Bullish Life: What Do You Feel Guilty About Today?


A teenage student of mine has a problem – she is involved in the worst unpaid internship in the world.

Her mom made her go into a local doctor’s office and, explaining that she had “nothing to do” all summer, request to work there. She does not actually want to be a doctor (her mom wants her to be a doctor).

The doctor’s office doesn’t really have much useful work she can do, but they’ve kindly exposed her to all facets of the business: this resulted in getting squirted with blood during someone’s wisdom tooth surgery.

She wants to just stop going there and never speak to them again. But she can’t! Because … wait for it … the doctor’s office is located in her family’s apartment building. Awkward. How New York.

I offered some suggestions. For instance, “Thank you so much for allowing me this opportunity! This has really helped me see that this isn’t for me – I’m a little squeamish and should really explore other career options.”

I have written before, on many occasions, about women who have trouble being direct, even when they are obviously in the right. In Bullish: How to Communicate with Chutzpah:

For instance, I once worked for a company that was late in paying me. My contact at the company had an elaborate plan to slip the invoice into a magical stack of invoices so that the person who pays the invoices would think that the invoice had been fast-tracked by the person who makes the magical stack. What? No one has done anything wrong here. I did the work. Everyone likes it! You got the money approved before you asked me to do it. Now I would like my invoice processed! You should ask the lady who signs thing to pay the invoice! Yay! There isn’t even a problem here.

(See also: Bullish Life: Breaking Free From Terrible Situations. And if you haven’t read my four-part series on asking for more money, I think you should do so and consider asking for more money. Not just for yourself, either – are you getting emails from the Obama campaign asking for money and wishing you had money to give? I want you to make more money for your future self, and for all of us. See Bullish: How to Ask for More Money, Part I and Part II, Bullish: How to Ask for More Money Q&A, and Bullish: How Negotiating a Raise is Like Dating.)

My student didn’t like the direct option. (She had also once told me a story about a “friend” repeatedly cheating off her paper, and the incredible lengths she had gone to – changing seats, buying a new pencil box to block the friend’s view – to try to stop this without having to say anything.)

My second try at advice was that she say something like, “I’m sorry I misjudged – I need to end this internship earlier than we discussed so I can do my summer reading for school. It’s a lot more work than I anticipated.”

This is basically true (she does have a summer reading list) in the same way that, “I love working here, but I need to have a job that allows me to contribute to supporting my aging parents” can also be basically true, even though you shouldn’t really need that kind of excuse to want to be paid market rates for your work, or better than market rates for being more awesome than other people in the market.


I also said, “You’re talking about this like it’s some terrible thing you’ve done that you need to worm your way out of. You know, you haven’t done anything wrong here.”

She said something like: “But I feel so guilty!”

I said, “I think this is a really common girl thing.”


“Yes. Adult women I know struggle with this all the time. I have never heard this from a man.”

I write Bullish articles all the time about being direct and making ballsy but reasonable demands and how to get your head in the right place to be able to do this painlessly and effectively. In Bullish: Seven Sentences to Boost Your Career and Life, I recommended the phrase, “It’s not possible.” In Bullish: How to Ask for More Money, Part II, I suggested, “It would be illogical.” Both clauses are best delivered collegially and matter-of-factly, followed by a “but” and an attempt to reach a compromise or satisfy demands in some other way.

When I get letters from men (somewhat rarely), most of them take the tone, “Oh, it’s good that you’re telling women this thing that we’ve been passing down from father-to-son all this time.” You can sort of feel the beneficent nod the letter-writer made as he was writing.

I asked a small panel of men about feeling guilty for no reason. I said, “A woman I know is feeling guilty about quitting her unpaid internship. I told her she shouldn’t feel guilty because she isn’t doing anything wrong. I think this is a girl thing.”

(Obviously anecdotal) responses:

  • “Yeah.”
  • [huge grin] “No, we don’t get that. We like getting away with something.”
  • “We like it when we’re walking away from things, even if we’re a little wrong.”

Um, that explains … a lot, right? I didn’t even ask any known assholes about this. Just (seemingly) normal guys.

So you can only imagine if I had asked some total douchebags: “That’s how you get bitches to do what you want. Wait, I just violated the douchebag code of silence! KEEP THIS TO YOURSELF.”

So, how many times per week (per day?) do you feel guilty? How many of them are justified?

Next time you find yourself feeling guilty, ask yourself, what, exactly, your crime was.


Make sure you’re comparing yourself to a baseline for a competent, above-average human (and no more). For instance, are you feeling guilty because you said you’d get something done but something else popped up unexpectedly? Human beings can’t actually predict the future and should not feel guilty about this. Sure, all human beings are supposed to be able to foresee things like, “If I drive drunk, people might die.” And competent, above-average humans are supposed to be able to forecast things like roughly how long a project should take if nothing totally crazy happens. But sometimes, totally crazy things happen.

If your guilt is unjustified, let it go. If you have to close your eyes and imagine yourself blowing it away like dandelion fluff, please do. Or say, “Oh, I was having an irrational guilt feeling.” Don’t own it. Treat it like hiccups. It’ll go.

More importantly, next time you find yourself acting like a guilty person, stop – other people can smell this.

If you have to ask “What would a dude do?”, do so, even if you ultimately end up pursuing a middle-ground approach. But please don’t go around wheedling and pleading and underhandedly manipulating when you could just say, “This isn’t working for me, but thanks so much for the opportunity,” or, “Because we’ve had a lot of unexpected employee absences, I’ve written this revised workflow document with a new deadline,” or, “Would you please put this invoice in today?”

Unnecessary guilt helps no one.

First published on The Gloss.


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