This week, I’m answering two letters about leaving jobs that are no longer a good fit.
‘How Do I Look for a New Job Without My Boss Finding Out?’
Dear Boss,
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. While I believe she would counteroffer if I resigned, I know it wouldn’t address the bigger picture of flexibility, culture, and work-life balance that I’m seeking.
Recently, I applied for a role that seems to align almost perfectly with what I want right now: a hybrid schedule with three work-from-home days, more time off, a family-friendly culture, a roughly 20 percent pay increase, and more. I was referred by a former colleague who left our industry for similar reasons and has spoken very highly of the culture at the company.
The initial screening went well, but I’m anxious about how to get through the interview process without alerting my current employer. The next steps include a 45-minute video interview, followed by a half-day in-person interview with peers and managers (including a team lunch), and a final meeting with the CEO. My current workplace has little tolerance for time off, even when legitimate, and missed days are noticed and judged. While I have an office and could technically close the door for a video call, I sit directly across from my boss, who keeps close tabs on my day. Thin walls make privacy difficult.
I know I’ll likely need to call in sick at least once, and I’m uncomfortable with lying, but I don’t see another option. Calling off multiple times over several weeks would be highly unusual for me and would almost certainly raise suspicion. My biggest fear is going through all of this, not getting the job, and then returning to a workplace where trust has quietly eroded because leadership assumes I was interviewing elsewhere.
How do people navigate multi-round interview processes when their current job offers so little flexibility? Is it reasonable to protect my own interests, even if it means bending the truth temporarily? And how much risk is simply unavoidable when you’ve outgrown a role but haven’t secured the next one yet?
Calling in sick is the way.
Is it ideal to lie and say you’re sick when you’re not? No. Should you simply be able to say you have an appointment and leave it at that? Yes. But when you work for a company with “little tolerance for time off” and where time away is “noticed and judged,” this is what you have to do — and they’re setting themselves up for it by operating that way.
There are all kinds of reasons you might need time off that you’re entitled to keep private and that you shouldn’t be judged for by your employer or colleagues: medical appointments, legal appointments, illness, family needs, mental health, and on and on. If your office makes you feel like meeting those normal needs is frowned upon … Well, that’s an office that’s in denial about the fact that it employs humans with lives outside of work, and it’s also an office that is pretty much forcing people to lie when they do need time away. So this is the situation they’ve created, and you shouldn’t feel guilty about adapting to it.
Given the number of steps coming up in this interview process, the smartest thing would be to tell your boss that you have a minor medical situation that you’ll have multiple upcoming appointments for — “Nothing to worry about, but I’m going to need to take a few half-days in the coming month to take care of it.” That way you have one overarching narrative explaining multiple absences rather than needing to come up with new reasons each time, and your boss is more likely to mentally lump them all together rather than wonder why you’re suddenly taking a bunch of days off. (Dental work in particular is useful for this, since it can require multiple visits without sounding alarming.) Again, the deception isn’t ideal, but that’s on your employer for forcing your hand.
‘When I Quit, My Boss Will Try to Guilt Me Into Staying’
Dear Boss,
I started my job almost six years ago and became my direct boss’s friend; we started occasionally getting dinner and hanging out outside of work.
The problem is that this guy sucks at work. He’s lazy, petty, and can’t take criticism. I’m one of the only people at our location who even tries to be nice to him nowadays (largely because the thought of being rude to anyone gives me hives), and he’s latched on to me because of it.
I’ve decided that it’s time for me to move on to another job, but I’m terrified to tell him I’m quitting. Realistically, I know the worst he could do is get mad, but he’s my “friend” still, so I’m worried he’s going to try to guilt me into staying, which I’m very susceptible to falling for. I hate disappointing people or feeling like anyone is mad at me. I know that’s a me problem, and I recently started therapy, but it’s still troubling me and I feel like getting a reality check might help.
This is a good thing to work on in therapy because, while it’s not unusual to feel nervous or even guilty about leaving a job, it is not normal to worry that your boss will successfully manipulate you into staying after you’ve accepted a different job. So if you genuinely worry about that, definitely raise it with your therapist!
But meanwhile, the keys to making a clean break are to (a) have an easy way to explain why you’re leaving (“this opportunity fell in my lap and it’s just too good to pass up”) and (b) be ready with prepared phrases to use if your boss tries to talk you out of leaving. For example, regardless of what your boss says, you can just cheerfully say, “Yes, it’s been great working with you and I’ll miss you!” followed by an immediate subject change, like “I’m going to go make a list of transition items that I need to cover before I go, I’ll see you later.” Or “I’m actually really excited for the change,” or “All things must end!,” or “It’s the best decision for me, but you’re right that transitions are rough. Anyway, I’m going to go share the news with Cecily and Frank but wanted to tell you first.”
And remind yourself that it’s very, very normal for people to leave jobs, and the only way to move on to a better situation for yourself is to steel yourself to talk to your boss and get through your notice period. Your boss can’t make you stay; this is 100 percent within your control.
Find even more career advice from Alison Green on her website, Ask a Manager. Got a question for her? Email askaboss@nymag.com (and read our submission terms here.)