When Quitting is the Boldest Move You Can Make

My client had been circling the question of whether to quit her company for months. Despite outward success and a recent round of ample funding, the company's mission had pivoted far from what she cared about. On top of that, she and her two co-founders were split on fundamental issues—not just on what they were building, but also on how they worked together and the culture they were creating.

There were ample reasons to stay—a sense of obligation and commitment to her business partners, for starters. Not to mention attachment to her tenured team. But under all that was the more genuine fear: What if she made the wrong choice? What if she quit and the company took off? What if she stuck it out and it went nowhere? She couldn’t fathom leaving, but as we explored, there was no denying a very clear decision emerging from within her. A call to build something different.

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Witness What's Already Here

Whatever shows up in your consciousness—that's what wants to be known, understood, and tended to. Be it the desire to quit, fear of getting fired, or replaying an argument with your spouse—if the experience is alive within you, you can either handle it directly, or carry it around like heavy luggage. The more unaccepting or unconscious you are of what lives within you, the more it persists and leaks out in other ways.

Quitting isn’t inherently a problem. But letting it run silently in the background can be. It drains your energy and robs you of the joy of a day’s work well done.

So if quitting is here—and it might even sound like “I can’t quit”—then it’s time to meet your Quitter. 

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Meet the Quitter

For example: I asked my client to look for ways she was already quitting. Putting judgment aside, she was pretty quick to own her impact:

• She wasn't "going to the mat" with her partners on issues that mattered to her
• She was dragging her feet on a key project
• She was constantly tired and experienced herself as 'checked out'

By disowning the part that wanted to quit, she was already stepping out on her business.  Not naming that truth wasn’t protecting anyone—and it was slowly draining her. 

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Below the Line Traps

On the surface, my client’s issue looked like indecision. But underneath, I sensed she already knew what she wanted. She just wasn’t willing to own it yet. 

When we’re stuck below the line, our choices get clouded by fear, obligation, and identity. As we explored, my client realized she had a series of stories running:

• "I'm not a quitter." 
• "I'll disappoint people I care about." 
• "I need to be financially responsible." 
• "Real entrepreneurs stick it out."

We all inherit ideas about how life is supposed to go—and we build our sense of self around them. Especially in career and leadership, identity runs deep. But when we're stuck in story, we're not available to choose consciously. We’re reacting to ghosts from our past. 

The fear of getting it wrong is rarely about the future. It’s about the stories we’ve absorbed—about who we think we’re supposed to be, and what we think we owe others. These are the invisible contracts that keep us in limbo. Until we see them clearly, we can’t make a real choice—we don’t have true freedom.

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What Happens When You Don't Listen

I know this terrain intimately. 

My most notable experience with quitting was when I left WeWork at its all-time high valuation. I had a title that mattered to me, a generous equity package, and the respect of my colleagues. I had even built a team that made my day-to-day workload feel almost easy. But I was unfulfilled by the work and disillusioned by my experience of leadership. 

I was quietly quitting long before that was a phrase. For many many months, I felt the energy drain out of me as I showed up for work, but wasn’t fully there. I told myself I should find a way to make it work—the company was headed for IPO, the work was interesting enough, I had close friendships and community through my work. But if I was honest, I was just done. It was time to move on. 

One Friday after work, after recounting and lamenting the situation for the hundredth time to my now-husband, he challenged me: “Does this all come down to what other people think?” 

The question, put point-blank, shook something within me. If I was honest, I was staying to appease others and to maintain an impression I thought people had of me. I was outsourcing my sense of self and trying to preserve an image by keeping a role that I didn’t even want. What did I care what anyone else thought of my career decisions? I’m the one living this life, and if I have any choice about it, I want to feel invigorated by my work each day. 

Finally—golden handcuffs be damned—I was ready to give notice. 

I should note, my career took a few more twists before I really committed to living life on purpose—doing work that feels fully aligned with my soul—but that decision to leave was a key step in my journey to arriving here.

Looking back, it's easy to see: staying in a situation that is misaligned internally diminishes aliveness. And that serves no one—not your company, not your family, not you. 

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From Trapped to Choice

When we finally tell the truth about what’s holding us back, we can see the story that’s been running the show—and decide if it’s one we truly subscribe to.

The story keeping my client stuck was simple: true entrepreneurs don't quit. Walking away meant she was weak or uncommitted. Once she saw this story for what it was, she could question it: Is it true? Does it serve me? Who would I be without it?

She’s not alone. Many leaders say things like, “I have bills to pay and people relying on me. I can't just quit.” This is a common response to entertaining the Quitter—and a compelling rationale for not pursuing what’s calling you.

To that, I’ll ask: Where are you speaking from? Hint: If “there’s no choice” is in your vocabulary, that’s a strong clue you’re operating from a below-the-line context—stuck in fear, obligation, or identity preservation.

To be clear, the feeling of having no choice is different than consciously choosing to stay.

When we collapse into “I can’t…”, we succumb to victimhood. When we own “I choose to stay because my current priorities are financial stability and supporting my team,” we reclaim agency. And through agency, we can re-design, co-create, and engage with possibility.

Then you can ask yourself: What would need to shift for staying to be enlivening?

For my client, that might look like initiating key conversations with her business partners.
For me, it might’ve meant reimagining the scope of my role.

Sometimes creating a relationship with your Quitter reveals a way to stay—renewed, re-engaged, and alive. Other times, it clears the path for a clean, empowered departure. Either way, the moment you shift from “I can’t…” to “I choose…”, your Quitter stops running the show. 

You’re no longer trapped by circumstance; you’re back in authorship of your life. 

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Choosing Freedom

Here's the thing: You can't screw this up.

When your life is dedicated to curiosity and learning, it isn't about choosing the right thing to do—to stay or go. It's about what lessons you get to learn. When you operate from the principle that life is your ally—that every experience is perfectly designed for your growth—the pressure to “get it right" dissolves.

This isn’t a feel-good mantra. It’s a radical shift in how you relate to uncertainty and outcome.

You get to decide when it's time to get off a ride—and how. To her credit, my client was incredibly intentional with her exit: owning the impact she was having and staying available for feedback and feelings. And of course the journey didn't stop when she quit. After leaving the company, she continued to process the experience, getting further into alignment with herself and her next chapter.

If you choose to claim authorship as you play the game of life, then it isn't about right or wrong choices, it's about maximizing learning by staying curious. You’ll find yourself free to ask better questions:

• What do I want to experience in this lifetime?
• Who do I want to be as I navigate this circumstance?
• If there is no “right” answer, what do I most want?
• What is my life’s work? Am I living on purpose?

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The Practice: What will you quit today?

In my experience, many hard-charging leaders have a blindspot around quitting—be it quitting, flaking, disappearing, you name it. The more you identify with having grit, tenacity or being the reliable one, the more likely there’s an unowned part of you that allows you to check out or disconnect.

In this now-moment, can you identify something you’re wanting to quit? It could be a decision you’ve been punting, a recurring meeting on your calendar, a project that’s dragging on. Once you have it, take a moment to explore:

• What does ‘quitting’ energy feel like within you? Contraction, withdrawing, seeking distraction, etc.
• Can you find the one within who wants to quit or end this commitment? Notice what shows up here—a visual, a sensation, a part of the body lighting up.
• What does your Quitter want you to know about the situation? Just ask and listen; no need to argue or debate it.

Resistance has intelligence embedded within it. That part that says, “Enough. I’m done.” — it has a point. Can you hear it consciously? You decide what comes next.