Looking at the temptations of Jesus we see that He was tempted first with material things, comfort, and then vainglory and finally pride. What are my weakest points?
Here is something helpful from Thomas Merton for Lent:
"It is necessary that at the beginning of this fast, the Lord should show Himself to us in His mercy. The purpose of Lent is not only expiation, to satisfy the divine justice, but above all a preparation to rejoice in His love. And this preparation consists in receiving the gift of His mercy — a gift which we receive in so far as we open our hearts to it, casting out what cannot remain in the same room with mercy.
Now one of the things we must cast out first of all is fear. Fear narrows the little entrance of our heart. It shrinks up our capacity to love. It freezes up our power to give ourselves. If we were terrified of God as an inexorable judge, we would not confidently await His mercy, or approach Him trustfully in prayer. Our peace, our joy in Lent are a guarantee of grace.
In laying upon us the light cross of ashes, the Church desires to take off our shoulders all other heavy burdens — the crushing load of worry and obsessive guilt, the dead weight of our own self-love. We should not take upon ourselves a 'burden' of penance and stagger into Lent as if we were Atlas, carrying the whole world on his shoulders.
Perhaps there is a small likelihood of our doing so. But in any case, penance is conceived by the Church less as a burden than as a liberation. It is only a burden to those who take it up unwillingly. Love makes it light and happy. And that is another reason why Ash Wednesday is filled with the lightness of love."