I like this article- I started making a "five year plan" last year, and when it came time to start looking for jobs for this season, I was really pleased at how much the act of writing down the plan helped me shape my season. Much more so than in recent years, I felt like I was working towards a specific goal, rather than just filling my calendar and making sure I can pay rent.
From the article: "You have to clarify for yourself what you aspire to do with your career before you can communicate it confidently to others." Writing down what was important to me in a job and where I wanted to be in the future clarified for me what I wanted, in the short term and the long term. I don't feel tied down to this document- it's something that is going to change every year. But it was something that I wish I had done a few years ago. I think I would have made better career choices as a young stage manager if I had done this.
I made a template that works for me- it has goals/steps that I want to accomplish for the next 3-6 months, 6-12 months, and beyond 12 months. It has longer-term (five year) goals, skills I want to develop, qualities that I value in a workplace, and personal goals.
Writing this all down really helped me realize what I wanted, and allowed me to take more concrete steps towards getting there.