“I’m done with paper pushing, this work feels meaningless,” a client told me last week.

After 10 years of practicing law, she’s done. She’s been thinking about a career change for five years, but several things have kept her stuck.

And she’s not alone. I hear similar stories from associates to equity partners. What keeps so many lawyers who want to pivot stuck?

Here are four common reasons I see.

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1. Sunk Cost Fallacy

Sunk cost fallacy is the tendency to keep going down a path because we’ve already invested time, energy, or money, even when we know it’s no longer right for us.

Lawyers invest a lot in their careers: it starts with the LSAT, then law school, followed by the bar exam, then the interview process, then the time it takes to develop competence and expertise. The idea of a career change can feel impossible. Most lawyers I talk to who want to leave the law have spent years thinking about it before they finally take action.

One of my friends is leaving law after 25 years—after building an $8MM book of business. When I asked her how long she had wanted to leave, she said, “Since I was a fifth-year associate.”

In my own 15-year career, I changed firms and practice areas multiple times to try to make law “fit.” And while my final years aligned more with my strengths and values, I still felt like I was trying to shove a round peg into a square hole.

Even after I finally achieved the work-life balance I wanted—and genuinely liked my colleagues and clients—I faced the truth: the work itself was never a good fit.

If you’ve been thinking about a career change for a while but haven’t taken action, consider whether the sunk cost fallacy could be holding you back.

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2. Worrying About What Others Will Think

Many lawyers who want to leave worry what their friends, colleagues, or family will say.

These fears may run deep.

One of the most powerful parts of coaching is helping clients explore the root of those fears and access the courage that’s already within them. As a coach trained in Internal Family Systems (IFS or “parts work”), I’ve found this model to be an effective way for lawyers to get clear on what they truly want, meet their fears with curiosity and compassion, and move forward with confidence.

As one client shared:

“I would not have had the courage to apply to this job or the courage to brag about myself or my experiences if I hadn’t been on this journey with you as my coach. I am so grateful for you. Even if I don’t get the job I am so proud of myself and how far I’ve come in my self-confidence. Thank you Jessie.”

(Spoiler: she got the job—and starts next week!)

A perspective I often share when fear of judgment shows up comes from hospice nurse Bronnie Ware, who identified this as the most common regret at the end of life:

I wish I’d had the courage to live a life true to myself, not the life others expected of me.

Having trained as a death doula, worked as a hospice volunteer, and lost my parents when I was in college, I find contemplating mortality to be one of the best tools to help us make the hard choices in life.

As Steve Jobs said:

Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything, all external expectations, all pride, all fear of embarrassment or failure—these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.

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3. Believing They Have No Transferable Skills

This is a common myth and it couldn’t be further from the truth. Lawyers develop skills that are valuable in a wide range of industries and roles. Just to name a few:

• Critical thinking – analyzing complex problems and making sound decisions
• Strategic problem solving – identifying root causes and creating results-driven solutions
• Clear communication – writing and speaking with clarity and persuasion
• Relationship building – establishing trust and navigating conflict
• Leadership and initiative – owning projects and turning ideas into action
• Emotional intelligence – reading people and responding with empathy
• Adaptability – learning new industries quickly and thriving in change
• Project management – juggling priorities and delivering under pressure
• Professionalism and integrity – demonstrating reliability and ethical decision-making
• Information mastery – distilling complex material into actionable insights
• Excellence and precision – maintaining high standards, even under stress

You have so much to offer. You just may need help translating your skills into a new context.

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4. Believing It’s Not Possible to Get Paid to Do Work They Enjoy

One client shared that her father told her, “If you enjoy 10% of your work, be grateful. They don’t call it work for nothing.”

That message stuck and shaped her decision to stay in law years after her heart wasn’t in it anymore.

I asked another client who felt stuck whether she believed it was possible to get paid to do work she enjoyed. She said, “No, I don’t think it’s possible.”

We unpacked the roots of that belief and then began identifying real-life examples of people she could relate to who were doing fulfilling, paid work they loved.

When I was contemplating my own transition, I created a vision board filled with women lawyers who had left the profession and built careers they loved. Seeing their stories helped me believe it was possible for me, too.

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If you’re a lawyer who’s been feeling stuck for a while, I want you to know: there is a path forward that aligns with your values, your strengths, and your definition of success.

You don’t have to figure it all out at once, and you don’t have to do it alone.

I created the Career Alignment Map to help lawyers like you take the first step. It’s a free guide designed to bring clarity, insight, and momentum to your career exploration. You can download it now to start reconnecting with what you truly want.

I’d love to hear from you: Have any of these beliefs or fears shown up for you in your career journey? Which one do you most relate to right now?