Books for the Messy, Winding Road

books for the messy winding road of young adulthood

Last Friday at the Influence Conference, I spoke about young adulthood. My session was called: “If It’s Not a Messy, Winding Road, You’re Doing It Wrong. (Or, Making the Most of Your 20- and 30-Something Years.)”

I explained in my session why these decades were “messy” and “winding.”


When I say “messy,” I don’t mean that you’re a mess and your life’s a wreck. I mean that these years are complex.

I’m not a big fan of drama, but the 20s (and to a lesser extent the 30s) are pretty dramatic years. It’s because they’re full of change. During these years, we change our work, our relationships, our location, our worldview…the list goes on and on. And change is always stressful, even good changes like landing a dream job or getting your first apartment.


These years are “winding” because personal growth during these decades isn’t linear. We don’t walk neatly down the path to adulthood; we meander. We backtrack. We have different personal timetables, and that’s okay. Sometimes we might look like we’re floundering. But real growth sometimes looks a lot like being lost.

Getting comfortable with messy and winding.

You all know I’m a bookworm. Reading helps me enter others’ worlds and understand their lives. Reading helps me grasp concepts beyond my understanding and visit places I’ll likely never see. Reading is both an adventure, and a welcome introverted escape.

If you’re trying to get a handle on what it means to walk through years that are messy and winding, these books will show you what that might look like. They not only accept the mess; they embrace it. And these authors grow, but not in a straight line.

A Million Miles in a Thousand Years, Donald Miller

Don Miller’s book is about how to live a good story. And the key element of good stories that we all try to forget is that they have low points. They have conflict. They start off really, really messy. For a story to be really good, really bad stuff has to happen to the protagonist.

But if the protagonist channels that bad stuff towards change and growth, an amazing story can unfold. Miller unpacks what this means for the big screen–and what it means for your life, and mine. (Also? Only $4.99 on Kindle right now. So worth it!)

Bloom: Finding Beauty in the Unexpected, Kelle Hampton

I somehow stumbled upon Kelle’s blog one late summer night, and soon found myself doing the ugly cry at my computer as I read the story of how her second daughter, Nella, was born with Down Syndrome. But Kelle soon found–with the help of her amazing, envy-inspiring friends–that this unexpected diagnosis was also a profound gift.

Kelle’s story is messy, and winding, and–beautiful. I loved (okay, hoovered) this beautiful memoir. Read it.

These are only 2 books about the messy and winding road–I could have shared 200! What books have helped you make peace with life, when it’s not going as planned?

photo credit

more posts you might enjoy


Leave A Comment
  1. I *loved* the Miller book – such a great way of looking at things, and so inspirational. It’s stuck with me, and I regularly think about some of his points and how I can put them into practice in my life. Haven’t figured it all out, but at least it’s got me thinking.

  2. Tim says:

    For fiction, one of the best stories about life’s messiness that I know of is Paul Zindel’s “The Pigman”. It was written in 1968, so may be a little dated. The leads are a bit younger than 20 and the Pigman huimself is a lot older than 30, but this one is mess and life through and through.

    For me, I didn’t find the 20s all that stressful. They were a meandering path with tons of changes, but not any more stressful than other decades and possibly less than most. My 40s, though – hoo boy, there’s a decade to talk about!


      • Tim says:

        Wait a few more years and you’ll be living the 40s, not just reading about them!


        P.S. I’m sure I’ll blog about something that happened in my 40s sooner or later. Today, though, I wrote about The Princess Bride turning 25. One neat coincidence is that my wife and I hit our 25 year mark last month too, woo-hoo! I did blog about that milestone a few weeks ago.

  3. When I first read the title of this post, I thought of “Bloom” immediately. I LOVE that book. I don’t have experience with having a family member with Down’s Syndrome or even being a parent, but it changed the way I think about finding beauty in life. Great recommendation!

    • Anne says:

      McLaren’s book really made an impact on me when I first read it. But I’ve never heard of A Sacred Thirst. Thanks, Leigh!

  4. Linda says:

    All things Austen…somehow her books help me remember that life’s not fair, but it can still come out okay.

    Calm My Anxious Heart by Linda Dillow helped me to remember that God is good in all things. Elizabeth George and Cynthia Heald are two authors that I’ve also found helpul in my daily walk.

  5. mandie says:

    I’m not even kidding that I wish I’d been there, if only to hear you speak on this messiness I’m living in. Want a mentee? I’m totally in.

    I am always wanting someone to give me the answers on how to navigate this adulthood thing, and as the oldest child, I so wish I wasn’t- I’d have given much to have an older sibling(and might still feel that way). 🙂

  6. Joy says:

    Madeleine L’Engle’s Circle of Quiet amongst other things is a favorite book about the messy challenges of caring for a family in our thirties.

  7. Alia Joy says:

    I know this is like serious writer heresy but I just can’t get into Donald Miller. Everybody raves about him and I could barely finish Blue Like Jazz. I might have to give this one another try but I didn’t get very far last time before I just couldn’t turn another page. However, I love L’Engle with a serious stalker-like obsession.

Leave a Comment

Your email address will not be published.