Previously, I wrote about 3 questions that I think are helpful in making career decisions.  I see these as pretty objective questions, and ones that can really help you evaluate the fit for an opportunity or a career path.

There are two other questions that I think are important to ask – probably more important than the first three.  But these questions are pretty subjective, and it’s less about finding the “right answer” and more about feeling comfortable with the answer, and knowing when circumstances have changed such that the answers are no longer satisfactory.  Rather than going into too much detail, I’ll share some thoughts on do’s and don’ts to consider when you think abotu these questions for yourself.

Question #1: Am I doing something that I think really matters?

do: Have a realistic view of your mission in your job.  As a VC, my mission (and fiduciary responsibility) is to maximize the returns to my limited partners by making the best investments I possibly can.  It’s not necessarily to be the nicest guy or best friend to entrepreneurs or be involved with the sexiest companies.  I think a lot of these things are helpful towards this end.  But they are not the primary mission of this profession.

do: Try to connect the dots.  I think it’s important to think about the broader impact that your job has to people you may not see or know.  It’s important to connect the dots, and think about whether you are motivated by the good ways that your career touches other lives, and feel ok about the bad things too. At Ebay, I was always pretty inspired when I would visit trade shows and see how many Ebay sellers were physicaly handicapped, or just folks who were able make a living buying and selling stuff they really cared about.  On the less rosy side, changes that we would make on pricing or the search algorithm on the site could completely tank a seller’s business overnight.  That was the good and the bad, but overall, I felt that what we were doing was really important and meaningful.

don’t: Assume that things stay static. Simple enough… it’s important to constantly reasess.  Good situations sometimes become bad ones, and bad situations can turn around.  IT’s important to have enough patience to stick with it when it seems difficult, but also move on if it’s not working.

Question #2: Am I happy and growing because of the people around me?

do:  Know what your non-negitiables are. For me, I avoid people that I think are jerks or are unethical.  This is clearly a judgement call (and some of you may think I’m a jerk or are unethical – if so, please let me know!)  But I think you need to go with your gut on this.   I once was offered a job for a startup that was growing like a weed.  The role was interesting and the company was well positioned in an attractive space.  But I thought the CEO/founder was a complete jerk.  And I realized that life was way too short to have to deal with a guy like that.

don’t: Be lazy.  It’s very easy to think “I like everyone at this company.  It’s comfortable.  It’s a great fit for me!”  But being comfortable does not = the best people or the best environment for growth.  I think teams with high performers often have people who are very stubborn or have quirky styles.  They may not be the most natural fit as teammates or colleagues, but they may make you a much better person and performer in the long term.

I could go on and on about this… but I’ll stop now since the suggestions in my comments are usually much better than the post itself.