When to quit your job without feeling like a failure

Introduction

Samantha knew she wanted to be a corporate lawyer since high school, so she worked extra hard—excelling in college, scoring high on her LSATs, building her business acumen in law school, securing competitive internships, and networking. Her ambition? Becoming a partner at a top law firm.

Fast forward seven years. Samantha is a senior associate, well on her way to making partner. But something has shifted—her enthusiasm is gone. She finds herself questioning everything:

Initially, staying late felt like “paying my dues.” But late nights turned into all-nighters. Weekends disappeared. My inbox never stops. I told myself that working nonstop was just part of success. But when I found myself drafting contracts at 3:00 AM and dreading Mondays, I had to ask: Is this really the life I want?

I can’t remember the last time I spent quality time with my best friend or my family. I’m always exhausted. And yet, I feel guilty for even thinking about leaving. Shouldn’t I be grateful? Am I weak? But also… when is enough, enough?

If you resonate with Samantha’s thoughts, you’re not alone. Many high-achieving professionals chase success—believing it will bring fulfillment—only to find themselves feeling trapped. But how do you know when to quit?

A powerful way to approach this decision is by using the Acceptance and Commitment framework, which helps you make choices based on values rather than fear.

Separate yourself from the fear of failure

When deciding when to quit your job, self-doubt will probably creep in. You might hear an inner voice saying:

“What if my next job is worse?”
“Quitting means I wasn’t strong enough to handle it.”
“If I quit, I’ve failed.”
“I just need to try harder.”

These thoughts can feel overwhelming, but that doesn’t mean they’re true. Instead of letting them control your decision, try naming your inner critic and recognizing the common doubts that keep surfacing. Thoughts aren’t facts; they’re just mental noise shaped by past experiences. Observe your emotions without reacting, picture them as waves passing through, and ground yourself in the present by pushing your feet into the floor, stretching, or taking deep breaths. Engaging your senses—by noticing one thing you see, hear, smell, touch, or taste—can help you regain clarity.

By separating yourself from self-judgment, you’ll gain the confidence to determine when to quit based on logic and values, not fear.

Check in with your core values

When deciding when to quit your job, ask yourself: Is this career still aligned with who I am? Many professionals get caught up in chasing external validation—titles, promotions, prestige—without checking if their work aligns with their core values.

Take a step back and reflect on what a fulfilling career looks and feels like for you. Consider what your top five career values are and whether your current job allows you to live by them. If your job aligns with your values, are there small adjustments that could make your work experience more fulfilling? If it doesn’t, then it may be time to ask yourself if you’re holding on for the wrong reasons.

Writing this all down will help you make a values-driven decision about when to quit, rather than one fueled by self-doubt.

Make space for uncomfortable emotions

Deciding when to quit is rarely easy. You’ll likely experience a mix of emotions—guilt, anxiety, fear of uncertainty, relief, and even excitement. The key is not to suppress these feelings but to accept them as part of the process.

A great way to practice this is through the mindfulness exercise “Leaves on a Stream.” This technique helps you observe your thoughts—without attaching to them—so you can make a decision that serves you.

When you acknowledge your emotions without letting them control you, you’ll gain the confidence to recognize when to quit in a way that honors your well-being.

Take committed action: When to quit vs. when to stay

Once you’ve clarified your values, it’s time to take action—whether that means staying or quitting. Either way, making an intentional choice will feel empowering.

If you decide that quitting is the right choice, start by assessing your financial situation and ensuring you have a safety net, such as a 12-month emergency fund. Exploring new opportunities that align with your values will also be key, whether that means networking with people in your field, connecting with recruiters, or researching different industries. To make the transition smoother, develop a well-thought-out exit strategy, including a resignation plan and an on-ramp timeline for what’s next.

If staying in your job feels like the better decision, consider what specific changes would make your work experience more fulfilling. Would switching to a different project, team, or department create a better fit? Would setting stronger boundaries around your time and energy help? Take some time to reflect on what has prevented you from setting limits before and think about how you can get support to implement them consistently.

Whether you choose to quit or stay, the key is to take small, intentional steps that move you closer to a career that aligns with your values.

Quitting isn’t failing—It’s choosing you

Deciding when to quit is one of the most important career decisions you’ll make. And contrary to what your inner critic might say, quitting doesn’t mean you’ve failed.

If your job is draining you, misaligned with your values, or forcing you into an unsustainable lifestyle, quitting is an act of self-respect. Walking away isn’t giving up—it’s choosing yourself.

So, if you’re at a crossroads, take a deep breath. Reflect on your values. Trust your judgment. And remember—success isn’t about staying in a job at all costs. It’s about building a career that aligns with who you are.

I challenge you to identify what’s truly holding you back and take one small action toward clarity. Need support with values-based career decision making? Reach out for a free consultation.