When is it Time to Cash Out?

Written By @Hookslide23

I could simply copy and paste last weeks column right here, over there ▶️, down here ?, or maybe even here ?.  Everything I said last week holds true now: I bet my standard 3-pack of underdogs, and only one prevailed victorious.  Thankfully, it was the Green Bay Packers; I secured a price of +185, so my losses were minimal.

(Yes, I wish my market entry was better and snagged the Packers +200, but we’re staying positive.  We have to stay positive!)

Underdogs are still taking a beating this season, and as I said in last week’s column, the statistical odds are against that trend continuing.  I still believe that, and I’m not budging from my strategy as the season pushes forward.

But this raises the next obvious question, a question I get asked frequently:  “Where did you get that sweet jacket?”  That’s a good question, but an even more important question (for this column anyway) is, “When is it time to cash out?

That’s really a question that only you can answer, and it’s a question that hinges on how you answer another question: “Why are you betting on sports, anyway?”

If you’re betting sports for excitement, an adrenaline rush, or to give yourself a reason to watch games you wouldn’t normally, then it’s probably not the money intriguing you.  In that case, decrease bet size, prepare yourself to lose and enjoy the sweat.  You can cash out at season’s end.

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If you’re betting sports to make a little extra cash, or partake in a hobby where money doesn’t always leave your wallet, set goals and cash out when you get there.  I’ve had NFL seasons in the past where that was my purpose, and once I had reached my goal, I packed it up until the following season.  (This is also my personal policy when dealing with emails from rich Nigerian princes who promise to send me millions if I give them my bank account information.)

Of course, I didn’t hit my aforementioned goal that season until two weeks before the Super Bowl, but still!  I knew when to quit.  (Free tip: when you finish in the black, do what I did that season and take your significant other out for a nice dinner at a swanky restaurant.  It’ll make the next betting season go smoothly.)

If you’re betting sports because you have unique handicapping skills, it’s the majority of your income, and you just flat-out enjoying beating the market, then this likely doesn’t apply.  You’re in it for the long haul no short-term streak is going to unhinge your confidence because you’ve proven to be a winner over a significant sample size.

Setting goals is very, very important (not just in sports betting).  It provides a way to measure progress, and will act as a lifeline in a racket where it often feels like you’re just a hampster on a wheel.  Win some, lose some, win some, lose some, but how do you know when it’s time to treat yourself to that steak dinner if you’re not tracking results?

I really wish I would’ve taken the Packers when they were +200 at BetOnline.AG.

See you next week, kids.