If you look at your immediate network, you may find people that have had to weigh similar options. Ask them how they made a decision. Also, find out their opinion on whether or not they would choose the same option again.
2) Look at your options under a microscope and from 2000 feet above.
Again, the key is to keep an open mind and look at your situation on a more detailed level and also from a wider perspective.
For example, suppose you are making a decision on whether or not to watch the new comedy movie that just came out over the weekend. You may visit Rottentomatoes or IMBD to look up actual reviews from viewers like you. Additionally, you may also ask your friends who have watched the movie what they thought about it. These are examples of looking at your issue through a microscope.
From a wider perspective, you may ask a couple experts in the movie business about how well the movie performed at movie screenings or how well they fared with other industry specific statistical measure. Taking a look at how well it did at the weekend box office is also another measure you can consider.
In certain situations, looking at it in a microscope is sufficient, but in more uncertain situations it helps to look at it from 2000 feet above.
The key is to consider all angles of your option and learn from the experiences of others and determining the odds for situations to play out. In the movie example, you may ask yourself, "what are the odds of me enjoying the movie?". Looking at your options under from varying perspectives will help you estimate your odds.
3) If possible, sample test your options.
There is no written rule that says you have to pick one or the other. Why not test your options in real life? Sometimes you can over-analyze your options. If what you are deciding between doing does not have a lot of statistical data or has not been done by enough people, just test it.
For example, suppose you are interested in starting your own eCommerce business. You've heard stories that if you start a new business, you should put 100% of your efforts on it. That means giving up your job to focus on it. But, you realize that you will need some way of supporting yourself after your savings runs out. One of your options could be to test the eCommerce business and see how well it does for a few months, before deciding whether or not you should quit your day job.
Still can't make a decision? If all else fails, ask yourself how you will feel about the decision 10 minutes from now, 10 months from now, and 10 years from now.
If all three time frames align then you have a no brainer. Looking at it from three different time frames helps you take out the short-term emotions that may initially sway your decision one way or the other.