Nick Carraway Nick, you are a sensitive, thoughtful, and intelligent man who has the potential to learn a lot from the current challenges you have presented. The questions you ask are astute and show a willingness to change and a vast array to tools with which to deal with change. Your self-awareness and insight are admirable, and are your core strengths. This self-improvement plan will help you capitalize on your strengths, and also become more realistic about your boundaries and limitations. Do not feel these boundaries and limitations are faults, because they are not. They are part of what makes you a unique and interesting individual. First I would like to answer your core questions in turn.

What advice can you give me about how to organize my life to achieve my goals of financial independence and spiritual fulfillment?

The financial independence you need will come, if you can outline your career goals. You are on the right path, which is why you are now on Wall Street. But where do you see yourself in the next five, ten, and fifteen years? In a leadership position? In an advising or consulting role? As an entrepreneur? If you cease putting any limitations on yourself, where would you like to be? Where would you be most comfortable? I believe you are conservative enough to know this but remember the importance of saving and not being frivolous like Gatsby: "If you would be wealthy, think of saving as well as of getting."

As for spiritual fulfillment, there are deeper issues going on. I certainly see that you would benefit from being more assertive. For example, you could have told your girlfriend back...

I think a lot of the dishonesty and falseness you see in New York are qualities that are mirrors of your shadow self. It is a good time to explore these issues. You will have more compassion for others and be less hard on yourself, even as you are willing to change. This combination of factors will bring you much spiritual fulfillment. Also, learn what made you bored in the Midwest. Boredom is a sign of spiritual impoverishment. As Thoreau puts it, "As if we could kill time without injuring eternity."
2. What advice can you give me so that I'll be sure and stay in touch with these positive traits in my character as I get involved with new people in New York? I know that this is a place where society accepts a lot of drinking, gambling, and philandering. How can I avoid these temptations without being rude to new people I meet?

Be yourself. When you develop enough self-confidence to be yourself with grace, others will gravitate towards you. You do not have to be like others, or conform to their social norms.

3. Do you think I should try to help Daisy? Or should I avoid getting involved?

You should wait until you are more comfortable; there is no need to meddle or interfere at this juncture.

4. Do you think this is a good thing for me to do on weekends? After a hard week's work I need a break, don't you think? Should I go or not?

I think that going to parties is a healthy thing for your social life and for your career. It does not mean you have to get drunk or lose yourself. It does not mean that you need to attend every party. It…