From Regret to Resilience: Coaching Reflections on The Midnight Library

Have You Ever Wondered, “What If I’d Chosen Differently?”

If you’ve ever found yourself looking back on your life thinking, “What if I’d taken that job?” or “If only that hadn’t happened…”—you’re not alone.

I recently read The Midnight Library by Matt Haig, and it beautifully captured this very human experience. It brought up reflections I often explore with coaching clients—regret, choice, and the surprising power of hope.

In this post, I’ll share how the story inspired me personally, as a coach, and how its lessons might support you if you’re feeling stuck, weighed down by the past, or unsure how to move forward.

What Is The Midnight Library About?

At the heart of Matt Haig’s novel is Nora, a woman caught between life and death. In this in-between space—The Midnight Library—she’s given the chance to explore alternate versions of her life. Each book on the shelf represents a different path she could have taken, a different decision she might have made.

It’s a moving metaphor for how we carry regret. And it’s powerful.

Why Regret Holds Us Back

In coaching, I often hear clients say things like:

• “I should’ve done things differently.”

• “I missed my chance.”

• “If only I hadn’t messed that up.”

Regret can feel heavy. It has the power to keep us frozen in the past—grieving lives we didn’t live, or punishing ourselves for choices we made when we were doing the best we could.

I’ve definitely had moments in life where I looked back and thought, Did I make the wrong choice? Should I have taken that other path? I used to revisit certain decisions on repeat, as if I could rewrite them into something neater or more successful. But over time—and through my own coaching journey—I’ve come to see that I always made the best choice I could with what I knew at the time. Everything else is a story I’ve layered on top. That realisation changed everything. The past isn’t fixed, but our interpretation of it is often far more rigid than it needs to be. And when we soften that story, we create space for compassion, and ultimately, for change.

But what The Midnight Library shows us is this: Even the lives we fantasise about might not have been “better.” They’re simply different. Every path comes with its own challenges.

This realisation can shift everything.

The Power of Choice in the Present

One of my favourite lines from the book is:

“You don’t have to understand life. You just have to live it.”

It’s simple, but it hits deep. Because so many of us feel like we need to have everything figured out before we can move forward. We wait for clarity. For certainty. For a perfect version of ourselves or our lives.

But here’s the truth: you can choose again—right now.

That’s the essence of transformative coaching. You don’t need to rewrite your entire past. You just need to pause, reflect, and ask, “What’s the next best choice for me?”

Hope Lives Here, Too

Despite the book’s darker themes—grief, loneliness, despair—The Midnight Library ultimately offers a message of hope.

It reminds us that we’re never as stuck as we think we are. That even in our lowest moments, possibility still exists. That our lives can take a new direction, even if the path ahead isn’t fully visible yet.

And that is one of the most powerful shifts I see in coaching.

Your Story Isn’t Finished Yet

So if you find yourself holding onto a “what if” or an “if only,” I invite you to gently ask yourself:

• What if I didn’t need to have it all figured out to begin again?

• What choices are still available to me right now?

• What would it look like to move from regret into resilience?

You don’t need a magic library to begin changing your life. You just need a willingness to explore—and a safe space to do it in.

Want to Go Deeper?

I’d love to hear what this brought up for you.
Whether The Midnight Library is on your reading list or already a favourite, I invite you to reflect on your own “what ifs”—and consider what’s next.

And if you feel coaching is next, let’s begin with a free, no-pressure chemistry call. You bring your story—I’ll bring the space to explore it.