There are a considerations built into this question. When something of value is at risk, the pressure to play well goes up. It gets worse if the amount lost impacts your lifestyle (the rent money, etc.). Basically, the decision to bet (and how much) on your skill depends on how the loss would affect you.
If you don't get all hyperactive (fast breathing, high heart rate, copious perspiration) when you place a bet on your competence, you need not worry about the outcome, positive or negative. A comfortable amount, wagered on your abilities against a similarly skilled opponent would be OK. The thrills and chills of a competition make the Green Game more interesting.
Some people can only play their best under this kind of pressure. Others, when exposed to this type of challenge, literally see their game fall apart. They just crash and burn.
If you find the thrill fascinating and can afford to lose, try it out. Just keep the bets within reason. And, be aware that there are predators out there that will make sure you lose AND lose more than you can afford. Among buddies, some friendly bets can be used as an ongoing scorecard.
Weekly tournaments are probably the most common form of gambling. You pay your entry fee (usually a small amount) and are assigned opponents that test you in ways that does not occur in day-to-day pool hall games.
Tournaments are an excellent way to identify weaknesses in your game against individuals of similar skill levels. From those experiences, you can develop practicing programs to strengthen those areas. Over time these contests are your gauge on how well your game is improving.
If you do decide to gamble, here are some general rules:
Don't carry into the pool hall more than can afford to lose.
Learn how to match up against your opponent so that it will be a fair challenge - i.e., ask for or give an appropriate handicap (number of balls, number of games, etc.)
Don't put down a large bet against someone you've never played before.
You will not get rich gambling, so don't expect that winning or losing will change your life.
If you lose, consider it entertainment. If you win, buy a good dinner.
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