Oh trust me, I know how you feel, because I am in the same situation as you. Anyway, what I am thinking is I think we should rebel against people we don't like instead of trying to please them. The thing about pleasing people we don't like is that they can NEVER be pleased. No matter what we do, they will continue to demand for more and more.
One middle way is being "badass" without any confrontation. If you are relatively silent (you don't tell your "offending" opinions about reality) and you don't give a shit (you are somewhat detached) then people will actually like you and think you are cool. However this can still be a complete waste of your time and effort if you are tiring yourself with this for the wrong party.
Not giving a shit is much better than rebelling against someone (although not giving a shit is easier said than done for some). Acknowledge and then totally ignore his/her bullshit. If you can not avoid giving a shit (as a fault of the other person/pushy fuck) then you can confront, this is still better than rebelling.
For example, I'm an asexual and my mom wants me to get married and have kids. She also wants me to work in office jobs for the rest of my life when I'm actually a creative right-brained person, can you believe it?

She doesn't care about my happiness, she only cares about trying to live her unfulfilled dreams through me.
People have too small goals and they reach next to nothing as a result. Your mother has too tiny goals and she tries to give you a little bit bigger than hers was. I'm pretty sure she wants good for you but she probably doesn't know how to live a *good* life, she is just guessing that her idea *might* enable you to live a better life. In one thing she is right for sure: she should have pushed much more earlier in her life (but much harder than she thinks so). Many people find this out at midlife and near to the end game but that time it is usually too late and they still wouldn't have the knowledge to do it (lack of knowledge as a result of laziness and risk avoidance).
There are several problems with a not large enough goal:
- It is not a dream.
- You aren't interested in it enough to make efforts for long enough to reach it, you will give up with it several weeks/months later without actually doing anything to reach it (because you aren't really interested in it to make efforts).
If your goal is large enough (it is a dream) then you will feel the motivation to reach it even years later if you haven't yet reached it. What do you think, how long time would be necessary for me to wake up and say: "I don't anymore want to be free.". Even if I reached only half of my dream: let's say I spent only 20 years instead of 40 with work/slavery in my life - that would be a great achievement thanks to striving for a huge goal.
You have to find out what makes YOU happy and you have to go for it even if it seems to be difficult or impossible to achieve. It is often only lack of knowledge that makes things seem to be impossible to reach.
I know I'll never be able to achieve everything I want to, but I'm pretty sure I've found a way I can break free of the rat race. It's gonna take a couple of years though.
There is no such thing as "achieving everything". In fact, if you achieve all of your current goals then you must find some other goals to shake up your life instead of dying of boredom or sinking into a life full of alcohol, drugs and bitches (although I would like to try this at least for a shorter period of my life...

). Even if you don't achieve anything (but you will, since smart failures imply learning a lot) it is much fulfilling to spend even a decade by fighting for yourself than embracing a never-ending bad situation.
My main concern is that my exit ramp doesn't lead directly into just another but different rat race.
Read the "E-Myth". Its main topic is that people who are fed up with their job and start businesses are often only good technicians without having experience with entrepreneurship (strategy) and management so theiy end up in a worse situation then their job was: theiy become the slave of their own (shitty) "business". With some preparation and self-education this can be avoided.
Trials and errors. Many people make the mistake of giving it a single shot and then give up. If you fail you can start over, it is still better than giving up and going back to slavery. You can never reduce the chance of failures to 0% but failing many times and learning from it will definitely help you to push your error rates (far) below 50% and that is enough. Learning how to run a business is much like playing poker, not like playing the lottery. After some time you find the ways and you will be good (take a look at serial entrepreneurs, they are the proof that my statement is right).
Another problem: many people think about very serious things and people in suits when they hear the word "business". This is complete bullshit and it unnecessarily demotivates many from trying to get money from other sources than selling their time. Most business owners at the top of the hierarchy wear no suits at all and you may not even meet them in their company/office building. Some people like suits even in everyday life but at work it is often the outfit of slaves who work a bit higher on the ladder. A business can be as simple as buying something and selling it for somewhat more money but this is just a simple example, it can be anything that gives good investment/return ratio. There are endless number of ways to make money. One has to choose some of them based on expectations/skills and evaluate them (trial/error). One has to invest effort/time/money to do this.
The things I want the freedom to do actually require significant investment from others, so the only way to preserve that freedom is to choose those others and the attendant circumstances with care. Otherwise, extricating myself would be relatively easy.
Becoming successful requires only your efforts but help may come in handy (or hold you back - this is a typical reason why so few people make it through). "Extracting yourself" is difficult even if you are alone and you are a natural born lonely wolf.
Then the crack closes up for another few generations and reality presents a seamless front to keep us in our rightful place.
There have always been such cracks in history. The only thing that changes is the number of cracks and the difficulty finding them. On the other hand it is not a "rightful" place. From life you get what you negotiate for yourself not what you deserve. Some people are lucky and born into a rich family but luck is always part of a game and it changes only your starting point (that is a significant factor). It isn't your fault if you have born as poor man but it is your fault if you die as one.
Most of us want what the 'rat race' brings, like a home and family, social status, an education, good health care, annual holidays, and a sense of belong and contributing to society.
To sacrifice all this for radical freedom is rare.
And most of us wouldn't know what to do with radical freedom if we had it, except for those driven to write new literature, or compose new music, or make scientific discoveries, or create new ideas, or found new companies, or to commit to the spiritual life, or found religious Orders.
I also wanted it and being a laid back lazy ass ISTP I was very envy of others when it came to their mediocre life that was much better than mine. My life became very-very shitty quite early and I received huge shocks that forced me to behave crazy and try things I would never try in a "normal" mediocre life. After researching and trying alternative ways I've realized that it is much easier to reach better than mediocre life than most would think but you have to be able to push against expectations.
No, most of us want the security of treading well worn paths, we want the security of mouthing cliches that have already been in too many mouths, we want the security of striving for the milestones set by our society, and when we die, we want society to say we had a well lived life and left a generous estate. Let's face it, we want the security of being good girls and boys. We figure that if we do as we are told, we will be looked after.
Lies + inauthenticity + false assumptions. You indeed get nice things from a mediocre life but you have to pay way too much for it. Alternative paths have a lot of treasures and I'm pretty sure that most people wouldn't switch back to mediocre after being able to taste something else.
This is very difficult for Americans to face because they have a mythology of radical individualism where the maverick is celebrated and the faithful worker is called a loser. Or worse, you regard yourself as a rat in the rat race.
Good. At least they celebrate for the right reasons and this part of the media is not lying.