I’m in my mid-twenties and I’ve found that whenever I start a job, after a few days or so, I start feeling trapped and stuck.

I fear the regular routine of the job, being stuck in the 9-5 (or whatever my hours are) and being forced to work for the money versus doing something I love with a mission I care about. I’ve tried working for things that I believe are doing great things for the world (kid-focused startup and working with kids, which I’ve learned I’m not good at) and I still feel like that. Any kind of job with routine (even varying retail jobs and the like) scare me and thinking about applying to a job with more challenge in it (not getting that out of my current job) but that same routine worries me that I’ll be stuck there for a year or two working on building my skills for the better but still trapped inside a prison even if it is at a well-funded startup.

I’m an INFP programmer who loves logic and hopes to start my own startup someday as I get frustrated with not being able to make my own decisions. I’m not sure if I should go forward with my plan to find a job with that routine while I get great to build my skills for my own startup someday or if I should try to find something without that routine and if so, what? It doesn’t feel like most people have that same reaction to the stability of doing the same thing every day. About the only thing I know is I’m sick of not having money and I need to find something that allows me to have that. What should I do?

I was wondering if you had any advice at all about how you overcame eating disorder/ other problems when younger? 

Because I’m 21 and bulimic and kind of like a failed university student, as in I’m meant to be in my fourth year now of Arts/Law in Sydney, but I haven’t completed a single subject this year and have a history of withdrawing from subjects/ only doing part-time loads because I essentially feel afraid that I’m not going to do well enough so I don’t even try.

And I’m kind of at a point now where it feels like my life is over, and I have no future in anything, and I’m fat, and can’t seem to do anything and that I’m completely alone (even though I somehow have a really lovely boyfriend, but we are currently fighting because I keep feeling like he doesn’t want/ like me because I don’t feel worthy and he feels really upset that I don’t believe his words/ actions that are apparently evidence that he does like/ want me.)

I am on the 6-8 week waiting list to go to a residential/ inpatient psychiatric hospital to try and deal with the Depression/ Bulimia. But still, until then, and even after then, I just don’t understand how/ what I’m meant to do?

I am a 41-year-old single mom who needs to change the direction of her working life as a matter of mental survival. I’m a classic ENFJ kind of person and have been working behind a desk in isolation (I work in a suite of offices but the nature of our work is to remain quiet and alone) and it’s been wearing down my sanity.

I am absolutely in love with advertising and have always been but when I was young I didn’t choose to study it; it was too intimidating for me then. I’d love to be an ad account executive someday but getting started seems impossible from where I’m sitting. I’m reading everything I can get my hands on (marketing, too – it’s much drier but important to understand the basics) and bothering ad people for advice on how to get my foot in the door.

I have about two years to update my skills (before my daughter graduates from high school and I can focus on a career and/or live wherever I need) but very little money in which to make that happen. I can’t be a full-time unpaid intern; I have to pay bills and feed two people. I can be an evening and weekend person who is poorly paid, but with the abundance of free labor out there it’s tough.

I have a BS in Psychology, an MSW in Social Work and a strong background in writing and research. By nature I’m a collaborator, diplomat, convincer and intuitive, but those qualities can’t be put on a resume. I am not stubbornly stuck on working in advertising; something that is stimulating in a similar way would be wonderful, as long as it’s focused on people and ideas.

If you have any thoughts or advice for me I would very much appreciate either.

I love your posts about how to succeed in the work world as a woman with Asperger’s. Perhaps you could use your unique perspective to give non-asperger’s individuals some insight into how they should work with people that do have it? I think that for your socially adept readers that who have learned to recognize the signs of Asperger’s, it would be nice to have some concrete advice on how to interact with co-workers that seem to have it.

I am learning to adapt to my co-worker’s preferences (I believe he has Asperger’s) and am trying to be considerate, for example, by not making too much pointless small talk. More guidance as to how I should conduct myself would be just the kind of post I’d love to read! I feel like many of your posts detail how people with Asperger’s can learn to fit in the social world they live in – but how can I work to make it more comfortable and easier for them?

I graduated from college with a degree in English in 2008.

I started a temp job at a goverment agency. My boss loved me and even recommended me for
a position in another department. Unfortunately, since it was temporary I could not stay. Then I interviewed for an admin position at a top 100 company in Rochester, NY and I was hired over an internal employee by my manager. Unfortunately this position wasn’t paying my bills and student loans, so I obtained another position at the University of Rochester as an admin. My job was to provide administrative support to the chief physician of the department. This is probably the most miserable position I have ever had; and instead of leaving when I knew I should, I ended up being let go by my company.

After that I started a temp postion at a company I loved, and I earned some great references. I was offered an interview for a customer service position but I ended up turing it down for a temporary editorial assistant position in Baltimore, MD. I was sort of thrown into this position as the editorial assistant and coordinator were leaving in a week. After a short time, they claimed that my Excel skills were not up to their standards, and I was let go from this temporary assignment.

I recently had the same experience at another company as a temporary employee. –I’m not certain how I can have so much success (being hired over an internal, being recommended for alternate departments, generally being well liked and respected) at some companies and being denied employment at other companies as a temporary employee.

Do you have any insight into temporary employment vs.full time opportunities? At the last temporary position I had I felt that I was let go due to a personality conflict with another employee. I am an incredibly conscientious person and I honestly do not feel this was my fault. It’s hard for me not to take these things to heart as I felt that I was the one being mistreated, but because I was a temporary employee it was ultimately their opinion over mine.

I’m about two years out of college and I was wondering if you had some advice for me. What would you do if you were offered a job at the same office as your boyfriend? I interviewed at the same company, but at a different branch. It looks like I may be offered a position at his location.

I am a big fan of your blog. Thanks for all that you write. I was actually pointed to your blog by my former boss (a good boss) who took a lot of interest in helping me to develop at my previous company…until about my last year there, where her focus shifted elsewhere.

That’s why I started the job I am in now–plus it got me back to the industry I want to continue building my career in, which is pharma.

Now, I am dealing with a boss who doesn’t understand what it is that her team does all day and therefore, cannot provide constructive feedback or guidance. Please note that this is not the person who I originally reported to when I began working here, but there has been quite a bit of tumult and restructuring in the last year and I have landed in her purvue. In addition to not providing direction, she also passes most of her work down to me. And it is unclear, even to people around me that at her level who have made comments to me about the situation, what she is doing on a day-to-day basis. My frustration level is at almost a 10, and I need help in managing up.

Can you point me in the direction of a blog you may have posted on this subject? Or, if there isn’t one, can you consider writing on this topic?

I was recently reading your interview advice for a phone interview I had for a teaching position at an elementary school in Michigan. Apparently I did really well and the interviewer subtly indicated that I would be invited to an in-person interview, which is really great. The only problem I have is that I wear a veil over my face, I’m Muslim. I was reading your advice on acing interviews and I’m not sure how to increase my likability factor, or to make myself more like the interviewers. Short of taking off the veil, do you have any ideas for how I can increase my likability and still get the job with the veil on?

In every job I’ve had, after a brief initial buzz (maybe two weeks) I feel despondently bored. This will happen when the role is well suited to my ENFJ personality, if I’m good at the job or even when I’ve initially felt really passionate about the role (like working for a children’s charity). And so I leave with this sense of incompleteness. I’m 33 and I’m torn between pushing through and finding that one amazing something or accepting that, as my father says, I’m just scared of hard work.

I’m re-reading the book, Do What You Are, and, as an INFP know I need to find work that is meaningful and feels authentic. I struggle with the part of me that also feel a great need for adventure, travel, and spontaneity. This seems missing from a lot of the research I’m finding. Are some people just genuinely restless? How can you tell if the urge to live/travel elsewhere, make new friends and lovers in foreign places, is your authentic self coming out or a form of escapeism?

©2023 Penelope Trunk