Life has a plan on its own

First, how do you know you are too focused on planning your life? - When you go to bed at night feeling dissatisfied about the amount of things you were able to do work you were behind on, fun you missed out on, etc. This might have been zero to very little. - When you find yourself putting dates around the key milestones of your planned life for which exact times make no sense, e.g., the age you will be when you are married, have your first child, earn your first million dollars, etc. all this - and much more - happens in due time. So don't waste your time planning when these things should occur, there are too many factors outside your control. Just knowing you want them is sufficient. Just don't put deadlines on them.

And when you cross off items on your plan and realize they do not bring you the satisfaction you had hoped for. Perhaps you have been trying a bit too hard to make assumptions on what makes you happy and lost some of the spontaneity required at times to discover things through serendipity and mysterious (but wondrous) circumstances. Perhaps the plan in this case might have constrained your perspective and artificially limited the choices you considered in important areas, e.g., mates, jobs, places to live, missions to dedicate yourself to, etc.

Also second, when are you planning enough? I'll rephrase that as "what are good criteria or parameters to draft a life plan?", i.e., a plan that is "light weight" like tech people would call it, while accomplishing what you make those plans for: to make you happier, wiser, deeper as a human being than you otherwise would have been without a plan. So when you can say yes to all the below, I'd say your life plan is good enough for now. Because when it comes to life planning, start with humility and respect for that awesome power you are dealing with. Life is chaotic. Life defies your expectations. Life may also be the subject doing the planning for you, not an object you can impose your will on, even if the self-improvement gurus will have you think differently.

Do you remember John Lennon, who probably had it right with his line "life is what happens while you're busy making other plans." So instead of something you plan, it might be the residual of all you haven't and can't think about just now. A life plan is not the same as a bucket list. A life plan should be about the most important things you want to do or have before your numbers is called and you make your exit from this realm. A life plan contains the few "must haves" and informs you about who you are as a person that's valuable. A bucket list contains the infinite "nice to haves" and is a subset usually of pleasure-seeking or, in its most rudimentary form, a bragging list to whomever is concerned.

A life plan is finite, so keep it short so you can get it done. Hence, prioritize the number of check boxes on your plan to raise the odds of them becoming a reality. I literally mean to think of something like "Top 5 things". How to choose? Try and use values to guide you on what should be on the list of the top 5. When you ask yourself "why" for each item until you get to the root, that root should be an underlying value. For example, if family matters to you, consider the classic "find a life partner" or "bring children into the world".

If freedom matters, consider items like "be my own boss, answer to no one". Boil your values down to the few most important ones you must have lived to feel good about yourself. Then derive life plan elements that embody those values. If you do not know your values, your first item on your life plan must be to discover your values. Your second item must be to test that these are truly your values. If you can manage this colossal feat, the rest is cake.

Revisit the list periodically, perhaps once a year but not too frequently. A lot can happen in a year and revisiting in those intervals can give you enough time to make changes to accommodate your new mindsets, circumstances or goals. Your values themselves may not change, but what can change is the prioritization, i.e., what matters most to you in any given year. Also cultivate humility to question your life plan checklist when you sense your values shifting as you age. For instance, you may value freedom, power or recognition more than anything when you are in your early twenties.

By the time you turn thirty or forty you may prioritize stability, contentment, peace of mind or impact on others. Again, always follow your values with your life plan. If your plan never changes, chances are you are either not being entirely honest with your values and changing self. I have yet to meet someone who was the same person at the beginning of an eighty year period (not that I have been around all those years to take notes, of course).

Try and build in slack. A belt too tight makes for an uncomfortable walk. And you have a long walk ahead. This refers to your concern about enjoying the "now and here." Every worthwhile life plan must have an item that reads something like "Take risks", "Do something crazy once in a while", "Have fun" or "Stop and smell the flowers." Without these things - and without having done any of them - you have had a life plan, but you have not truly lived.

Moreover the point of a life plan is to help you become the person you were meant to be. It also should allow you to live well or better than what is otherwise just an existence. To live well is to live in accordance with the values you cherish and protect at your core. But to live well you first have to live. To live you have to commit to having experiences. To experience you have to go out and do stuff. You should be out there doing stuff all week. Thankfully, no matter if it turns out good or bad, it all counts as experience. If you find yourself not having done any stuff this past week, chances are you are too busy with that aforementioned life plan so that's a good stopping point then! Cheers!