To plan for success, often it makes more sense to plan how you might fail, figure out what might cause those failures, and then don’t do those things. That’s true for getting pilots home safely during combat, and also true for planning your career.
“For example, let’s say you are trying to figure out ‘How can I have a great, fulfilling career?” Instead, ask yourself ‘How can I have a terrible, worthless career?” and whittle away at the choices that you know will ensure that outcome: Stay in a dying industry. Stay ignorant of emerging technology. Continue to be a rent-taker as opposed to adding value. Prioritize near-term income over long-term value. Continue working with people that treat you poorly. Continue to think like a junior team resource. Be reactive to opportunity as opposed to proactive. And so on.
“Now you have a list of actions to avoid. Avoiding them begins to move you away from failure and closer to reaching your goal.”