I wrote these up a couple of Lents ago, but I think they are still helpful in our discernment of how we may enter into this 'joyful season.'
1. The classic models of fasting, praying, and giving alms are the best starting point. Concentrate on one or do something for each.
2. Make it too challenging and be set up for failure; make it too easy and lose interest.
3. All spiritual practices can be misused to focus on self rather than God. Be careful.
4. "Giving up" something that is already objectively sinful doesn't count; ascetical effort at reorganizing our lives to eliminate occasions of sin does.
5. Spiritual practice and prayerful ascesis that also serves physical health is nothing to be ashamed of.
6. Everyone knows that Sundays don't count, but don't make the Sunday relaxation an occasion of backsliding.
7. Doing something is easier than not doing something.
8. Doing something for others is more blessed than doing something for yourself. But if you habitually fail at spiritual self-care, this principle isn't an excuse to continue.
9. Pelagianism is a heresy, but the idea of it is not an excuse for laziness.
10. The engineering principle known as the "airplane rule" is useful here: complexity increases the rate of failure. Conversely, simplicity increases robustness.
11. Secret practices are better than ones that will be obvious to everyone. Secret saves us from both vainglory in success and embarrassment in failure.
12. Succeeding in observing a practice does not mean it was a spiritual success, and failing does not necessarily mean spiritual failure. Successes used poorly can be spiritually ruinous, and failures used well can be providential occasions for learning humility and honesty.
13. Concrete is better than vague.
14. This is not about our doing or accomplishing something, as if salvation were another thing for us to "do" or "get." It is about surrendering and responding to grace. As Paul says, "God is the one who, for his good purpose, works in you both to desire and to work." (Philippians 2:13)