I thought i was doing it right

I wouldn't allow my options to lose much value. Maximum 50$. I sold for $100-$300 depending on confidence. I've had quite a few options go very high in value after selling later in the day. Whenever I hold i somehow always sell before profits come in. I stay up to date with the news, watch live traders, and learn as much as i can while not trading. I analyze my strategies to figure out what works and what doesn't. I managed to make 1500 on pure accident. Then 2k the next day. Then just down, and down, and down. Even while trying to be safe. A true regard I am. I'll never quit but I have things to reconsider. Advice and thoughts are welcome. Every failure is a lesson I'm plenty aware