I never thought I’d have a spiritual director. Now that I’ve benefited from conversations with one, here’s why I think everyone should take this step in their spiritual lives.
One morning last winter, I woke up early enough to see the Chicago sunrise. I stumbled out of bed, threw on four layers of clothing, and walked 10 minutes to Kathy Osterman Beach on Chicago’s North Side. I arrived at the beach to a stunning winter sunrise and watched as the sun tiptoed above the horizon. I looked around at the few dozen others around me, also taking in the view. A man on the pier smiled at me. “Best show in the city,” he said, then turned and left to begin his day.
Later that day, I was talking on the phone with Sister Jessi, my spiritual director, while walking through my neighborhood. At the beginning of the conversation, she asked where I’d seen God in the past month. I shared that I’d been having a period of spiritual dryness, no doubt exacerbated by long, dark days and the pandemic.
As an afterthought, I mentioned the moment at the beach that morning. I shared how beautiful it all had been. “Hmm,” she said. “Tell me more about that.”
I told her how impossibly colorful the sky was — that yes, I’d seen God there. And then the words started tumbling out. We were a group of strangers there together on the beach, looking at something beautiful, and the experience was made even more lovely by the fact that we were all sharing it together. It had been so long since I’d shared a moment of awe with strangers — observing the sunrise held echoes of what I’d been missing since Covid shut down concerts, art museums, and football games: human community.
“Well,” Sister Jessi said, “that sounds like prayer.”
I first met Sister Jessi during my service year in Chicago and was immediately drawn in by her humor and kindness. So, when she posted on a Facebook group that she was open to serving as a spiritual director, it only took me half a second to send her an email. I was excited to have the opportunity to talk to her once a month! It was only after the email was sent and our first session was scheduled that I began to get nervous.
Having a spiritual director had always seemed like it was for Gold Standard Catholics — for people who pray the rosary, follow all the rules, and attend daily mass. Me? I’m a Catholic who is skeptical about the Church and prays sporadically. If I attend Mass, God is pleasantly surprised. I thought I wasn’t worthy of spiritual direction, that I wouldn’t have anything to say, that I’d disappoint whoever had the misfortune of directing me. To say I’d gotten myself into this on a whim would be an understatement.
I pressed “join” on my first Zoom spiritual direction meeting with more than a little trepidation. Would she give me homework? Would she tell me I wasn’t praying enough? Or tell me what to do and how to do it?
It turns out most of our conversations are like the one about the beach. Sister Jessi helps me to see where God was present when I didn’t see God myself, which in turn helps me see God more clearly in the days that follow. When impostor syndrome creeps in and I doubt my worthiness, she gently redirects me to a more compassionate understanding of myself and of God.
Sister Jessi rejoices with me when my relationship with God gets a bit deeper, and she helps me think creatively when the relationship feels stale. I always end our sessions feeling at peace, even if I have no more answers than I did at the beginning of the hour.
So, if the thought of having a spiritual director has even crossed your mind, my first piece of advice is this: Do it. Think you’re not religious enough to have one? Do it. Think it’s a little weird and scary? Do it.
The most important thing I’ve learned about the process is to find someone with whom you connect both personally and spiritually. Ask friends for recommendations. Think of holy people in your life — and they don’t have to be a nun, priest, sister, or brother.
Sister Jessi explained that “good spiritual directors won't try to ‘direct’ you or tell you what to do. They expect people to explore and try out different spiritual directors to find one that's a good fit. As with any new relationship or new endeavor, it can be awkward at first, but you will eventually find what works for you. The only way you'll know what spiritual direction can be for you is if you give it a try (or maybe two).”
Having regular spiritual direction conversations has been more welcoming, more freeing, and more fulfilling than I ever thought possible. As Sister Jessi says, “At its core, spiritual direction is just a conversation between two people about God, faith, and life.” And, really, what’s so intimidating about that?
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