Planning is an inexact art. Anyone who says different is delusional or a liar.
What this means, practically, is that a plan that makes no allowances for slippage, screw-ups, and unexpected setbacks is bound to fail. A plan that doesn’t account for possible causes of failure damns itself to being, at the very best, inexact.
The heart of the issue here is that even the best plan isn’t really likely to stay intact when it interacts with reality. People are stubborn, disinterested, and generally not likely to make other people’s plans work out right. Most people aren’t even all that interested in making their own plans work out right.
Far more important than the details of any given plan is the strategy that underlies it. The most exact of plans are in some ways the worst. Because the world is likely to penalize a plan for its intricacies by quickly stomping all over them, a strategy is the real long-term plan.
A strategy is a hard thing to build, because the excitement of exactness can distract you from evaluating the saneness and workability of the strategy. It’s easy to fixate on how you’ll use your first million to grow your next ten, without noticing that your strategy for that first million is the empty hope of hitting the lotto jackpot.
Good strategies are dead simple, and verge on the banal. Trying to write a book? A good strategy is to write. Your plan should be something like: write at least 1000 words a day until I have a book. A bad strategy depends on finding a literary agent who will give you a topic to write a book about, and then get you a fat advance while you write the book that will make you a millionaire.
The simpler the strategy, and the plan that grows out of it, the more likely it’ll actually stick. Intricacies breaking apart can be discouraging, but the quotidian effort will always be there for you. Effort to make the world pay attention to the work is sane; a plan built upon the world giving you its attention in a specific way is destined to failure.
As with caring, a good plan is an internal one. You can only control what you put in, and what you get out is up to the fates. Certainly you can direct your effort in a way that’s likely to get more generous results, but you can’t ever control the response of the world to the work you do.
The other easy-to-miss trait of a good plan is that it is rooted in reality. If you can’t currently run 100 meters, planning to run a marathon a month from now is insanity. If you rarely meditate and can’t currently sit still in meditation for five minutes, a plan to start meditating three hours per day, everyday, eternally, is insane.
Start small. It’s fun and easy to dream big. Millions in the banks are more fun to dream of than thousands or hundreds, but if you currently have a negative net-worth, getting to zero is the best first step. Then you can aim for a few hundred socked away for a rainy day, then a few thousand. The dangers of an unrealistic plan are hard to overstate. Nothing is more discouraging than the sense that you’ve expended tremendous effort but moved only a minuscule distance toward your goal.
A good strategy is written in a sane way, toward a sane goal, and rooted deeply in the knowledge that the specifics of the plan will need to change with time. Build one of those, start to execute it, and don’t be afraid to re-plan as the world gives feedback. That’s how you really change your life.