Free as a Bird: Jack Dorsey Resigns from Twitter | communication analysis

Jack Dorsey resigned from his position as CEO of twitter on 11/29/21 and posted his resignation email to twitter. (This post is also featured on my new substack, which is how you can subscribe to my mailing list — free, of course)

Let’s analyze it line by line, recalling the 3 elements of communication: what we are saying (the words that are coming out of our mouth or that appear written on the page), what we are really saying, and then the most important element, what’s been left unsaid.

First, the subject line. It’s Fly. The word is never repeated in the body of the email but it is the most important part. It tells us that Dorsey is seeking freedom, that he has felt caged (like a caged bird unable to fly) and that leaving twitter is going to be exactly that, release from the ties that bind his wings and his ability to soar without constraint. This is so important. It is the crux of the entire email and its significance can not be overstated.

The body of the email begins, “Hello team, After almost 16 years of having a role at our company .. from co-founder to CEO to Chair to Exec Chair to Interim-CEO to CEO … I decided that it’s time for me to leave. Why?”

Now Jack Dorsey doesn’t have to explain himself to anyone. He could have called the team together on Zoom or Teams and announced his resignation or even at the office in person, for old time’s sake. But he wants to set the story straight with a written statement of account. He doesn’t want people to say, “well in the announcement, he said …” and then paraphrase to the best of their memory. But what’s most interesting here is that he wants to assert autonomy: “I decided that it’s time…” not the Board, not shareholders, he decided. And no one else.

“There’s a lot of talk about the importance of a company being ‘founder-led.’ Ultimately, I believe that’s severely limiting and a single point of failure. I’ve worked hard to ensure this company can break away from its founding and founders.”

Now, google says a SPOF or single point of failure is any non-redundant part of a system that, if dysfunctional, would cause the entire system to fail. Clicking on the link, we learn that one example of a SPOF is “people that cannot be replaced in case of emergency.” Oh. Ok. Maybe that’s why most companies treat the CEO role as a revolving door — in goes a marginally decent leader, out goes a newly minted millionnaire a few years later. S/he’s just a figurehead. Is that Jack’s point, that becoming too dependent on one person could cause a breakdown of the entire twitter system? (Not asking rhetorically; we’ll come back to it.)

He continues, “There are 3 reasons I believe now is the right time [for the company to break away from it founders].”

“The first is Parag becoming our CEO. The board ran a rigorous process considering all options and unanimously appointed Parag. He’s been my choice for some time given how deeply he understands the company and its needs. Parag has been behind every critical decision that helped turn this company around. He’s curious, probing, rational, creative, demanding, self-aware, and humble. He leads with heart and soul, and is someone I learn from daily. My trust in him as our CEO is bone deep.”

WOW. Bone deep. That is trust. As you may know, I have written many times that there is no such thing as trust, only reduced risk. That’s why banks call your borrowing and repayment history a “credit” report but have their risk team analyze the likelihood (the statistical probability) of you paying them back. That being said, most people don’t think this way and haven’t even considered that element of the nature of “trust.” I suspect that Jack Dorsey is has. As a Sigma male in an Alpha leadership role, he is also likely to know that one of the most powerful ways to influence somone from that dominant leadership position, is to build them up (give compliments) and make them feel that you have invested in them. This can make them feel beholden and indebted. In other words, if Jack says, “Parag, I would trust you with my LIFE (or my company, my baby that I built from the ground up),” then perhaps Parag will feel that he should emulate Jack and be as good a CEO as Jack was. There is often an element of quid pro quo in a glowing annual review, and this is a review of Parag’s entire career at Twitter if there ever was one. Interestingly, calling Parag demanding is not a compliment. This could be Jack’s way of giving “feedback,” pointing out an area of potential future growth. “Exacting” is the complimentary diplomatic way of saying demanding because it means the person has high standards for themselves and others. Demanding means … well, you know the connotation.

He continues:

“The second [reason Jack is saying now is the time for him to leave] is Bret Taylor agreeing to become our board chair. I asked Bret to join our board when I became CEO, and he’s been excellent in every way. He understands entrepreneurship, taking risks, companies at massive scale, technology, product, and he’s an engineer. All of the things the board and the company deserve right now. Having Bret in this leadership role gives me a lot of confidence in the strength of our board going forward. You have no idea how happy this makes me!”

Ok so he was worried about weak spots, but the weakness he was most worried about was the power dynamic among members of the Board. Bret as the captain at the helm of the ship/board is a huge relief to him. He doesn’t mean happy here in the joy-filled sense. He means relieved. (But why?)

“The third is all of you. We have a lot of ambition and potential on this team. Consider this: Parag started here as an engineer who cared deeply about our work and now he’s our CEO (I also had a similar path … he did it better!)”

I’m curious as to why Jack would say that. Is he referring to how he himself left Twitter in 2008 and then came back in 2015 whereas Parag came, stayed, got promoted, and is now CEO with no lapse in employment at Twitter? Why compare the two paths? While life seems to be a series of decisions we make, upon further reflection, perhaps Life is the one making the majority of the decisions. Do we all have our own life? Or does Life have a bunch of us? Regardless of Jack’s thought process behind this ebullient (excessive!?) praise of his successor, it’s a display of submission whenever we put ourselves down. He probably was intending to sound humble and complimentary, not self-deprecating. Nevertheless, what we accidentally say can be as meaningful as what we end up saying. 

He continues: “This alone makes me proud. I know that Parag will be able to channel this energy best because he’s lived it and knows what it takes. All of you have the potential to change the course of this company for the better. I believe this with all my heart!”

In sales, they teach you that you’re really selling belief in the product or service, that what success boils down to is the transfer of this belief. Here, Jack is transfering his belief in his Sigmatic (engimatic + Sigma) way. Love is very powerful (some would say the most powerful force in the universe and I would agree) and with his words, he is transferring belief in Twitter and his love for Twitter as a company to his former employees. BUT there’s something else here. Something concerning. Why does he want the course of the company to change? And for the better? Because something is wrong. He’s broadcasting loud and clear in this message to every single employee (thousands of people, let that sink in for a second! Nay, a minute!!) that steering the course is something they can all still do even once he is gone. And he is hoping and praying they WILL. How do we know this? Because he says he believes this with all his heart. This hurts to read. I know I often joke in an over the top way on youtube on occasion, exclaiming, “It hurts! It cuts like a dagger!!” (melodramatic pantomime of a dagger in my heart). “Twist! And back around!” but in all seriousness, that’s how I feel when I read this paragraph. It just hurts.

Now this is where some background is necessary. What is wrong? What is really going on here?

Something bad happened. Or rather some one. Right before the Pandemic started. In early 2020, an activist investment fund called the Elliot Group (founded and run by Peter Singer: remember that name) bought up a huge share of twitter stock in order to leverage one of their employees onto the board (oh, that’s why Jack was so worried about the strength:weakness ratio of the board) which would in turn give the Elliot Group’s mole — er, I mean, employee — the power to demand/pressure all the other boardmembers to vote in a new (and improved) CEO and vote out Jack Dorsey.

What is an activist investment fund?

An activist investor is a major investor (generally someone at the head of a fund or firm) who buys shares of a company’s stock with the goal of changing its policies or leadership.

Thanks, yahoo finance.

Want to know something really interesting about Peter Singer? He poured a shit ton of money into Marco Rubio’s campaign in 2015 in order to derail the populist support garnered by Donald Trump. Want to know something else? Singer sent an email to all employees of the Elliot Group on February 1, 2020 telling them they should plan ahead for a long term cov!d nineteen related quarantine. I mention this merely in passing, not because it bears any relation to the pendulum swing in content moderation policy that took place at Twitter between 2018 and 2020, once Elliot Group, in March of 2020, used its status as one of Twitter’s top 25 investors to install their employe Jesse Cohn on the Board of Trustees. 

Once Elliot Group had a literal seat at the decision making table, Twitter employees read the writing on the wall and could see that there was a bounty on Jack’s head and someone was gunning for him. All the media outlets swore up and down that it was because there was no way one man could be the CEO of 2 companies [Twitter and Square] at the same time and not for some other nefarious reason. (And I mention this merely in passing and not because I think the real reason was to use duress to achieve a new content moderation policy that would come in handy to justify eventually booting Trump off Twitter altogether, and to justify censoring any tweet which questioned an official “safe and effective” narrative regarding other matters. And not to go on and on about it, but for fun, let’s compare the 2018 policy, see below, where twitter declared itself literally NOT the arbiter of truth …

… to the new and improved policy 2 years later where certain special tweets got warning labels and became un-retweetable or force-deleted. Example:

But back to pre-lockdown March of 2020. The employees of Twitter love(d) Jack. And they were pissed off that some vulture capitalist dickhole (er, I mean, philanthropist) had it in for their boss. They even started a hashtag, #WeBackJack, to defend their guy.

Take a look at this loyal guy, Empinto, below — he’s ready to physically fight to defend Jack. That is how beloved a leader he was at Twitter. (Seriously, check the hashtag. This is just one example).

And as a brief update to the drama, the Elliot Group plant, Jesse Cohn, stepped down from his position on the Board in June of 2021. Stock value up, and even an edit button available via subscription coming down the pipeline. Mission accomplished.

Which brings us back to November 29, 2021 and Jack’s resignation letter. As he was saying: “Parag is CEO starting today. I’m going to serve on the board through my term (May-ish) to help Parag and Bret with the transition. And after that … I’ll leave the board. Why not stay or become chair? I believe it’s really important to give Parag the space he needs to lead. And back to my previous point, I believe it’s critical a company can stand on its own, free of its founder’s influence or direction.”

Ok so, not quite. Jack, in typical Sigma fashion, wants (desires) autonomy.

Sigmas either want total control over executive decisions or total freedom from being responsible for the effects of other people’s poor judgment and subsequently the even worse decisions made based on that judgment. Contrast this with an Alpha male who demands total control, final approval of decisions made all the way down the ladder, and who chuckles at the idea of freedom (even in theory). Jack isn’t going to take a role with less power of influence, no authority, and watch (in potential horror) as Twitter is fundamentally changed from his original vision or even his 2015 vision from the sidelines.

“I want you all to know that this was my decision and I own it. It was a tough one for me, of course. I love this service and company … and all of you so much. I’m really sad … yet really happy. There aren’t many companies that get to this level. And there aren’t many founders that choose their company over their own ego. I know we’ll prove this was the right move.”

So much to unpack in this one tiny paragraph. “I own it” is a colloquial way of saying we made a mistake. (As in the case of one person accusing another of doing something wrong, and imperiously demanding, “You did it, own it!”) But he doesn’t mean that, nor does he mean, “I take responsibility for it” as in the 90’s HR-speake, “take ownership.” Yet it’s still an interesting reveal. What he literally means is that he possessed the decision — as in possessive pronouns. The decision was HIS and not the Board’s and he’s making such a big deal of reiterating it now because of how much love and loyalty everyone in the company showed him a year and a half earlier using the #WeBackJack hashtag. But he (unconsciously) uses the “I own it” idiom because this resignation on some level is a mistake. Not Jack’s mistake. So whose? Peter Singer and the Elliot Group’s mistake. 

Jack says it was a tough decision, “of course.” Of course. The phrase of course is almost always extraneous. (Except when we are using it to say, yes, e.g. Can I bring a friend? Of course!) And usually means we are exaggerating or straight out lying. The other day I was re-reading a text I had sent saying why I couldn’t attend an event I’d been invited to. I didn’t want to disclose the real reason I couldn’t make it so I said (lied) something else was the reason, “of course.” I was kicking myself after the fact going, why did you say of course??! Lol!! By the same token, we can deduce that it was not a tough decision for Jack at all. He was ready and this may even have been a long time coming. Again, Fly is the subject line of the email and the Twitter cage will soon feel very empty indeed for everyone left inside. 

Jack also says he’s really sad … yet really happy. You be the judge: does he mean really as in very? Or really as in actually? I think he means he’s very sad but actually happy. He’s sad, again, because he knows his people will miss him terribly and he’ll miss them, but he already told us why he’s happy (in the subject line), and I posit that he’s actually very happy. He’ll soon be free as a bird. (The Sigma feels they have become an extension of what they have created; the Alpha feels what they have created is an extension of them.)

Now why does he say, “I know we’ll prove this was the right move”? We know what it means when someone has something to prove — and it’s not good. In the power dynamic, we are in the inferior position. We might even have been set up to fail, and are fully aware that there is a premeditated strategy being implemented to thwart us which makes us we feel compelled to defeat this dastardly plan and prove the haters wrong.

He then signs off with, “We’ll have an all-hands meeting tomorrow at 9:05 AM Pacific to discuss it all. Until then, thank you for all the trust you’ve placed in me, and for the openness to build that trust in Parag and yourselves. I love you all.


And Jack seriously and sincerely DOES love them all. A lot. Deeply. As in the type of leader who wanted to make the workplace environment a joyful place for each and every employee. And he was beloved in turn. I mean adored. Go to twitter right now and search the hashtag #ThanksJackDorsey. He is going to be deeply missed. Now for the post script.

“PS I’m tweeting this email. My one wish is for Twitter Inc to be the most transparent company in the world. Hi mom!”

Quite the fascinating P.S. Our mother holds the strongest image of our self and vision of our future; indeed she is usually the first person to know we exist (when she discovers she is pregnant with us), and the focus this one human woman will hold for years, day in and day out, this picture in her mind of the very map of our personality strengths and weaknesses, is powerful enough to induce failure or produce success when we are young. Jack loves his mom, yes, but this final reference to her in a work email sends a profound signal indeed. He is anchoring his very decision to leave twitter in their shared vision of his character. If someone said to him, “Why would you leave twitter? It just doesn’t make sense.” Well, now they have the reasons – the 3 very specific ones he just delineated via mass email. If someone mused, “This just seems out of character, it isn’t like you to buckle to external pressures to leave something you love.” Well, it’s exactly his character to put the success of an entity he created and loves above his own desires and no one understands this character strength better than his mom. She may even have been the first person he told of his decision to leave twitter, and she probably said, “You do what makes you happy. I love you no matter what.” We should all be so lucky!

And now, I hope you enjoyed the meat and potatoes because it’s time for dessert.

  • Not once in the email do we see the phrase “thank you.” That’s amazing. He doesn’t say thank you because (wait for it) he’s not thankful.
  • There’s not a hint of nostalgia. Not one anecdote from the earlier days. Because he wouldn’t go back if he could. There’s not a drop of nostalgia for 2006 anywhere in his heart or mind.
  • He mentions the company’s founders plural (because there were 3 originally) — except once, when he says, “its founder” singular. A slip. But he knows Twitter is his creation. It’s HIS. “I own it.” Yes. And it will always be his, like the company Apple will always be the brainchild of Steve Jobs. 
  • He says that his one wish is for Twitter Inc to be the most transparent company in the world. Because it is anything but at the moment.

These are all dots that connect to tell us the larger message. As we know, Dorsey’s real victory in his battle against Peter Singer was achieved once the Elliot Group backed down and their boardmember was replaced back in June of 2021. At that moment, Jack had effectively “won.” Any pressure on the board to replace Jack and any pressure on Jack to resign would then have stopped. So if he doesn’t have to leave, then we can deduce that he’s leaving because he wants to. How do you think someone who believes journalists should act as fact checkers, not social media companies would feel about getting a phone call from the Press Secretary telling him the President wants him to delete a journalist’s account? (Alex Berenson, on 8/29/21.) I think that would cause a terrible internal conflict at a deep level, one that could only be relieved by reverting to the core values that the person was raised as a young person to uphold as sacroscant: freedom of speech, freedom of the press, freedom to be free.

It appears that Jack Dorsey is ready to leave the nest for complete autonomy and freedom.

I hope someone gets a chance to tell Jack, “you are non-redundant.” After learning about Peter Singer and his remarkable similarity to an evil villain, I hope losing Jack does cause twitter to systemically fail. (Imagine a microblogging platform that makes microblogging words people actually want to read so cumbersome that it eventually becomes not profitable and thus defunct.) When they beg him to come back and save Twitter (again) in 5 years, he can turn around and say, “no, never.” Now, did you catch the dig? The quip about Twitter being the most transparent company, in the world? LOL. That’s a big screw-you to the people who operate in the shadows of secrets and lies all day. The policies of Twitter now are the opposite of transparent. The algorithms are secret. No one knows how they got swept up or why they got banned when someone else didn’t get suspended for engaging in the exact same type of behavior. Finally, the lack of any reference to gratitude is remarkable. He says he’s proud, but “proud of you” is bestowing praise from the superior position in an unequal power dynamic. “Thank you” is giving gratitude, as part of either an equal exchange or giving from the inferior position in an unequal power dynamic. He’s decidedly not thankful for the opportunity to leave his brainchild in the hands of people he hopes will realize they can steer it clear of icebergs.

So, where does that leave our Sigma Protagonist? Well, Jack loves Bitcoin

Will he become a Bitcoin salesman, so to speak? A Bitcoin missionary? Bitcoin is a unique concept. I’m reasonably curious and able to read and understand new concepts, but I could not (at this point) explain the blockchain or how Bitcoin works without getting confused mid-explanation. He can, he does, and in a very magnetic confident way. If you, dear reader, are interested in learning more, may I recommend these 2 articles below that shed a great deal of light on the subject and made me feel enthusiastic about Bitcoin replacing the dollar as the world’s reserve currency which could end the finance of endless war. (Some of you know that I often refer to world peace as the absence of war, and world joy as the presence of joy. I believe that one could lead to another, as part of my spiritual regimen and Bitcoin seems to have a lot to offer in terms of achieving both goals.)

Bitcoin is Time 

Bitcoin and The End of Super Imperialism 

Check out this one little paragraph from the second piece: 

[Bitcoin] stands a good chance to eventually be the next reserve currency. Will we have a world with bitcoin-backed fiat currencies, similar to the gold standard? Or will people actually use native Bitcoin itself — through the Lightning Network and smart contracts — to do all commerce and finance? Neither future is clear.

But the possibility inspires. A world where governments are constrained from undemocratic forever wars because restraint has once again been imposed on them through a neutral global balance-of-payments system is a world worth looking forward to. Kant’s writings inspired democratic peace theory, and they may also inspire a future Bitcoin peace theory.

Under a Bitcoin standard, citizens of democratic countries would more likely choose investing in domestic infrastructure as opposed to military adventurism. Foreigners would no longer be as easily forced to pay for any empire’s wars. There would be consequences even for the most powerful nation if it defaults on its debt.

In closing, enjoy this video to see what the future holds for our Sigma Male:

Thank you reading!


2 thoughts on “Free as a Bird: Jack Dorsey Resigns from Twitter | communication analysis”

  1. Wonderfully written. Congratulations Sarah, you outdid yourself with this one. You made me see Jack from a different angle. I’ve noticed lately that he’s “different” but not a “Sigma” different until now.
    You are good, really good and as someone who thinks (he knows it all) you made me feel like I still have so much to learn (in my defense I’m still young ;). Overall, Thank you so much for your “teachings” and insights you are making an impact (directly or indirectly) through education and I’m looking forward to what you’ll share next.

    Liked by 1 person

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