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If You Bet The Farm, Be Sure To Have More Farms

Fellow Riskologist,

The other day, I was driving through a Native American reservation on the way home from a short weekend trip when I spotted a casino. Fancying a little blackjack, I stopped in to play a few hands.

There was $100 in my wallet, but I only cashed in $20 for chips. The strategy? Play until it was gone or until I doubled my money. Either way, it would be a quick round of fun on an otherwise long drive.

Sitting down at the only open table, I said hello to the gentlemen there and placed the minimum $5 bet. Damn, lost it. Another $5. Damn, lost it again.

I thought to myself, “Ah hell with it,” and went all in—the final $10 on the next hand. That’s when the luck turned, and I won. Back to even.

Over the next half hour, the three of us watched our piles of chips rise and fall like the tide. After awhile, though, I was back down to just $20 in chips in my corner. I was ready to get back on the road, so I went all in one last time. I lost. Darn it!

One of the fellows at the table made the “whomp whomp” sound you hear when a contestant loses on a game show, and the other wished me better luck next time, reminding me I could have played longer if I hadn’t “bet the farm” on that last hand.

I thanked him for the condolences and advice as I left the table. What neither of those guys knew, though, was that I’d squirreled away $40 worth of chips into my pocket when the cards were good—removing the temptation to wager them again.

I’d already doubled my money and was just playing with extra until it ran out. I cashed out my $40 and hit the road back to Portland.

Now, this was no high stakes game of poker, and whether I lost my original $20 is mostly inconsequential. But I couldn’t stop thinking about what the other player said to me as I was leaving the table. “Sorry for your luck; shouldn’t have bet the farm.”

He didn’t know I had two more farms in my pocket, four more in my wallet, and thousands more spread across other accounts and investments.

This low-stakes round of blackjack underscores the importance of using the right strategy when you take any risk in life.

Many amateur risk-takers incorrectly assume the way to get ahead is to make one big play with everything you’ve got—you have to bet the farm. You either end up a hero, or you go down in flames.

If you’re a Smart Riskologist and know the odds are highly in your favor, this actually is a good strategy and an excellent blackjack player who can count cards will do this and win more than she loses. But when you’re striving for something more uncertain—a new career, a big adventure, an important relationship—it’s a terrible way to play the game and it’s a terrible way to tend your farm!

Instead, the path to success lies in making many small bets knowing you’ll lose most of them but you’ll eventually stumble onto a few worth going all in for.

Rather than keep one big farm with all your pigs, cows, chickens, and crops in one place, you keep many little ones—at least in the beginning. You don’t know which farm is going to produce the best yield, so you compartmentalize and spread your efforts across several.

This gives you the confidence to “bet the farm” in small doses to see what works and what doesn’t. If you lose one, there are more to fall back on. If you find you’re an excellent hog farmer, you can sell your cows and vegetables and buy more pigs.

This applies to many areas of life.

  • Maybe you’re saving for retirement? You don’t know what stocks to pick, so instead of taking an uneducated guess and crippling your future, start with an index fund that invests in the entire stock market. Eventually, as you gain knowledge and learn how to value businesses, you can start going all in on stocks you can positively expect to make money.
  • Trying to pick a college major? You’re not sure what you’re into yet, so why not try lots of things? As you get a better feel for what get your juices flowing, you can start investing more and more of your time into that and letting the other things eating up your schedule go.
  • Want to start a business? If you haven’t done it before, you probably won’t get it right the first time. But you also don’t have to. By trying out a number of different microbusiness ideas and changing your strategy as you learn, you can make small, incremental gains that add up without betting the farm and losing on one bad decision.


As I left the poker table, I was happy to know I’d won myself an extra farm even if I looked like a loser to the other players. But even if I’d lost at the casino that day, I was even happier to know I was driving home to much, much more.

If you’re going to bet the farm, be sure to have more farms.

Yours in farm-tending,
Founder, Riskology.co