Hi Penelope,
How are you? I’m an author and executive recruiter (currently at [big impressive company]), and have a book coming out next month. I’ve been told it’s bad form to request a review from a big-name blogger without first building a relationship, but that seems a bit backwards to me (or perhaps just disingenuous). I’d love to get a book review from you and am wondering if you’d be willing. Please let me know if you have any questions or what I can do to be of help.
Are there steps that you recommend taking when beginning a freelance career in the middle of the recession that perhaps wouldn’t be done if the economy wasn’t such an unknown? I’d like to know if there are any specific precautionary steps that one should take, such as having 6 months of expenses covered, etc. etc.
Thank you for your help. It’s very scary to think about going freelance. I’m procrastinating, but I know I need to start pitching for work.

I have blown work relationships with more people than I care to think about because of my bad temper. Now I’m struggling in my career. Part of it is the shrinking jobs and pay but I know it’s more so because of the bridges I’ve burned. I’m good at my job and I can be pleasant and fun –when my buttons aren’t being pushed. I’m actually very capable, responsible and smart. It’s just that I have issues.

I’m in therapy and I know it has to do with being criticized and having emotionally abusive parents. I get easily wounded and insecure, and I lash out.

Right now I should be using some of the many contacts I’ve developed along the way, and the influential people I know. (You can’t tell from looking at me that I have this problem and I have lots of friends.) But I fear using some helpful contacts because I know those people know the people I’ve had incidents with and I worry they know about it. Ugh.

I’ve been with a social media marketing start-up for a little over a year now. Our founder has made a lot of bad choices. Partly because he doesn’t know social media and also because he put his faith into a poor sales team.
We are now at a make it or break it point. I feel like I know what it would take to make a successful social media marketing company, but it would be entirely different from our current company, which may not fall into the vision of the founder.
Also, I currently do all the social media fulfillment for our clients. Everything. I’ve invested a lot of my own money in reading business books, seeing Seth Godin speak, and spend most nights blogging and reading articles on Hacker News. Yet, as long as the CEO/owner is in charge, I lack faith in the direction of the company.
Is it worth rebuilding the company or better to just start my own? How do you know when you should leave a start-up as an employee?

I’m a 22 year-old working in New York City. I have a decent-paying job as a journalist that is (to me) meaningful, challenging, intellectually stimulating, and offers a lot of opportunity for growth, on-the-job-training, and networking with others in my field. I can afford my rent and I have health benefits—money would be tighter if I had student loans, but I don’t.

The negative: I’m from the Midwest, and I really loved my life there. Since moving to NYC to start my career, I’ve been miserable: I left a loving partner and amazing friends behind and am lonely constantly. I don’t feel like I can connect with most people my age because they are still in school or are bumming around in retail jobs or living with their parents. Everyone I work with keeps me at arms length because I’m 5 to 10 years their junior. My job takes up most of my life, making it hard to schedule things in advance or take an evening or weekend class that meets regularly. I have no idea how I should be spending my free time. I am constantly homesick.
I feel like my career is on the right track, but I’m afraid that living in NYC as a sad and lonely 20-something with no ties will become unbearable and I’ll give up. I’m probably a few years ahead of the curve in life but I don’t know how to appreciate it or take advantage of it.
Is this a non-problem? When I write it out I feel like I’m just whining over nothing, but I feel really deeply effected by this.

I am a 35-year-old queer lady working in IT. I  have been out at work as a lesbian for 10 years, and always felt comfortable doing so.

But now I’m hitting a new challenge in my life. I was recently unemployed for a year, and during that year my female partner went under treatment for gender identity issues, and changed genders to male.

The relationship has worked out for us, so I am now a queer lady partnered with a queer-identified man. The word “queer” seems to be the best identifier for me: I have a nuanced enough identity that I don’t identify as “bisexual.” I’m not in a “lesbian” relationship. And I’m into my partner, but not most guys.

In the last few months, I have found myself starting at a great new job, but find myself plagued by the feeling of being in the closet.

Having a girlfriend was always shorthand for saying that I’m gay at work, but now I have a boyfriend who doesn’t want the whole world to know — upon first meeting — that he used to be a woman.  If I told my coworkers the whole story — which might be too much right now anyways — I would be ‘outing’ him before he has even met most of them socially and has a chance to decide what he wants them to know.

How does someone like me avoid this feeling of being in the closet?

Socially I’m in a whole new world here.

I worked at a company for about 3 years, which was fine through the recession, but a new manager came on board with whom I fought constantly. Yelling and screaming matches were the norm.

Fed up, I quit and recently accepted a new gig. Now, just a month in, I hate it. It’s not for me, it’s a big company and has extensive travel requirements and other tasks that I don’t even want to deal with.

So, problem is that now I’m job hunting again – but with weight of not being able to get good recommendation from last employer and the new one is only a month in, not an easy story to spin.

Any suggestions on how I can fix this?

I am an older mom who is busy supporting a family and working as an ICU nurse.  I don’t want my daughter to repeat my lifetime of mistakes.  She is bright about many things but in school I feel she is an underachiever and does just enough to get by.  I have had many financial setbacks.  I lost my home, lived with in-laws and now live in a house that was a fixer-uper and I was never able to do the fixing up. I could go on and on. But enough about me.

How do I guide my teen to choose a career path that will be suitable for their abilities and potential. I have depleted all my savings just keeping the family going so its going to be a community college to start out.  She is 16 and very responsible.  She has had three jobs in three months. Now she’s working at her third, job as restaurant hostess.  How do I be the guidance counsellor, where do I start?

My husband is one of those people who didn’t go to college. Instead knew what he wanted to do (become a chef), set a goal, and began working in restaurants where he moved from dishwasher in a cheesy steak house to head chef in a respected restaurant.
He then decided a more “regular” job would be better for us and him, and now is in sales. A job opening was forwarded by a friend, and one of the requirements is a college degree. This is a job he could do not only well, but excel at, and he’s done everything else on the list.
He seriously regrets not getting a degree, but I know from experience, and having to deal with recent college grads as interns, that a college education does not a productive employee make.
How does he get around this? Or work within it?

I’m a management consultant with an MBA and a technology focus. Every time I try to choose an area to specialize in, I get interested in something else. I really don’t care very much what subject matter I’m working on. What I like about my work is rapidly learning new things, making sense out of ambiguous situations, high pressure to deliver, meeting a lot of new people and the prestige and good salary/benefits that allow my husband to stay home with our kids. There is enough work to do at my company that so far I have always taken new projects in totally different areas just based on what interests me and avoiding too much travel.

But I don’t think I’m going to be able to progress and become a leader if I don’t choose a niche – and I can’t see myself ever finding a new job with such a broad focus. I do eventually want a new job to avoid travel and to build a more lasting network. For that I am pretty sure I need to specialize and become an expert in something. But how do I choose what?  It can’t just be random or I’ll have a hard time committing.