The Workologist: You’re Ready to Quit, but When Should You Actually Do It?

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Send your workplace conundrums to workologist@nytimes.com, including your name and contact information (even if you want it withheld). The Workologist is a guy with well-intentioned opinions, not a professional career adviser. Letters may be edited.

I have been contemplating quitting my job for the past six months or so. I’m finally certain about the decision, but I can’t seem to find the right time to tell my boss. It didn’t seem right just after the holiday break. Then I came down with the flu and missed several days, putting additional stress on my team. Plus the company is in the middle of kicking off several big new projects, and my role would be integral.

Our company is small, and I have a close relationship with everyone, my boss included. I don’t think anyone suspects that I am even thinking about leaving. I have had a couple of amazing years here and expected to stay longer. But I’m burned out by long hours for not enough money and don’t find creative satisfaction in the work any more. It’s starting to affect my personal and professional relationships.

I don’t want to blindside my boss, but I fear postponing this conversation, as that may just overcomplicate things. I would love some advice.

ANONYMOUS

The problem here is pretty clear: You like your colleagues, but you really don’t like your job. You’re right that postponing the conversation will not make it any easier. Eventually, in fact, it’s just going to make you bitter: You’re suffering for the sake of others who are blissfully ignorant of your unhappiness.

If you have something else specific lined up, let that dictate the timing. If you don’t, then decide on the timetable that’s best for you and stick to that as closely as possible. Be selfish about this. If a job is having a negative impact on your personal life and you can get out of it, you need to do so promptly.

When you announce your decision, tie it to a concrete final date. You can choose to be flexible if requested, but anchor the discussion to a specific time frame; don’t start out with something vague or squishy.

You really don’t owe anybody a detailed explanation for your decision, and my suspicion is that you’re better off keeping that vague — just say you’ve had a valuable experience with great people, but you’re burned out and it’s time for a change. In other words, treat the organization and this situation with respect, but make sure that you and your decision are respected, too.

CreditGracia Lam

Managing a Problem Volunteer

I am the administrator in a small church. The only other full-time professional is the pastor, and we have a part-time custodian. We depend on volunteers to help with everything else around our services and community programs.

We believe that one of our volunteers is undercutting the custodian. Small things are being changed — the heat is turned on or off inappropriately, windows are left open. The volunteer always shows up while the custodian is working, to point out problems and take over fixing them. The custodian is retiring, and we suspect this volunteer wants the job. We don’t see that as a good fit. And we’re worried that the volunteer will drive off a new hire with similar meddling.

My question is how to handle a volunteer of more than 30 years who has tremendous institutional knowledge and truly cares — but is becoming a problem. I suspect he is lonely and unaware of appropriate boundaries. We want to be kind and welcoming. We are stumped.

LOU

In general, a problem volunteer should be treated the same way you’d treat a problem employee. Be respectful, but firmly explain what needs to change and why. Put this in the context of more general appreciation and the sincere hope that the person will understand that this is nothing personal.

Of course, you don’t want to upset or alienate a well-meaning and perhaps vulnerable parishioner, however problematic he may be. But ultimately, avoiding the issue isn’t really doing him any favors. And it certainly isn’t fair to your part-time employee.

Maybe the custodian transition offers an opportunity. Explain to this eager volunteer that you’re bringing in someone new — and that it won’t be a parishioner. (This makes the decision feel more like a policy than a judgment, and avoids directly suggesting that he wanted the gig.) Note that while you appreciate his attentiveness, you are counting on his help in giving the new employee the time and space to do the job. Then shift the conversation to other useful activities that this volunteer might focus on instead. Suggest ideas, but make sure to listen, too.

If you’re sincere in expressing how you value him, I suspect he’ll get over any initial upset and respect your candor and appreciation. It does sound as though he simply doesn’t get the boundaries — and that means that, ultimately, you will have to show him.

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