I wish it didn't, but the Lenten season always sneaks up on me.
The prayer and contemplation that I would like to put in prior to the season typically manifests itself as an "O crap. It's Ash Wednesday" and a cursory review of things that are filling up where the Spirit should be.
In high school, it was typical to give up chocolate or caffeine. One year at university, I gave up email and instant messaging (this was before both were a common necessity for classwork). I've practiced fasting and turned the TV off. Given up secular music and committed to purchasing only necessities. And admittedly, my eyes where often not fixed on the goal during those seasons, but rather my on own personal appearance of holiness.
And of course, Lent is supposed to be about Jesus...
It is a time of reflection and refreshment through sacrifice. It is a time to remember the wondrous life of Christ, His death on the cross and His resurrection to new life.
Lent is a time when Jesus asks us to the garden to pray, saying, Pray that you will not fall into temptation and again, Why are you sleeping? Get up and pray (Luke 22:40,46).
If you don't typically commemorate Lent, I would recommend it to you. Take something away for a season or add in a new habit. Care for the orphan and the widow. Love your neighbors and seek first the kingdom. Render to Caesar what is Caesar's and to God what is God's. And let us run with perseverance the race marked out for us, fixing your eyes on Jesus the author and perfecter of your faith. For the joy set before him, he endured the cross, scorning its shame, and sat down at the right hand of the throne of God. Consider him who endured such opposition from sinners, so that you will not grow weary and lose heart (Hebrews 12:1-3).