Lots of intelligent responses here. Can't unpack them all, but here are some thoughts:
Why should you need or want to have stellar career success or any of the other accomplishments? If it would be really meaningful to you then I’m pretty sure you would find the motivation and grit to at least try. But maybe you dont because you don’t care enough because the life you have is good already.
This comment reminds me of exercise. We all know we should exercise. We can decide to exercise. We can commit to exercise. But activities that feel less pleasant than their alternatives are very hard to maintain. The "burden" of an easy life is that there is always something more pleasant to do, tempting one away from whatever one resolves is important.
Seems more probable to me that you're afraid of the unknown.
Unknown as in worrying that getting out there and failing a little might upend the whole happy life which was obtained by being a privileged person who only has to pursue the default paths in front of him? Maybe. But the known fear is becoming trapped in slackerdom. More on that below.
what matters is living according to your personal core values and you can start that NOW. You will probably be happier if you take some "think time" to identify and write down your core values. Then structure your approach to work and whatever else you do to be consistent with those values. The ennui will likely evaporate.
Tried that, but this comment in this context makes me wonder if I missed one. Perhaps "doing my best" or "being excellent" is a core value? And perhaps I'm not doing it. Which leads to...
You must be accomplished or competent to a pretty high degree in one or more areas to get to that...
Accomplishment, competency, riches, and being a slacker are all relative terms. The world is full of people more brilliant and talented than me who are sitting on their arses, and if there was something I try to run away from, it would be being like them. A life is a terrible thing to waste. Waste just seems wrong when so many are suffering. To be this lucky and to waste it... the phrase "whistling past the graveyard" comes to mind.
I assume "necessity" situations will become less common as I have more security and especially once I no longer have the responsibility of a job. Will this make me soft? Will it make me boring? Maybe.
The risk of becoming "soft", lethargic, disorganized, dim, and overall "boring" is truly something to fear. Today, I envision myself retiring
to something - I have a vision of the future life and it involves hard work. Yet, how do I expect to accomplish this - to be this person - when I don't possess those traits
now?
My guess is that all you have accomplished so far (and they are great accomplishments) have come easily to you without a lot of effort and it's been comfortable to go with the flow. Did you more or less do what was expected of you, in terms of career, marriage, etc. or did you buck expectations and do what you really wanted to do, regardless of what anyone thought? I think what you are lacking is mental toughness, which people develop to get out of an uncomfortable place or to get something they want very badly. Apparently, you never needed to develop this, so coasting is your default course. A question I once heard (can't remember who asked it), is "What do you value more than your own comfort?" Focus on answering this for yourself. If the answer is "nothing," that's okay, just stop torturing yourself with why you're not doing "more."
That's pretty much my theory. In terms of others' expectations, I'd say I grew up with a strong emphasis on academic achievement (which I did) but not careerism (which I didn't). However, I made some maverick career moves, changing careers 3 times when my own expectations weren't being met, and each transition took effort. So it's a mixed bag.
I can name lots of things more important to me than comfort - but despite my values, comfort is hard to resist. This is like how one can value fitness but have a hard time competing with the taste of chocolate and bacon. Another example is how the world seems to be filled with keyboard warriors who have VERY STRONG OPINIONS and yet these deep convictions rarely translate into donations or volunteer hours. On this forum, we hear from people all the time who have large houses, expensive cars, and devastating food and beverage habits, but who say they value financial freedom. If luxury is an addiction or a weakness, so is comfort.
You don't have major adversity in your life until you do.
This is another problem with being weak-willed. My string of luck must necessarily run out someday. Loved ones will die. Health will fail. Externalities will come along and create danger. Will I be ready? Or will I crumble under the first bit of serious adversity I've ever faced, like the person who's never exercised in their life who has to run a mile to flee the erupting volcano?
If your life is too easy, why not make it harder? Ease doesn't make a fulfilling life.
This is something I've considered, just for the sake of exercising grit. I could train for an athletic event like a half marathon. I could relocate to somewhere where everything is difficult and awkward. I could take on an ambitious project where others are depending on me. I could do one of those escrow accounts where if you don't accomplish your goal in a certain amount of time, you lose your money.
I tell myself the barrier with finding worthwhile hard things to do is time. That's a BS excuse. I could be doing ten squats every day with one minute of time. I could be learning Spanish in diez minutes a day.
...maybe you're high in trait neuroticism, and you worry and plan and hedge. That's okay, just adjust your risk tolerance as your wealth/stability increases. This won't be comfortable but life isn't supposed to be comfortable and there will be times when it is not, regardless of your prior efforts.
Good point. Much of my luck, success, and lack of struggle is a result of mistake avoidance. While friends and acquaintances crash and burn, I just keep zig zagging through the wreckage somehow. I meticulously research everything as if studying for a bachelor's degree in Jack-of-All-Trades, and can be quite a bore with my chitchat about how to properly calculate the ROI of a mortgage refinance, why you should only buy cars with timing chains and not timing belts, and why taking a "dietary supplement" is usually a bad idea. I could probably be accused of liking to stay within my circle of control a bit too much for my own good - only moving beyond the circle after having expanded it. Being risk averse has served me so well for so long it has become habitual, but I guess I'd like to have a solid offensive game as well as a good defense.
Neurotic personality trait is an intriguing explanation. I will have to look further into this direction so thanks for the lead (meticulous research ahead, of course).
I've recently found out they have a name for this - executive dysfunction. Often associated with ADHD.
Another intriguing explanation! Now I'm all over this article and its links:
https://en.wikipedia.org/wiki/Executive_dysfunction
