I am ENFP according to personality tests, ADHD according to psychotherapy, and 26 according to the calendar. I have been doing account management type work for the past couple of years, which admittedly was a terrible idea as details, timelines, and keeping track of projects are all things I, as an ENFP, am inherently terrible at and also make me feel like my soul is being sucked away. I also have had a number of issues with several bosses because I don’t fall in line with their demands just because “the boss said so” or because “this is the way we do things around here,” which has resulted in some, ahem, parting of ways (i.e. kicks to the curb).

I think eventually I’ll need to work for myself, but creating some kind of freelance career right now while working from home sounds so boring and lonely, not to mention less financially solvent. Brooklyn is expensive! I want to start solidifying my career because I know I want kids (at least five years down the road) and I want to have the flexibility to be with them, but I feel like I’m not gaining any traction in my career because so far, my job description has been at odds with who I am.

Here are my current thoughts and I’m interested to here which, if any, you think would be my best bet.

1. Find a new job that is more people-oriented and focused on big ideas rather than details (and where I work for a boss that I can respect)  – I’m considering Sales because it’s with people or content writing because I can write

2. Go back to school to get my MSW and become a therapist – it’s people-oriented, flexible, and I think it’s meaningful work with a purpose

3. Go on ADHD medication so I can fit into the box at work and theoretically be more successful

Thanks!

Apologies for the super long post, but I started writing and had to get it all out. Your post about Leaving your options open sets you back  really resonated with me and I recognise that that’s where I am but at the same time seem utterly incapacitated to do anything about it.

So I am a classic case of having a well progressing career that is suddenly turned upside-down by having kids. Back when I had the career coaching with you was when I was first trying to make sense of what to do. As a result of that I tried new things like the start-up with Claudia, where we failed fast and I learnt a ton. Then exploring options with the tech camps which looked more promising but then (with your coaching advice) I was able to evaluate that the marketing & PR wasn’t all I thought it was cracked up to be. In between doing this I think I was taking every class of yours I could afford:dream job, freelancing, blogging, negotiating, etc.

So with money becoming an issue again, I went back to focussing on my main work which is running an open-source software consultancy with my (INTJ) husband. With what I had learnt I was able to see that we needed to do more marketing. So I started blogging, albeit still sporadically. And I started going to the industry conferences, and I think I shared with you how the blogging course helped me write a great article which I turned into a talk which got early-bird acceptance at two of the conferences I submitted it too. And then like magic, companies, big big companies doing really interesting work started coming up to me to ask us to do work for them.

So now we have our choice of great work coming in, working side-by-side with great people at big & small companies, operating as freelancers where we can notionally control how much we do and still balance out with spending time with the kids. And it’s absurd that it sounds so perfect on paper, and it should be, but it isn’t in reality.

I have been killing myself over the last year to be a good mother, figure out my parenting style, take my business to new heights and deal with medical emergencies and deaths in the family. More recently I’ve had to add couples therapy to the list because the marriage part has been one of the parts that has suffered. So now I know I need to cut back but already seem too exhausted and don’t trust I have the perspective to make the right decisions. My husband who I normally rely on for helping make these decisions and is much more a black & white thinker like you is fed up with my inability to give things up and say no to people. I have been slowly and painfully getting better at saying no and getting rid of some clients/projects, but still have too many.

I was hoping you might have some clarity on the situation and see the bigger picture to help me focus on one goal. So far this is the list.

1. Focus on clients in the embedded space – this is our original speciality and where are backgrounds are perfect for but when the work seemed to dry up 5 years ago we lucked into the science sector. With the renewed marketing we are picking up 2-3 big new clients who are happy to pay us well for consulting. Also with the promise of the ‘internet of things’ this seems like an attractive space (although noisy) space to stay in. I want to grow and hire some people, but my husband thinks it is not worthwhile in the short term. It feels like a chicken&egg.

2. Focus on Science – we have been working for 5yrs with a big scientific facility in this space and now things are growing. We decided to become founding members of an open source science working group and have a bit of technology we wrote for the science company which they are happy for us to package and sell services to other companies. Ironically with that technology we are attracting companies in embedded space. We don’t have the phd credentials for the science space but I do have a friend who does who I might be able to bring on board. The work is very cool and looks like it will have added bonuses of getting to visit some great facilities.

3. Hardware product – then I have a good friend who came up with a little bit of hardware, ran a couple of kickstarters and got it initially funded. The product is great, with some fanastic usps but he completely lacks any marketing or a business plan. I am the one-eyed leading the blind but I feel like it has massive potential either in the education space or even as part of a low-power solution for industry. I feel like a product will always have more potential than consulting – is this even true and does it matter? I do talks about the technology and have set up a project at a school next year to get it in front of kids to try it out, but again haven’t made any progress because I am not committing. I like this option when I imagine it works well in the future for spending time with my son who is such an engineer already.

4. Other?? Focus on a personal brand – so if you ask me what I really love to do it is problem solving and personal development.

If I try to imagine what I want in 5 years I could see it being something like heading up an open source foundation or some random foundation. And then I think well if I want to do that I need to build a brand and I should be spending time blogging to build that up. And ever since I did your How to Write About Your Life course I have been haunted by the idea of writing a personal dev blog disguised as a tech blog. So then I spend time here and there trying to write stories.

OK so now writing this all down I don’t feel I’ve done it justice – I see so many little nuances and things to over-explain. I feel like I don’t know what’s involved for each path and how it will fit in with my family life so how can I decide. So do you think a coaching call would be the right way to go, or is the answer blindingly obvious to you? BTW, I am enjoying the pitching seminar (just watched day 1 so far) but I can’t help but feel it is another thing I am doing that I should not be because I haven’t made any proper commitments and so I am stressed, anxious and exhausted while I have to force myself daily to meet the commitments I have already made.

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: https://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.)