A Simple Strategic Planning Method
Step 1: Timespan
You can only move so far in a certain period. I'm getting ready to graduate school this year so my planning for today will be short; about 6 months.
Step 2: The Best
if everything goes right, what should your life look like? This is our "ceiling", so you likelihood of hitting it should be well below 50%. Write out at least a paragraph, ideally a full page describing in excruciating detail your ideal situation a that time.
Step 3: Negative Visualization
A fantastic resource from Stoicism with a perfect message. Imagine the worst case scenario. What if nothing goes right? The likelihood of this should also be well below 50%. Tim Ferris gave a TED Talk on it, so it must be useful! Really though, it's super helpful. Don't skip this step.
Step 4: Filling it In
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I like to construct two middle of the road scenarios. One a bit more bad and the other a bit more good. You can make as many as you like here, but I wouldn't get hung up on making more than a handful at the very most. The likelihood that one of these options occurs should be over 50%.
Step 5: Major Factors
Are there parts of your not worst-case scenarios that need to be put into place well before they actually occur? Are there any single factors that differentiate scenarios. List these out on your paper to create a key factors list. Monitor these as time goes on. If any of them occur in advance of the end of the timespan, consider whether their outcome requires a revision of your current plan.
Using your new scenario-based plan
For the time you've outlined ask yourself which scenario you are on track for only when you're doubting yourself or in crisis. It will help show you the path toward your current ideal. Don't obsess over it though. The scenarios are just a projection of what could happen. They're a reference tool for strategic planning, not a crystal ball.