Should I quit my job, or stay in my current one?

This week, a client came to me with a big decision: She received an attractive job offer that seemed like a perfect escape from her current, toxic work environment.

But, like many people, she was torn. She loves the team she built and believes in the product she’s selling, and she was reluctant to “throw in the towel” after putting in so much hard work building her function.

She’s not alone in her dilemma; when it comes to career moves, it’s rarely a simple choice.

Deciding whether to leave a job - especially when the current situation feels unhealthy - stirs up a whirlwind of emotions: loyalty, unfulfilled dreams, guilt, burnout, hope, grief, excitement, fear, and uncertainty. To avoid jumping out of the frying pan and into the fire, it’s essential to examine these feelings thoughtfully and make a strategic decision that genuinely supports your career and life goals.

Below are 11 questions we discussed to help her make the best choice.

If you’re contemplating a similar move, these might help you find clarity too.

1. Why Would You Stay?

It might seem counterintuitive, but ask yourself why staying might still be an option. Is there anything left to gain from your current role, such as growth opportunities or fulfilling projects? This question can reveal if you’re truly done with the position or just needing a change.

2. Why Would You Leave?

Sometimes the reasons to leave aren’t as clear-cut as they appear. Is it the people, the culture, the workload? Understanding why you want out will clarify whether the new role genuinely offers a better path.

3. How Different Is Your Job Now from the One You Originally Signed Up For?

If the job you’re currently in has evolved significantly from what was promised or expected, it could explain your dissatisfaction. Reflecting on this can help determine if your frustration stems from changes outside your control.

4. If You Were Interviewing for Your Current Job Today, Would You Take It?

Imagine you were offered your current job right now, with full knowledge of what it’s like. Would you still accept? This hypothetical helps you assess if staying aligns with your values and goals today.

5. On Any Given Tuesday, What’s Your Current Stress Level, and Are You Willing to Keep It There?

Taking inspiration from productivity expert Ali Abdaal, ask yourself how your day-to-day (not just big-picture) stress levels feel. This can help you gauge whether it’s sustainable for the long haul or if change is necessary for your mental health.

6. Are There Positive Changes on the Horizon in Your Current Role?

Sometimes, the factors making your current job intolerable are temporary. Are there upcoming changes—like new leadership, added resources, or redefined roles—that might resolve some of your issues? Understanding the trajectory of your current role can help inform your next steps.

7. What Would Have to Be True for Staying to Be a Good Option?

This powerful question, borrowed from strategy expert Roger Martin, helps you think about the ideal conditions for staying. What would make your current job worthwhile? This can help clarify what you’re seeking, whether in your present role or a new one.

8. Is the Answer to Question #7 Likely to Happen Anytime Soon?

If your conditions for staying aren’t reasonably achievable or negotiable within a realistic timeframe, it might signal that a change is necessary. Evaluate if you’re hoping for something that’s out of reach.

9. Are You Running “From” Something or “To” Something?

Evaluate whether you’re leaving out of frustration or if you’re truly inspired by the new role. Is this next opportunity genuinely better? Compare your current Tuesday baseline with what you expect in the new role. What data do you have to confirm this?

10. Does the New Job Fit Your Ideal Job Matrix?

Examine the new opportunity against your ideal role criteria:

• Does it align with your purpose or interests?

• Does the job description match your skills and ambitions?

• Are the people and work culture a good fit, including the manager?

• How well do pay, benefits, work/life balance, and flexibility align with your goals?

11. How Confident Are You in Your Prediction of the New Role’s Fit? Do You Need More Information?

How much trust do you have in your assumptions about the new position? It’s wise to gather as much intel as possible about the company culture, team dynamics, and role expectations to “de-risk” your decision.

Wrapping Up: A Strategy-First Decision

Working through these questions can reveal more about what you truly need in your next role. For my client, the process confirmed that her current company is in decline, the workplace culture has turned toxic, and her well-being is at stake. In contrast, the new job offers a stable product, growth potential, a supportive boss, and similar or better pay.

Ultimately, I encouraged her to trust her instincts and make the leap, but your own reflection may lead you to stay.

Either path you choose, taking the time to ask the right questions can mean the difference between escaping a toxic environment only to fall into another challenging one - or moving on to something genuinely better.