There's many aspects to living philosophically, mainly subjecting ones' existence and will to constant questioning. Not to be confused with 'questioning oneself', this practice allows one to confront his own understanding of reality with that of reality itself while assessing his own free will into the same equation. Let's see what Epictetus has to say about it.
To maintain our prohairesis (moral character) in the proper condition – the successful accomplishment of this being necessary and sufficient for eudaimonia (‘happiness’) – we must understand what is eph’ hêmin (‘in our power’ or ‘up to us’; see Handbook 1 and Discourses 1.22.9–16). If we do not do this, our prohairesis will remain in a faulty condition, for we will remain convinced that things such as wealth and status are good when they are really indifferent, troubled by frustrations and anxieties, subject to disturbing emotions we do not want and cannot control, all of which make life unpleasant and unrewarding, sometimes over- whelmingly so. This is why Epictetus remarks: ‘This is the proper goal, to practise how to remove from one’s life sorrows and laments, and cries of “Alas” and “Poor me”, and misfortune and disappointment’ (Discourses 1.4.23)

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