One of the major challenges of the Saturn Return is to identify what isn't working in your life and then acting upon that to make real changes.
Perhaps the biggest challenge is admitting that something isn't working. It is odd that this is a challenge because most likely what isn't working is causing us pain, frustration and taking up the space that could be filled with something that gives us pleasure and satisfaction.
Enlightenment came as I listened to an interview with Kristin Neff who teaches about Self-Compassion. She explained that if we have been using self-criticism as a motivator then we become afraid of failure because we know we will beat ourselves up.
It is a very short step from admitting something isn't working.... to blaming ourselves for what went wrong, for taking that path in the first place, for not trying hard enough, for mistakes made along the way. And if our inner coach is a slave-driving, drill sergeant, then we know we are about to get internally blasted.
The effect of this is that we can tense up, hunker into ourselves and resist taking anything that looks like a risk - anything where failure might be lurking. The other effect is that we hold onto things for far too long - long after it is clear that it is not working for us - trying to stave off that label of failure, to delay those harsh, punitive words, the endless, internal put-down.
Saturn does not need to be such a hard task master. It is not Saturn who is judging us. Saturn as teacher points out that much of our learning is through trial and error - we learn from our experiences. We need to try things out and see how they fit - whether they work for us or not. When something isn't working Saturn encourages us to cut our losses. To take the learning of what didn't work and try something different. Saturn teaches us that knowing what doesn't work is an essential part of the journey to knowing what does work.
In the tarot there are many cards that touch on Saturn matters - but it occurred to me that if we are afraid to admit something is not working, we can get stuck in the 5 of Cups. We can become fixated on those fallen cups, trying to force them to stand up again. The tough love of Saturn encourages us to let go and rejoice at what is working - move on with the cups still standing.