Should one feel guilty for being ambitious?
Harmful ambition vs. beneficial ambition?
Is being ambitious necessarily bad?
If not, how can it be good?
Thoughts?
Desire for advancement in the dhamma is a necessary motivation, but the path is conditioned while the goal of the path is unconditioned, so that necessary ambition is eventually abandoned. For all practical purposes ambition is necessary.
“Brahman, there is the case where a monk develops the base of power endowed with concentration founded on desire & the fabrications of exertion.”— SN 51.15
In the context of the higher fetters ambition is known as conceit for the level of one’s own practice and is a necessary motivation right up until the last stage:
“‘This body comes into being through craving. And yet it is by relying on craving that craving is to be abandoned.’ Thus was it said. And in reference to what was it said? There is the case, sister, where a monk hears, ‘The monk named such-and-such, they say, through the ending of the fermentations, has entered & remains in the fermentation-free awareness-release & discernment-release, having known & realized them for himself in the here & now.’ The thought occurs to him, ‘I hope that I, too, will — through the ending of the fermentations — enter & remain in the fermentation-free awareness-release & discernment-release, having known & realized them for myself in the here & now.’ Then he eventually abandons craving, having relied on craving. ‘This body comes into being through craving. And yet it is by relying on craving that craving is to be abandoned.’ Thus was it said. And in reference to this was it said.”—AN 4.159
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Added:
This is a really excellent talk by Ajahn Brahmali, that is directly relevant to the Opening Post. It just keeps getting better as it goes on, so watch/listen to the end 
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Ambition is craving:
DN33:1.10.38: Another three cravings: form, formlessness, and cessation.
These cravings give rise to grasping:
DN33:1.10.46: Three searches: for sensual pleasures, for continued existence, and for a spiritual path.
Only the third can lead to the end suffering.
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In the context of dhamma practice distinction should be made between suttas that refer to the path (conditioned) and the goal (unconditioned) and western Buddhists are prone to overlook the former and focus only on the latter. Such suttas can often be identified by who delivers them or who they are addressed to. For example both those I have quoted above are spoken by Ananda so can be expected to deal with the view from the path, while unless identified otherwise those spoken by the Buddha deal with the arahant’s view. Western Buddhists should therefore base their practice on the suttas describing the skillful use of conditioned phenomena such as desire, craving and spiritual competition rather than erroneously imagining practice from a position where nibbana has already been attained and such qualities have been abandoned.
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A wonderful find!
To be looked into. Thank you for sharing.
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