How can I make up for bad decisions in my 20s?

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?

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Bored at work? Maybe you’re not doing your job

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.)

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Should I leave my expensive college for a cheaper one?

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.

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When is it time to shut down a startup?

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?

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How can I get a job I’m overqualified for?

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.

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I can’t stop worrying about not having enough money

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???

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I’m in the US for a job. Should I do an arranged marriage in India?

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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Dealing with an indecisive boss

So far my new job is going really well. I have days when I’m so engrossed in what I’m doing that I don’t even notice the hours ticking by. It’s a much better fit than my last position.

Anyway, I have a question for you. What’s the best way to handle an indecisive boss? I am very good at making decisions, and I don’t have any experience working with somebody who is so bad at it.  In addition, I have limited patience for people who constantly put off making decisions or change their minds 5 million times. Especially when it messes with my deadlines. At the same time, I’m new to this company and I don’t want to come across as bossy or bitchy. Do you have any ideas for ways I can speed up the process without stepping on any toes?

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Will time off for travel hurt my career

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.

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Showing multiple careers on LinkedIn

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.

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