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In the French language, I'm searching for a natural way to say,

How do you expect to break a habit by willpower alone which you couldn't for the last thirty years?

and I'm having difficulty in how I should say "How do you expect to --- ?". Is "Comment peux-tu espérer --- ?" natural French? Here's my try,

Comment peux-tu espérer arrêter une habitude avec une volonté seule que tu n'as pas pu pendant les trente dernières années ?

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{Your version}: Comment peux-tu espérer arrêter une habitude avec une volonté seule que tu n'as pas pu pendant les trente dernières années ?

Unfortunately, your phrasing does not sound idiomatic enough as is. I'd avoid using a relative pronoun here in favour of the conjunction "si".

Given the rhetorical nature of the expression "How do you expect to ...?", I'd go for the structure "Comment veux-tu que ...?". How about:

Comment veux-tu qu'on se défasse/débarrasse d'une mauvaise habitude ancrée rien qu'avec (de) la volonté si on n'y est pas arrivé depuis une trentaine d'années ?

Or, less literally:

Tu essaies de t'en défaire, cette fâcheuse habitude, depuis quand déjà ? Une trentaine d'années ? Le temps est révolu où la volonté suffisait pour ça.

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    Note that using "on" brings an extra level of undefinition that isn't in the OP's question
    – Laurent S.
    Aug 6, 2018 at 15:16
  • About "on", I don't know if I rightly understand it, but "on" is used when speaking of a general statement, am I right? I was not speaking about any personal statement. "You" was intended as a possible everyone, not someone personal. Thirty years of a bad habit is difficult to break for anyone. This is what I wanted to say. Is this why "on" is used?
    – Carol.winter
    Aug 6, 2018 at 17:29
  • @Carol.winter Yes, if that's what you have in mind. If you want to make it sound personal, on the other hand, you should stick to "tu" throughout, as shown in my 2nd version. By the way, I forgot to include the idea of "alone", so I've just edited it in.
    – Con-gras-tue-les-chiens
    Aug 7, 2018 at 22:41
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"Comment peux-tu espérer..." is correct. Another way to phrase would be "Comment comptes-tu..." or (older vocabulary) "Comment escomptes-tu..."

In my opinion the problems in your translation are with the rest :)

  • the expression closest to "break a habit" would be "rompre une habitude", "se défaire d'une habitude" or "se débarrasser d'une habitude" (not that arrêter is completely wrong, but doesn't sound idiomatic)

  • "which you couldn't do for the last 30 years" is a bit of a sarcasm — it stands in stark opposition to the beginning of the sentence. That may benefit from the opposition being marked explicitly in French by an "alors que".

  • Personally I perceive the emphasis of your original sentence to be on the fact that the person has been trying to kick the habit for 30 years. To translate this emphasis in French, using "ça/cela fait 30 ans que..." sounds appropriate.

Here's my suggestion:

Comment comptes-tu te défaire de cette habitude par ta seule volonté, alors que cela fait trente ans que tu essaies sans succès ?

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  • "escompter" is really outdated from where I see it... your example will be much more actual simply with "comptes" : "Comment comptes-tu te défaire..."
    – Laurent S.
    Aug 6, 2018 at 15:14
  • @LaurentS. Ajouté, merci
    – qoba
    Aug 6, 2018 at 15:16
  • Thank you everyone. I'm surprised at so many different ways to say this. @LaurentS. About "comptes" you proposed, is it okay too to say, "Comment peux-tu compter sur la volonté pour te défaire de cette habitude"?
    – Carol.winter
    Aug 6, 2018 at 17:21
  • @Carol.winter it's grammatical but has a slightly different meaning. In English it would be "How can you expect willpower to help you break this habit", meaning that willpower would be the agent breaking the habit, rather than the person being talked to breaking the habit using willpower. Sounds a bit less natural to me, as a result.
    – qoba
    Aug 7, 2018 at 21:42
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i would go like this:

Comment veux-tu te débarasser d'une mauvaise habitude par la seule force de la volonté alors que cela fait trente ans que tu n'y parviens pas ?

willpower would translate in something closer to "strength of will"/"force de volonté". and i would use the verb "parvenir" to show the distance between the unreached goal and the beginning. "comment peux-tu espérer" would also fit for the start, but shows a more sophisticated level of language. "comment veux-tu" sounds more classic/idiomatic/familiar/natural.

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  • I will give an upvote to this one because the provided example is the most natural compared to other answers. There are many valid combination that still would be natural though
    – Laurent S.
    Aug 6, 2018 at 15:18

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