Dear Penelope,
I am the new syndicated columnist for Careers Now from Tronc (Chicago Tribune and LA Times online content agency). I found your website and would like to get your input on a question that I have to answer for my next installment of the column. The only catch is that I will need your input by the end of the day this Friday. The answer doesn’t have to be long–I only have room for about 300-400 words

THE QUESTION:

How do I go about making a career change from corporate America to something meaningful?

–Kathleen Furor

I really enjoyed your recent blog post about taking a break, but I was wondering what a break that is not constructive looks like? I’ve been thinking about taking a year off of work to go to grad school, or to travel, or to do both, but, as a longtime reader of your blog, I know that you aren’t a fan of either. Do you have any advice for a way to structure the break so that you end up in a better place on the other side of it?

I know that I’m approaching a point in my life that I need a break and to change, but I’m not quite sure that grad school/travel would be a way of avoiding problems instead of changing in order to be better able to face future problems. If it helps, I’m an INFP.

I’m an INTJ, and I have a quick question.

I’m a Ph.D. student of theoretical physics and as usual, I discuss my research with my supervisor. Because she doesn’t bother to get into the detail of calculations, or maybe because she doesn’t care enough, sometimes she makes obviously stupid comments, and such things make me angry a little. So I feel she thinks I’m arrogant, even if I don’t get angry and try to explain (explaining stuff is a little hard for me…). But I’m not. I do appreciate when she has some good comments (which she does sometimes…).

So can you help me to avoid such misunderstandings?

After 12 years of not a single date, desire, need or want for a man/companionship in any way, my coworker and I unintentionally fell in love. Loves me for who I am, your happiness is my happiness and all that jazz.

Problem is, he is sort of married. Not legally married but wears a ring, they share a child and a home. However, it’s an insane partnership where both have hurt each other in every way, constant fighting, one of those “were staying for the kids” relationships at this point. Mostly bad with good moments.

I lost my virginity to him. We told each other we loved each other and had sex all within a 3-month span. Lots of late nights in the office, however we only had sex the one time. When he kissed me I actually lost my breath and went weak in the knees. When we had sex, it was perfect in every way. He was wonderful to me.

The problem with all of that is, he has completely changed on me, even though he swore he wouldn’t and I’m miserable. I don’t know what happened, but he won’t talk about it even though he knows I’m an ENFJ and my two needs are communication and quality time.

One day he will sneak a handhold in from across the desk and tell me he loves me. The next he won’t even let me speak to him.

I decided for myself weeks ago that I was done, this was over, I deserve better, this is bullshit, etc. The hell of it is, I not only have to work in the same building, but we are the COO’s of the companies only two departments that go hand in hand.

I have constant anxiety.

I think what I’m struggling with is, I can’t decide on a story. Either I was a complete and utter fool who was someone’s mistress and lost my virginity and this was the biggest mistake of my life. Which is a hard pill to swallow when you have pride yourself on being a strong, smart hard worker with a healthy dose of confidence. This is very new, and if I’m being perfectly honest, pathetic feeling to me.

Or, as my friends like to tell me, I waited until I was almost 30 to have sex with someone I loved. With the person I have loved more than anyone in my entire life. And it was wonderful. And with all the growing and learning I’ve done, how could that be a mistake?

The real problem is this: I have worked my ass off to get this position. Worked my way up from the bottom, nights and weekends, many sacrifices, etc. I love my job. I am fantastic at it. I was made for management. I have hand chosen my team, and they are amazing. I have never worked so hard before in my life but somehow never tire.

I don’t know that I can with having to see him every single day. Because then it hasn’t really ended. I don’t have the luxury of choosing to not see him or talk to him.

So, should I stay or should I go? Would leaving be giving him even more power? This is more change in my life (in a very big real way) because of him? Should I stay in spite him, stand my ground and what not?

I bought my own house two years ago, I’m not making a lot of money but its the most I’ve ever made and am more than comfortable, financially speaking. I have no prospects job wise but a healthy savings.

Wherever you go, there you are, that’s a thing. I know leaving won’t resolve this but at least I wouldn’t be tormented by him and his games 10 hours a day.

I am a 27-year-old cis-gendered female INTP with mild Asperger’s and a good job at a nonprofit. My organization is doing good work and actually effecting some positive change in this insane community of people. This isn’t really what I want to be doing long term (I am interested in Data Science and Machine Learning) but it is a good job and a good salary while I do personal and contract work in my chosen field with the hope of being able to enter that field as a career.

I have had a lot of different experiences, some have been successful and some haven’t, but what I have learned thus far follows:

  • I am highly empathetic in spite of my social dysfunction and people tend to like me even though they find me odd.
  • When I am not liked it is because people perceive me as cold, overly-rational, and arrogant. This is common among people with Asperger’s, especially women.
  • I am really, really smart.
  • I have a penchant for organizational thinking, resource management, and strategy.
  • Many organizations are completely dysfunctional because the people in charge are not good at the aforementioned things.
  • I am good at managing people as resources, but not very good at managing people as people.

I believe in my organization. I also believe that it is totally dysfunctional. In my experience, most nonprofits are.

Specifically, I am mismanaged as a resource. My direct supervisor (who is at the director level) has never had a direct report before me – and she does not know how to manage people either as people or as resources. The reason she was given an assistant is because she is doing two (completely different) full-time jobs at once – one of which is in line with her experience and career and the other which is not her area of expertise at all.

The problem is that she is unable to effectively delegate – so we have a situation where she is totally overwhelmed and I am completely bored. I have asked her repeatedly to allow me to take some things off her plate, but she is unwilling to trust my ability to do anything on my own, which basically amounts to her having a ton more work by virtue of having an assistant rather than having less. It’s maddening.

So there are two major problems: 1.) I am totally unsatisfied in my job and 2.) this mismanagement of resources is a waste of my salary – which this organization sorely needs.

One of my boss’s jobs is development, which is the second position that sort of fell into her lap and isn’t what she is good at or wants to do. I believe that it would not take much improvement on the part of a new, more experienced development director to pay for the difference between my current salary and his/her hypothetical new salary – the going rate for a fairly experienced development director at this kind of organization is only about $30,000 higher than what I’m making now. I want to suggest to the executive director that I leave my position and they use my salary to hire someone new at the same level as my current supervisor to ensure that both jobs get done well and fully.

I would like to stay at this organization if they can find a place for me where my talents are beneficial and I am permitted to take on interesting projects and learn new things, but regardless of where I end up, the organization doesn’t need me to be in my current position, and because of my boss’s difficulty with being a manager, I’m actually hurting the organization by being here more than I am helping it.

So my question is this: How the hell do I propose this plan (fire me, reduce the scope of my current boss’s job to something she can manage without an assistant, and hire a person to do development who actually knows what the hell they are doing) in a way that the board and executive director will take seriously?  I am aware that this suggestion is brazen and likely to really piss off my current boss, but I also think it is a good solution to a very real problem that needs to be addressed.

When I joined my current company a few years back, I started working on a special project that I have experience in, but the tool I was using was relatively new to me. As expected I spent my weekends and free time at home learning and excelling in it.

After two years, a newly employed fresh grad joined and I trained her as the management wanted me to do so. I work in senior capability and my lead is also a senior who has no clue about the work I do. But I trained her as well. They hired a new senior person who does not have any experience in the line of work I do.

As I believed the go over and above crap, I did a project as my manager VP asked me. I did a good job but my manager found some silly reason to criticize and scream at me.

I was asked to provide pictures as proof when I needed to work from home due to major repairs at home, but they gave the new colleague permission to work from home half days for the whole week as her teenage kid has holidays.

Fast forward the manager changed, and my colleagues got licensed to use the tool I was using so that they can also do the same work. As they started bombarding me with basic questions I guided them to the online documentation and videos available (I learned from them) as I already provided 2 sessions on that and also scheduled a session again but they canceled it and keep asking me questions.

No one else is learning anything new and sharing. They have no time to read and watch the video I provided. Within four months time, the new colleague complained about me behind my back but now she comes to me sounding innocent asking how to questions.

She won’t share any info. She already managed to take a high profile project which was promised to me by the VP. Once I was told I’m the highest paid in my team. Now part of my work is getting assigned slowly to my colleagues. My boss says everyone should know everything on the team so he wants me to train others but the work my other colleague is doing is not shared or no knowledge transfer sessions or training on it.

Do you think I better start looking for another job?

The new hire wants to manage me. He’s supposed to be my co-worker. He’s in his thirties. Every conversation we have he’ll ask questions that are to “see the way I think”.

Am I just being competitive? Do I have to put up with him? The CEO hasn’t said that he’s my manager. The CEO has asked me to take more responsibility in managing the operations team.

I work as a housekeeping supervisor at a hotel in Massachusetts. The general manager of the hotel had invited a prostitute to stay in one of the rooms at the hotel for sexual favors as payment for her stay. She also used the hotel room for clients and drug use.

The reason for me finding out all of this is because she was to leave the hotel one day earlier (Per: The general manager). She was not willing to leave the hotel at check out time, so check out time was extended until 2pm (Per: general manager). 2pm rolls around and she has not left yet and I asked her to please pack up and leave. She was not willing to leave, she was promised 3 days at the hotel. I advised her that I was going to have to call the police. She got very angry and upset.

She told me she had text messages that proves that she had a 3 day stays at the hotel by the general manager. Come to find out it was true, and along with that being true all the messages she had were all about the G/M picking her up to bring her to the hotel, sexual acts, lunch dates, all the conversation were between him and the prostitute.  I do have a copy of all the messages.

The G/M does know that I’m aware of what was going on. He is not willing to speak to me about this issue, he keeps ignoring me and I want to resolve it. What do I do? Do I report this? How do I go about this situation. He put all of us housekeepers at risk when cleaning the room. There were used needles laying around and condoms everywhere. The place was a mess. Please get back to me with some advice.

Do you have any recommendations on how to deal with two colleagues hooking up in a company smaller than 15? In larger settings it happened and was okay because it usually wasn’t with people on your team, or that you worked with on a regular basis.

We’re dealing with this while we’re all in France. two of the youngest team members (23 and 24) (he is a subordinate and good friend of the CEO, and she’s the CEO’s EA) hooked up pretty early, and the behavior has just increased and made everyone uncomfortable. She’s currently using him as an errand boy, partnering with him to get a lot of her work done.

My boss asked me what we think we should do, but I don’t have a clue on how to handle this at such a small scale. The relationship has definitely been affecting work dynamics, and we’re all dreading the implosion for when things go sour. We both agreed that while they are two adults and should be allowed to do their own thing, we’re dealing with two very immature individuals, so there aren’t high expectations for this to work out in a positive way.

Do you have any recommendations on how to handle this? What should the policy be moving forward?

I’m 25 years old and I work in a senior advisor position within a government.  I help form decisions with some of the most senior elected officials that appear on TV news hour. I navigate political warfare, and I make more than the combined salaries of my parents.

But somehow this meteoric rise churns in my stomach since by night I inherently reside in another galaxy. I’m a hobbyist performer in breakdance/funkstyles/hiphop culture. I share communal practice space and session 3-4 times a week after work. I’m more in-tune with the grassroots arts organizations and people that meet what we call a “struggling artist” profile. I do local outreach with them in fact.  I know and can recite all the lyrics of Notorious B.I.G’s Big Poppa, prefer high top sneakers over oxfords, and generally grew up with this type of environment since high school.

I find myself in a space in life right now where I simply don’t have a place called home in the realm of social circle. Don’t get me wrong, I can mingle with the best of the suits in a networking session, but I’m genuinely not interested in hearing about how fast your Porsche 911 can go. In the same way I admire the artist community, I couldn’t find myself fully relating to some arts educators who tell stories about literally saving children from suicide by teaching them dance.

I feel there’s something wrong with me. I wake up many mornings wondering if I should pursue other things. Do “successful” people at mid 20’s ever face loneliness? What if I don’t find myself fitting in with the country club?