Call it what it is: exit guilt
One in four leaders are carrying it
Listen here.
This is the fourth in a five-part series on the blockages that keep us parked in the “safe” jobs when we should be thinking about what’s next. We’ve covered money fears, who you are without your title, and prioritizing your most important relationship. This week, we’re talking about a blockage people don’t talk about much. It also produced some of the strongest emotions in my survey.
“Don’t ask what the world needs. Ask what makes you come alive, and go do it. Because what the world needs is people who have come alive.”
— Howard Thurman
“It’s kind of like breaking up with a girlfriend or leaving your parents’ house for the first time.”
That’s how one leader described the thought of leaving his career. A breakup. Leaving home. Those are words for losing something, and he used them about a job he’s free to walk away from at any time.
Another one went to sports: “It’s like working your tail off for years to earn a spot on the first team and then walking away when you’re on top.”
No one is pushing you out. The job is good. Ten thousand people would be thrilled to have your role. But that’s the whole problem: how do you give up something this good without feeling ungrateful?
Almost one in four survey respondents named some mix of love for the job, loyalty, and guilt. Nearly three in ten named doubt about timing.
Joe still can’t answer it: “I always tell myself, I will know when it’s time, but will I really?”
We promise ourselves we’ll just know. And waiting to just know is how five years go by. Then ten.
What would change in your life if you dealt with this question now instead of when your health or age forces you to?
I shared in the first issue that I spent more than two years thinking about leaving before I actually did. I always thought the math didn’t work for me to leave and build a coaching practice. But my financial advisor settled it for me in a handful of meetings last fall. I didn’t need to question his math and run more financial models on my own — that’s what I trusted him for.
Maybe for you, it’s guilt over leaving your teams to fend for themselves. That makes sense. They’ve relied on you. You’ve fought political battles for them. You spent decades being the one who shows up when they need you. That’s just good leadership. And it doesn’t switch off just because you’re ready to do something new with your life. So you keep feeling responsible for people who are capable of swimming the deep waters on their own.
If that’s you, here are three permissions you can give yourself:
Permission to think about it. Thinking about your next season is not quitting. You planned your career. You planned your kids’ education. You’re allowed to actively plan for life after corporate.
Permission to prepare. A financial review, the conversation with your spouse, a small test of a business idea on the side. None of that is turning in your two weeks.
Permission to be replaceable. They will put someone in your place as soon as you walk away. That’s exactly what happened to me. No one is irreplaceable, not even a CEO. That’s proof you built something that outlasts you, which was always the assignment.
And if you still feel guilty anyway, hear how one retired leader described leaving. Sam sometimes felt guilty in the middle of the day for not being at work. Almost two years in, he still has dreams about the job. But this is also true: the guilt fades. Years of internal wiring stay with him, but that doesn’t mean he made the wrong choice.
James said the hardest part for him was “actually believing my value didn’t come from my job performance.” That one hit home with me. If your worth was never tied to the badge, leaving is how you find out where it really comes from.
If you can feel it in your bones that your time is approaching, whose permission are you waiting for?
Your homework this week: tell one trusted person outside of your work circle that you’re actively thinking about your next season. Your second mountain. Your next act. Actively working on it will give you ideas on what can be next in your life.
See you next Sunday.
Note: I am excited to offer a free masterclass on August 4th at 6 PM CST called “Don’t Quit Your Job (Yet).” This isn’t necessarily for people who are ready to retire, although you could be. It’s for people who know what’s next is coming and want to be well prepared. Follow this LINK to save your seat!
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