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?

I’m 29. I’m pretty sure I have Aspergers and I’m pretty sure my mom does too… I was doing research because of the latter (my mom having it) before the first (me having it) slapped me hard across the face. Not that I’m upset by it. God no. In a way I’m thrilled to finally read about others with VERY similar quirks. I find myself suddenly obsessed with this aspect of my life.

My husband thinks there is no reason for me to get a confirmed diagnosis. He doesn’t mind my antics and what will it really “do” other than jack up our insurance premiums. I did take the Aspie Quiz and a few spectrum quizzes online and I had borderline scores. Should I just go to the doctor?

Something that’s been nagging at me recently is how much younger I feel than my professional counterparts. I’m new on the job at full-service agency – I’ve previously only been in the digital space. I think most ad agencies skew young, but mine has been in traditional media for over 30 years and has a LOT of industry veterans.

I’m younger than virtually everyone I’ve interacted with so far, by quite a wide margin. I feel very self conscious of that fact when I’m in client meetings, speaking with vendors, and brainstorming with my creative team

Do you have any advice on how to feel confident in these situations? I’m terrified of somehow losing the respect of my cohorts by doing something inadvertently offensive or immature, as viewed by an older demographic.

I wish I’d seen your blog and had a wider, less fearful view of the world in my 20s. I was just trying to get out of poverty and then get out of my head, so I followed my scholastic abilities right into nowhere with an M.A. in English and lots (lots) of debt.

I’m a really good poster child for your warnings.

What if you’re in your mid-30s, and you made the wrong mistakes (or took no risks other than borrowing on the future) and you find yourself entrenched? I (and probably lots of others) could use your no-holds-barred take on it. Planning any Make the Most of Your 30s When You Didn’t Make Your 20s Count seminars?

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 going to be a junior this fall at a too-expensive liberal arts college. I am considering pursuing a MS degree from Boston University (they offer some online classes) in international marketing.

Should I transfer to a cheaper college (because I can get a good education at UCSC for a better price) or stay at the one I’m at?
I’m concerned that transferring to the JC then to the UC (I don’t have enough credits currently) would make me seem indecisive and hurt my chances of getting accepted.

I’ve just read your post on how to know when to leave your startup on VentureBeat, and I wanted to ask you a question, if you don’t mind.
We completely bootstrapped our start up for 1.5 years. We’ve got a beta product, about 5 companies using our product successfully, and over 600 companies signed up to try it.

The problem is all three of our co-founders are at financial and emotional exhaustion and the two married ones including myself at marital exhaustion.

We are working to raise seed round, but we keep hearing that we don’t have enough traction just yet (paying customers will be highly desirable) and our runway is only a month at most. At the same time, we don’t want to give up, because we get a lot of very position reviews from people signing up for our product.

I was wondering if you might have any general advice? You seem to be able to raise money, do you have any advice in regards to that?

Thank you so much for your work! I have found your advice to be extremely helpful in my job searches.  Please keep up the good work!

I have an interview this Friday for a job that I badly want.  The recruiter just called me and said that they were intrigued by my resume and want to meet me but are concerned that I might be bored with the position.  I am curious how you suggest responding to such a question if it should arise in the meeting Friday.

Thanks in advance for your response.

I recently lost my job and am at my wits end. My nerves are shot and my anxiety is high!  I was encouraged and inspired by your blog and postings. However, when money is an issue and bills are mounting, how do you stay focused enough to pursue other interests when so many other matters seem to take precedence at at time like this???

I came to US 5 years ago for school and working for a fortune 500 company in Chicago and make a decent living. My parents are in India and wanted to marry someone of the same religion, caste etc (too much for ppl here to understand) Well. I visited my parents last November and they made me meet someone. She was smart, have same views about things I care for, but something about her physical looks bother me. I said yes to my parents after meeting her for couple days I was there, thinking I will get over the fact. But I never did.

Whenever we skype, it keeps bothering me. There were twice I told her I’m not ready for the wedding w/out telling the actual reason and she convinced me everything is going to be alrite.  I have my wedding in 1 month. It’s been couple weeks I even skyped but use whatsapp and phone every day. All invitations are sent out and my entire family is excited for me to go there and get married. I’m having strong back thoughts. In my family calling off wedding means they will actually disown me.

I need your opinion on what I should be doing. Why do I need your opinion. Because I want to know what you think is the right thing to do, from a person who doesn’t know me and would tell me the truth – I could just think of you. When I ask this question to friends who know me they don’t give me a frank answer and some convince me I’ll be alrite after the wedding and some say it’s too late and will be embarrassing for the entire family if I do that.

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