What to do when faced with a big, uncertain decision

“In any moment of decision, the best thing you can do is the right thing, the next best thing is the wrong thing, and the worst thing you can do is nothing” – Teddy Roosevelt

Sometimes it’s hard to figure out what you want because it means making a big decision that might be very impactful to your life – such as getting married, having kids or changing jobs. The same ideas apply, but I find a bit more structure can help.

The first thing to keep in mind is that life is complex, which means there is no single “right” answer to the question you are pondering, so don’t expect to find one. Instead, you are trying to find the answer with the highest probability of success.

It is also important to think about your mindset. Even if you are struggling with a difficult situation, don’t dwell on it as a “problem”. It is simply the next chapter in your grand adventure, and a lot of people (myself included) find that the current “problems” often become the best stories once you get past them.

Once you have the right mindset and approach, it’s time to get to work:

What information do you have to work with?

Do an inventory of what resources and information you have that can help you make your decision. It’s important to differentiate what pieces you are confident in (the “facts”) and what is less so (the “assumptions”).

Think of additional pieces of information that would be helpful. How can you get those? Ask “journalist” questions: Who, What, When, Where, Why and How?

More specifically, if you want to launch a successful business, study other successful businesses. The same goes for marriages, job changes, or other complex decisions. Find ones that worked and look at the facts and assumptions in those situations. Compare the two for likenesses and differences, with the goal of finding items that can help in making your decision.  Be sure you cast a wide net to find potentially useful information.

What are the potential options and associated outcomes?

Start brainstorming potential action options (“what could I do?”). List them out without worrying about the outcome. The goal here is quantity over quality. Even if you think it’s a bad idea, write it down anyway. Often great creative solutions come from what looked like bad ideas at the beginning.

Once you have your list of potential actions, go through and write up 3 possible outcomes – the most likely outcome, the best possible outcome, and the worst possible outcome.

Now filter the list and improve. You want to find the outcome with a likely scenario that you consider “good”, a high (or at least medium) probability of an amazing outcome, and a low probability of a negative outcome. Go through the list of possible actions and pick the 3-5 that seem like the best matches to that criteria.

Once you have those ideas, see how you can make them better. Specifically ask two questions: “What can I do to increase the probability of the best-case scenario?” and “What can I do to limit the downside risk (or make the worst-case scenario less likely)?” This is a great place to ask family, friends, or your network for advice on how to improve the options.

After you have the options flushed out, comes the most important part – you need to make the decision.

If you are having difficulty deciding, remind yourself that stalling or otherwise not deciding is actually a decision. There is a cost to not making the decision, so make sure you know what it is.

11th Piece of Advice: If there is a decision to be made, make it actively. No decision is a decision.

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