Determine what you want to plan or prepare for. The future is a big place with many eventualities, but chances are that you want to address a specific situation, problem, or opportunity. Define this end to the best of your abilities.
Use your intuition. Not all decisions are rational or carefully analyzed, and intuitive guesses can often be quite powerful. What feels right? What do you think will happen? When you use your intuition, you draw upon your experience and knowledge in a different way than when you make a rational analysis. Listen to your first instinct. Intuition often works best before you've had time to study any details, so pay attention to it, even if you do not act immediately on it. Intuition may clue you into emotional factors and subtle cues that you might otherwise miss. If something feels wrong about a situation or you just don't like somebody, don't ignore it, even if you can't put your finger on the problem. Use intuition as a "lead" rather than as a solution. Investigate what might be causing your hunch or gut feeling and dig deeper until you find it.
Consider what you already know. Prior knowledge comes from many places. Have you tried something similar before? Do you know how somebody is likely to react? Have you seen something done or could you read about others' experiences with a situation? Could you ask others? Can you try something out or gather data that might suggest what could happen?
Detect your own bias. People tend to bias their guesses and actions in certain predictable ways. For example, recent events may play a larger role in influencing decisions than they warrant; or, you may be more likely to believe something just because everyone around you believes it. If you think this sort of thing is happening, start looking closely at hard evidence (like facts and numbers) and question your assumptions. Consult the list of cognitive biases for common presumptions and biases and see if any apply to you.
Invent hypothetical situations related to your objective. Ask yourself "what if" for various possibilities and imagine possible outcomes, possible courses of events that could result. Especially, think about the possible consequences of different courses of action.
Consider the worst-case scenario. What is the worst thing that could happen? Evaluate the possible risks. Is the worst case something you and others could tolerate? Could you clean up a mess, try again later, apologize, lose a bit of money, or cope with criticism or rejection? Is the worst case something you could plan for, avoid, or mitigate? Is the worst case too risky or too undesirable? How likely is the worst case, and how likely is an undesirable outcome?
Consider the best-case scenario. What is the best thing that could happen? Evaluate the possible rewards. What can you do to bias the outcome towards the best case? Where should you set your goals? How likely is the best case, and how likely is a desirable outcome?
Think of possible actions to take. If you are trying to think ahead, it is probably because you want to decide how to respond to some situation or need, so think of possible responses.
Evaluate those actions. Based on your experience and knowledge about how such events usually turn out, choose or narrow down which action to take.
Prepare. Whatever you have to get ready, be it people, equipment, facilities, plans, or simply courage, get it ready. Writing can be a powerful tool for preparation. It helps you remember your plans, and it helps you to see them completely. Use a calendar or notebook, checklist, chart, whatever helps you.
Try it. Act according to your forecasts and your plans. Then, let life take its course. See what happens. By taking note of the outcome, you will have more experience and knowledge to draw upon the next time you must make a decision such as this one.
Adjust. As you see what does transpire, adjust your actions or responses as best as you can. You may not have the opportunity to change course after you begin, but you do have the benefit of acquiring new information or results. Use them to decide how to modify your actions in the present and the future.
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