Reading: Your Job: Knowing When It’s Time to Leave

Not long ago, I received a text from an executive who had recently resigned from his C-suite position. He couldn’t stop talking about how great he felt. “I can’t believe I have the headspace to pause and evaluate what I want,” he said. I’ve even started looking after myself — exercising, meditating, and getting enough sleep — in ways I’ve never done before.” 

I couldn’t stop smiling because I knew exactly what he meant.

I started my coaching firm, Conductive, in 2010 after years of working on Wall Street as an executive for a major bank. I was ready to embrace a new phase in my life. And for that, I had to go through my own executive departure, a career transition that might have left many people feeling anxious and drained. Instead, my transition made me feel energized, optimistic, and confident about the next stage in my life. What I learned was that it is not always the most logical, easiest or safest road that I am going to travel. When I am faced with decisions,  I know that to reap great rewards, I need to push outside what is comfortable, muster up my courage and trust that with every step my vision will unfold.

Know When It’s Time to Move On

Here’s how it feels.

Something stirs inside of you. You feel restless. You perceive that there’s a lack of alignment between what you’re doing professionally and who you want to be. 

It can be a subtle thought that builds over time and slips into your consciousness directing your interests elsewhere, like when you’ve been driving for a long time and you suddenly ask yourself, “how did I get here?” Or it can be a seismic shock that hits you when you wake up one morning or in the middle of the night.

You start to ask yourself about your situation: How aligned am I with my company’s vision and direction? Could my energy be better spent realigning to the present or reimagining the future?  

No matter how the perception emerges, you are suddenly aware that there is a lack of congruence between your wishes for the future and your professional life.

With some trepidation, you share your thoughts with a few trusted friends and associates. Some sympathize and say “yeah, I have those thoughts, too.” Others protest, saying they cannot understand how you could even consider walking away from such a great career.  And yet others just jump right in and tell you what other direction is right for you.

Several months later you start feeling guilty or disloyal for even considering abandoning a team or company that has relied on you for so long. You might even believe that you can turn things around, that you can change the company and everyone around you to make things perfect again. 

You might even feel betrayed by your company for putting you in this situation. Or angry at yourself for allowing “them” to do “this” to you or for being too slow to realize that a big change is necessary. 

Maybe there’s even a sense of shame or selfishness for putting your needs ahead of others.

And of course, there is fear. Fear of the unknown; fear of failure; fear of disappointing others or that you’re not providing for them.

Know this: Thinking about leaving does not mean you will. It simply allows you to assess the situation. It even allows you the possibility of re-embracing your current role. 

Leave with Confidence, Clarity, and Conviction

Leaving a job you love can be disruptive and chaotic if you are impulsive or reactive. But the truth is you have the ability to press pause and assess your short and long term goals. You have a right to design your ideal future.

Begin with these two questions: If I choose to stay, what are the changes that I want to lead? What are the conditions and culture that I want to create?  

If you opt to leave, ask yourself: How do I explore the wide range of possibilities available to me? Could I take a sabbatical or “gap year?” What steps do I have to take to make that a reality?  

Remember that as you prepare to move on, your company will, too. That means you will be invited to fewer meetings and your decision-making opportunities will diminish. This may lead you to feel isolated or unappreciated after being at the epicenter of all vital decisions and actions for so long. It might shake your sense of identity.  

Allow Yourself to Grieve For an Old Job

Leaving a job is like leaving a deep relationship. When you consciously choose to depart, you will feel a sense of loss — for the relationships, the influence, the legacy. 

Part of your leaving plan should include shifting your focus and energy from anger or questions about “what’s going to happen to me?” to “how I can best prepare those around me for my departure?” This is important because you’ll be remembered for both leaving and how you left.

During her final weeks, a client of mine prioritized mentoring as many people as possible. ] She helped to address her team’s concerns and feelings about the upcoming transition and worked proactively to ensure continuity. She said a proper good-bye to former peers and direct reports over lunches and coffees.

As a result, her colleagues were genuinely excited about her next step. They responded with an abundance of support.

She emailed me on her final day. “I walked out today feeling on Cloud 9!”

Whether you leave or not is your decision. How you leave and how you will feel after you leave is something you can plan for.

You don’t need to have the answer in front of you for the next phase of your life. But you can dream big, own your decision, and embrace your journey.