Recently I was contacted by a young alumna from my college who requested advice on breaking into the movie business.  This woman was different from the usual newbies in that she was contemplating a big career change.  She was a successful investment banker who wanted to leave her job and chase her dream of becoming a creative producer of independent films.  So, I started out warning her as others have done for me when I first started – if you can make a living doing anything else and don’t hate yourself for doing it, then don’t build your livelihood around film as it is such a difficult and mercurial business.But in saying this to her, it got me wondering whether following one’s true calling and being able to make a living at it is a luxury or the only way to be truly successful at anything.  (Following one’s calling while being funded by parents/spouses/sugar-parents doesn’t count as there’s no skin in the game)  Some happiness theorists, consider this experience of being so positively connected to one’s work that you lose all sense of time aka “flow” as a critical component of achieving satisfaction in life (along with strong personal relationships). Granted we all need to work to cover the basics of food, shelter, clothing, healthcare and kids for some.  But to what extent is work a means to an end vs. a basis for our sense of purpose in life?  Do you work to live or live to work?  Or maybe both?
DHH: My 16 year-old son and I were just talking the other day about career choices. He said, “I think I’d rather do something I like than something that makes a lot of money.” I explained that, when I first started wanting to write plays, I didn’t expect to make money from it, and certainly never expected to have shows on Broadway. If you do something you love, you’re more likely to work hard, achieve more, and it won’t feel like work. Then, at some point down the line, there’ll be a decent chance you can find a way to make some money from it.

Work and life, in my view, are inseparable. We spend a huge part of our lives working, right?  So a good work life is a huge part of having a good life.

QUENTIN: I do agree with David that work and life are inseparable if you are a creative person. If you’re a writer, most likely you’ll be thinking about ideas and storytelling all the time. When I take a job as a means to an end, I am always watching the clock and I know clearly that it is a job. But when I’m doing what I want to do, regardless of financial gain, I’m really living a good life. Great advice, David!


ALFREDO: I forget who said it, but here’s the quote: “Do what you love and you’ll never work another day in your life.”That’s the gold standard.  That’s Approach A.  And kudos to anyone who can pull it off.Approach B, which a very close friend of mine has taken, is this: work and passion do not mix.  Period.  Do not let money come between the two. So all his life he has worked at whatever jobs demanded the least of his time and mental energy: video store clerk, UPS store guy, storage warehouse worker, etc., and in his free time he has painted, written, read, watched TV, travelled – on his terms.  His basic attitude is, “work” gets the lesser part of me, free time gets the “best” me.One caveat: he has no one to support but himself. Me, I’ve split the difference.  I have a family of four to support, so what I did is this – in the same year, I jumped into screenwriting and opened two bars.  I’ve been fortunate: over the years I’ve earned roughly the same amount of money from both, but the bars allow me the luxury of not being desperate about getting screenwriting jobs in the lean years – desirous, ambitious, covetous about them, sure – but not couch surfing down to my last cup of Top Ramen desperate.  And as Elaine said, show biz is feast or famine, so you gotta have a Plan B to keep your sanity, unless you really, really love Top Ramen.
PHILIP: I couldn’t imagine working at a job I didn’t feel passionate about and loved. But as a child of immigrants, I know what a privileged and lucky position that is. My parents came to America and worked at a job that was by no means their dream job so their children didn’t have to do that. I realize that’s the case with most of the people in the world–they work at jobs they’d rather not do to support their families and to make a living. I think that takes a certain type of strength that I probably don’t have because I don’t think I could do that. My parents made me get a series of “menial” jobs as a kid–cleaning the public restrooms at the park, washing dishes at their friend’s restaurant, etc… to hopefully instill in me an appreciation of what most people have to go through but I think it was a way of also saying that if I worked hard, I had a chance to do more with that with my life. Or at least that was the lesson I learned. And as tough as the artist’s life has been at times (yes, I really, really learned to love Top Ramen), I don’t think I could trade it in for a well-paying job that I would hate.
JUSTIN: I totally agree with the idea of striving to make your living doing what you love.  But the truth is that it’s a match rarely achieved.  I’d go with the Kenny Rogers/The gambler rule on it– got to know when to hold, when to fold, when to walk and when to run.  And at the end of the day if you can’t make a living doing what you love it’s okay.  You’ll still be able to do it, but instead of a job it’s called a hobby.
ROGER: I too, much like Justin alluded to above, agree with the idea of striving to make a living doing what you love.  And after almost 20 years of trying, and watching others try, to unite personal passion with stable, paid work, I too have come to the conclusion that it is indeed a match rarely achieved.  Especially over consistent, longer periods of time.I think Offender Alfredo phrased it best from the pragmatic point of view – have a Plan B that will enable you to financially weather the more money-lean creative years of your Plan A.  Such a plan will enable you to keep your creativity pure and your spirits high.  Worrying about money sucks.  Take the money out of the equation and you can live to fight another day and you’ll most likely be able to love and enjoy your creative process without any unnecessary outside pressures.

And I think Offender Justin phrased it best from the more spiritual point of view – if you ultimately can’t make a living doing what you love, it’s okay.  It’s not a failure.  Just re-engineer your life so that you can take care of your pragmatics and section off enough free time to consistently and continually indulge in your passions and capacity to create.  Be flexible with your expectations and what your definition of “success” looks like and create the time and space for you to experience your creative flow.

My personal scorecard?  I think I’ve done ok with the pragmatics.  I have lived a frugal life and saved and invested much of the money I earned in Hollywood.  I have created my version of  Alfredo’s “opening 2 bars.”  Though now, being married with children, I certainly wish to up my financial game so that my 2 baby girls can experience more choices in their many years ahead.

As for the spiritual, I sucked at it for quite some time.  If anything, I had insanely high expectations of my career.  And when certain ideals didn’t materialize in the manner I expected, I found myself wrestling with disappointment, anger, and depression.  That being said, I am a much humbler person now and someone who is much more aware of keeping my expectations in check.  If anything, I am learning to enjoy and appreciate the day to day beauty of the journey, no matter where it may lead.