I'm curious about people's opinions and experiences regarding how permissive modern western world is to egolessness.

By modern life I mean a life where the respect you get is not independent of how high you are in the ladder of material success, your accomplishments in material world, and how much social status and influence you have.

By egolessness I mean an attitude that values giving more than taking, sharing more than having, humbleness more than pride, helping more than competing, accepting more than fighting, having guards down rather than up etc...

If people have problems with the word egolessness and the way I defined it, what we call it is not that important. Question is applying the described attitude to modern life.

Very good question.  I also like your description of egolessness which is basically a relaxation of the push and pull of likes and dislikes.

I think it depends upon the type of job you have.  If you're a caregiver of some kind then it would be welcome but in many other competitive jobs it definitely is an invitation to be a doormat.  I was warned about this by psychologists I talked to and I have been bitten.  I'm currently learning how to do a better job of being a little pushy in areas where one must do so without becoming a monster.

This doesn't mean we have to go in the exact opposite direction and be as psychopathic as possible.  There are many in society that eventually have to get punished for being criminal and even if the punishment isn't harsh enough (Wolf of Wall Street) then you still lose reputation.  Lots of people who achieve status find it hollow and as any meditators know everything is impermanent.  There is also a danger in being so competitive that you have nothing but enemies.

The balance is to be dangerous in your skills but to not join the dark-side which should be similar to a lot of martial arts philosophies.  You can also look at your family and close relationships.  In those relationships it would be good to be more egoless so you can nurture a family.

What I like about egolessness is that you can still pursue tasks and goals and be pushy but you don't have to be immoral.  Everybody understands healthy competition but like anything there has to be moderation.  I also find egolessness allows more energy to pursue tasks.  One doesn't have to sit around and do nothing.  You can pursue activities while reacting less and less to perception.  If you have failures along the way towards your goal, being egoless will help you tolerate them much more.

I think your name "Trial and error" is very apt.  You have to try these practices out and learn to move between a self and non-self point of view which is recommended by teachers like Rob Burbea.  Negating a self point of view can also be an aversion.  Bascially you have to be able to defend yourself and your property.  An egolessness way of doing this would be to accept that people have egos and push beyond your boundaries and that the natural response is to push back.  

Eg. Look at competitive sports and how many talented players will have sportsman-like habits versus some who over do it and get punished or ostracized.  Find the right balance.

The way status works is that not everyone can have status if everyone is equally with status.  So most people aren't going to achieve that even if they try their hardest.  If a person tries their hardest they might gain status but the people perceived to be below them will probably look at that person with envy and contempt.  There are famous people who have no private life.  If they mess up everyone in the world knows about it and enjoys schadenfreude.

The best thing is to pursue skills and use them in a postive way and if status happens upon you then don't lose what got you there in the first place.  If status is taken from you but you don't need it then it won't be as big of a loss.

Thanks for the perspective, there are helpful things in there.

"By egolessness I mean an attitude that values giving more than taking, sharing more than having, humbleness more than pride, helping more than competing, accepting more than fighting, having guards down rather than up etc..."

I do accept that people have egos and it's a common habit to want to push back with our own egos.  But I also think that as we mature, we do less and less of that.  People can do and say all sorts of things but how you respond is up to you, you do not need to be a door mat nor be a sociopath, there are other more balanced options like just not getting sucked in at all to such things.  Have the kind of pride that is the desire to do a good job and improve yourself and if you are in a good field for you where you like it and have decent skills, then you will be competitive in your field with that mindset, but you do not need to worry about where everyone else is on the ladder in order to do a good job yourself.  In the end, you compete against your own self and all your own issues.  And you can certainly help people when appropriate and not be a doormat.  IMO, help them when you think help would be good for them and it's reasonable for you to do that. And if you look at confident successful people, you often can see relaxed people who do not have guard up.  They are just confident that they will be able to handle what comes when it comes and do not feel the need to worry too much about things before that.   They also tend to have a good instinct for knowing what is true and what is not true and acting accordingly.  I have certainly met some very successful competitive people in various fields who were confident successful straight shooters, neither pushy nor door mats who did help others around them when appropriate and also were respected by those around them.  It think it's a big mistake to conceive of our options as either predator or prey, there is a 3rd option which is neither of those.  I also think it is a mistake to think of egolessness or evolution as leading to a kind of weak defenseless state in which you could easily become prey by others around you.

It seems possible to be egoless but take things, keep things, show pride, compete, fight, be guarded etc You would behave in that way for some other motivation than ego. For example you might take back human rights, show pride in being part of a minority, keep a passive income, take people/organizations to court, surprise those acting immorally etc.

It requires receiving if other people are to get the opportunity to give, consolidating wealth to allow for investment, being proud to motivate a group, competing to master some skills, fighting to protect the innocent, secrecy to defeat abuse.

I guess my point is that those behaviors become problematic when they are enacted in service of the ego. Someone who does not behave in those ways may still have a big ego and be morally corrupt as well. 

For example not wanting to be judged as greedy leads some people to not accept help. That can be the ego playing a game of pretending to be "nice" or what some people confuse for "egoless"

I may be well off the mark here but I hope some of it can be of some use.

You do have very good points, sorry for the late response.