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?

I have never had the compunction you have for creating businesses and being an entrepreneur and all of that…but maybe I need to do that anyway to be more financially successful. I grew up just wanting to be a part of the entertainment industry – which I have been for 10 years. That’s my bliss. But I listen to you and other successful entrepreneurs and business oriented people who are making big money and I think “Why can’t I have been born with their innate sense of business sense and wealth accumulation?” I admire you for your success and sense of how to earn money. I want to earn 45K/year and have health insurance – something which is becoming increasingly more difficult to do in the US
Should I just go to business school and get the MBA even though that is not my passion but will ultimately provide (theoretically the means to an end)?

I need help earning more money. I’m a workhorse, great at ideas, and a very creative artist. Self-employed artist for 11 years. I’m busy rebuilding my financial life post-divorce.

What I need is more income to support my good ideas. I’d like to be able to hire an assistant so I can do the idea making, while someone else makes the machine work. I’ve got a new business I’m busy launching as well.

I would like you to mentor me, or coach me toward this. I can offer you ART in trade. I’m rich in art, great at color.

I would like to say that I am interested in kick starting my career or starting a business. But that would be a lie.  My interests lie in writing, social work, community development and someday teaching theology on the seminary level.

However, the reality is that I’m scraping by, I have considerable college debt, and in the not so distant future will have parents to take care of.  I know little about business, how to get a good job and even less about start ups.

What would you suggest for a guy like me?

I am a huge fan of your work, and I recently started to consider starting my own business. I was wondering if you have ever published a list of your favorite books for starting a company?

I just got off of a call with a very type A recruiter who asked me whether I pay for health insurance myself and if I had children who were covered under it. I’m not confrontational, therefore I didn’t tell him outright that it was an inappropriate question.

What would you recommend I do?  I want to apply for the job, but if his aggressiveness and inappropriateness is any indication of the type of people I would be interviewing with then I’m not interested.

Do you ever get in trouble for writing what you write? Does your family call you on the phone to yell? Do your friends ever tell you they will stop talking to you because of something you wrote?

I have only one year of work experience, Should I lie and say I have three years?

Can you take a look at my blog [link redacted] and maybe give it a mention on your site?  I am desperate for my blog to take off, so I can write for a living, which has always been my ambition. I am focussed on writing. I write every day. I am trying to tie the blog posts together, give it a narrative and make it more novel-ish. I have no idea if this will work. Any advice on that front would be welcomed…

My husband and I married young and, while he worked and graduated college, I chose to stay home with our kids. We both agreed being home was best for our family, but I wanted more challenge (and money) than that offered, so I opened a home-based child care. I have been doing this for the past 8 years, quite successfully. While I have enjoyed the job and feel like I’m good at it, I am, once again, ready to move onto something more challenging (not to mention, I would really like my house back).

My question is this:
I am about to quit and go back to school. I have been looking forward to going back to school for many years but, honestly, I don’t have any idea what I want to do.  I don’t feel like I have the luxury of time because my goal is to get a degree and get me back into the job market as quickly as possible, but I want a job that will be stimulating and useful. My husband keeps saying just having ANY degree is the goal… is that true?


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