I just read your article “How to Build a Career As An Artist”. I found the article helpful but I was hoping for a little more advice. I feel like every thing in our society is career driven.

Since I got my Associates in Arts in 2012 I have been working and saving so I can move out of my mother’s house and continue my education in an art school in California (I had the intention of being a prop maker). But now I’m 24 I have no idea what I want to do, and I am fearful of pouring a bunch of money into a school for a career that is always described as so inconstant.

I am creative and I love to make art in many mediums but like the Bruce Lee quote I feel “crammed and distorted by the classical mess.” Every one I speak to asks me what job do I want but really I cant answer that I just want to create. I don’t care if its alone or in a team or what environment it is specifically. It doesn’t have to be prop making or costume design or painting I’ll be happy as long as I’m creating and working with my hands and not at a desk all day.
Any advice or suggestions would be great. I’m just feeling very frazzled and conflicted and thought you could help.

This is going to be a tough one for you. And I keep asking myself WWPD? (What Would Penelope Do?)

I am going to be 50 years old in July. I am currently working as a Behavior Specialist for developmentally disabled adults.  I got this job after almost completing my master’s degree in behavioral health (didn’t finish cause I got divorced and had to pick up another job and raise three kids on my own – husband was financially ruined). 

Anyway, I am good at what I do but I don’t want to do it anymore. I loved it for quite awhile but I am burnt. And the industry is changing and heading in a direction I don’t have the energy to be a part of.  Truth be told, it wasn’t my true calling and I knew it.  I was meant to be (get ready) a comedic actress.

Wherever I am, wherever I’ve worked, people gravitate towards me because I am entertaining.  I am truly funny but not in an annoying way.  I wrote some material and did one stand up gig.  I had one “fan” in the audience yet got lots of laughs and applause.  I stopped there.  Why?  I have no fucking idea.  It was the best 5 minutes I can remember.

I write, occasionally, but have been quite lazy about it. Make excuses constantly.

On a great note, I got remarried and I could potentially quit my job – NOT WORK AT ALL – but I’m scared.  Scared to be too dependent (again) and scared I won’t find another job if I want to.  I also still have those 3 kids I am responsible for!   And I am scared I won’t buckle down and write/perform like I always promised myself I would if I had the luxury and time to do so.

Anyway I went to Quistic and took the personality test.  I am a ESFJ, if that helps.  It really did give a good description of me.

Thanks for listening,

I have two major passions in life: Animals and Reading/Writing.  I worked with animals for about 10 years, doing kennel work, dog bathing, and eventually, dog grooming.  I love working with dogs, the only problem is that the way owners of grooming salons focused on money more than the love of the dogs ate away at me, so I made a career change. I went from being dog groomer to being a Media Coordinator for an Ad agency, a small 11 person company with only two people in the Traffic department: myself and my manager, who would be training me.

I thought it would be a great fit because I love editing and I’m a very organized person, looking for a new challenge.  The biggest problem arose when my manager,  who was training me (or supposed to be…I mostly just watched what he did, which is a terrible way for me to learn, personally) QUIT out of the blue after 2 weeks of “training,” leaving me to run the department myself, still not sure what I was doing (although I asked a million questions) and trying to deal with the pressure of people saying “you should know this” when I was never given a chance to “know” anything.

This lead to me quitting after two months without another job lined up because the pressure was breaking me and making me miserable. Now that I’m out of there and living on my nice nest egg I made while grooming, I’m struggling to figure out how I can put my love for reading, and writing int o a full time job where I can be happy and be respected.  I have a book review blog and do some editing for a publishing company, but I’m struggling to find a way to make a living reading/writing and getting over the fear that another job will sandbag me like my other one did, which lead towards history repeating itself.

Is there any way you can throw a line or two of advice my way?  I would GREATLY appreciate it.

I am 27 female INTJ (English and Creative Writing graduate) working in a lowly job in an English public sector. Words cannot describe how I hate my job and how little opportunity for development it provides.

I am married, only due to the fact that I could not possibly support myself on my shitty wages. I hate even the thought of having children and frankly, staying at home and taking care of anyone makes me feel sick. My marriage makes me feel sick and I would love to leave but…

I have childhood issues (my parents never loved me and do not love me now either) which render me almost impossible to live or function on my own – I always need a safety net, otherwise I feel like I am drowning. I have been in therapy in and out (currently in) for the last 14 years and the more I explore the more I find out that my biggest issue is that I cannot simply be myself. That I feel insecure to do so. It does not help that I cannot seem to find a job that would give me that security. Obviously, my role in life is not to be a home-maker. I need a career. But I generally hate whatever happens to me and whatever I do. So I keep thinking more and more I should just settle for something for INTJs that is well-paid because if I am not going to enjoy it, I might as well earn good money for doing it. Because I generally do not mind what I do as long as I can do it independently and that I deem it worthwhile.

I do admire the advice you are giving on career, however, it is hard to understand why you decided to have children. But hey, I might turn 35 and maternal instincts might kick in – biology is a mystery and is not to be treated lightly.

I was always drawn toward older men and it was a mistake to marry someone my age and maybe if I met someone my age I would look at the prospect of having kids more favourably but maybe it is just my insecurity talking. Either way, I would love some advice on how to get a career/forget about a relationship for now. It is sad to think that despite having 3 long-term relationship I have never had sex with anyone I love but it is even sadder that I have never enjoyed anything that I have done at work.

Just to be clear, I am not disrespecting anyone (regardless the gender) who chose family over career/the other way round. I think it is amazing that some people posses the self-knowledge that helps them making decisions they are happy with, whatever they are.

I am a 29 year old introvert (ISFJ) woman who struggled with the responsibilities and expectations placed on me by being a gifted kid. I am the first person in my family to attend a four-year university and graduate, which I did with a high GPA and multiple awards.

Immediately after graduating I entered an environmental advocacy fellowship program that is prestigious and competitive, but it made me miserable. I was depressed, gained weight, and entered into a terrible and destructive relationship during that year because I so badly needed any type of support. I’ve worked in environmental NGOs ever since.

Now my job is communications and media relations, which is also prestigious and competitive. The highs aren’t high enough to justify how low I feel when things are bad. I see more gray hairs every day. I am afraid to quit because I am finally making decent wages – $44k per year – and have another 18 months to pay off a loan.

I came across this post and it got me thinking: http://mailbag.penelopetrunk.com/2012/03/04/how-to-find-meaningful-work/. I want a job making 45-50k, not in politics and not in the environmental field, where I can work well with people AND not have my family members disappointed that I’m not living up to my potential. I want fewer gray hairs and more days where I go him smiling. I think human resources or office manager or something like that appeals to me, but I have no idea how to make the transition or even be considered for those jobs.

I’m in the process of revising my resume and your advice is blowing my mind because it makes so much sense. Thank you for pointing things out and being funny about it.

Here’s my question: Your advice seems focused on the business world and I work in the nonprofit sector. How different are these worlds, really? Are the same recommendations transferable to those of us working at relatively small nonprofits? There is so little room for growth in most of the positions I come across, but the only other option I can discern is to job hop. How would you advise young twentysomethings to advance their (my) nonprofit career?

During our coaching session, you said I should be working at a startup. But I don’t know what sort of position I should be looking to apply for. So the question is: What sort of position should I be looking for in a startup? What sort of position is ideal for me? Will just any position do?

This is probably going to seem like one of the most big-headed questions you have been asked but I need your advice on finding a truly challenging job role.

I have applied to, and been employed in, far more jobs in my lifetime than can possibly be considered healthy. There is a common theme, if I am not initially overqualified I will always without fail come to terms with the job abnormally quickly. While in essence this seems like an advantage from the outside it is anything but; within a few weeks I will generally have mastered most aspects of the role, (assuming that the job contains no seasonal responsibilities,) in a few more weeks I start picking my duties apart in order to tailor them to my work style and within a few months I have the entire position down to a fine art. Which is where things get sticky, after this point I simply get bored and my motivation goes entirely downhill and I am either forced to take a new position or to exit the company entirely before my lack of focus begins affecting my performance.

This process has never taken longer than 6-7 months -often occurring even sooner- and as there are often no opportunities to move on to a more challenging position within the same company I end up leaving to find something else. While I have amassed several glowing recommendations in this fashion I’ve still never held a job consistently for longer than 8 months, and, it’s a cycle I can’t help but want to break.

Basically, I’m just asking what are the most challenging positions you have come across? (That don’t involve a start up. I’d rather save that rabbit hole for a few years down the line.)

I am a regular reader of your blog and a huge fan of your work.  I started following it in 2007. I was drawn to it because I was/am that classic twenty-something: lost.  I immediately found my post-undergrad job to be unsatisfying and boring.  I started in corporate finance.  I have since upgraded to an analyst position in asset valuation at a financial services firm.  I have been here three years and although I am not miserable, I daily yearn for something more.

I am in the process of researching NGO’s in Nepal.  I want to move there for 2-3 months to work in women’s empowerment.  I want to volunteer in Nepal because (a) I have spent the majority of the last five years making money for myself and my employers, not contributing much to humanity, (b) I want to immerse myself into a new culture and I find the Nepalese culture intriguing and (c) I want a hub to explore Asia (primarily after my commitment is fufilled in Nepal).  I have been to Asia twice and traveled throughout Europe in college so I am very confident in my traveling skills.

My biggest hesitation here has probably crossed your mind: what will I do upon my return?  I don’t know.  I am hoping that while abroad, I will be presented with new opportunities that will lead to my next step or, at the very least, my time overseas will shed some light on my next career move.  I am fairly certain that I do not want to stay in finance and I do not want to come back to Chicago, which is where I’ve lived for nearly five years.  One of my inclinations, among many, is to pursue a career in writing, using my material from a blog that I will keep while in Nepal and afterward.  My priorities of traveling and exploring will come second to writing my blog to ensure that I have a product when I return to the US (if I return).

What are your thoughts? Am I completely insane to pick up and leave (with approximately $10K in the bank) after building so much career equity in the past five years?  I am so lost and without a clear direction on my next “job” and I feel drawn to do something drastic and unconventional like this.

I went to art school and have been working in the creative industry for about five years now. I am going back to school this Fall for nursing though because I didn’t want to purely do art for the rest of my life. I see myself has having dual careers, nursing as the main one (day job) and art as the freelance one.

My question is about my LinkedIn profile!  Should I make my LinkedIn profile for nursing only? Art jobs boil down to the portfolio, so I think having a separate online presence will be enough for freelance. Yes, I think I answered my own question. I don’t think I should mix the two because it will confuse nurse recruiters.