Where Should I Live?

My boyfriend, JP, and I are looking at five different cities to which to move in the next two months, and it seems like you have experience in many of them, including New York City. Right now we are near you — in Madison. Could we take you out for coffee to ask you about your experiences living in all the cities you’ve lived in?

2 replies
  1. Penelope Trunk
    Penelope Trunk says:

    First of all, you will not get good responses from people if you want them to help you and you want them to do it over coffee. Email is so much easier than going for coffee. If I don’t know you, or anything about you, I don’t want to take two hours out of my day to go have coffee with you. And this is true for anyone who values their time. This seems so obvious to me, but every day someone who I have never heard from before asks me to have lunch or coffee. This is not a good way to start a conversation.

    The best way to get a good answer from someone is to make it easy for them to help you. This question makes it nearly impossible for me to give help because you are not divulging any information.

    Still. I will try. Because I like to think that I’m nice.

    I have written a couple of posts that you will find immediately helpful:

    Do You Belong in NYC? Take the Test.

    How to Decide Where to LIve

    In general, though, it is very very difficult to align anticipated lifetyle and anticipated career for any given city. So do this: Look at what you think you’ll be doing in the city (as in, how much money will you spend) and then look at the kind of job you’ll have to have in order to support that lifestyle. Usually there is a disconnect in a most of the cities on the list. Move to a city where these two things align, and don’t be delusional about it just to get to the city you think you SHOULD want to live in.


  2. Susan
    Susan says:

    Wow! I just discovered the mail bag. So much excellent reading to go with my coffee and buttery toast. And re: this post. What a relief. I always feel pressure to conduct face-to-face meetings with potential clients, mentors etc. but avoid it because I hate it!! It’s awkward, unnecessary and awkward. I always feel like I’m copping out if I rely on email, fb etc. to communicate. But I’m not! Yay!

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