Good to read your post Jordan and good to talk to you on chat the other night.
What I hear from reading between the lines is someone who feels restless despite having done well in life.
It sounds as if you have come from a difficult family situation with alcohol playing a part and yet you have, to use your words, “great salary, bills paid, vacations here and there, a beautiful gf, supportive friends and family …” Many people on here would be very happy with that!
Yet it is not enough – and you feel you need to gamble to gain more … what exactly? I think a clue maybe in what you said about your big win … “I was ecstatic to tell my gf and family of my winnings …” The ecstasy was not in the win itself but in the telling of this to your loved ones … I wonder if the remorse is linked to the shame you feel about losing – about not being able to tell of your losses to anyone close to you?
It is clear to me (and I trust to you too) that you have a problem with gambling – and I am glad that you don’t feel the need to chase losses. Gambling – like substances is not going to fill the need that you have which I think is something like raising self-esteem.
I think if you could find some way of talking about these feelings to a counselor or supportive self-help group, this would help you to move on with your life and accept the great things which are happening to you without feeling the need for more. Most counselors will offer a first session for free or at a discounted rate and I feel it is important to find someone you feel you could work with – which is often more useful than the type of counseling on offer.
In the meantime there are a number of self-help books on addiction and its links to low self-esteem, mainly concentrating on alcohol but you can read and adapt – John Bradshaw is one author to look at and there will be links to several more.
Great that you have come here to share your story and I hope you can find the time to let us know what happens in the future. I wish you well.