From Burnout to Golden Handcuffs: Why Legal Pros Stay Stuck in Jobs They Can’t Stand

What’s really keeping legal professionals in jobs they hate. And how to break free.

By Chere Estrin

Let me guess. You wake up, drag yourself out of bed, gulp down that cup of burned office coffee, and dread logging into yet another pointless Zoom meeting run by someone whose idea of leadership is reading PowerPoint slides aloud, badly. But you show up anyway. Every. Single. Day.

Why? Because you’ve got bills. Maybe a mortgage. Maybe a spouse who’s “finding themselves” on your dime. Maybe kids. Or maybe just a serious addiction to overpriced takeout and handbags you never use.

I get it.

Let me be the first to say: I have been there. When I sold my first company to a $5 billion public corporation, I thought I’d hit the jackpot. I had a big title: Sr. Vice President, (thank you very much), a huge contract, golden handcuffs, and a direct line reporting to the CEO. I was supposed to run the legal staffing division and turn it into a massive profit center.

Instead? I ended up in what I now refer to as “Corporate Purgatory.” Think Dante’s Inferno but with HR compliance modules and last-minute midnight flights from Los Angeles to Florida for pointless 45-minute meetings that could have been an email. Turnover was 120%. No one stayed. Ninety-five percent of the entrepreneurs who sold their companies to this Goliath jumped ship within the first year. I should have done my homework. But there I was, trapped in a velvet cage with a smile on my face and a scream in my throat. I was literally crying in the shower every morning. Not a pretty picture. 

Eventually, I broke my contract, took a hit to my buyout, and walked away. Best. Decision. Ever. I will never again stay in a job I hate. That’s not just a cute quote for your vision board. It’s my mantra:

“You have to get up in the morning and love it. Otherwise, don’t do it.”

So, let’s talk about why people stay in jobs they hate, and more importantly, how to get the heck out.

1. You’re Addicted to the Paycheck

Let’s be honest: the number one reason most people stay in miserable jobs is the paycheck. You’re not staying because of a deep love for the billable hour reports or because your manager truly inspires you. You’re staying because the direct deposit hits like clockwork and the 401(k) has a decent match.

Here’s the truth: misery is not worth a dental plan.

Sure, there’s some stability in staying. But at what cost? If you’re spending 40+ hours a week at a job that leaves you exhausted, demoralized, or plotting your escape to a remote cabin in Montana, no salary is worth that.

If you died tomorrow (morbid, but stay with me), the law firm would replace you faster than you can say “exit interview.” So, why are you sacrificing your sanity for a place that wouldn’t blink twice if you disappeared?

2. You’re Wearing Golden Handcuffs (and They’re Cutting Off Circulation)

High salary. Plush benefits. Generous bonus. Primo parking spot. Those perks are real and seductive. But they’re also shackles. Golden, yes. But shackles, nonetheless.

I’ve seen so many people sit in misery because, on paper, they’re “living the life.” And yet, they loathe every minute of their day.

Here’s the kicker: If you were the last person on earth with no one to impress – no LinkedIn followers, no in-laws, no social climber friends – would you still stay at that job?

No, you wouldn’t.

So why are you still there? Prestige and loyalty and so called “job security” isn’t worth it if it comes at the expense of your happiness, health, and peace of mind.

3. You’re Afraid of the Unknown

Risk is terrifying. I get it. But guess what? So is wasting your life doing something you hate.

I hear it all the time:
“But what if the next job is worse?”
“But what if I don’t like my new boss?”
“But what if I have to learn a new system and I just can’t?”
“What if I don’t get the money I am making now?”

OK, but what if the new job is better? What if your next boss is someone who actually supports you? What if learning something new makes you feel alive and happy again?

That mindset, the one that tells you to stay put because the devil you know is better than the one you don’t? That’s what’s keeping you stuck, not to mention negative thinking.

4. You’ve Grown Comfortable with Complaining

This one stings. Some people just like being miserable. They don’t want to change. They want to complain. I have had one candidate from a major firm who has been on the market for 10 years. She keeps complaining about the lack of growth at her firm but when presented with a great opportunity, decides to stay where she is. Is this sounding a bit familiar?

They don’t actually want a better job, they want better gossip. You know them. Maybe you are them. They’re the first ones to say, “I hate Mondays and thank god it’s Friday.” They know every dysfunction in the office, and they treat complaining like a competitive sport.

Here’s the thing: Complaining is not a career strategy. It’s emotional constipation. You were not put on this planet to gripe endlessly about Tom in Accounting and how he impacts your job.

5. You Don’t Want to Disappoint Others

Your parents want you to stay because it’s a “great job.” Your friends are impressed because you work at a prestigious law firm. Your significant other or spouse is fearful for their own income and lifestyle. Your LinkedIn looks fabulous.

But you’re miserable.

Let me tell you something: People who truly care about you don’t want you to suffer just to keep up appearances. You don’t need anyone’s permission to walk away from misery. You’re not here to impress your college roommate or your cousin Minnie. You’re here to live your life.

6. You’re Trapped by Lifestyle Creep

Oh, the trap of the expensive life. The BMW lease. The designer wardrobe. The high-rise apartment. You built your lifestyle around your income…not your happiness.

Now, you’re stuck. You can’t imagine taking a lower-paid job, even if it means peace of mind. So, you trade your freedom for granite countertops and Whole Foods groceries.

It’s time to Marie Kondo your life. If your lifestyle doesn’t spark joy, change it. You’d be amazed at what you can live without and how much happier you can be without all that baggage.

7. You Think You’re Too Old to Start Over

I hear this one every day:
“I’m too old to start over.”
“Nobody will hire me at this age.”
“I’ve invested too much in this path.”

Nonsense.

First of all, age is not a career death sentence. It’s a power tool. You’ve got wisdom, experience, grit. Use it. (Get my eBook: Hot Flashes, Cool Resume: Still Brilliant. Still Billable. Not Done Yet. Chere@EstrinLegalStaffing.com)

Secondly, sunk costs are not a reason to stay. Just because you’ve spent 10 years doing something doesn’t mean you should spend the next 10 suffering through it. That’s like eating a bad meal because you already paid for it. Just stop.

8. You’ve Developed a Seniority Complex

You’ve been at your firm longer than the plants. You’re proud of your tenure. That’s not nothing.

But don’t confuse loyalty with a life sentence. Staying solely because you’ve been there longer than anyone else is like staying in a bad relationship because of the wedding photos. It’s nostalgia, not strategy.

9. You Think Hating Your Job Is Normal

This one hurts my heart. Somewhere along the way, we’ve convinced ourselves that hating our jobs is just how it is. That it’s normal to dread Monday, fantasize about sick days, and count down to retirement.

But here’s the truth: It doesn’t have to be that way.

You can actually like your job. Really. You can be challenged, valued, supported, and excited about your workday. That’s not a fantasy. That’s a goal. And it’s achievable.

10. You’re Living in a Negative Motivational Environment

Psychologists call it a “negative motivational environment”, where your emotions are manipulated by fear, guilt, shame, or obligation. These workplaces don’t just exhaust you, they drain your soul.

They feed on your self-doubt. They make you question your worth. And worst of all, they make you believe that this is as good as it gets.

It’s not. You are not meant to merely survive your work life. You’re meant to thrive.

What’s the Real Reason You’re Still There?

Let me let you in on a little recruiter secret. When candidates say they’re “looking for a more challenging role,” it’s almost never the real reason. They’re bored, they’re burned out, they’re micromanaged, they’re underpaid, they have excessive billables or they’re surrounded by incompetence. And sometimes? All of the above.

Sure, sometimes it’s a streak of hard tasks, like Dr. Grant Hilary Brenner explains. His research showed that people quit not because of hard tasks but because of long, punishing streaks of them. Called “task sequencing,” the solution is surprisingly simple: break up the misery. Managers, are you listening?

Still, too many people stay because they’re waiting for the right moment, the perfect time to leave, the day someone gives them “permission.” One of my good colleagues has been a manager at her job for 10 years. She’s not totally unhappy. Just getting terribly, terribly bored with routing and repetitious assignments and no further growth opportunities. She keeps saying, “When I am ready……..” Stop waiting.

What to Do Instead

If you’re sitting in a job you hate, and you’ve read this far, congrats. You’re ready. Now do something about it.

Here’s how:

1. Acknowledge That You’ve Changed
   Who you were when you took this job is not who you are now. Give yourself permission to change your mind.
2. List What You’ll Still Have If You Leave
   Your identity is bigger than your job title. You’ll still have your friends, your family, your talents, your grit. You are not your paycheck.
3. Get Real About What You Want
   Not just “a better job.” What does that mean to you? More money? More purpose? Less toxicity? Less overtime? Define it.
4. Make a Plan
   Update your resume. Send me a draft and I’ll help you with it. Start networking. Take a class. Talk to a coach. You don’t have to quit tomorrow but you can start preparing today.
5. Remember: The Firm With The Job You Hate Can Replace You
   Quickly. Easily. Without remorse. So stop giving it so much of yourself.

Parting Thoughts (And a Good Ole Fashioned Pep Talk)

Listen, I’m not saying to quit your job tomorrow and move to Bali. (Unless that’s your dream. In which case, send pics.)

What I am saying is: Stop settling. Life’s too short to spend 40 hours a week watching the clock and silently screaming.

You deserve work that makes you feel alive, not work that makes you feel like a hostage.

As Steve Jobs said, “Everything around you that you call life was made up by people no smarter than you.” That means you can change it. You can build it. You can do better.

So go ahead. Take off the handcuffs. The door is wide open.

Walk through it.

Looking for a new position or – thinking about it? Send me your resume and let’s chat. 

Chere Estrin is the CEO of Estrin Legal Staffing and founder of The Estrin Report. She’s been featured in The Wall Street Journal, Fortune, and CBS News. When she’s not placing legal professionals in amazing jobs, she’s writing about how to thrive—not just survive—in your career.  Chere@EstrinLegalStaffing.com