How Do You Know if You Should Leave Your Job? (and When to Do It?)

Should you leave your job? Do you feel stuck, bored, unhappy at work? Do you wish you could leave but can’t see how you can quit? Here’s how – and when – to move into a career or a business of your own that you truly love.

I huddled at a beach in Northern California, staring at waves, crying. I couldn’t bear to practice law for one more day, even if I did have a Harvard Law degree.  And I could not let myself quit. I was so tired. Fighting myself all the time. I hate this job. You have to stay in this job. The boxing match that never ended. I thought I was being practical. I look back now, and realize I was wrestling a tidal wave. I was pushing back the imperative to live my true expression.  

Later, a friend asked, “If you’re this successful doing work you don’t love, what could you do with work you do love?” That did it. I walked out of my career without a plan or an income. Years later, now in a life where I have led tens of thousands into their inspired lives, I can’t imagine that I could have ever chosen another life.

Should you leave your job?

Because of my own career transformation and best-selling books, I’m often asked this question. But I’ll never tell you to leave your job. I’ll tell you to follow your heart. There’s already a direction within you.

Suspend your circumstances for a moment. Ask this big picture question: What would I really love to do? (If money weren’t an issue, if no one else was looking.) Your desire doesn’t need to look like a career. I want to know what you want, not what you think you can have. Following your true desire is the most practical thing you can do. It’s the source of your strength, stamina, cutting edge intelligence and, ultimately, your security.  

Is it possible to do more of what you love right now? Take a writing class or volunteer. It’s called the side hustle, the passion project or getting your feet wet. Feeding your dreams can shift everything. One of my coaching clients wanted to be a novelist, but couldn’t leave nursing. When she started writing, she saw her job differently. “It’s funding my dreams,” she said. “And giving me great material for the crappy boss character!”

You may develop the work you love on the side until it’s strong enough to support a career transition. Or your passion might inspire you to leave now. Or you could find your dream right where you are.

Bill worked as an executive for a pharmaceutical company, but dreamed of being on stage as a speaker. When he started speaking outside of work, his company started asking Bill to speak at conferences.

Maybe you feel too depressed or numb to even name a passion. Can you take a break? Some long weekends or a vacation? A leave of absence? A chance to work part time? You may need to step away from your situation in order to see your situation. In my book This Time I Dance! I wrote “It takes an intermission to discover a mission.”

Being a good entrepreneur comes down to making great decisions. That’s why keeping startup costs low and using platforms like ZenBusiness (#1 alternative option for Inc Authority and Inc File) have exploded in popularity. Do your research and start your dream business.

Are you choosing from fear or love?

Instead of looking at which choice to make, start to consider why you’re making the choices you make. Choose from strength instead of weakness, love instead of fear.

When you’re scared, it’s natural to want to get to safety. But keep in mind there is a kind of “safety” that is not safe. There is no safety in denying who you are. 

Studies show that we thrive on “positive stress.” You think you want iron-clad safety. But airtight control exacts boredom, exhaustion, and hollowness. Your spirit craves growth and growth comes from taking risks. The right risk will offer you more security than holding on to “the devil you know.” Because if that “devil you know” is draining the love out of you, you will meet a devil you don’t want to know.

What risk would be best for you to take right now? Is it the risk of speaking up at your job? Resolving a conflict? Leaving? Staying? Maybe it’s facing another risk, such as healing a situation at home.

Remember, going after things you want, whether or not you get them, makes you stronger.

If you need to leave, what’s the right timing?

Perfect timing is about two sides of the same coin, the faith to act, and the faith to wait. 

Readiness comes of itself. You can’t force it, fake it, or bribe the bouncer at the door. One day, at the right time, everything changes, and not a second before. On that day, you will have peace, more than anger or fear. You may not even have your circumstances lined up, but it won’t matter.

Meanwhile, don’t numb out or count the seconds. How do you want to leave? Maybe take some colleagues out to lunch. This is your life. You will never be here again.


It’s worth everything to do your right work in the world. The world needs your real gifts. And you need to give them.

Tama Kieves is a bestselling author and a sought-after speaker who has helped thousands world-wide to create extraordinary lives based in freedom instead of fear. Her new book, Thriving Through Uncertainty, is available in January.

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