The Messy Middle: Why Feeling Stuck Might Mean You’re Exactly Where You’re Supposed to Be
Jan 08, 2026
There are episodes I record that feel timely, and then there are episodes that feel necessary. This conversation with Lindsey Schmidt was the latter.
Lindsey is the founder of LS & Co-Conspirators, and when we first met, we immediately bonded over something that so many of us are quietly navigating: the messy middle. That in-between season where things aren’t falling apart, but they’re definitely not neatly put together either.
If you’re building a business, raising kids, navigating motherhood, leaving a career, starting something new—or all of the above—you’re probably in it. And if you’ve ever wondered, Is it supposed to feel this confusing? this episode is for you.
What the “Messy Middle” Actually Is
One of the most powerful takeaways from this conversation is the idea that the messy middle isn’t a failure state—it’s a transition state.
Lindsey describes it as a season of unraveling before rebuilding. Before you can create something new—whether that’s a business, an identity, or a different way of living—you often have to pull apart what no longer fits. And that process is exhausting, disorienting, and mostly invisible to the people around you.
That’s why so many women feel like they’re “doing nothing” during these seasons, even though internally they’re doing some of the hardest work of their lives.
Why We Feel Stuck (Even When We’re Not)
A big reason the messy middle feels so uncomfortable is because we’re holding paradoxes at the same time:
- Excitement and fear
- Freedom and the need for structure
- Growth and grief
- Confidence and self-doubt
We want clarity, but clarity rarely comes before action. It comes from moving through uncertainty, not avoiding it. Lindsey shared that many people feel confused during these seasons—not because they don’t know what they’re doing, but because they’re standing between who they were and who they’re becoming.
That liminal space can feel lonely, especially if you’re used to being competent, confident, and “put together.”
Motherhood and the Ultimate Identity Shift
We spent a lot of time talking about how motherhood amplifies the messy middle in ways we don’t prepare women for.
Pregnancy, postpartum, identity loss, generational patterns, and the mental load of modern parenting all collide at once. Lindsey shared candidly about becoming a mom while still operating at a high level in corporate America—and how impossible it became to separate “work Lindsey” from “mom Lindsey.”
That moment when you realize you can’t compartmentalize your life anymore is often the breaking point—and also the beginning of something new.
For many women, motherhood forces a reckoning:
- What actually matters now?
- What am I no longer willing to tolerate?
- Who am I if I’m not defined by productivity or achievement?
Those questions don’t come with immediate answers—but they’re the ones that lead to meaningful change.
You Don’t Have to Do the Messy Middle Alone
One of the strongest themes of this episode was the importance of support. Lindsey talked about how transformation—whether personal or organizational—rarely happens in isolation.
Having even one person who can hold space, reflect back what you can’t see, and remind you why you started can be the difference between staying stuck and moving forward.
This is something I’ve seen over and over again in my own career. The seasons that felt messiest were also the seasons where community mattered most.
The Messy Middle Is an Invitation
What I loved most about this conversation is the reframe: the messy middle isn’t something to rush through—it’s an invitation.
An invitation to choose:
- What you want to carry forward
- What you’re ready to leave behind
- How you want your life and business to actually feel
You don’t need to have it all figured out. You don’t need a perfect plan. You just need the willingness to stay present, stay curious, and take the next honest step.
Because the truth is—you can’t design the next chapter of your life without spending some time in the middle.
And as Lindsey so beautifully said, that’s often where the magic is.
