Sometimes I think it can be easy to pray it safe in life; to pray in a way that protects the safe, comfortable world we sometimes rather live in.
To pray with boldness and expectant faith is hard, not to mention really scary sometimes.
Honestly for a time as a teenager, I used to think if I prayed "boldly" or directly asked to know God's will for my life it would mean I was going to the convent. Not really the best understanding for discernment 101, but it was where I was at the time.
As my understanding of prayer has grown over the years, it has also greatly simplified. I used to think prayer was about using the right words before God or seeing how many spiritual books and journals I could use or collect. It was more about the doing instead of just being with God.
A prayer that's really messed me up, even totally wrecked my life has been the Serenity Prayer.
I have to admit all I knew was that is is associated with Alcoholics Anonymous. That and I thought it seemed a bit new-agey. Still working on the judgmental thing ;)
When I started to really listen and reflect on the words, they began to mess with me. On a daily basis, I began confronting and acknowledging all the things in my life that were outside of my control (which are many). Then I was slowly able to discern the difference between what I can and cannot change.
Often times when I felt like I didn't know how to pray, these words helped settle my soul. When I was able to accept the people and situations I could not control it brought me a great sense of peace. I am learning (as the full version of the prayer reads) to "Live one day at a time, enjoying one moment at a time. Accepting hardships as the pathway to peace."
Maybe praying boldly will look different for you than it does for me. It could be just sitting in silence 10 minutes everyday or maybe it looks like saying "Lord, I want whatever You want. No matter the cost." Whatever it is, pray with boldness.
When we allow prayer to wreck us from the inside out, it allows God to do that deep soul work that is needed in each of us. I know I have seen that time and time again in my life.
If you are looking for some help in understanding and applying the way of serenity to your own life, I highly recommend this book.