Parenting Through the Messy Middle

Hope for Parents of Teens with Health Challenges

Jan 05, 2025

Halfway through my teenage son’s haircut, I’m nervous about the results. Almost nervous enough to interrupt the barber, grab a shaver, and clean up my son’s head myself.

Because my son looks like a mess, with half his head shaved, while the rest hangs awkwardly to the side. His sideburns stick out and that cowlick on the back of his head is still arching towards the ceiling.

Then I remember: the middle of anything, including a haircut, is often the ugliest part. It’s the time between starting something new and seeing the ultimate results of our dream.

It’s the messy middle. Those moments when we know a transformation is coming, but we aren’t quite there yet. We have faith that something better is on the way, but the process is sloppy and uncertain. We believe we can create something beautiful out of ashes, but as we sweep up the ashes, we’re still sitting in a mound of dirt.

Sometimes parenting teens, especially teens with health challenges, feels like a long, unending foray into the messy middle.

The Messy Middle of Health

Our nineteen-year-old daughter, Ellie, groaned when I greeted her on New Year’s Day.

“What’s wrong?” I asked. This is a tricky question because Ellie has chronic health conditions, so something is always wrong. She has also struggled with anxiety, depression and an eating disorder.

“My stomach hurts bad,” she said, pulling her comforter tightly around her shoulders.

“I’m sorry,” I whispered, plopping onto her bed. After eighteen months of chronic pain, there isn’t much more to say. We’re in frequent communication with multiple doctors, and Ellie takes more prescription medications than any teenager I know.

“It’s just that…” She sighed. “I really hoped that after that procedure, I’d feel better. Maybe it’s silly, but I wanted to start the New Year without this pain anymore.”

I rubbed her back. “I hear you. I think we have to give it more time to see if the procedure helped. At least we have that new specialist soon.”

Ellie didn’t answer, but I could hear her unspoken questions. We’ve already waited so long. When will healing come? I’m scared to hope because I’ve been disappointed before. What if I never get better?

Ellie and I are living in the messy middle of her extended health crisis. Although we’ve assembled a team of solid doctors who’ve prescribed the right medications, healing feels awfully slow.

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The Messy Middle of Mental Health Recovery

In the space between the initial disclosure of a health challenge and the assurance of stable recovery, we may feel stuck. We may wonder if our teen is making enough progress. Their poor choices, unhealthy patterns, and addictive behaviors leave us feeling discouraged. We might question if therapy is really making a difference, if we are on the right path, if our teen’s care team has an effective approach. If we’re deeply discouraged, we might even doubt whether our teen is willing or capable of recovery.

Maybe we don’t just doubt our teen or the recovery process. We may blame ourselves for our parenting mistakes or for our teen’s health challenges. Perhaps we blame institutions like school, church or a treatment center. Ultimately, we feel alone, abandoned by God, and scared to hope for something better.

Sometimes our messy middle might appear invisible to everyone except us. To the outside world, our teen seems to have recovered from the mental health challenges that once paralyzed them. Even though they function like a typical teen, we notice the ways they secretly struggle. Maybe we’re concerned about their under-eating or overeating, their use of alcohol or drugs. Maybe anxiety still handicaps them. We wonder, will our teen ever make it out of this messy middle, to a healthier, more authentic way of being? Are they willing to do the hard work of recovery?

Many “Messy Middles”

If the phrase “messy middle” sounds familiar, you might have heard it from a variety of sources, all of whom talk about the tension of walking through this space.

In The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture, author Scott Belsky guides managers in navigating the challenging middle stages in their business. Belsky writes:

“No extraordinary journey is linear. In reality, the middle is extraordinarily volatile — a continuous sequence of ups and downs, flush with uncertainty and struggle.”

Professor, author and speaker Brené Brown uses the term “Day 2” to describe the messy middle of any experience, the place where we feel lost and discouraged.

“Day two or whatever that middle space is for your own process is when we’re in the dark, the doors close behind us, we’re too far in to turn around and not close enough to the end to see the light. In my work with…veterans, they talk about this kind of dark middle piece as ‘the point of no return.’ It’s an aviation term coined by pilots for the point in the flight where you have too little fuel to turn around and return to the originating airfield, so you have to go forward.”

From a Christian perspective, author and former pastor John Ortberg describes a different messy middle on the Saturday between Good Friday and Easter Sunday.1

“It’s a strange day, this in-between day. In between despair and joy. In between confusion and clarity. In between bad news and good news. In between darkness and light.”

Reflecting on these perspectives can help us to locate ourselves. Just realizing that our family is in the messy middle feels empowering. It helps us make sense of our feelings of confusion, frustration, and fear. And it reminds us that the middle is a necessary part of the journey.

Surfing the Messy Middle

My children love to body surf. On occasional trips to the ocean, we have paddled out far enough to wait for a massive swell that carries us back to shore. Spitting out salt water, with sand in their hair, my teens crow about the best ride so far.

Therapists have taught us the term “urge surfing.” It’s a technique to ride out an unhealthy urge (such as an addictive behavior), rather than giving into it, until the urge passes. For this to be effective, it’s important to have insight into our triggers, awareness of the urges and tools to manage them.

I suspect the same principle applies to parents like me, in the discomfort of walking through the messy middle. Often, I desperately want to change the situation, to “fix” my teen or at least speed up the healing process. While my advocacy for Ellie is well-meaning and sometimes helpful, I cannot control the healing process. I cannot escape the messy middle. Sometimes my best choice is to accept my daughter and her health, just as she is, even if I’m unhappy with her current reality.

No one said that recovery would be easy, quick or linear. When we can accept and even expect that our teen’s path to healing will be turbulent, we will be less shaken by it. When we focus on the long game with recovery, we can recognize our teen’s overall growth, rather than focusing on the moments when they regress into old behaviors.

A Faith Perspective

John Ortberg talks about Saturday as the day of silence from God. In other three-day Bible stories, trouble characterizes the first day, and deliverance characterizes the third. But on the second day, the Biblical characters wait, wonder, and agonize. They can’t see that hope is on the way.

In response to those times when God seems silent, we have a few options.

We can choose despair - assuming that we will always live in a “Friday” reality.

Or we can choose denial, which looks like forced optimism, platitudes, simplistic answers, or ignoring the problem.

Our third option is to engage with God honestly, with all our agony. A quick scan through the psalms reveals that most psalms are complaint prayers. Apparently, God is okay with our honest expression of our pain and confusion. Expressing our grief and anger helps us heal, regardless of our beliefs about God. But I also believe that as we pour out our heartache, God is faithful to meet us.

The Magic of the Messy Middle

Brené Brown says that in the creative life, the messy middle is not just a neccessary part of the journey. It’s where the magic happens.

In my best moments, I wonder if the messy middle for our struggling kids is also full of a kind of magic we can’t quite see or touch, but one that is powerful. I hope that Ellie’s struggles are shaping her heart to know compassion and empathy for herself and others. If we can find God’s love and goodness in those times of despair, the messy middle can hold gifts for us too.

I’d love to hear how you’ve negotiated a “messy middle” in parenting, in the creative life, or in your own personal journey.