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If I were to challenge a great intellectual, who knows his area extremely well, on one of his points he has made; thinking about how I can repudiate his argument, how I will phrase my counter-argument, how I will back it up, and, above all, whether or not I should open my mouth in the first place could be an intimidating experience, one which induces a lot self-doubt and entails a great deal of reluctance and second-guessing.

What would be a good adjective to describe that experience and capture all the connotations I pointed to?

Thanks!

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    A "humbling" experience, perhaps? – Curtis H. Nov 27 '14 at 1:59
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    It is relevant to the scenario, but does not quite capture the sense of 'risk' in the attempt at a counter-argument. Thanks for your comment! – asef Nov 27 '14 at 2:19
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    A subjugating, trying, nerve-racking, self-questioning(triggering), challenging... life threatening, and, of course, doubt-inducing experience. – user98955 Nov 27 '14 at 6:27
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I think you said it yourself in your question. It is an intimidating experience.

to make timid or fearful (source)

to overawe or cow, as through the force of personality or by superior display of wealth, talent, etc. (source)

Another option might be daunting.

to lessen the courage of; dishearten (source)

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Forbidding

1 : such as to make approach or passage difficult or impossible

-- merriam-webster

In such a situation, one might pause, take a deep breath, gather resources, and plunge in or forge on.

So you would have

An experience that induces self-doubt is a forbidding experience.

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You can consider dubious.

causing doubt, uncertainty, or suspicion : likely to be bad or wrong

Below is an example that exactly fits to your situation:

Someone with not half his years, not a tithe of his experience, and none of his expertise in the subject, will challenge him. Often the challenger will be someone who has an ax to grind, or someone who has had some dubious experience, or someone who has uncritically accepted a contradictory statement, or someone who has strung together a few texts taken out of context. I have met them all!

[Exploring Proverbs: An Expository Commentary By John Phillips (2002)]

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Confounding - adjectival form of:

con·found verb \kən-ˈfau̇nd, kän-\

: to surprise and confuse (someone or something)

: to prove (someone or something) wrong - merriam-webster.com

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And please break up and/or rephrase that sentence. It is too long and complex; plus, it begins with an "if" which is never resolved. The simplest fix is to add "; it" before "would". To make your sentence more organized and digestible, I would be inclined to set off your list of doubtful thoughts as parenthetical, either with actual parentheses or with em-dashes, thus: "(thinking about...,...first place)" Or "—thinking about..,....first place—" As for word choice, I like "daunting", as it seems to best capture most of the elements you mentioned.

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