Q: I’m a young mother working for a company that prides itself on being “family friendly.” Nonetheless, I was pressured into work travel several times while trying to exclusively breast-feed my then-infant; I’m often given more projects than can be reasonably executed in a typical workweek (forcing work evenings and weekends); and even though my boss agrees we should hire soon, recruitment initiatives keep getting stalled.

Is this workplace really family friendly? How would you define the term if it is not supposed to mean that priorities and responsibilities involving children will not be compromised? — California

A: “Family friendly” is one of those phrases that, like “economic opportunity” or “freedom” or “stable genius,” can mean many things to different people. It sounds like your employer thinks it means, “I won’t retaliate against the fact she is a mother by firing her or paying her a garbage salary.”

It’s unfortunate that you had to take the job and actually start working to figure out that this is what “family friendly” means to this one firm. But now that you are there, what can you do?

Go to a cafe with a standard sheet of paper. Think hard about two goals: what you want your career to look like in five years and what you want your home life to look like over the same period. List 10 items under each goal that you feel you will need to check off to get to where you want to be. For the bottom half of each list, either hire an assistant to help you and/or aggressively fudge it.

For instance, you should outsource as many personal tasks as you can, like paying bills or buying groceries. And Holy Mom of Gosh, do not clean anything ever at all if you can help it.


Even if you are short on funds, it is worth it for you to go into (potentially further) debt at this time to pay for as much day-to-day help as you can get. You should use the pain of any outlays to motivate yourself to ask for a raise at every opportunity. The firm is really who should be paying for the re-righting of your capsized work-life balance. Because they lied.

As for the job, check back in a year or two with your lists. If the job isn’t going to get you there, look for another one. But keep in mind you will never change this firm’s ridiculous definition of “family friendly,” and you should not bother trying to. That said, you can do any future employee a good turn when you interview them by defining this perniciously vague phrase in the context of this particular firm much more precisely.

Passport to plutocracy

Q: I have enjoyed my career as a seasoned, high-level executive assistant in the financial sector. As such, my responsibilities include travel planning.

Recently, an associate in my firm planned a personal holiday from New York to Chicago and requested his return from Chicago, stopping in New York, then on to London on a multi-leg ticket. He failed to bring along his passport, even though his final destination was international. This resulted in the purchase of an additional domestic-only ticket.

Later, HR told me that it was my responsibility to ensure that the executive brought his passport. I feel that since he is an adult, and a seasoned traveler, he should have been responsible for bringing along proper travel documents. I may lose my job over the brouhaha, so would appreciate your objectivity. — New York City

A: It is hard to tell from your description of the situation, but the question of the hour is simply: How much does this person make on an annualized basis including base salary, bonus and deferred compensation? Trigger warning: The following answer is going to be gross.


If it’s more than, say, $10 million a year, you might lose your job over this, even if it’s totally unfair. (And to be clear, I am not condoning this.) If it’s less than, say, $1 million a year, you can safely laugh in HR’s face for even implying that you should be fired for this executive’s pathetic lapse in judgment.

The more money a financial executive makes, in other words, the more they are excused, at least in dysfunctional corporate cultures, for behaving like a spoiled child. The problem is, the job descriptions for executive assistants to senior finance personnel don’t typically mention baby-sitting.

I might also point out that a person who doesn’t know better than to not bring their passport on an international trip probably shouldn’t be trading in any size, or really making any important decisions at all.

Dino might

Q: My boss is a fearful dinosaur who has drained all joy and sense of accomplishment from my workday. I stay because the pay is spectacular but my job leaves me hating my life. I’ve worked there a year.

My workplace used to be a stodgy government agency and, until recently, was run like one. Since then, most senior management left or were replaced by people who value innovation and change. Only my boss stayed, waging a secret war against the replacements by thwarting their efforts with missed deadlines and eye rolls. She’s on the cusp of retirement but has no life outside of work. I get emails from her at midnight.

I feel like I’m in the wrong job but I don’t know if there’s something I can do to turn things around. I’ve never missed a deadline and my performance review was solid. Still, I feel like this woman’s sole purpose as my manager is to keep me from advancing or even succeeding slightly. I honestly think she hates my guts. Is there something else I can do? — Ottawa


A: First, lose the bit about the dinosaur. It’s ageist — which is weird, since the dinosaurs are dead, not old! But regardless, I’d suggest another word.

Look, your situation is simple as can be: You can either stay and suck it up while you wait out the full life cycle of your boss’s career, or you can leave.

Or, to continue with our totally offensive dino metaphor: This woman is more senior than you are. You can wait like a good little mammal to evolve until your prehistoric boss exits the scene, or you can quit her rightful territory and seek out an environment populated by other junior furry creatures like yourself that suckle their young.

Work Friend is a cheeky New York Times advice column to help with careers, money and the sometimes grim, sometimes hilarious maze that is the contemporary office, from a rotating cast of advice-givers.