Before You Quit Your Job

It’s probably the question I’ve been asked more than any other over the last fifteen years.

“Should I quit my job?”

I can rarely answer that question right away because I first need to understand how your work fits into the larger context of your life.

People often shrink their lives down to work and maybe one other category: family, a relationship, or self-care if they’re lucky. Work becomes dominant and the most obvious place to look when something feels off. But it’s hard to know if work is actually the problem until we’ve right-sized it within the rest of your life.

Maybe you should quit your job. Or maybe you’ve allowed work to crowd out everything else, and the answer is getting back to living. Logging off at 5:00 to make your kickball game. Signing up for the improv class you’ve been talking yourself out of. Taking the pottery class, joining the run club, or making room for hobbies unrelated to your career.

Maybe you should quit your job. Or maybe you’ve been postponing your personal life because work is the easiest place to pour your energy. Instead of refreshing your inbox, maybe it’s time to refresh your dating profile. Instead of saying yes to another late meeting, maybe you need to say yes to invitations where you might actually meet someone.

Maybe you should quit your job. Or maybe you’re exhausted because you’ve built a career around overfunctioning. You overdeliver before anyone asks, anticipate others’ needs before your own, and quietly carry work that was never yours because you learned your value comes from being indispensable. If that’s the pattern, a new employer won’t solve it. You'll simply recreate the same dynamic at the next company: overperforming, overfunctioning, and eventually wondering why you're exhausted all over again.

I hear a version of this question from aspiring entrepreneurs all the time. They assume leaving corporate will eliminate everything they dislike about working, but many of those same patterns follow them into business ownership. If setting boundaries with a manager feels impossible, setting them with paying clients usually feels harder. If you’ve been avoiding difficult conversations at work, entrepreneurship doesn’t magically make you better at having them. Often, it amplifies what was already there.

That’s why I spend much less time deciding whether someone should quit and much more time understanding what they’re trying to leave behind: the company, the manager, the work itself, their own patterns, burnout, or a season of life asking for something different.

Those are very different problems, and they don’t all require the same solution.

What I’ve found is that most people don’t need someone to tell them whether to stay or go. They need help diagnosing what’s happening, separating circumstances from patterns, and figuring out what bridge needs to exist between where they are today and where they want to be.

Sometimes that bridge is financial. Sometimes it’s emotional. Sometimes it’s building confidence, learning to communicate differently, creating better boundaries, or developing enough clarity to make leaving an intentional decision rather than an escape.

Sometimes the bridge is building the business while you're still employed. It’s keeping the paycheck while you find your first clients, test your offer, figure out who you want to serve, and learn what it takes to run a business. The goal isn’t a dramatic leap, but to build enough evidence that when you leave, you’re walking toward something you’ve already started rather than away from something you no longer want.

I think people often assume the only choices are to stay or leave. In reality, there are usually a dozen options in between. My job is to help people see those options, build the right bridge, and make a decision from clarity instead of urgency.

This is the kind of work I do with clients every week. We untangle what's actually happening, identify the real constraint, and figure out what bridge needs to exist before making a decision. Sometimes the answer is to leave. Sometimes it's to stay. Either way, the goal is to make the decision from clarity instead of urgency.

If you're sitting with this question yourself and want someone to help you think it through, I'd love to work with you.