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12 / The Should Factory

January 8, 2023

Welcome to Issue 12!

In The Lord of the Rings: The Two Towers, Gandalf & Co. show up at the doors of Rohan only to find Théoden King, a frail and pale shadow of the King they expected. Sitting beside Théoden is Grima Wormtongue, the embodiment of the word scumbag. Wormtongue has been poisoning and paralyzing the mind of the King.

Contrast Théoden King with Wormtongue with the same man in The Return of the King screaming, “Spears shall be shaken…Ride now! Ride for ruin and the world’s ending!”

Each of us has our own Wormtongue taking up residence, at least part-time, in our minds. And this inner SOB does its damndest to keep us small, scared, ashamed, and weak, keeping us from becoming versions of ourselves so strong even we’re surprised.

Every single coaching program I’ve come across makes this distinction. Conscious Leadership Group calls it “Above the Line” (Théoden King calling the shots) and “Below the Line” (Wormtongue/Saruman). Reboot calls it “Right Side of the Street” vs. “Left Side of the Street.” I’ve heard “Learner vs. Judge,” “Curious vs. Furious,” “Scientist vs. Litigator,” and ye olde “Angel vs. Devil.”

And one of the easiest ways I’ve found to find out you’re letting your inner SOB drive the car is when we use the word “should.” Should is a word we use to shame ourselves and others. I always chuckle at the phrase, “Don’t should yourself.”

I spent hours writing and rewriting the preamble and big idea for this week’s Hoo Boy. I couldn’t get them “right.” The ideas are rich and useful, and I wanted to give them a couple more weeks to ripen.

Like clockwork, my inner SOB was spinning up its propaganda machine, The Should Factory. “I should have set aside more time,” “I should not have committed to writing two essays for each newsletter,” “I should have known the first week back in January was a bad week to write and edit,” “I should have set a different schedule,” “I should have spent my evenings writing this week instead of going to the gym.”

Sometimes The Should Factory shares some truth. Maybe I am playing with fire, trying to write two essays every other week. But should comes with a hidden message of cruelty. If I weren’t somehow broken, stupid, lazy, or weak, I wouldn’t be scrambling to write a last-minute essay thirty minutes before my newsletter is supposed to go out.

But I am, and having gotten to the end of a last-minute preamble, I’m pretty happy with what I managed to put together in an hour. I know The Should Factory is a House of Lies.

If the only thing you take away from this week’s issue is to pay more attention to when you and others use the word should, that will be enough. Should is a sign we’re letting our inner SOB drive the the car, and that SOB is like our personal Grima Wormtongue, whispering Sauruman’s black magic in our ears, blocking us from unleashing our true inner strength (Ride Now!).

Reads & Resources


Tip no. 3 in this piece by James Clear, author of Atomic Habits, is “Reduce scope, stick to the schedule.” And that’s exactly what I did this week. I spent hours writing two different essays than the one you read above. I wanted to throw in the towel, spend next week honing the essays I drafted, and play the UNO “skip card,” but instead, I reduced this week’s scope, and stuck to the schedule, thereby making sure to keep the habit.

From Twitter

Sales and marketing are easy to measure, but engineering? Whenever a team plans out a month, quarter, or year, questions invariably come up about how to measure an engineering organization (especially if the team is trying to do OKRs). This tweet screenshots part of a blog post by Will Larson, CTO at Calm, and I think it will be helpful to any engineer, engineering leader, executive, or CEO.


This playlist won’t be for everyone, but it’s the playlist I’ve been using to get shit done for the last month or two, and I’ll be adding to it over 2023. It’s big, upbeat, loud, and intense.


There’s a phrase that’s borderline cliché now that most startups don’t die of external wounds but self-inflicted ones. In my experience, that’s all too familiar. Thankfully, Dr. Matthew Jones has identified ten core causes of ineffective partnerships and laid out strategies for fixing or addressing them in his book.

Dice Roll

In May of last year, Sequoia Capital published a 52-page deck to all of their portfolio founders full of reflection on past downturns and strategies for approaching the next 12-24 months. I liked one part in particular: “Prepare your mind. Prepare your team. Prepare your company.” If you’re a founder or CEO, I recommend setting 20-30 minutes aside to scroll through and take notes.

That’s all for this week. I’m looking forward to what’s next!