (My favorite scene in baseball involves a bases-loaded stretched-out triple to the gap — the entire field explodes into action, and even the most disciplined teams descend into madness during the play.)

However, my superstitious rituals started getting out of hand. I remember noticing, as the pitcher wound up, that there was a big dirt clod a foot in front of me. So I quickly stepped on it, and got back in position. Ball one.

Then, I saw another dirt clod, big as a shoe, to my left. Bam, got it. Ball two.

Then, oh Mother of God, I realized that I was surrounded by dirt clods. They were everywhere.

And they all needed to be stomped.

For weeks, I was able to attend to the endless task while warming up before each inning, and I was careful to always be back in position during the game before the ball arrived at the plate.

But those fucking dirt clods kept multiplying. Pretty soon, I was out there dancing and stomping like a Dervish before every pitch, muttering to myself and looking like a complete idiot.

At the same time, my fear of somehow not pacifying Lady Luck really got out of hand. I was so convinced that my performance at shortstop depended on crushed dirt clods that it affected my already meager skill levels. And began to bleed into life outside the ballpark (to the point I couldn’t have a dime in my pocket — bad, evil coins! — and stepping on a sidewalk crack would ensure a full day of nameless horror.)

I woke up during sweaty nightmares full of taunting clods and grounders skipping between my legs while the galleries laughed and laughed…

And I am so proud of what I did next. I was just a kid, but I figured what the hell — if this superstition crap was gonna get me, let’s give it full access. So, the next game, I just let the dirt clods be, and put myself at the total mercy of the Gods of Superstition.

And I had a normal game.

At that point… at that tender age… I made one of my first life-long vows. I vowed to never fall victim to superstitious rituals again. If I ever suspected that future outcomes depended on me performing some unrelated task or action…

… then I purposely violated that ritual. Just to see what cosmic wrath awaited.

I’ve never been let down. Cosmic wrath has, for decades now, demurred from crushing me. And, in fact, I feel I’ve led a fairly “lucky” life… as in, being pretty happy about how things have turned out. The “bad” luck I’ve experienced almost always presented amazing lessons to learn, which then helped me get even more done. And any “good” luck I’ve stumbled upon is just icing on the cake.

I can’t even imagine what kind of nervous, stress-addled nutball I’d be today, if I hadn’t crushed those superstitious feelings early on.

Superstition is fear. Fear of the unknown, fear of being out there all alone with no magical back-up. This hurts you twice — first, it sets you up to accept failure as a “punishment” rather than as just one of many possible outcomes…

… and, second, it robs you of any sense of accomplishment when you win. It ain’t the rabbit’s foot. It’s you, and the preparation and skill-building and focus you put into the task, that made things happen.

I like mystery, don’t get me wrong. I have a very deep spiritual side, and I do not believe for a moment that I’ve got life “figured out”.

However, I do know that superstition sucks. And it’s got nothing to do with finding a big break.

Feelin’ Lucky Point #2: While in college, my wayward pals and I gathered up our meager extra bucks and drove to North Shore Tahoe to try a little “adult level” gambling. We were all experienced poker players, so we weren’t exactly babes-in-the-woods…

… but I’d never been inside a real casino before. It was exciting, and I had no illusions that I would return a rich man.

However, a very important lesson was awaiting me.

My friends all trooped into the Crystal Bay Club through a side door, but I wanted to go in properly, through the main gates. Before I reached the entrance, however, a guy slightly older than me approached…

… and offered me his very nice leather coat for ten bucks.

It was snowing. He had on a tee shirt under his coat. I raised my eyebrows.

“I just need ten bucks to get even at the tables,” he said. “C’mon, it’s a good coat.”

I was barely 21, and in no position to either judge the dude or offer advice. So I declined the offer, and went into the casino.

That scene has stayed with me my entire life. Right there, in a feverish 30-second encounter, was a mini-soap-opera on addiction, and all the insanity that comes with a belief system about “changing your luck” or “getting back in the game”.

Now, I enjoy gambling. I’ve tried most of the vices available in modern civilization, and gambling is one of those once-in-awhile pleasant departures from the grind of living sensibly. However, I can get the same thrill from playing dime-ante poker (with a $2 max burn) with longtime friends… or working to win spare change from Pop and siblings in our frequent rummy games… or playing a quarter-a-hole golf… as I ever got from an all-night crap game in a sordid Vegas low-life casino. (The now-demolished Frontier, if you must know, had a never-advertised $1 craps table with 10x odds that attracted players from all over the globe. I went a few times with a pal for the pure Hunter Thompson story-value, and it was like being in a Fellini movie, surrounded by grotesque hard-core gamblers from far-flung corners, drinking heavy and praying for one more long roll before the sun came up…)

I love competition. Against another player, against the odds, against all rational possibility. But it’s not a lifestyle, and it’s no Master Plan to live a good life. It’s just training.

The lesson: Go up against impossible odds once in a while. Learn how your gut handles the pressure, learn how your mind works in losing situations, learn how your system reacts to pulling off feints or destroying your opponent.

These are good tests, both to judge where you’re at as a human being in an unpredictable world… and whether you can evolve new skills required for advanced gamesmanship (which include losing well, assessing risks, and understanding why so much of life follows game-like rules).

You can do this playing chess, too. But I like the added risk-taking of having money involved — even dimes and quarters.

It’s that attitude — of seeing how I played a hand given the stakes (and losing a quarter to Sis is easily as bad, emotionally, as dropping a Franklin to a blackjack dealer) that led me to the “Gun To The Head” theory of professionalism. With a gun to my head, I wouldn’t dare write an ad that strayed from the proven fundamentals of great salesmanship.

However… and this is important… one of those fundamentals is TAKING RISKS with your knowledge of the market, the prospects, and the competition. You can’t “play it safe”. You just don’t take wild risks that don’t have a chance in hell of working.

But you DO risk things… like pushing the boundaries of what your client and marketplace expects.

And I know my gut, and I know how much risk I’m okay with taking… because of all those gin rummy and late-night poker games where I had to make decisions loaded with consequences. (I was very, very lucky to grow up in a loving but INSANELY competitive family. Sis taught me to never pass up a chance to gain the upper hand, and never offer mercy. It’s the best kind of competition, and it mimics real life in the business world.)

So, yeah, pray for the Jack of Spades, and feel lucky if you grab it and win the hand. And know, from experience (not guessing) that sometimes you can win with skill and a good plan…

… and sometimes you can win by sheer wild fortune, without having a clue what you just did. (Or, just as easily, lose to someone else the same way.)

Just be sure to learn your lessons when they land in your lap. Both the good ones, and the painful ones.

Feelin’ Lucky Point #3: Last point.

One of the best moves I made, early in my freelance career (when I was living month-to-month), was to stay hyper-alert to anything that might be an opportunity to make money as a writer.

Today, after an exciting and fruitful 30-year-career, I can confidently tell rookies that maybe — MAYBE — one or two big opportunities will arrive in their lives. But these opportunities will not announce themselves. They will come as whispers on the wind, easily missed.

And they will often arrive as confused, non-obvious situations that defy logical possibility.

I first met Gary Halbert at a party at Jay Abraham’s house that I had no intention of attending. I was leaning toward not going, and then heard that Halbert was going to be there… for a short time (as was his habit).

Now, I barely knew about Halbert. He had just come back on the direct response advertising scene (after a vacation in Boron, courtesy of the The Man), and had just started publishing his newsletter (which he continued to write right up until his death a few years ago).

I was in a very different part of the advertising world at that point, working with corporate clients and agencies. But I felt drawn more to the entrepreneurial side, where Gary excelled. Less rules, more risks, more payoff if you won, more fun all the way around. (Being a “fun” dude in a corporation pretty much ensures you’re never gonna get anywhere, you know.)

And so, I sensed that meeting Gary was something I needed to do. Even with no idea of the consequences. So I went to the party, and introduced myself to him, as he sat with his new red-headed girlfriend in a corner, happily insulting everyone who ventured near.

He was the most arrogant, abrasive, and manipulative guy I’d ever met… and I liked him immediately. We did not “hit it off” right away… and it would take another year of dancing around each other before he asked me to join him in his marketing adventures. And, just to complete the story, I had to turn my back on a fortune to do so — I was one of the rising stars in the corporate direct response world (working with game-changers like Jim Rutz, Gary Bencivenga, and Steve Barwick), and fees were rising like crazy.

But I took one look at the boring life I’d lead as a writer for the big mailers… and another look at the sheer pandemonium and excitement of a stint with Halbert…

… and never looked back.

Was it “lucky” of me to meet, and eventually become one of Gary’s closest friends? There was a brief window there, where this could happen. I didn’t plan it. But I jumped on the opportunity when it presented itself (and pushed my skill levels even higher during the time we sniffed each other out, knowing I needed max professionalism to earn a spot on his team).

No superstitious rituals needed. No banging my head against the wall, and no lamenting the cruelty of Fate.

Maybe Luck exists. I’ve certainly felt lucky before… both with good luck that thrilled, and with bad luck that crushed my spirit.

But the best lessons I’ve learned along the way all point to a very Zen-like answer: The universe is both precise and rational… and totally unpredictable and full of surprises.

And here we are — fragile little bundles of brain and guts and nerves, easily smashed by large rocks and bad business moves alike. Sometimes struggling, sometimes cruising, always one event away from being in a totally different and scary situation.

I’ve “created” Luck out of thin air, and I’ve had it slam up beside me unannounced and deliver a bounty. And I’ve had it vanish just when I needed it most, or stupidly assumed it would hang around forever.

I’ve built up my relationship with Lady Luck over a long time. She’s not as much mysterious, as she is unpredictable.

Don’t rely on her. But don’t ignore her, either.

Get to know yourself… and how you handle the vicissitudes of stress, risk and life’s amazing surprises… and your relationship with Luck will take of itself.

Stay frosty,


P.S. I dunno. That’s just my take. What’s your relationship with Lady Luck? Are you where you are today because of a stroke of luck, or nothing but hard work, or a combination of the two?

How did you learn to play the game of business?

The comments section is open.

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