Here is a practical thought experiment that might help you: picture yourself many years from now, on your deathbed; would you have more regrets of having gone down path A or B?
That is not very practical, as you don't know how the future will turn out. If they start a startup and succeed they'll likely be happy about that decision. It's very hard to figure out expected outcomes for actions, and it's not very productive to think about worst-case (or best-case) outcomes.
I don't think I explained myself very well. You don't need to predict the future. You just need to estimate the amount of regret you would have by NOT doing something.
Living a fulfilling life is about minimizing regrets. People regret not trying to initiate relationships with potential soulmates. People regrets not trying working on a business idea that could have been very successful. People regret not spending more time with family. Etc. The regrets you will have on your deathbed are probably regrets you will have carried your entire life, and thus regrets that will have haunted you and hampered you from living a fulfilling life.
It turns out that in many cases, regrets are independent of the outcome. For example you may not know whether a relationship with a potential soulmate will fail or succeed. But you will probably have more regrets by NOT giving it a shot at all.
>Living a fulfilling life is about minimizing regrets.
While I very much agree with your advice on thinking of how you'll feel on your deathbed, I would be careful in your phrasing. People often make poor decisions about the future because they are overly concerned with whether they will regret a decision or not. You will find many who believe that focusing on regret will get in the way of life satisfaction, and it is a perspective worth considering.
For me, it makes sense to make some achievable goals (relationship, career, hobbies/activities, etc). Then start paring and prioritizing. Without the latter, I will always have more things I would like to achieve than is possible, and will always have regrets - it's rather pointless.
I think you're taking it too literally. Let's say you are 60 years old, in perfectly good mental health, and are diagnosed with a terminal illness and will not live longer than a few months.
I rarely do this exercise, but it has been helpful at times. It's a lot simpler to do if you're older (late 30's or higher). You can look back at your pursuits over the last few decades and can actually see things like "Oh, I've been learning new programming languages for so many years now. How useful has it been?" If I extrapolate for another decade or two, will I be happy at age 50 or 60 with the outcome if I continue with these activities?
I have many more pursuits than I can do in this life. When you're younger, you usually don't limit your options because you feel you have a lot of time. When you're 40, you can easily say "I've been doing this for 20 years. If I don't change/prioritize, I'll soon be at 60. Is this stuff worth doing at the expense of other pursuits?"
This year I ticked off two bucket items. I had been putting them off for too long. IMO, it is worth thinking that way.
