November 18th, 2022: Greetings from Austin! The past few weeks have been very productive and very leisurely at the same time. I’ve trying to set some stuff up for next week which is my planned “every seventh week off” and starting to take it easier drifting into the holidays.

+ I got a copy of Venkatesh Rao’s Art of The Gig this week and re-read both volumes over two days. It was excellent and is a must-read for anyone that might wants to become an indie consultant. You can grab the book here.

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#1 Writes TikToks as Poems

This podcast is the most downloaded episode in the first seven days and that honor is well-deserved.

Mid-pandemic, Kyla messaged me to get my thoughts on whether she should leave her job. I said some vague things about building up cash before leaving and making sure she really will like self-employment.

She left a week later and I’m glad she did. As she said in our conversation, “if I had lived my life without knowing what I could have done, I would have been very sad.”

Sadness minimization is the new regret minimization.

She’s since gone all in on writing and creating videos about the economy, markets, and finance, all told through her unique lens.

She alone made me rethink my perspective on short-form vertical video. It’s not that the format is bad, its that most people are unimaginative about it’s potential, especially in covering “serious” topics like finance.

If you’ve ever spent more than an hour learning about finance you really how much of the “news” coverage is absolute bullshit. “Stocks rise on oil news", or “stocks drop on President’s talk” really mean “these two things happened today and we needed to write something but ultimately, we don’t care about going deeper.”

Kyla goes deeper and in her explorations, she coined the term “vibecession” to describe the phenomenon of the last year of a tight labor market and strong household financial conditions with the fact that people actually felt miserable about it all.

I also just love the passion she has for what she’s doing.

She cares.

Which is rare in today’s world. So many people all the way up to people like SBF ultimately don’t give a shit about what they do. The joy of learning, growing, or getting better has taken a backseat to money concerns.

I almost headed down that path too and I understand how alluring it is.

But this sucks and she writes about why this sucks in a recent issue:

Our passion crisis is broadly a function of tapping into the uncomfortable parts of ourselves - in order to find out what you love, you have to be vulnerable. You have to care - and caring itself is an act of rebellion in a world that seems to constantly want to put you down.
And it’s really beautiful to care - but man, it can be difficult. The act of being engaged in the world outside, of having art that is really your soul on a canvas, or perhaps in a song (or video) or maybe it’s a car that you’ve been fixing up, or maybe it’s that little plant on the windowsill - caring, at any level, is so deep, so raw, it was actually the original money

We talk about this all and also talk about how she thinks of designing her Reels and TikToks as poems, which she apparently has never revealed before.

🤯🤯🤯

What are you waiting for? You can listen to the audio here:

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#2 David Senra’s Founders Podcast

I’ve been listening to many of David Senra’s podcast episodes about famous inventors and founders throughout history. I’ve filtered the many amazing episodes through my own curiosity about how people think about work.

Here are some quotes that stuck out:

Dee Hawk:

“Life is not about control. It’s not about getting. It’s not about having. It’s not about knowing. It’s not even about being. Life is eternal, perpetual becoming, or it is nothing. Becoming is not a thing to be known, commanded, or controlled. It is a magnificent, mysterious odyssey to be experienced.”

David Ogilvy

"It’s tragic to see men and women wasting their lives in work that they hate or do badly. It’s never too late to find out that you’re doing something you don’t like, and are not very good at. Then you’ve got to take hold of yourself and decide what you would like to be doing most and then do it for the rest of your life.’

and

"On the other hand, I believe in lots of vacations. When one of my partners gets abrasive, its usually because he has worked too long without a vacation...the partners in a service business should be given sabbaticals to recharge their batteries"

Henry Ford:

“Life, as I see it, is not a location, but a journey. Even the man who most feels himself “settled” is not settled—he is probably sagging back. Everything is in flux, and was meant to be. Life flows."

“I had to choose between my job and my automobile. I chose the automobile, or rather I gave up the job, there was really nothing in the way of a choice...I quit my job on August 15th, 1899 and went into the automobile business”

"That thinking first of money instead of work brings on fear of failure and this fear blocks every avenue of business"

Emerson:

"A foolish consistency is the hobgoblin** of little minds, adored by little statesmen and philosophers and divines. With consistency a great soul has simply nothing to do"

George Lucas

“being able to step out of whatever you’re in and move forward rather than being stuck in your little rut...People would give anything to quit their jobs. All they have to do is do it…They’re people in cages with open doors.”

Some more here in this thread which I’ll be adding to over time:

Paul Millerd @p_millerd

Been diving into the historical figures on @FoundersPodcast and it's striking how almost all of them have similar thoughtful reflections on work, and finding things that matter to them (including David) These seem to be hidden in plain sight secrets. Some that stood out👇

#3 Cal Newport & Our Relationship To Work

Cal Newport seems to have recently stumbled into writing about our broader relationship with work:

Knowledge workers were already exhausted by their jobs before the pandemic arrived: too much e-mail, too many meetings, too much to do—all being relentlessly delivered through ubiquitous glowing screens. We used to believe that these depredations were somehow fundamental to office work in the twenty-first century, but the pandemic called this assumption into question. If an activity as entrenched as coming to an office every day could be overturned essentially overnight, what other aspects of our professional lives could be reimagined?

and

The final mismatch I identified concerned the way in which modern knowledge work subverts our instinct for skilled effort. It’s not that knowledge workers lack ability but, instead, that the relentless, mind-warping distraction that defines the modern office makes it difficult to apply these abilities in a satisfying manner. The talented marketing executive wants to focus her energy on writing a brilliant campaign, and would find great fulfillment in doing so, but finds herself instead thwarted by the constant ping of her in-box and demands of her calendar

This is more or less what I’ve been writing about for the past few years and it’s also cool to see that he’s less landed on the same fundamental starting point:

If we hope to replace this mishmash of conventions with something more fulfilling and sustainable, it makes sense to start by asking fundamental questions about what “work” meant throughout most of human history.

It’s impressive that Cal has gotten to this point. I think it is hard for people that have succeeded in the traditional system and have work they like doing to ask these kinds of big questions. I used to be a big fan of Adam Grant’s work writing but as soon as I left the traditional system, I couldn’t really find much wisdom from him. He and many other work writers are really focused on making tweaks within the current system.

I’m more concerned about thinking about the bigger picture, especially as we see more people shift toward work that looks like mine.

After watching a recent video I actually emailed him my book. Not sure if he will read it but if anyone knows Cal, tell him to come on my podcast! I sense it would be a fruitful discussion.

#4 The Girl Boss Meme

Katherine Dee writes a reflection on the pitfalls of the “girl boss” meme:

It’s not so much that millennials were just fed a bunch of lies and need to fix their behavior; it’s that their environment didn’t allow them to behave any differently, and they attacked anything but the root cause. The “girl boss” makes sense in an environment where you’re going to have to work a soul-sucking job no matter what; why not add a veneer of glamour to it? In a world where day care is an expensive necessity, there is a womblike comfort in telling yourself stories about how staying childless is an “act of heroism” or even a ticket to happiness.

An interesting reflection of things people have been talking about privately for a long time.

#5 Freelancing 101

In my continued “for fun” YouTube efforts, I made this video about taking the leap to freelance, including questions to assess your interest, what it really feels like, and how to craft a “weird identity”:

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TikToks as Poems, Famous Work Quotes, The…