Wednesday, February 1, 2017


Creative Career Design

After three shake-me-up events in the middle of last year (2016 was hard for everyone), I've been on a major new life track, trying to figure out a new pathway for myself.  What do I want to accomplish with my life?  What's a good career for me?  I've been reading a lot of books, writing a lot in my journal, and generally talking to everyone about everything.  Here's some notes that I have been sending to people when they ask me about "my process", which has been many months long already.

Books: So many, but here are two excellent ones: Creating A Life Worth Living  and The Subtle Art of Not Giving a Fuck: a counter-intuitive approach to living a good life.  The latter book is pictured, it's one of the best books I've read in my entire life; highly recommended.  Unlike a lot of self-help books, it's not filled with feel-good bullshit, or spurious details of the authors life.  There are no wasted words, or wasted chapters - the book needs to be the 224 pages that it is.

In non-book stuff, here are some exercises that I've done, that I've found super helpful so far:

Ask yourself "What will have the most impact on the future of humanity?", and then drill down into those answers to see what you're interested in doing.  This is a question from Elon Musk.

Write down all of your goals (20-30).  Choose five that are most important to you.  Stare long and hard at the other 25 and promise yourself you will never do them, because those the things that will distract you and ruin your life.  This is an exercise from Warren Buffet, via Carol Lloyd (author of one of the books above), who instead says: organize the goals in a hierarchy, see if everything you are doing is actually in service of just one goal.

Create a list of every job (or job-like thing) you've ever done, and list all of the things that you hated about each.  Then list all of the things that you loved about each.  Are there any similarities across different jobs in each group? Hopefully this gives you a bit of picture about the kind of career that you would enjoy - not just what you would be doing, but all the other things that matter (esp. people/relationships, but also: environment, culture, how you are managed, work/life balance, etc.etc).  This one came from my life coach.

Future Fulfilled.  If you've got an idea for a big project/accomplishment, "begin with the end in mind" and write down what your life / the world looks like in X years, if things are wildly successful (X = whatever span is appropriate - some things obviously require a lot longer than others).  Then, project back in stages, with "milestones" at intervals before that period.  Each milestone should be far enough backwards from the last that the situation is pretty different, but close enough that there are just things that have to be true if the next milestone is going to be accomplished.  Work your way back all the way to now.  It's amazing how quickly things can get really detailed as you get close to now.  I got this idea from my friend Paul, who got it from Landmark Forum.

Experimental Mindset - from the above four things, you should be able to construct a list of possible careers for yourself, and a variety of ways in which you might evaluate the success of those options.  Now, devise ways to run "experiments" for each of them, in order to gather data and see if each option might possibly look like you want your life to look like.  Run the experiments, and evaluate.  This of course starts to make things really real.  This one is my idea, but really, there are no alternatives to an experimental mindset - if you are going to do anything, you are essentially doing this, so you might as well be doing it consciously.

Pathway.  I got this one from Tim Ferris, his question: "How can you make it so that even if you fail or quit, you still win?" While you are doing the experiments, or leading your life, pay attention to all the side effects.  When you are working towards a goal, often you end up doing a lot of other things, gaining a lot of skills, meeting a lot of people, etc.  Often times, you ultimately end up failing at your goal.  But, all of these side effects usually end up being super important in your life - that person you met becomes the person you start the next company with, or that skill you built ends up becoming your next career, or whatever.  So, when you are thinking about your potential experiments, consider carefully how you can still win (walk away with some great side-effects) even if you ultimately do not choose that path, or that experiment fails.  Does the pathway you're on lead to lots of great side-effects, or it is relatively barren? How can you get more and better side-effects in everything that you do?

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