'How Do I Quit My Job?'

"I'm looking for advice on how to pursue a new job discreetly, particularly when the interview process requires multiple rounds and my current workplace has very little flexibility. I've been with my current employer for ten years. I started here before I even graduated from college, and I've grown tremendously. It's a well-regarded organization with a prestigious name, and I genuinely believe they care about their people."

"That said, it's time for me to leave. I'm no longer challenged, the work doesn't excite me, and at my site things are fairly old-school: no work from home, less vacation than many other employers, no flex hours, and we pay for our own downtown parking. And while my pay is decent for my field, the same role in another industry would pay significantly more with better benefits."

"My boss is kind and well-intentioned but very emotionally invested in me staying. She frequently tells me she never wants me to leave, and I think she would take my departure personally, even if she tried to be supportive. She doesn't see the lack of flexibility or benefits as an issue and has framed concerns I've raised as criticism of the company itself."

Use personal email, phone, and devices for all job-search activity and adjust LinkedIn visibility to avoid alerts. Schedule interviews outside work time—during lunch, before/after hours, or on personal days—or request remote interviews when possible. Ask recruiters for condensed interview rounds or flexible scheduling to minimize on-site absences. Line up private references and inform them about confidentiality. Avoid discussing the search at work and do not use company resources. Decide in advance how to handle counteroffers based on priorities like flexibility, compensation, and culture. Prepare a concise resignation and transition plan that preserves relationships and performance until departure.

Read at The Cut