Friendship and the Courage to Let Go

by May 26, 2017Courage, Cultivate4 comments

We’re delighted to have Bailey Gillespie as our guest blogger today,
sharing her intimate perspective on courage, friendship, and letting go.

Recently, I was listening to an episode of the lively That Sounds Fun Podcast, where songwriter Ellie Holcomb shared how “the work of the believer is to remember.”

For some reason, this rang all sorts of bells inside me. We usually use the word remember to signal retrospective acts, like remembering our pasts. But lately, I’m learning how it can also signal the act of looking forward. Whenever I sense that my internal landscape’s been derailed by conflict, I need to revisit and remember where I’m going and why. And this brings me to friendship.

Growing up, I had four lady-friends who were my people, my kindred spirits. We walked through all those things you walk through during the special coming of age and coming of faith years—laughter, silliness, heartbreak, spectacular birthday parties. It fills me with gratitude when I remember the vital roles some of my dear ones have played in my life.

One sweet friend who now lives by the sea once said something that changed the trajectory of my faith life, bringing clarity and revelation to a muddled mess. Another showed up at my doorstep one night when I was too depressed to get out of bed. We’ve laughed, cried, complained, and ate our way through Fresh Mex’s salsa bar. They were the best of the best.

Fast-forward to May 2017, and life looks very different.

Three are married, two have more than one kiddo, one lives on the East Coast, and the other three live an hour away. It was like one day I woke up and realized I was alone on a desert island. This realization hit me harder perhaps because I’m single and have a pretty independent life without the constant presence of a family. But there are lots of times when I turn to do something and wish I could pull along one of these girlfriends, only to realize I can’t.

As an INFJ baby, in Myers-Briggs language, relationships mean the world to me—sometimes to the point of idolatry. Two anti-virtues I’ve wrestled with like crazy this year are possessiveness and jealousy. Since I can remember, I’ve found myself trying to hold onto people more tightly than I should, and it always costs me something. Lately, these anti-virtues have become monsters, eating me alive until my heart twists into a posture that believes everyone is out to get me.

This is wholly opposed to sacrificial love.

Jesus knew what it was like to love and lose friends. He knew the taste of betrayal and the on-again, off-again loyalty of his beloved Peter. He knew the sweet fellowship of his people and how hard it would be to leave them behind. But he didn’t let companionship become an idol. He didn’t let possessiveness of his earthly friendships derail him from his greater mission of obeying the Father. Ultimately, his mission was to love others in ways they couldn’t return, culminating in the most selfless act of love he could ever give—his death.

That’s a hard act to follow.

Up until now, I haven’t quite been able to reconcile the change in certain friendships. I think maybe I’ve forgotten where I’m going. Along life’s journey, friendships are meant to be beautiful markers of God’s provision, but they shouldn’t be mistaken for our first love. Instead of mourning the loss or transition of a friendship, maybe what I need to learn is how to see it as a chapter in the multi-volume story of our lives. This is a posture of freedom.

Sure, I’d like to believe certain friendships can withstand the chasms of space and time. But it’s only natural that as your story continues to move forward, certain characters will slip in and out of the spotlight.

Jesus, remind us that the work of the believer is to remember: both the goodness of what we’ve known and the mission of what’s ahead. As Hebrews 12:1-2 says, help us to “run with perseverance the race marked out for us, throwing off everything that hinders, fixing our eyes on Jesus, the pioneer and perfecter of faith.”

Give us the courage to let go.

Bailey Gillespie is a writing instructor and project coordinator at William Jessup University. She lives in Rocklin, California and loves connecting with people over health, creativity, and faith. Recently, her writing has appeared on The Rabbit Room and The Deeply, Co. You can read more on her blog at


  1. Joy

    So many good words here …so much truth to hold onto. I love your phrase, “anti-virtues” and the thoughts on friendships becoming idolatry. Unfortunately, I understand that all too well. Very timely post. Thank you!

    • Bailey Gillespie

      I’m so glad to hear this, Joy! Thanks for your encouragement.

  2. Sheri Schooler

    Thank you for sharing! We moved across the state about a year and a half ago, I had many close friends that I enjoyed my time with. Since moving I have found it difficult to cultivate those close friendships and often feel like an outsider. I know in whom I believe, and he is ultimately my closest friend. I think I too have some of the feelings described in this blog and need to ask my savior for forgiveness!
    Again thanks for the share.

    • Bailey Gillespie


      I’m so glad this post resonated with you! I believe it’s so common to feel the pang of separation from the people that we love. I know God will be faithful to continue bringing special people into our lives if we have eyes to see and the bravery to be open to it. I hope you find some new, meaningful friendships soon!

      Take care.

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