Breaking up Is Hard To Do
Last month, I finally read Careless People by Sarah Wynn-Williams. Late to the party, yes. But with three book clubs, I’m doing my best!
As I read her account of working at Facebook (for 7 years!), I kept coming back to one question:
Girl. Why were you still there?
She describes leadership decisions that conflicted with her values and a work environment that became increasingly difficult to tolerate. Yet she stayed.
There were practical considerations, including health insurance. Leaving a job can have real consequences, and I don’t want to minimize those.
But as I kept asking why she hadn’t left, I had to turn that question back on myself.
Because I have stayed too long, too.
Especially in relationships. I’ve made excuses, waited for things to change, and given situations more time when I already knew they weren’t serving me.
It’s much easier to recognize that from the outside. When you’re the one inside it, there’s history. There’s hope. There’s the memory of how good it used to be, or, even more heartbreaking, how good you thought it could become.
And there’s the thought of having to start all over again.
The same thing happens in our careers.
Maybe you’ve stopped learning. Maybe you’re consistently overlooked. Maybe the work no longer aligns with your values, or you’ve been waiting on a promotion that always seems to be one more conversation away.
But the paycheck arrives. You know the people. You know how to do the work.
So you give it a little longer.
And then a little longer.
Sometimes we stay because we’re happy. Sometimes we stay because we’ve learned how to live with the disappointment.
We stop asking whether the role still fits. Getting through the week becomes enough.
Leaving feels uncertain. Staying feels familiar.
In my last newsletter, I talked about continuing to invest in your relationships, skills, and community while you’re happy in your work.
This is the next question:
Are you choosing to stay, or postponing the decision to leave?
Staying can be a thoughtful decision. You may need the income or benefits. You may be gaining experience that will help you make your next move. You may have a clear reason to stay through a particular date.
But that decision deserves a check-in. Especially if another year has passed and you haven’t asked yourself whether those reasons still hold.
If this feels familiar, ask yourself:
⇢ What keeps happening that I keep explaining away? Look for the pattern you’ve learned to tolerate.
⇢ What would need to change for me to want to stay? Be specific. More support? Different work? A credible path to advancement?
⇢ What evidence do I have that those changes are coming? What has actually happened since the last promise or conversation?
⇢ If nothing changed over the next year, would I still choose this? Give yourself permission to answer honestly.
Then take one step that gives you more options—even if it feels uncomfortable.
Reach out to a former colleague. Look at roles you’d actually want. Update your résumé. Work out what you’d need financially to make a transition. Have the conversation you’ve been avoiding.
You don’t have to resign tomorrow to begin making a decision today.
And you don’t have to wait until you’re completely miserable—or until someone else decides it’s time for you to go.
You’re allowed to say, “This has been an important part of my life. And I’m ready for something different.”
You’re allowed to be the one who says goodbye.
Join the LinkedIn Convo
For decades, the career playbook looked something like this:
🎓 Go to school.
💼 Get the job.
🪜 Climb the ladder.
🏢 Chase the corner office.
Then Gen Z came along and collectively said...
"Yeah... no thanks."
Ya’ll, Career Minimalism has officially entered the chat.
Remember when someone you met once at a conference could endorse you as an expert in strategic planning? Those days are long gone.
LinkedIn’s new Hiring Assistant is looking beyond long skills lists to find evidence of what candidates have actually done. In this week’s Monday Market Brief, I broke down what that means for your profile and the quick skills audit you should do now.
Want to catch it each week? Head to my LinkedIn profile and ring my bell (in the upper right-hand corner)!
Give yourself a moment to ask: If I were choosing today, would I choose this again?
Your answer doesn’t mean you have to leave tomorrow. But it deserves your attention, and one small step toward figuring out what you want next.
As we settle into autumn, remember that you’re allowed to change with the season, too. Travel in grace, knowing you are surrounded by love.
Work with me 1:1 → Step into a focused alignment experience to clarify your direction and intentionally reposition your leadership. I’m currently scheduling for late October and have 1 spot left!
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