If I were able to theoretically sit in a room filled with all of the different versions of me before and after all of the major decisions in my life, I would love to hear what my future selves feel about my current positioning in life and if my past selves are proud of the decisions that I have made to get to where I am.
I have adopted the way of thinking in recent years that no matter the outcome of a decision, you will be a better person for having gained the experience of whatever it was that was in question, even if it was objectively a negative experience. Until recently, I had viewed things as so profoundly quantifiable that I was discounting the qualifiable benefits that may be more difficult, if not impossible, to fully measure.
It is important to act, speak, and think in ways that are true to yourself. What I mean by this is heavily weighting the future few years' versions of you along with the recent few years' versions of you. I will explain what I mean by this more numerically by the following: For the sake of being able to conceptualize this, consider that each of your birthdays represents a unique version of you (that in this thought experiment corresponds with your current self). Next, for math's sake, consider that you live to 100. Let's say you are about to make a major life decision and you have 100% that you can distribute among the 100 versions of you (including your present self). Some people may say that 51% (a simple majority) should always be allocated to your present self, and others may say 100% should be your present self (the you-only-live-once types). On the opposite side of the spectrum, you may have people who feel only 1% should be allocated to their present selves, with 99% allocated to their retirement many years away. Lastly, we may have individuals who are living in regret of who they have become, giving the majority of the weight to previous versions of themselves.
My current allocation is as follows: 5% to my early years, 15% to my previous three years, 30% to my present self, 35% to the immediately following five years, and 15% to the rest of my years after the next five.
Some of my allocation might make sense to you or be similar to how you would allocate yours. My thinking on allocating 15% to the previous three years is because I feel it is very common to immediately cast aside previous versions of ourselves in thinking that we have new information and experiences and are better for it. Consider any ideologies your previous selves held that have been adjusted in recent years. My views on many political topics, for instance, have evolved over time. At the same time, I am trying not to discount my previous selves.