Hmmmmm. I live in a fairly easy going part of the world - Dunedin, New Zealand - a small university town in the country's South Island. I am a recording artist/musician, run a web-site and sell my product online (in little sporadic bursts ) And no, this isnt an ad. It relates. Ha ha. Thus environmentally the conditions surrounding my life are very much more relaxed than say, a stock-broker's in Frankfurt. These conditions are a good compromise between the absolute hermit/mountain dwelling devotion of a chinese daoist monk in the 14th century and the ruthless hustle of late modern capitalism. I am blessed to have the time and space to at least attempt to live a daoist lifestyle whilst participating in a system i simply must play ball with. I have attempted to gradually reduce outlandish desires and their many variations from my everyday life - noting the cumulative stilling of my being with each new reduction. Being a musician i have been able to observe first hand the folly of excessive ambition. I have observed many artists approach insanity as they over-estimate the happiness desire and ambition can bring - beautiful, creative people ultimately depressed and their soul destroyed when the industry fails to provide for them. Actually - that was ME fifteen years ago (without the beautiful bit). It was these experiences that pointed to the wisdom of rejecting ambition - of yielding , of just being content with simple acheivements - financial or artistic or personal. Just living a quiet, (as 'uncool as it might seem to those crazy nihilists i know) simple, self-contained life - in tune with the seasons, yielding to and neutralizing situations and people that try to stir this up, yet, as Jacksquat mentioned, including others/society/community in your environment - yielding-to to while one participates-with. To live in the Way as a city dwelling westerner one needs first an income/roof over ones head. So, i suppose - do what you gotta do. In some countries - welfare is available, in others - you better flip burgers or something. But make sure you can pay the rent. (I often think back to the 19th century with its aristocratic rich kids spending their days drugging and invoking demons - lucky lucky them). Second, one needs to actively reject/neutralize the ubiquitous and mind-numbingly repetitive barrage of multi-media advertisments, to not buy into their messages, to not let them aggravate ones passions, to be courageous enough to be happy with what one has - in a word:voluntary simplicity (VERY subversive). Third, one needs to monitor and be mindful of oneself, ones mind, thoughts, emotions, habits - to gently keep oneself in check. Observe the interplay of yin and yang in the world. Observe it in oneself. Join a tai chi group - there you may meet others like you. One needs to know the skills of re-using and recycling. One might grow ones own food.
As far as my 'success' with these methods is concerned - well - from when i discovered Daoism up to now, I have calmed down so much - my friends always tell me this ha ha, but of course i still have much to iron out. But i am only young and the path is lifelong. One must focus less on results and more on process - one of the main tenets of tai-chi. i think the thing may be to not actually give up ambition or effort . It is to make them real - aligned with nature - harmless and with longevity in mind.
One will find oneself more and more at odds with the modern capitalist agenda. daoist quietism, self-containment and wholism is absolutly anathema to it. If you live in one of the northern hemispheres great cities, maybe you could consider moving to the country, or to new zealand. ha ha.
So, for me, it took a brush with the madness of rock'n'roll and many horrible first hand experiences to teach me the futility of ambition. Ugly, plastic, unnatural human ambition.