I’m a 20-something woman in NYC looking to change/start a career.  My work history is retail and cooking in restaurants. I’m an ENFP. I’m interested in an office job so that I have more opportunities for success.  So far, I’m interested in office manager job descriptions (which is the closest thing to entry level I’ve seen).  Is there something more entry level than that that I can try applying for?  Do you have advice for how to get an entry level job in an office? I feel even though I don’t have experience in an office, my cooking and retail skills do translate.  And since I’m a 90s kid, I’m perfectly tech literate.  How can I best convey that on my resume/cover letter and in an interview?

Penelope – I am 5 months pregnant with twins and have been showing for awhile now.  I’ve been asked several times by coworkers and have lied, but I’m going to have to stop lying sooner than later because it is so obvious at this point.

My question for you is how I should tell the President of the Company who I report to directly.  While he talks about diversity in the workplace as a positive thing, he has proven to always be more comfortable with promoting people who look the part (meaning older men who have put their time in) and has made comments about other women and how they care more about their kids sports tournaments than they do their job (which may or may not be true, but has definitely given him a bias).

Currently, there is only one female SVP and no female EVPs at the company.  The President has always been very fair to me and I have moved up the ranks in a very short period of time.  I am currently a VP and I have had conversations with him this year regarding a promotion to an SVP this fall which at my company would be significant since there are only 5 SVPs total and 2 EVPs.

I want to ensure I stay on this SVP track and would like to address that during this meeting but am not sure what message that gives.  Does bringing the promotion up show my insecurity and lack of faith in the system?  Should I just continue to act the part and assume the promotion will come as promised?  Part of me feels like that is naïve but then I think what would a man do and I doubt he would ever question the promotion was in jeopardy.