For starters, I (and neither does anyone else) know the amount of money you deposit or your circumstances so I won't comment on whether it's irresponsible or not.
However, I refuse to believe that in all those deposits (unless they're ridiculously low amounts) you haven't had a win worth cashing out. I think you need to review your stake sizes and perhaps the games you play; are you playing high-volatility games at high stakes? If so, perhaps decrease your stake or play less-volatile games.
I also think it's worth asking what you define as "winning" is.
Edit: I just saw your response to
@Boulder where you have effectively confirmed you win enough to cash out, but continue playing to win more and then lose it. Y