How to Know When It’s Time to Leave a Successful Career
My decision to leave my corporate career wasn't a gradual realization or a carefully weighed decision. It was instant and visceral—a knowing so clear it bypassed my logical mind entirely.
When I learned my boss announced his retirement, I couldn't imagine the process of proving myself once again or navigating yet another reorganization. If I was going to prove myself to anyone, it would be to me.
But here's what's important: that moment of clarity didn't come out of nowhere. It arrived because I'd been following intuitive breadcrumbs for years – small, seemingly insignificant nudges that my inner wisdom had been laying out for me all along.
Throughout my corporate years, I took music lessons and night classes. On weekends and vacations, I explored courses, attended retreats and read voraciously about topics that had nothing to do with my day job. Art, creativity, wellness, nature, spirituality – a reading list I dreamed about exploring deeply one day.
At the time, these side interests frustrated me. While this was a way to scratch a creative itch while maintaining my "real" career, I still needed to give my main attention to corporate work. But looking back, I can see they were something more: my soul's way of preparing me for what was next. Each topic I explored and small step I took built the confidence I needed to eventually trust the timing of my departure.
Are you in a similar place right now – successful by every external measure, yet feeling a persistent tug toward something you can't quite name? The question isn't whether you should listen to that tug, rather it’s ow to know when it’s time to act on it.
The Myth of the Perfect Time (and the Voices That Keep You Stuck)
Let's start with an obvious truth: there is no perfect time to leave a successful career.
If you're waiting for absolute certainty, a clear vision of what's next, or unanimous support from everyone in your life, that horizon will never arrive. The "perfect time" is a myth that keeps capable, intuitive professionals stuck in careers that no longer serve them.
But it's not just the myth of perfect timing that holds us back. It's also an array of external voices and perceived expectations that have shaped our choices since the beginning.
“Get a good job after graduation. Climb the ladder. Don't waste your education. Think of the benefits, the security, the retirement plan. You'd be crazy to leave something so successful.”
These aren't just casual suggestions. They're deeply embedded expectations from family, society and the professional culture we've inhabited for decades. They become the lens through which we evaluate our choices, often drowning out the quieter voice of our own knowing.
I gave these voices and expectations undue weight. While I never believed my corporate job was my purpose, I had no idea what my calling was. This caused years of confusion and frustration. Yet I was also able to realize other dreams—international travel, home ownership, and the freedom to eventually leave and pursue writing and entrepreneurship. Looking back, it all unfolded perfectly. There are no regrets.
Here’s an important lesson I learned: you can honor what your career has given you AND know it's time to move on. These aren't contradictory truths. They're both valid, and holding both is part of the paradoxical wisdom that best serves this transition.
But how do you actually know when that time has come?
When Your Body Knows Before Your Mind Does
Your inner wisdom doesn't speak in spreadsheets or five-year plans. It speaks in quiet whispers, gentle prods and physical sensations that are easy to dismiss when you're trained to prioritize logic over intuition.
But here's what most people don't realize: you're already fluent in the language of intuition. You use it every single day.
An intuitive nod is that subtle "yes" feeling in your body. It’s many forms include a sense of expansion, lightness or rightness. It's the opposite of the "no" feeling, which can feel constricting, heavy or unaligned.
You experience this constantly, often without realizing it:
The friend’s name pops into your mind. When you call, they say, "I was just thinking about you."
The alternate route you suddenly take to work that helps you avoid unexpected traffic.
The book that opens to the exact passage you need to read in that moment.
These aren't coincidences. This is your inner wisdom guiding you through life’s small decisions. The same phenomenon that helps you navigate daily choices is available for the bigger ones – you just need to learn to trust it.
When it comes to knowing if it's time to leave your career, your body often knows before your mind is ready to accept it. Here's what that might look like:
Physical exhaustion that no amount of vacation seems to cure
The feeling that you're operating on autopilot rather than growing
A recurring thought that won't go away, no matter how many times you rationalize it
A daydream about a different kind of life that keeps showing up during meetings
A pang of envy when you see someone living with more freedom or creativity
These aren't signs of weakness or ingratitude. They're signals that your soul is ready for the next chapter, even if your logical mind is still building the case for staying.
The Practice of Following the Breadcrumbs
If thoughts of leaving your long-term career both thrill and terrify you, here’s something that might ease the pressure: you don't need to have your entire next chapter figured out before you can trust that it's time to leave.
When my boss’s retirement was announced, I knew one thing with absolute certainty: my corporate career was complete. I also knew it was time to get busy to ensure the timing of my own departure was rational and well-thought out. I didn’t want to jeopardize decades of hard work for a rash decision.
I also began to explore my breadcrumbs – all those night classes and weekend explorations. With careful reflection, I found that the small steps I took toward what interested me built my confidence and prepared me for the transition, even though I couldn't see where they were leading at the time.
You don't need the whole map. You just need to follow your next breadcrumb.
Honoring What Was While Stepping Toward What's Next
One of the most important insights I can offer you is this: you don't have to vilify your career in order to leave it.
My corporate career gave me incredible gifts – the ability to travel the world, a home I love, and the freedom to retire early. I'm genuinely grateful for all of it. And I also knew, with absolute certainty, that my season there was complete. Both truths can coexist.
You don't need to manufacture a crisis or wait for burnout to justify your departure. You don't need to have a calling waiting in the wings. You simply need to heed the inner call when it presents itself with absolute certainty that one chapter is ending and another is ready to begin.
The courage required for this transition isn't in making a dramatic leap. It's in trusting the timing that only you can feel, and in taking small, intentional steps while you're still employed.
Maybe it's signing up for that course you've been curious about. Maybe it's blocking off time for a creative practice or giving yourself permission to explore your interests. Maybe it's having an honest conversation with your partner about what you're feeling.
These small steps aren't distractions from your "real" work. They're the foundation of what's next. They're how you build the confidence to eventually trust your organic timing.
The Question Only You Can Answer
No one else can tell you when it's time to leave. Not your partner, your financial advisor, nor your well-meaning colleagues who think you're crazy to walk away from a successful career.
This is the question only you can answer, and you'll answer it not with your mind, but with your heart and how it feels in your body and soul.
Your inner wisdom has been whispering – maybe for months, maybe for years. It's been leaving breadcrumbs, sending signals and creating moments of clarity in the quiet spaces of your life.
The question isn't whether you should listen.
The question is: are you ready to trust what you already know?
Journal Reflections: What’s the first feeling that arises when you think of leaving your current role? What small breadcrumb have you ignored or dismissed? What would your sage self say about your timing decision?
P.S. Ready to explore your next life phase? If so, I've created a special gift just for you! It’s a guide called 5 Questions to Explore a Soulful Second Chapter. It contains the type of reflective work that gave me the courage to make my midlife transition. You can download it for free at athenawellness.com/reimagine.
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Email Kathy: hello@athenawellness.com