I recently decided to leave my job at Google to pursue a career in visual arts. I fit your mold; I cannot afford to be long term unemployed. In fact, I have a year of conservative living without income before I will be compelled to go back into the formal work force. That is unless this all works out which, of course, is the plan.
That’s the first step.
Figure out how long you can be unemployed. In doing this, make sure you consider grossly expensive new costs of health insurance and the cell phone bill your employer is probably currently paying. I did a serious reevaluation of my current expenses and implemented life style shifts before I left.
Determine if this is enough time. Enough time for what? If you don’t know then it might not be time to leave. It was important to me that I would be learning more, taking more risks, meeting more people, and failing more out of work than in work, a high bar leaving a place like Google. Ultimately I believe I am making myself more valuable to potential employers by doing what I am doing now. What do you want to accomplish with leaving? Maybe you know that where you are currently working it is too comfortable or too soul-sucking to really ever find your vocation. If you need to leave to put yourself in a place to be more open to that calling, then leave. But make a plan for discovery as well.
Treat unemployment like a job. I learned this one from a good friend of mine who left her job at Mathworks to get a Ph.D. If you are leaving to “do something” then make sure you do it by getting up every morning, getting dressed, and holding hours. Don’t let your days fill up with errands. I suggest picking one afternoon a week to deal with the life errands and keep the rest of the time sacred. Create value when you are unemployed. Write that book. Make that movie. Have something to point to for if you are planning on returning to industry.
Don’t hedge with your life. Read Seth Godin’s The Dip. I know too many people who arbitrary calculate chances of success before making a career change. If you are leaving “for” instead of “because of” something, you will feel the difference when you get up in the morning. If you leave “for” something, are willing to change your life until you get there, and follow through on it, you have the best things in the world to worry about.
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