I’m not big on gambling. But I’ll play a few hands of blackjack or watch some spins of the roulette wheel when it’s close by.
I was at a casino this past weekend, and got myself a stack of twenty $1 chips to spread around the roulette table. 
I won a few bets. Lost some. Eventually I lost all $20. 
No big deal. I was alright with losing the $20 I’d put on a game of random chance. 
The problem for me was, it wasn’t fun. Games of chance are supposed to be fun — they’re games, after all. 
Did losing contribute to my no-fun experience? I’m sure it played a part.
The house always wins… 
“Unless,” said Danny Ocean (in the movie Ocean’s 11), “when that one winning hand comes up, you BET BIG. And then, YOU take the house.”
I sat down at the table again and tried a different style of play that actually was fun. 
I put $20 on the table again. But, I told the dealer (is that what you call the roulette person?) that I wanted $5 chips this time rather than $1s. 
I bet $10 on black and $10 on “even.” Split it. 
Treaded water for a few spins. 
Got down to my last $10.
Bet it all on black. 
Started hitting. 
Doubled my money. Then, I doubled it again. Lost some. Resumed multiplying.  
Left the table with 5X what I’d started with. That’s not enough to fund my retirement, but it’s a start. 

***

What made my first run at the wheel boring was that I was playing the game too small. 
Win or lose, there wasn’t much to gain OR to lose, no matter what numbers came up. That’s how it is when you play small: no possible outcome changes much of anything for you. 
When I started betting bigger, the game came alive. 
Did winning help? Of course. 
But even had I lost, at least I would have been out of my money quickly, and could go find my next adventure instead of slowly bleeding out one excruciating dollar at a time. 
Betting bigger, I gave life to my experience. And I gave myself a chance to either wipe out quickly or take the house, $10 at a time. 

***

Many people lose in life not because they want to lose, and not because they don’t try to win. 
We lose because we live our lives in small bets: efforts that not only minimize our downside when losing, but also make our upsides helplessly low. 
Even when we win, the payoff fails to move the needle. 
We lose because we live our lives in small bets: efforts that not only minimize our downside when losing, but also make our upsides helplessly low.
Even when we win, the payoff fails to move the needle. 
Small bets have their time and place. Not every move in your life is going to be a swing for the fences. 
But, as Danny explained in Ocean’s 11, the winning hand will eventually present itself — and that’s when you need to push more chips onto the table. 
If you lose, at least you’ll lose quickly. No wasted time in getting to the point. 
But if you win… 
Where in your life do you need to make bigger bets? Where are you playing too small too often, thus giving yourself no real chance to ever win big? Reply and let me know — I read all responses. 

Tale the following masterclasses on aiming bigger and playing to win — 
#919: How To Bet On Yourself
#389: Risk Taking- You Can't Dunk Without Jumping!
#1342: When In Doubt, Take The Risk! 
#952: How To Bet On Yourself -- And WIN
#836: How To Mentally Minimize Risk

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