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Let's think this through...on the one hand, you're judging yourself for not having fulfilled the potential you think you have ACCORDING TO OTHER PEOPLE and on the other hand you're bemoaning you're too nice a guy to have GOTTEN A WHOLE LOT OF ATTENTION.

Which do you want? Other peoples attention or none at all? The real trick to becoming all you can be is to NOT CARE how much attention other people give you...

Here's a thing to reflect upon. You were clued in enough to get into college (OK...you haven't completed it YET). You're smart enough to have got a job (OK....it ain't your dream job YET). You're proactive enough to have sought advice from your GP and your boss (OK...they haven't been the ones to sort your issues YET). All these things are impermanent and can form the foundation of your future dreams/goals if you want them to be.

And put this into perspective...to a lot of ladies, your lack of experience / nice guy / lack of conceit / appreciation for their company will become a bigger and better asset as you age. Women at 25 think they want all bells and whistles - in their 30's they start to twig the value of a GOOD man (at least, the ones worth falling for do).

Here's my advice - forget hookers. Forget looking outside for someone else to fix your problems. Look INSIDE. Take a deep breath, get very STILL and stop fixating on the past or the future. Fix on the NOW. You're healthy. Intelligent and articulate. Employed. Canadian. That's not half bad :)

If you're into taking your life into a stiller, more fulfilled place, I can't recommend Eckhart Tolle 'The Power of Now' enough. Read it twice and let it sink in. I guarantee it'll make a much more significant difference to your life than a 100$ hooker. Link to book on Amazon.ca

I've read that book. I've tried living in the moment and lost a job, because I wasn't really working efficiently.

Since that, I've also read a few books on mindfulness, such as:
"Mindfulness (Kindle Enhanced Edition): A Practical Guide to Peace in a Frantic World"
http://www.amazon.com/gp/product/B004TTHD9O/ref=oh_aui_d_detailpage_o09_?ie=UTF8&psc=1

Choose the Life You Want: The Mindful Way to Happiness
http://www.amazon.com/Choose-Life-You-Want-Happiness/dp/161519195X

and was trying to practice mindfulness and observation a lot (maybe, sometimes, too hard), but the thing is, by following the books to the letter puts me in a state, where I can't do anything I want. I can eat and probably go to a shop, but I can't put myself to work or even exercise in a focused way. Also, in this year, life has taught me that doing is more important, than observing. Having dreams is alright, it seems.

By focusing on the external world my thoughts go into complete disarray and just observing them doesn't do anythng, because I don't do anything. For example, I'd lie in bed since morning till night just observing my breath, watching life passing by.

That's why I switched back to the "doing mode", at least it lets me function and not let down the people that depend on me (including employers).

What would you say about this or advise me? Thanks.

I know many people who loved and swear by The Power of Now, but it didn't do it for me. Too spiritual. I recommend two books by the Arbinger Institute. Leadership and Self-Deception: Getting Out of the Box and The Anatomy of Peace. They are both written in a narritive style so they were easier reads for me while still giving the insights and more specifically, the actions, that helped me.