@Moreira Yes, there are many hippies and bums in Hawaii. But I did not say living on the beach like a bum. I said buying your own land and building a small shack. That is very doable if you save up some money. In Hawaii you can even live off the grid using solar panels and a rainwater catchment tank. Heating and A/C are virtually unnecessary there.
See my Hawaii solo retreat blog videos.
Also, you don't need to slave. Learning how to make money is not hard. There many ways to earn six figures per year and enjoy the process. You just need a vision to do it. You can't be doing it out of a desire to become a bum. Cultivate a desire to genuinely contribute to humanity. It is so much more fulfilling and pays well when properly designed.
Learn some business, sales, and marketing skills. This is easily acheieved online through courses, workshops, audios, and books.
You also need a plan for getting old. Your health will worsen and so will your ability to work. Healthcare ain't cheap. Don't take stuff like healthcare for granted. Without government you'd probably die in your 50's or 60's due to lack of healthcare, disablity, etc.

I don't know who trungpa is.
If a teacher is an asshole, then yeah, I'd say he's got some devil in him. He has more work to do. He can be awake but he has a repressed shadow which needs work.
There are also degrees of awakening. Such a perosn may not have awoken to absolute Love for example, which is why he's still an asshole. It's pretty easy to realize no-self without realizing God or Love or Goodness and be an asshole.
Which is why a good Zen master will drive his students to go deeper after their first kensho. The first kensho is just the beginning. A good master will not let a student stop at the first kensho. There is what's called post-satori practice.
"If you cannot weep for a person who is crying, there is no kensho." -- Yamada Koun

Ken has a very robust grasp of awakening and nonduality, and much more.
His work is not just about awakening, it is about stages of development and various kinds of pathologies in this work.
Awakening is independent of one's stage of development. Both are important. To awaken but still be stuck at a low level of development is very common and dangerous.
If your teaching only emphasizes awakening and nothing else, it is a narrow and incomplete teaching which will produce a lot of problems if it's taught to lots of people.
Stages of development are extremely important and yet they are virtually unknown to most teachers and traditional teachings. Which is why so many spiritual practioners come out half-baked.
You cannot understand stages of development by sitting on a meditation cushion, even if you are the best meditator in the world. Introspection is not enough.

The dirty secret is that you can't help but be aware 100% of the time. Notice that you are always aware! It's impossible not to be aware unless you're dead.
Past and future cannot exist without awareness.
Nothing can exist without awareness.
So you are already 100% aware all the time.
You just need to sit down and be quiet and you'll notice it.
That's why do-nothing works.
And why distractions and addictions make up your lifestyle.
If you remove every single distraction and addiction in your life, you are pretty much guaranteed to become enlightened automatically.
But you're not gonna do that, are you?

You're not gonna be able to sustain more than 40 hours per week for long. Programmers burn out and destroy their health all the time.
You should research why we have a 40 hour work-week.
Where did it come from historically?
Do you know that Henry Ford and other industrialists of the early 20th century actually commissioned studies to find out the optimal amount of the time their factory workers should be working to produce the highest output and thus earn them the most money?
And you know what number they came back with?
40

When you meditate, stop manipulating your experiences in any way. Just sit and accept everything as it is.
Do you see that on a meta-level, what's happening right now with you, is that the ego believes it can control this process. It's trying really hard to be a good meditator. It thinks it can stop mental images from arising. It thinks that mental images are somehow undesirable.
All of this is of course ludicrous because the ego doesn't exist and has no control. The manipulations are just additional layers of delusion of which you have no control.
Whenever you notice the urge to control something in your meditation, just drop the need. Soon you will enter a kind of very deep, calm flow state and you'll actually start smiling because you're finally accepting reality exactly as it is = happiness.

@FunBun Emotions are very tricky. What's required is mindfulness practice over them, and also getting to the bottom of why you feel the need to emote in those ways. See, those emotions are how the ego-self survives. So who you are results in those emotions getting acted out. Changing who you are will change those emotions and vice versa.
Psychedelics are one of the most powerful tools for showing you a way past all that egotistical acting out. See, right now you don't even know what it means to be free of it. So it will be very tricky to stop acting out.
You need to become deeply conscious that you are "doing" emotions as a means of ego survival. The emotions are there to keep the ego intact. The whole process is ruthlessly efficient and very tricky to stop because it is a matter of life and death from your POV.
To change those emotions you will have to REALLY change. To become like a whole new person.
How you define yourself is what then gets emoted. Take a look at how anger, fear, judgment, guilt, jealousy, etc. are serving to maintain your self-definition, your self-image, your persona. How would you have to change your self-image such that your habitual angers, fears, judgments, and guilt no longer needed to arise?
What are all those emotions defending?
This is a big can of worms which will take some serious work to sort out. But it's worth it.

The trouble with that approach is that it's sourced from a deep neurosis. You're basically in conflict with yourself, disowning parts of your psyche, and trying to bull your way through towards some idealized future which -- even if it comes -- will be deeply disappointing because you will one day realize that you whored yourself out for success. If you use this approach, you will become the stereotypical businessman who makes a killing on Wallstreet and then hangs himself one day from the ceiling fan.
All your achievements in life are ultimately pointless and produce very temporary doses of satisfaction because of hedonic adaptation. What you need to do is to learn how to derive joy from being, not from doing.
A good approach for you would be to do almost the exact opposite of what you suggest. Which means, practice self-compassion, self-acceptance, and a slow relaxed, easy-going pace. Learn to enjoy life rather than enjoying some idealized future.
All that said, I don't mean that you don't take action. You still take action. But from a place of self-acceptance rather than a place of lack, as you're doing now.
This is another one of those counter-intuitive moves I always talk about.

@MM1988 Notice how egoic your perspective is. Just the fact that you are evaluating the fairness of life based on how much sex you do or do not get, is absurd. As if the universe cares about how much sexual pleasure you receive. No one cares about that but you. It's got zero importance at all in the big picture.
Also notice how you assume that if you don't have sex, then some other guy will have sex instead of you. This is a horribly warped and biased way of looking at things. Most of the time when sex doesn't happen is has nothing at all to do with another guy stealing that sex. Sex fails to happen for many reasons, many of them valid. A lot of times sex fails to happen because it was not supposed to happen, because the chemistry was missing, because you two were not a good match for each other, or simply because the logistics and timing was bad.
Nobody owes you sex. And nobody is competing with you for sex. Drop these toxic mindsets.
Relate to the whole woman. Right now you are relating to the sex.
The valid way of looking at things is: "Sexual pleasure has zero importance. If it happens, great. If not, oh well, I got important shit to do."

Be more mindful that you're using mindfulness mindlessly
I think you've defined mindfulness too narrowly, as something associated with focusing on your breath. When in fact it's much broader than that. You gotta be careful not to become a mindless meditation machine.
Try practicing mindfulness without focusing on your breath, and while doing activities such as light chores, house work, cleaning, showering, driving, watching TV, and even talking to people. This will push your mindfulness abilities outside of their currently constricted pigeon-hole.
And when in comes to doing practical thinking/planning, allow yourself to get into it and to flow. In pursuing mindfulness we tend to swing our pendulum too much to one side and demonize all thinking as evil. Thinking is not evil. This needs to better integrated in you. Thinking is useful in proper proportions and situations.
The only thinking that's really problematic is the I-thinking. That is, thinking about the me, me, me, me! all the time.

This is a problem of lack of authentic relating. The next time you relate to a human being, try to do it from a place of 100% genuineness. Only say exactly what you think and feel and not some polite bullshit. Then when you say "I'm sorry" it will be coming from an authentic sense of feeling sorry, and not just empty words, or even worse, lies.
In general, try to clean up your language so that whenever you say some words, you really mean them. << That's a great self-improvement exercise. You could turn it into a 30 day challenge. It will grow you a lot.
Re-watch my How You Lie video. It's addressing this very point. What you're basically doing right now with people is lying. And it makes you feel hollow inside.

There are a lot of weird state-experiences that can happen during meditation. You could have life-like hallucinations of giant spiders crawling around you, or of Jesus coming to bless you, or the Buddha, or people's faces can start to warp and distort, or you may see bright lights, or images of demons, or total blackness, or an explosion of energy in your head, etc.
All of that is called Makyo in the Zen tradition. Literally it means, "abode of the devil". It's all a distraction from truth. It makes you feel like you're making progress or gaining some deep spiritual insight when in fact you're identifying and getting lost in sensory phenomena. It's the devil playing tricks on you, testing to see if you're wise enough to distinguish between truth and illusion.
The important thing to remember is that enlightenment is NOT a state! It is not an emotion. It is not a sensory experience. It is not a high. It is not some blissful light, or any other thing you can imagine. Everything you can perceive or imagine is guaranteed to NOT be enlightenment.
Enlightenment is the Truth! It is what you are! You are it ALWAYS! You cannot ever not be it. You're IT right freaking now as you're reading this sentence. No special state is required. Truth is ALWAYS present. In fact, it's the ONLY thing that's present. It cannot EVER be lost. You already are enlightened! (You just don't know it.)
The only problem is that your mind doesn't know what to do with this. The mind only knows how to conceptualize. The mind only knows illusion. It cannot know truth no matter how hard it tries because truth isn't something that's known, it is BEING itself, and it is not an object. Absolute Truth is indescribable and unimaginable. It has no shape. It is not even an "it". It transcends even existence and non-existence. Absolute Truth is ETERNAL -- it NEVER changes. Ever!
Instead of trying to attain a grandiose meditative state (and I've been guilty of this myself A LOT), try relaxing your body and mind and focus on genuinely wondering, "Who am I really if I'm not the body?" or "What is true independent of all phenomena?" or "What is it that's aware of all of reality?"
Hint: don't neglect the possibility that you may literally be nothing at all
Ask yourself, "What is the only 'thing' that could be ETERNAL, untouchable, and indestructible?"
Also make a distinction in your experience between meditation and self-inquiry. Lean more towards self-inquiry vs meditation if you wanna get enlightened faster.

There is an important difference.
Firstly, let's make sure we're on the same page as to what contemplation means. Contemplation in the context of enlightenment work is equivalent to self-inquiry. Don't let the word contemplation fool you. It does NOT mean: sit there and think about stuff. << That is NOT contemplation, and that will not get you enlightened. Contemplation really means: directly experience your true nature right now! Focus deeply on only question: Who am I? or What am I? And probe it experientially for 30 to 60 minutes like a laser beam, never wavering.
Meditation is sitting down and literally doing nothing. Letting go of all control and letting your monkey mind run as you observe it. There is no goal in meditation. You just sit and accept reality exactly as it is, no matter what is happening. Meditation is helpful for enlightenment work, but it's not as direct as self-inquiry/contemplation.
 

Yes, this is called the Upper Limiting problem. You actually do have an upper limit for how much happiness you allow yourself to feel in a given day/week. Anything over that limit feels uncomfortable and even scary. Because fundamentally you haven't developed your psyche enough to open yourself up to being penetrated by love. Deep down the ego FEARS love and it fears life.
What to do?
Gradually practice expanding your ability to feel love and joy. Be very mindful of those moments when you have more love than you can handle. And stretch yourself a bit to stomach just a little bit more than the last time. Tell yourself, "I have the courage to open myself to more joy and more love."
Being happy is actually like a muscle. If you haven't used it for a long time, it's very weak. You gotta flex it gradually over the weeks and months and years to build it up to the point where you can wear a shit-eating grin on your face all day long for absolutely no reason. << That's not easy to develop to. You gotta really work out many of our inner demons.

@bmcnicho Sounds like you are right where you ought to be given your age and lack of life experience. I was/am very anti-conformist like you. Nothing wrong with that. It's just a part of your personality. It might mean you should be a leader, a boss, a solo artist, or just off doing your own thing. This is great. In this case you will have to build yourself up and lead yourself a lot before others start to follow you.
Don't be afraid to carve your own path in life. Maybe consider starting a business within a field you are passionate or curious about.
A traditional cookie-cutter college major or job is probably not right for you. You need something more custom, more your own.
Autistic is also okay. Just part of your personality type. You just need to find a career/purpose which leverages that.
The best way to pursue truth is via yoga, contemplation, philosophy, self-inquiry, and/or psychedelics. So I would build experience will all the above and see how that feels for you. If you really value truth you should love all that.
Try to think about what kind of career would be most aligned with your personality and the value of truth. It's basically that simple. Don't beat around the bush. Nail your top value.

One of the things that I find myself struggling with again and again is not necessarily facing the emptiness of being but the loneliness that tries to creep back in when I start to realize how few people are able to relate with the importance of solitude and doing the inner work. That's why I really appreciate this video: 
This is exactly the challenge that I face now. I don't have a large family. I'm not married. I don't have any kids. I don't have a significant other. Don't need one. I use social media sparingly. I'm a former programmer. I now work 20 hours per week in the mental health field and spend the rest of my time working on myself (by myself) as much as possible. I live a very minimalist life and have discovered a great deal of internal wealth in the process. But to be honest, even though I have made peace with solitude and practice facing the emptiness daily and practice experiencing being, there are times when I want to connect with others who are further along in the process. In person, that's looking less likely by the day. Online, maybe. I know there are some. They are hard to find. That neediness to connect with others that I'm observing in myself is counter to embracing the emptiness of being, and it comes and it goes, but it returns. I've started drastically limiting my social media use. It has become depressing to see how many people are completely offline inwardly as they immerse themselves online outwardly in non-stop dick and fart jokes or airy fairy spiritual memes. I know that sounds like a judgmental thing to say but that's how it feels. The more I work on myself, the more I feel less of a connection on those deeper levels with others, and I know that's part of the process, but Leo's right, it does get lonely. I'm not trying to condescend. I know it's fear that they are dealing with and that they are so terrified of sitting alone with themselves that they distract themselves endlessly and never begin to look inward. I was like that for a long time. I still need some distraction too but it does get lonely when you realize that there are very few who can appreciate the importance of solitude. It's a total paradox, but I actually feel less alone when I'm all alone than I do when I'm interacting with people who are operating on low consciousness levels which is almost everyone I know with the exception of just a couple of people who I have run into online. Can anyone relate?