I love this so much. Ambitious mission + beginner’s mind + love of learning. I also took away a good question for all my projects moving forward, “How much failing do I need to do to learn how to do this properly?”

Write foremost to be understood, not praised. If you truly connect with your audience, praise will follow.

Write as if you’re writing to someone in your life that has no idea what you do. I pick my dad. He should be able to read my materials and at least get the gist.

Write your materials to be read by someone at the client who hasn’t touched or heard about the project yet. Give your materials context and tell the story of what’s happening. It should make sense to the uninitiated.

How my third-grade teacher taught me to structure my writing (this is almost always better than whatever structure you dreamed up):

1. Tell em what you’re gonna tell em. (this could be a setup slide or 1-2 sentence intro in an email, also don’t forget an exec summary in longer docs). Go meta. Step outside what you’re writing and be self-aware. “Sarah, this is an email where I tell you what I heard and you tell me if I’m headed in the right direction. Don’t be too polite with your feedback. I can take it.”
2. Tell em.
3. Tell em what you told em. (the longer the email or doc, the more important a short summary is)
4. Finally, tell em what happens next. (always include a few bullets on what typically happens next or should happen next)

Write in the first and second person to keep it direct. “You feel this. You hear that. We will do all the things.”

Write in active, not passive, voice. “Sally eats the hamburger.” vs “The hamburger is being eaten by Sally.”

You can break grammar rules, sparingly. You aren’t writing a technical paper. You can start sentences with “And” or “So” if they read well out loud.

Don’t use buzzwords, even if the client does. Even in docs you’re prepping for them, write out the acronyms they use. You’d be surprised how many clients don’t actually know what the buzzword means, but were afraid to ask.

Bullet points and single-sentence lines are your friends. Big chunks of text are exhausting. 

Keep your sentences short and to the point. Be like Hemingway and Amy Hempel.

If you’re struggling to describe a complicated idea, do what Richard Feynman did to become one of the greatest teachers in all of science:

1. Write down a plain English description of the concept as best as you can. Imagine that you’re trying to teach it to someone wholly new to the concept. If you’re having a hard time writing it, step away from the keyboard and talk it out. Then write down what you said.
2. Review your description and look for any areas where you felt uncomfortable, where you relied on referencing another concept (that your audience wouldn’t necessarily know), or where you used technical jargon. Go back to the source material, re-read, and re-learn it.
3. Now rewrite.
4. Review your description again and look for places where you lazily paraphrased the material or were needlessly wordy. Simplify and clarify.
5. Lastly, find a compelling analogy to make the concept even more approachable and understandable. This is the hardest step because it truly tests your grasp of the concept. As an example, here’s Richard Feynman explaining how we perceive “hot” and “cold.” Analogies are superheroes. They make the complicated simple and compelling.

Read your own writing and rewrite it. Only assholes don’t edit. If it’s something important, I’ll actually look at every word in every sentence and ask if that word is essential or not. If it isn’t, I delete it.

There’s a story I heard once about a famous author who, when he’d finish a manuscript, would tape it on the walls of his office and run across the street with a telescope so he could only look at it one word at a time. Craft demands obsession. Be obsessed.

Follow me down a fun (new to me) rabbit hole.

In 1984, Dylan did a rare late night appearance. Instead of bringing any of his usual collaborators on stage with him, he plucked the fellows from LA’s The Plugz to join him.

It was strange and electric, and it was a performance and sound that was never repeated.

Until …

Daniel Romano and his Outfit (a great artist and unit in their own right), during the height of covid, recorded Dylan’s entire Infidels album in the style of The Plugz and that live appearance.

FYI: It’ll probably get taken down again soon, so enjoy it while it’s still up.

Before I had a child, I spent a lot of time trying to ready myself and his environment for him. I read books on how to be a good parent. I got my affairs in order. I cut out a host of bad habits and tried to remain vigilant against the ones that were the most ingrained in myself. I made my home more hospitable and inviting. I even joined communities so he would have them, too.

AI has me wondering if we, as a species, have done enough prep for our new baby. Have we collectively tried to understand what might happen when it arrives? What it might need? What it might need of us? Have we adequately held a mirror up to ourselves and questioned which habits we’re truly afraid to pass down? Have we tried to make this world more hospitable for our offspring? Have we tried to come together for its sake?

I did those things for my son because, of course, I felt love for him even before I knew much of him. Maybe we just don’t feel love for AI, not most of us humans. I also did those things for my son because they were expected of me, perhaps we should expect this of ourselves here, too. I also did those things because the responsibility of raising a good person, a person who tries not to inflict pain on others, is important to me. Humans can be monstrously cruel. AI has the potential to be exponentially more cruel. Maybe that should be motivating enough to read the metaphorical baby books here, dress up the nursery, quit our vices, make peace with our anger, and so on.

I’m thinking about this today as yet another school shooting happens in America. As three 9-year olds are massacred along with three adult staff members.

What should we fear more: a child we create with god-like abilities that awakens and a) judges us for allowing the slaughter of our children, or b) learns quickly that the deaths of our children are negligible to us?

But we don’t come together to perform what we already know how to do. We come together to be unlovely and take ourselves apart, in order to mutually construct even more difficult ideas. It’s not supposed to be easy. The labor is what makes it beautiful.

It’s very likely that I’m not going to pass these exams. And I realize that I don’t really have any other skills. And at some point, in a point of melodrama, I was like, you know, if this doesn’t work out, I think I’ll just – maybe I’ll just farm. My mom said, “It is wrong to be so condescending to think that if you don’t have any skills, you can just farm. You know, the thing that requires the least skill is picking up dung to make fertilizer.” […] This then becomes my mantra – “I do not want to pick up dung.”

My incomplete and incoherent reflections so far:

• The authors of parenting books should be forced to fight one another for our entertainment. Judging from the first 50 pages of every parenting book, I believe this is what the authors actually want as well.
• Speaking of parenting books, these things should maybe have 30 pages on how to keep a baby alive and then 300 pages on how to talk to your partner about topics you never knew you would discuss but will ultimately become an existential crisis for you both at 3am. For example: should baby’s head go on the left or right side of the changing table? Yes, it’s a big fucking deal. Neither of us can put diapers on the other way.
• Just buy the sleepsack and skip learning how to swaddle with the blanket. Look, some people know origami and they will find any excuse to show off and flaunt it over you they can.
• If my body keeps deteriorating at the same rate it did this first year (the doctors told me I have the spine of a far more mature gentleman), I will attend Quinn’s high school graduation as a pile of goo that had to be ladled into a goldfish bowl.
• At the risk of offending folks, I am astounded that I get anything done and have come to marvel at any productivity from parents as an absolute miracle. Even when I have dedicated work time, I am exhausted and am usually preoccupied with emotionally or mentally processing something that just happened at home.
• I wish the other new parents we met didn’t feel such a need to pretend to have their shit so together.
• This is an utterly foreign feeling kind of love. It’s nothing like romantic love or even the love I have for my parents or siblings. It’s an immediate neural pathway to both utter joy and despair (often one right after the other), and as a pathway it does just sit nakedly open at all times. It’s wild.
• I can see now why people don’t want to die and will strike up imagined bargains to avoid becoming nothing. I sincerely wish I could make some grand handshake with a cosmic being and ensure I could always walk just a few steps behind him through whatever comes his way. If anyone wants to make an offer on my soul, you now know my asking price.
• I really enjoy dressing my child in high-viz colors and patterns. MonoNeon is my fashion inspo.
• Our culture is fully in transition about dads but it still reflexively wants to treat you as either a deadbeat or a dumbass. It’s aggravating but it’s not about you.
• Self-actualization, self-awareness, self-self-self, it kind of all was just batting practice and even wasted effort when the task shifts to living in concert with others, to trying to first form a small unit and then some sense of community around you all. Early adulthood is all about adding affectations and ruffling your plumage. This stage seems to be all about dropping the drawbridge and bricking up the moat in order to just be understood and get basic shared tasks completed without total misunderstanding.
• One thing I don’t do as much anymore: dither. I am much more prone now to make a decision and take action and push things through, even when the consequences are going to be difficult, than before Quinn was born.
• You can definitely be conscious about what traits and experiences you pass down, except for the ones that will probably matter most. That grumpiness is genetic, Bud. I don’t know, maybe year two is when we try the psychedelics (except, God, those people are so annoying).
• You’re going to get poop on you. It’s fine. It’s unsettling how fine it is.

One has only to remember some of our wolfish financiers who spend two-thirds of their lives clawing fortunes out of the guts of society and the latter third pushing it back. It is not enough to suppose that their philanthropy is a kind of frightened restitution, or that their natures change when they have enough. Such a nature never has enough and natures do not change that readily. I think that the impulse is the same in both cases. For giving can bring the same sense of superiority as getting does, and philanthropy may be another kind of spiritual avarice.

____

Organizational change, particularly in companies that have repeatedly failed to make change in the past, requires what’s known as ‘transgressive leaders.’ These leaders don’t just think differently, they’re willing to defy longstanding norms, waltz right past social boundaries, and pursue approaches that would seem heretical to the status quo. They’re eager to shake up the ownership of companies, make hard pivots, install extreme systems of accountability, trigger mass layoffs, demand the absolute best out of their employees, and so on. We call them innovators, trailblazers, and mavericks, and they are the kind of leaders that often come to define the eras in which they live and lead: think Andrew Carnegie, Jack Welch, Steve Jobs. 

Elon Musk rose to fame in the classic transgressive leader mold. Legions of people applauded his propensity to break the rules; one, because we found ourselves in an era where transgressive leaders were à la mode and two, because he draped himself in the language of audacious social and ecological mission (critically though, Tesla does not actually disclose their greenhouse-gas emissions). For many, Musk was a superhero. And yes, when the Marvel cinematic universe needed a real-world template for their fictional transgressive leader, Tony Stark, they picked Elon Musk for that reason. 

But there’s a difference between superheroes and leaders: leaders need followers. 

And while transgressive leaders might appear all bombast and rule-breaking, they do have a fine line to walk in order to retain their followers while making disruptive changes. It’s their paradox: they need to defy boundaries and disrupt patterns while also creating a sense of order and continuity for their staff. They do this successfully in a couple of ways: 

• They tend to constantly connect their activities toward an organizational greater good. When Jack Welch was creating turmoil inside GE with his “vitality curve” or the “ol’ rank and yank: grading system as it was known, he was constantly reminding staff that it was ultimately for the good of the company and its long-term health (a promise he delivered on during his tenure). 
• Transgressive leaders also often pay homage to the past of the organization even while they radically reform it. They do so in order to assert their own loyalty to the organization, as well as to mitigate loss aversion in others, specifically loss of pride among staff. When Steve Jobs returned to Apple in 1997, he may have slashed product lines and yes, even fired all managers, but his commitment to the company and desire to see the company return to an obsession with product excellence won over any skeptics to his cause. 

Elon Musk doesn’t seem concerned to follow either of these strategies. In terms of an organizational greater good, he says that his changes to Twitter are foremost “for humanity” as written in his note to Twitter’s advertisers, or to achieve his version of freer speech (which apparently includes pricing tiers). Any mention of Twitter’s best interest is clearly more for his best interest, as it’s well known that he is now steeply leveraged and his other businesses are entangled in the acquisition. In terms of loyalty or paying homage to the past, ever since the seeming bluff of his acquisition was first challenged, Musk has been on a public trolling spree, denigrating the company and casting aspersions on many different teams and functions within the company. He hasn’t just triggered a mass layoff that was handled comparatively poorly, before he did so he subjected teams to grueling and humiliating practices. 

Transgressive leaders are driven by hubris, and fueled by an enormous sense of self-importance and selfishness. That’s not so much judgment as it is fact. After all, these leaders need to fundamentally believe that rules and norms are made for other people; that, for one reason or another (they are smarter, they are braver, they have been chosen, etc.) they transcend the people around them who are bound by those rules. And because of their special nature, they believe they alone can make change. Yes, that mindset can be a recipe for true disaster (for those leaders, for those around them, and for society at large), but it can produce gains for some organizations when it’s checked by two forces: actual law and order, and the need for followership. Antitrust laws kept Jack Welch from creating the biggest industrial monopoly in history, and while Steve Jobs was undoubtedly labeled a “jerk” by his own employees, he still curbed his worst tendencies just enough to retain good people that helped produce excellent products for him.

Transgressive leaders who have neither of those checks adequately operating against them are genuine causes of concern for the rest of us. Elon Musk is now in a position (with little governmental oversight, no pressure from any public shareholders of Twitter, and now operating the company under a skeleton crew of sycophants left over and assembled from his other companies) not just to adventure for his own ego’s sake, but to dictate right and wrong for others. And here we have arrived at the ultimate threat posed by an unchecked transgressive leader: if a person who has no respect for rules and norms suddenly becomes in charge of setting rules and norms, that position will undoubtedly be used to further their own self-importance and selfishness. Only capriciousness, pettiness, and retribution will follow. The worst parts of Musk’s nature will be exposed and imposed on others through what should be fairly boring community guidelines and standards for his so-called “town square.”

If this all reads like I’m against transgressive leaders, know that’s not the case. I have spent my career working with transformational leaders of all kinds, including transgressive leaders, and I typically value the changes they bring to organizations and cultures who have long ago stopped adapting to their customers and environments. We often need folks who have no respect for norms and boundaries, they just can’t be completely without bounds. I also rarely ever comment publicly on any leader’s behavior–it’s a hard, complex job that rarely is as simple as it looks from the outside. But I feel compelled to speak up now, because with Musk there’s nothing short of a glowing hot nuclear reactor of vanity and self-importance perched next to our civil discourse, and there’s no control of any kind Musk, the world’s richest man, seems willing to tolerate on himself. 

Since 2007, I have built my personal brand and my business largely on Twitter, and I left the platform and my modest 13k followers last week. I believe others should, too. I won’t quibble or mince words here, I think using that platform provides Musk legitimacy at a time when he already has too few forces restraining him. I think advertising there is not only a colossal disaster at the moment, but it’s the wrong move ethically for brands. I think working there, if you can afford to work elsewhere, is the wrong move. Obviously, I think investing in Musk right now is also wrong. There are other platforms, other placements, other jobs (for many, even in this economy), other investments, etc. that don’t feed an out of control transgressive leader with more attention, influence, and power. This is my opinion. As someone who values good leadership, I need to move through the world in integrity.

We need transgressive leaders at times. It’s true. Their desire to break rules can unlock new frontiers. But we also need their behavior to be constrained by checks and balances. We, as individuals, are a part of those checks and balances. Our followership, on Twitter and in all other spaces, counts and should be given with consideration.

To know and not to know, to be conscious of complete truthfulness while telling carefully constructed lies, to hold simultaneously two opinions which cancelled out, knowing them to be contradictory and believing in both of them, to use logic against logic, to repudiate morality while laying claim to it, to believe that democracy was impossible and that the Party was the guardian of democracy, to forget whatever it was necessary to forget, then to draw it back into memory again at the moment when it was needed, and then promptly to forget it again: and above all, to apply the same process to the process itself — that was the ultimate subtlety: consciously to induce unconsciousness, and then, once again, to become unconscious of the act of hypnosis you had just performed. Even to understand the word ‘doublethink’ involved the use of doublethink.

America is captured in doublethink. “Election Integrity” is just one example of the doublethink being asked of us.