Growing up made easier
My discernment journey was a meandering one. I consider it to have five phases, each with a corresponding lesson. This is my journey:
I consider my discernment to have begun in college. I had fallen away from the Church for a while. I was like an onion: my innermost desire (whether I knew it or not) was for God. My inner life, however, was not into my faith and did not trust God. My outer life still looked like a Catholic; I still went to church and even confession (?!), but in reality, I was steeped in sin.
The first rule of the discernment of spirits (which, of course, I had no idea about at the time) indicates that when a person is in a habitual state of sin, the Holy Spirit convicts and nags. And He sure did for me. I kept feeling restless. I didn't trust the LORD and His glorious promises, so I pursued and settled for pleasure and happiness instead of joy and fulfillment.
I have since found it impossible to discern God's Will for your life when you are separated from Him by grave sin.
Step 1: If you are not in a state of grace, get there ASAP.
I soon found out that my restlessness meant I needed major change in my life. I tried to trust God and broke up with a long-time girlfriend. That lasted all of two months, at which point I promptly got back together with her because I didn't actually trust God.
Here's the thing about trusting in God, though: God is love. As such, He is not capable of wanting anything except the best for us. Remember: love is willing the good of the other as other. In other words, because God is love, He wills our good. Put another way: God's will for your life is your good.
Step 2: You gotta trust God.
I knew that my way wasn't working, so I tried to throw myself at God. I toted with the ideas of NET (National Evangelization Team) and the seminary. My friends who knew me best were suspicious that neither was right for me. I sought their counsel, but I didn't actually listen to them.
Step 3: Ask people who know you well for advice. But then actually consider it.
I ignored my close friends and dared God to stop me as I tried to discern Him.
I interviewed for NET. They invited me to serve, but I (somehow) realized that it wasn't God's will for my life, so I turned them down.
I set my eyes on something bigger: seminary. I met with the Vocations Director several times and got halfway through the application. At the time, I was finishing a devotion to Mary. I felt uneasy about the seminary (which I attributed just to nerves), so I prayed a half-hearted novena of rosaries for Mary to help guide me. Another close friend reminded me that novenas aren't a substitute for really sitting and reflecting on God's will. I, of course, didn't listen.
Step 4: Pray novenas, but don't let them be your only method of discernment.
God humors the ignorant. On the eighth day of my novena, my now-wife walked into my life. She captivated me with beauty (remember, God lives in the true, the good, and the beautiful!). Thinking that I was going to be a priest, she approached me with hard questions about the faith (she was on the verge of becoming Catholic). I finally took a serious look at my faith. I learned truth. I also found joy again instead of restlessness. In my experience, God acts through joy (note well: not pleasure or happiness, but joy).
So I ghosted the vocations director (sorry, Father!), took a step and dated her. I dared God to stop me if that was His will (are you sensing a theme here?), but He never did.
There's a famous math problem called the Monty Hall problem, a game show in which you choose between three doors (one of which has a car and the other two of which have goats). Monty, who knows what's behind each door, then shows you a goat. He then offers you the opportunity to switch doors or stay with your original choice. With Bayesian statistics, you can prove that it's advantageous to switch doors.
What does this have to do with discernment? Being a statistician, I would say that it means you'll make better decisions with more information. So trust in God and take a step. He won't let you down.
Step 5: Take a step while trusting in God.