When a Job Goes From Dreamy to Dreary

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Morale Killer

Dear Work Friend,

About three years ago my company hired an incredibly toxic person to oversee my software engineering team. That person has slowly made things a living hell, taking what was creative work and transforming it into a dead-end, robotic job. As a result, 12 people have quit in the last six months — around 20 percent of the team. The only way to please this new lead is to jump through hoops and do exactly what we are told, and as evidenced by last year’s performance reviews, there is low probability that even that will get rewarded.

I’ve tried talking about the problem with my director and senior director, but no one seems all that concerned. I’m only a couple of years away from retirement, have a remote work situation and earn a good salary, so I’m pretty sure I want to stay. But I’m having trouble enduring the day to day. Do you have advice on how to suffer through?
— Anonymous

What you need is a group chat. The misery of working under a bad boss can be bearable if you have sympathetic and comradely co-workers. The loneliness of working remotely can be alleviated by a humane and motivating boss. But working remotely under a bad boss is the worst of all possible worlds: all the misery and toxicity and none of the enjoyably seditious long lunches or after-work vent fests over drinks.

So I would seek out and gather some sympathizers into an app — needless to say, a separate, nonwork app to be used only on personal devices. A good group chat of similarly disaffected and frustrated colleagues may not be able to wholly replace the cheering experience of making meaningful eye contact in a bad meeting or gathering in a galley kitchen to complain in whispered tones about a new policy. But having a text box to type your frustrations into, and receiving a supportive response, can go a long way to soothing the day-to-day frustrations of an unbearable workplace.

If you were at a different point in your career, I might even suggest that such a group could be a staging ground for an organized effort to remove your new toxic lead. And maybe it still can be that for whichever participants are staring down an indefinite future under this boss.

But one reason I suggest a group chat complaint sink rather than a more organized effort at workplace change is that I think your next priority should be recalibrating your own understanding of what you’re doing at work.

It seems like you’ve spent a long time operating under a particular kind of unwritten contract — do good, creative, enterprising work and expect acknowledgment and reward. That was probably extremely motivating and fulfilling during the growth phase of your career. To have that contract nullified in favor of something worse — do boring, hoop-jumping work and expect nothing — is a bummer.

But the bummer will be compounded by grief and frustration if you dwell on the way things used to be. If you can imagine your work as a dull new job — one you have no emotional connection to but that serves as a vehicle to retirement — rather than as the zombified version of a job you once loved, you might find yourself less frustrated. It might help you to do the bare minimum, rather than try to perform at the level of effort you’re accustomed to. Then you might be less surprised if you don’t get stellar performance reviews.

And when you still find yourself annoyed — well, that’s what the group chat is for.

Complaint Department

I have worked at a nonprofit for a little over two years, and during that time we have had three chief executives. Since the current one arrived in mid-2025, I’ve witnessed some sketchy, if not illegal, behavior: misuse of funds; the “layoff” of a staff member who was eight months pregnant because of a “lack of sufficient funding for her position” followed by the hiring of a man to do the exact same job; private board “sessions” about the budget that did not involve the entire leadership team.

I shared the evidence I had on the misuse of funds multiple times. After the last incident, they conducted a comprehensive organizational audit.

Luckily, I have recently been recruited for a different position and will be leaving the organization soon. My question is: Should I do anything with this information when I go?
— Anonymous

I think you’re obligated to do one thing: Quietly reach out to your former colleague and let her know, if she doesn’t already, that she might want to consult a lawyer about potential pregnancy discrimination. The claim is hers to pursue if she so chooses, but she can’t do anything if she isn’t aware of what happened after she left (which seems quite possible, given that she was eight months pregnant when she was laid off).

As for the rest of your complaints, I think the question facing you is less ethical than practical: How much time and energy do you want to spend pursuing satisfaction? You’ve already done the honorable thing by reporting your suspicions internally; I don’t think you can be blamed for deciding not to entangle yourself any further with such a seemingly corrupt and dysfunctional workplace, even in the pursuit of justice.

If you did feel obligated to go further, the next step would be to file a complaint with the I.R.S. — you want Form 13909, “Tax-Exempt Organization Complaint (Referral)” — and/or your state’s appropriate regulatory body. You could submit your evidence of misconduct — assuming it was lawfully obtained — and wash your hands of the situation, assuming (or hoping) the regulators will take care of it.

Beyond that, you could consider talking to a journalist who can assess if it’s worthy of an exposé.

But at some point I would worry about diminishing returns on personal investment. You should think about what satisfaction would be to you — An apology? A resignation? A perp walk? — and what it would take to actually obtain it. When you’re working for a dysfunctional organization, it can be a useful just-get-through-the-week coping mechanism to imagine dishonest or unprofessional colleagues finally held to account. But the justice that’s actually obtainable through more active or public channels often requires a lot of extra work and personal exposure, and the most satisfying outcome is rarely guaranteed.

Worse, sometimes transgressions that feel existentially wrong from within an organization can seem less awful from outside, and you can end up burning professional bridges and garnering a lot of quizzical reactions from outsiders. Put more bluntly: It’s going to be hard to convince anyone outside the world of your nonprofit to care very much about governance issues like private board sessions. In which case, the smartest thing to do might be to move on, and let the nonprofit’s deteriorating reputation exact its own justice.