After nearly half a century at the company he co-founded, Jerry Greenfield of Ben & Jerry’s is officially stepping down. His departure comes 47 years after he and Ben Cohen started scooping ice cream in a renovated gas station in Burlington, Vermont. Over the decades, Ben & Jerry’s became more than just an ice cream brand. It stood for quirky flavors, community values and social activism.
Greenfield’s exit is a reminder that even when you’ve poured decades into building a career or business, there comes a point when moving on is the right choice. And it’s not always about age or traditional retirement. Sometimes it’s about alignment, energy and opportunity.
So how do you know if it’s time for you to follow suit? Here are five signs.
1. Your values no longer match the work
Jobs often start with passion, purpose or at least a clear sense of alignment. But companies evolve. Leadership changes, market pressures mount and sometimes the culture shifts away from what first drew you in.
If you feel silenced, disconnected or pressured to act in ways that go against your principles, that’s a clear sign it may be time to walk away.
2. Stress outweighs fulfillment
A certain amount of pressure is normal at work, but when the stress becomes chronic, impacting your health, relationships or sense of self, it’s no longer just “part of the job.”
Burnout is costly. If your work leaves you more drained than energized, it may be time to put your well-being first.
3. Growth has stalled
Careers thrive on challenge and progress. When your role no longer offers room to learn, influence outcomes, or feel like your contributions matter, stagnation sets in.
That’s often the quiet signal that you’ve outgrown the position, even if on the surface, everything looks fine.
4. You have the resources to leave
One of the biggest practical hurdles is financial readiness. If you’ve built a safety net through savings, retirement accounts, or even a side business, you gain the freedom to leave without putting yourself in jeopardy.
Having a plan for what’s next, whether it’s consulting, starting a new venture, or scaling back hours, makes the leap less daunting.
5. You’d regret staying more than leaving
When you picture your future, do you feel excitement (or dread) at the thought of continuing down the same path?
If staying longer feels like sacrificing time, relationships or opportunities you can’t get back, then leaving may be the wiser choice.
How to evaluate your own moment
Deciding whether to quit a job is rarely simple. It requires looking beyond the day-to-day frustrations and taking a wide-angle view of where you are and where you want to be.
- Start by taking inventory of your current situation. What aspects of your work still energize you? Do you enjoy certain projects, colleagues or the stability the job provides?
- Consider what could be draining you. Pinpoint whether it’s the workload, the culture, the lack of growth, or simply that your values no longer align with the company’s. Clarity here will help you separate temporary rough patches from deeper signals that it’s time to move on.
- Assess your overall “exit readiness.” This includes financial stability. Do you have enough saved to sustain yourself for a while if you step away? Also, think about how you’ll handle the identity shift that often comes with leaving a long-term role. Are you prepared to answer the question, “What’s next?” with confidence, even if it’s just a transition plan?
- Remember that quitting doesn’t always have to be abrupt. Explore transition options such as reducing your hours, moving into consulting or pursuing a side business while keeping your current role. These approaches can provide flexibility while helping you test new waters.
Balancing quitting with practical planning
Even if you feel certain that it’s time to go, the logistics of leaving require careful planning and financial preparation is key.
Having an emergency fund or savings cushion can make the decision less stressful and buy you time to explore new opportunities without rushing. Then, consider the benefits you’ll be giving up, such as health insurance, retirement contributions, or stock options and map out how you’ll replace them.
For those close to retirement age, think carefully about how quitting might affect Social Security benefits, Medicare eligibility, or the long-term value of your retirement accounts.
Beyond the financial implications, it’s important to plan for how you’ll fill your time and sense of purpose after leaving. Work often provides structure and identity and without it, many people feel adrift.
Setting up new routines, goals, or commitments, whether through volunteering, part-time work, or personal projects, can help ease the transition. Quitting without a plan may feel liberating in the short term, but having a thoughtful roadmap ensures you’re not only leaving something behind, but also stepping toward something meaningful.
Quit or wait?
There isn’t a universal formula for knowing when to leave a job. For some people, holding on until retirement age makes sense. For others, stepping away earlier can be the healthier and more authentic choice. What matters most is that you recognize the signs and make a deliberate decision, instead of drifting along by default.
Quitting doesn’t have to mean failure. It can be a proactive step toward aligning your work with your values, protecting your well-being and opening the door to new opportunities. Whether you leave now, in a few years, or much later, the real success lies in making a choice that honors your priorities and the life you want to build.
