When Is It Time to Quit?

Years ago, during a rainy day meeting around New Year’s Eve, two colleagues and I surprised each other by making confessions to our boss, the Executive Director. I don’t remember who started it, but I do remember that – one by one and without any planning – we each declared that we weren’t happy and were considering quitting our jobs.

Our boss, in turn, surprised us. She didn’t react, protest, push, or pull. She listened with empathy and responded with curiosity. She asked us: “How could things be different? If you could have anything you wanted, what would you want?”

At the end of a collaborative and creative 2-hour conversation, we each had a newly redefined role and a new path forward. I remember feeling like it was a miracle. I remember how we all laughed in wonder as we reviewed the conversation, where we started, and where we landed.

And it worked… for a time. All good things must end, and one day it was time for me to leave, for real this time. I remember waking up in the middle of the night with the shocking clarity that I had learned everything I needed to learn from this job, and it was time to learn something more and different in a new role. It was just time.

For most of my clients, the decision to leave a job isn’t always so clear. It often starts with a rumbling of restlessness, fatigue from the Same Old Problems, or frustration that’s finally boiling over. Sometimes a client hits a wall of impossibility – they can’t do what they came to the role to do anymore and all the paths are blocked, for whatever reason. Many years ago, I had that experience too. I remember sitting at my desk realizing that all the doors for possible growth were shutting at that company. It was time for a change.

So… if any of this sounds familiar, what do you do? The answer is absolutely unique to you, but here are some tips I’ve learned from the last 18 years of coaching to get you started.

Reality check first.

Before you try to solve anything, it’s good to check in on your mental and physical state. One of my few rules is to never make a decision when you are sick, tired, or overly stressed. If you are burnt out and so tired you feel like you want to collapse or cry, please don’t try to do any deep meaningful inquiry at this point. You can’t find answers when you are so exhausted or emotionally overwhelmed that you can’t see straight. Get rest, take care of your body and emotions, and maybe take some time off. Once you’ve reset a bit, you’ll gain more clarity.

After some rest and distance, here are some approaches to play with:

1. Honor what you’re craving.
If you are restless, tired of your job, craving something different/new, etc. – there’s a good reason why. It’s important to listen to that. The conclusion isn’t always “I want to quit my job,” but it might be. Suspend fear of repercussions for a moment – just get honest with yourself about what you are feeling. We’ll decide what to do with these feelings later. But let’s start with self-awareness and attunement:

  • What do you feel done with? Why do you feel done with it?
  • What are you tired of? What’s no longer sustainable?
  • What are you craving or longing for?
  • What would feel like the best expression of your potential, capacity, experience, knowledge, etc.?

2. Ask: Have I harvested all the lessons I need to learn from my current role?
This part requires more soul-searching. My general rule of thumb: Don’t leave a job only because it’s terrible; leave a job because a) you’ve learned all you can from it and b) you are ready for something new. Going to a positive is more sustainable than leaving a negative. If you run from a negative experience without learning the most important lessons, you will manifest a new version of the same problems in your next role.

  • Is there anything else you need to do in this current role?
  • Is there anything else you need to learn or process?
  • Are you ready to graduate from this role and start something new?

3. Do a Thought Experiment: Is a rebirth of my current role possible?

  • Can I change – or advocate for changing – my role?
  • Is it possible to have new or different boundaries with my role?
  • Can I get more of what I want in my role?
  • What would I have to give up to experience more of what I crave? (This might be old habits, attitudes, types of work, certain meetings, etc.)

Sometimes, the answer is to have a more empowered and honest relationship with your role, boss (even if the boss is you), and/or employees or colleagues. Sometimes, my clients are done with their habits or old relationship to work – not necessarily the role itself.

Then again, sometimes I ask this question and my client’s answer is such a clear and grounded “no” that it propels us to the next inquiry.

4. What’s next?
Now it’s time to dare to dream. Do you need… a sabbatical or walkabout? A different version of your role somewhere else? A new company? Starting your own thing? A total career shift?

What do you most want? What’s true for you at this time? What’s most in alignment for you?

At this point in the inquiry process, the answers might be obvious. If it’s still hazy, consider accessing the following sources of wisdom:

  • Your own wisdom
  • A mentor in your field
  • A career coach
  • Taking time to do some blue sky thinking and visioning out in nature
  • Friends, family, partners, etc.

To help clarify your next step, check out How to Figure Out Your Next Career Move: Your North Star. It explores different concepts and inquiries to help you further define what you want. Then you can use your answers like a filter for any job possibilities you might be considering.

Whether you rebirth your current role or start a new one, I wish you all the best for your next adventure.

Would you love some more support to make a career transition? Schedule a session with me. New clients can receive a free 30-minute intro session.

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