There is a simple fact about people that most of us are very bad at remembering: we are typically poor judges of what actually motivates us. People spend energy going after things they think they want, only to end up unsatisfied. I'm not attempting to preach or act holier-than-thou. I'm just being descriptive. This is definitely a problem with me, and it's very likely one with you and many people you know. The person who actually knows what they really want and knows what really satisfies them is either 1) lucky or 2) reached that point after a lot of disappointment and self-searching.
So it's interesting (and sad) that people attach money and external rewards to games. We usually become good at games because we just like them a whole lot; material stakes don't have much to do with it. Few kids grew up watching Michael Jordan play and thought, 'I want a contract like his when I grow up.' They wanted to be basketball gods, for the sake of being basketball gods. Because it was awesome to learn and get better. It was cool.
But at some point, people want to add things to the game to "make things interesting" or "spice it up." And it works. It actually does work to put something on the line and threaten yourself with genuine loss should you fail at a game. Put a thousand dollars on a hand of poker, and you are gonna seriously care about that hand of poker (assuming you aren't a multi-millionaire and a thousand dollars isn't just chump change to you). Your adrenaline is going to spike, your palms will sweat, your heart will go nuts.
This is where it gets tricky. Let's say you love darts and your friend loves darts, so one day you decide to put a hundred bucks down on a game. And you get close to the end and it's neck and neck, and your buddy suddenly says, "hey listen man, if I lose this I actually can't pay rent this month. How about we just nix the bet?" You may or may not say yes, depending on how homeless you want your friend to be. What happens after is the interesting part:
If you decide to cancel the bet, you typically become significantly less invested in the outcome of the game. You may stop trying altogether, saying, "well, now there's no money on the line, so what's it matter?" This will even be the case if you're normally competitive. Why? Because ordinarily, the dual purpose of the game is to have fun and try to win. If you replace that with a new one, where you play the game to try and win money, then remove that, you have nothing left.
Some people DO continue to care and try their hardest because they are innately competitive and always want to win. However, most people most of the time will stop caring. This is the result of something called the Overjustification Effect. From Wikipedia:
"The overjustification effect occurs when an expected external incentive such as money or prizes decreases a person's intrinsic motivation to perform a task. According to self-perception theory, people pay more attention to the external reward for an activity than to the inherent enjoyment and satisfaction received from the activity itself. The overall effect of offering a reward for a previously unrewarded activity is a shift to extrinsic motivation and the undermining of pre-existing intrinsic motivation. Once rewards are no longer offered, interest in the activity is lost; prior intrinsic motivation does not return, and extrinsic rewards must be continuously offered as motivation to sustain the activity."
tl;dr: If you attach extrinsic reward to something to get people to care more, then remove the reward, people stop caring.
Seems obvious, doesn't it? Yet people insist on taking things they already enjoy, then adding money to them. Once they stop playing for money, they stop having fun. In fact, they have even LESS fun than they did before. This means that you might have cared about the game, just for the sake of the game, or your own learning, or the thrill of competing, and that was great. As you went on, you tried to increase it by putting more on the line, which seemed great, but then you realized you undermined the whole thing. That's not so great. Now playing is a job, a chore. You ask yourself constantly, "will this be worth it money-wise," and if you can't make enough money at it, you don't bother to show up. If you bother to show up, you goof off. Getting too used to money ruins the activity.
I'm not crazy enough to say there's something wrong with having resources available to you, or wanting to have sufficient resources to enjoy your life. Life has the chance to be a lot more fun when you don't spend all your time wondering if you get to eat this week. Which is exactly why you shouldn't make money a central (or even auxiliary) component of your games; you can't enjoy them if you are obsessing over the monetary aspect.
The thing is, it's really nice and attractive to think that you can make a living doing what you love, but the problem is if your living legitimately depends on it, odds are you're not going to enjoy it nearly as much. You will be constantly evaluating what you do in terms of "is this going to get me by," or "is this enough money for my investment," and that's going to kill your enjoyment.
There is a caveat here. If you KNOW that you don't need or even particularly want the money, or you genuinely don't expect to get it to begin with, you are drastically more likely to keep your interest for something. If you make $50,000 a year and you agree to do a commissioned painting for $20, that's such a small external reward that it basically doesn't matter to you. You might as well be doing it for free.
That's the key: if you might as well be doing it for free, you're more likely to enjoy it regardless of the existence of an extrinsic reward.
So this is my advice. If you aren't going to enjoy what you're doing, you might as well pick something lucrative. Then you'll have the financial safety net to enjoy your hobbies without worrying about the cost. That will let you leave the whole thing as intrinsic as possible.
Thanks for reading.