A few years ago, a manager of mine gave me the assignment to work on a 5-year career plan. I had never created a career plan before (not even to plot out goals for the coming year), so I was completely unprepared for how and why I should do this. Luckily, she shared her own plan as a guide, but I still agonized through the exercise. Over time I have become aware of how important this was for me to do. Looking and assessing where I was at the time, really thinking about what I wanted to be doing in the future, gave me the tools to make the right decisions to make things happen.

while i totally disdain the “save for your SUV / mortgage / life insurance” plans, there is some great advice in this article by erin malone how to map out your career.
2013-04-29: this is the kind of question most people never ask themselves, instead blaming the man for their life sucking.

What’s the last thing you did to advance your career or improve yourself?
On your 85th birthday, what do you want others to say about your accomplishments?
What would you be doing if paying the bills wasn’t an issue?
What are you passionate about that you’re not pursuing?
What have been your greatest accomplishments so far?
What’s the greatest value that you bring to your work?
What does it mean to you to be satisfied at work?
What’s your personal definition of success?
What about your work energizes you?
Where are you playing it too safe?

2016-10-04:

Designing Your Life is one of the most popular courses at Stanford. Taught by Bill Burnett and Dave Evans, the class teaches how you can use design thinking and techniques to shape your life and career.