I Don't Know How Anyone Works With Their Sibling

No offense to my brother but I couldn’t hack it

Peter Kramer/HBO
Cain and Abel

“You don’t choose your family. They are God’s gift to you, as you are to them.” That’s a quote I found on BrainyQuote.com, almost certainly misattributed to Desmond Tutu. Whether or not Tutu actually said that, the sentiment is true. The first part of it, at least. None of us get to choose our family, and most of us don’t get to choose our coworkers. In the Venn diagram of people who a) have families and b) choose their coworkers, a sinister group of people sits in the middle: people who choose to work with their siblings.

Since Jacob and Esau, siblings have been feuding. It starts when the younger child is born, and suddenly the older must vie for the attention that once belonged to them alone. A sibling can be a great friend and confidant, but on the turn of a dime they can become your most bitter rival. The good and the bad are what bring people together, but a deep familial history is probably not a sturdy basis upon which to run a business.

Look at some of the most notable sibling collaborations throughout history. John Wilkes Booth and his brother Edwin acted alongside each other, and one killed a president. Karen and Richard Carpenter started a band, and then Karen died. Dane Cook hired his half-brother Darryl McCauley to manage his money, and then McCauley stole millions from the comedian. Billie Eilish’s brother Finneas produces all of her music, which hasn’t resulted in anything bad yet but just has a weird energy. I would include the Winklevoss twins, but all twins are freaks so it actually makes sense that they’d work together.

Some of those examples hold more water than the others, and all of them seem to suggest that maybe no one should become famous. But look at the Murdochs. The children of the media scion have so publicly feuded over who will be their father’s successor that it gave us Succession. As we see on the show, no one can stab you in the back like a sibling. They know all of your buttons and will push them endlessly if they want to. It doesn’t seem like a conducive environment for getting your work done.

To test this theory, I asked my younger brother, David, a recent college grad who works part-time as a researcher, to write a blog with me. Early one Monday morning, we got on FaceTime to co-author the incredible blog, “Gillian Anderson Unable to Commune with Ghost of Margaret Thatcher.” An instant classic.

I will admit that when we started the endeavor I was worried I would be the problem — that my biggest flaw as an older sibling (being a bitch) would rear its ugly head. I feared that we would quickly slip back into the dynamic established when we were children, where I would go too far during a wrestling match, pull his hair too hard, and then beg for him to not tell our mom that it had happened.

To my surprise, that did not happen. David was more than game to spend a full five minutes thinking up what Margaret Thatcher’s ghost might have said to Gillian Anderson as she was preparing for her role. He also reminded me that Kristen Stewart actually had felt the spirit of Princess Diana while shooting Spencer, which gave us a nice little kicker that I otherwise would have spent a long time looking for while my brain short circuited. Shiv and Kendall Roy we were not.

Knowing that this was just my own personal assessment of our time spent working together, I called David afterwards to see if he thought we could run a successful business.

“Absolutely not,” he said. Ok, interesting.

While he described the actual experience as being “pretty tight,” he rightly noted that us knowing each other for 24 years would not exactly help the situation. “I think our sensibilities are so similar that putting two [of that kind of person] in the mix, you know, doesn't, like, balance anything out,” he said. That’s a very kind way for him to say that we are both Virgos who don’t like when someone tells us how to do something.

David did agree with my idea that given enough time we would eventually revert back to our childhood antics. “I'm rolling boulders down the hill to hit you,” he said, “and you’re throwing me into fireplaces.” I would like to take a moment to specify that it was the edge of one fireplace and there wasn’t an active fire going at the time. Either way, hopefully at our age these inevitable blows would be metaphorical, but you can never be sure (Romulus and Remus vibes).

Surely there are some siblings who work together well. David said he thinks the reason the Eilishes probably work so well is that there is a strong differentiation in their skill set, which I am inclined to believe. Unfortunately for us, our skills (writing, movie trivia, ordering the best dish at a restaurant) are very similar.

I guess it’s safe to say that you will not be seeing The Craigheads running a taco shop or a venture capital firm any time soon. That is probably for the best. A healthy work-life balance cannot possibly exist when your professional partner can tell your employees about the time you peed your pants at soccer camp.