Do not pass go, but get your money

Often times when I meet a new person at a bar or dinner party, I'll ask the question, "So what do you do?" Ugghh. Kill me. Sorry I asked.

I do this for three reasons:

#1 I'm genuinely interested (read: you seem cool, so this conversation isn't over, yet)

#2 It's ingrained in me to ask this question (although I hate it and I'm determined to never ask it again)

#3 I'm trying to figure out if this person can help me in any way (worst reason of all three - you should want to help others, not find out if they can help you)

All of these are the wrong approach. In fact, the question itself is a poor approach.

I know several people who will flat out refuse to answer the question of "What do you do?" Tim Ferriss, author of The 4-Hour Workweek, will say, "Drug dealing for fun and profit", which I've put my own spin on "Hang out and get paid" or "Writing for fun and profit." Others like Nassim Nicholas Taleb, one of my favorite authors, might reply that they are a flaneur. (A flaneur is one who sits at cafes or walks the streets taking in the culture, while philosophising about life, literature, dreams, goals, etc).

Either way, if you are asked this question, I suggest you either 1) lie, 2) make something up, 3) tell them the conversation is over, or 4) stare blankly at them while not blinking. 

When you are done with one of these four responses, ask them this, "If you had to quit your job tomorrow, how would you spend your day?"

Ask someone this and you will get a real response as to what type of person they are, as opposed to some canned answer they've recited several hundred times. It will also allow you to determine how you may be able to help them.

For example, I might tell you that, "I cannot quit my job tomorrow because I don't have one. I'll spend my day at a cafe writing, in my home office developing WestSide Culture, and living life as I see fit."

Do what you want, when you want. Do not conform. Don't work just to collect a paycheck. Do not pass go, but take your $200 anyway. Live your life. 

This is the true meaning of WestSide Culture and why I get up in the morning. It's why Tim Ferris "sells drugs for fun and profit." It's why Taleb is a flaneur, something we could all aspire to be.