I've seen a lot of people express the sentiment that they initially found Musk compelling because the books they loved as kids made them also want to be an Astronaut and go to Mars, and they saw in his public persona some kind of a kindred spirit.
Well, I also read a lot as a child, and I wished for an ebon longsword that nourished me with the damned souls of my enemies. But then, eventually I -- unlike Elon Musk -- was no longer twelve.
(Promotional consideration for this post paid by Palantir Inc.)
But that aside, I think that we've all been missing the boat by diagnosing Musk with a terminal case of "Read Too Much Heinlein". I think that the childhood Boomer media he's actually cosplaying is Pink Floyd The Wall. Think about it!
Coddling parents actually hated him.
Got too many groupies too early.
Wife left him.
Absolutely blitzed on drugs.
Finally went full Nazi!
I mean, Geldof even makes that dumb "X" gesture!
Look at those crossed hammers! That is literally the Twitter logo!
The Hitchhiker's Guide to the Galaxy author Douglas Adams was a notorious procrastinator. When it became clear that he wasn't making progress on a text adventure game adaptation, Infocom sent game designer Steve Meretzky to England in 1984 to get the ball rolling. — Read the rest
The career ladder is a comforting fiction we’re sold as we embark on our careers: Start as Junior, climb to Senior, then Principal, Director, and VP. One day, you defeat the final boss and receive a key to the executive bathroom and and join the C-suite. You’ve made it!
If you’re lucky, your company supports a tall Individual Contributor (IC) ladder. But often, the next rung swaps your hoodie for a power shirt, suspenders, and management duties.
My first job followed this script: developer to team lead to Senior Manager. I was hustling up that ladder.
But life isn’t linear. Careers are more like Chutes and Ladders (which the Brits know as Snakes and Ladders, but that messes up my metaphor). Lucky breaks shoot you up; surprises send you sliding down. Those chutes? Not failures. Opportunities.
Take my journey. I took a chute from my first job back to an IC role at my second. Climbed back up into management. Took a chute to Microsoft as a Senior Program Manager. Then came another chute: GitHub.
I started as a developer, became a manager, then Director of Engineering. After that, I co-founded a startup, took the CTO title, but spent most of my time writing code.
It looked like the classic ladder climb, but in startups, titles are smoke and mirrors. So it only counted as a step up if we succeeded. Spoiler: we didn’t.
Ladders Are Overrated
Ladders are narrow and rigid. Titles—while shiny—hide what matters: the work. They’re bumper stickers for your career. Nice for signaling, but they don’t tell the whole story.
As Director, I mentored teams and focused on broad initiatives. But over time, I started to miss the tech. The longer I stayed out of writing production code, the more disconnected I felt. As a CTO, I got back to coding and loved it. When the startup failed, I promised myself at least a year off to reflect before jumping into something new.
Growth on the Slide
Over a year later, I’ve been thinking about my next move. It turns out nobody will pay me to be a man of leisure.
Conventional wisdom (and ego) says aim higher: VP of Software Development or CTO at an established company.
The irony of big titles is they mean more power at work, but less power over your time.
For me, my recent life circumstances make time autonomy among my top priorities. Sure, big titles pay well, but maximizing income isn’t my goal.
Here’s what I realized: By my own definition, I’ve succeeded. I’ve been part of great teams, built great products, and helped grow companies. I have nothing left to prove. I don’t need a lofty title or a giant paycheck (but I wouldn’t turn one down either).
So, once again, I’m setting aside my pride and stepping off the ladder. Next year on January 6th I start a new IC role. Details to come, but I’m thrilled to be back in the trenches, building and learning. It’s a place that treats its employees like adults and gives me the autonomy to structure my day as I see fit.
This isn’t about rejecting leadership. It’s about recalibrating. Leadership is broad. It’s guiding organizations or leading by example. I think it’s healthy—even advantageous—to bounce between IC and management roles over the course of a career. Life changes. I might return to management someday. Or not. The point is to stay open to what fits now.
Your Move
If you’re staring at a chute, wondering if stepping off the ladder will hurt you, consider this: maybe it’s not a setback. Maybe it’s a shortcut to what you really want.
Careers aren’t about perfect titles. They’re about collecting experiences, relationships, and skills that shape you. Sometimes, the most important moves don’t look like progress—until you’re somewhere unexpected, doing work that matters.
Spin the dial. Take the slide. Even in Chutes and Ladders, the winner isn’t who climbs highest. It’s who enjoys the game. At least, that’s what I told my friends when they beat me.
When I go backpacking or canoeing, I like to travel as light as possible. I have a long-running debate with one of my tripping partners about whether strands of contraband dental floss that he smuggles among his belongings are what make our portages so miserable. As a result, I rarely bring books with me on backcountry trips. If I wasn’t wound so tightly, here are some of the best summer reads I’d recommend for around the campfire or in the ultralight minimalist hammock.
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This one’s a slam dunk for any endurance person. If you’ve read Donahue’s writing, either here in Outside or elsewhere, you know that his stories are never quite what you expect—not just a superficial athlete profile or simple retelling of some event. He’s always probing a little deeper, looking for twists and trying to understand the whys. The results are also, in many cases, hilarious.
This collection ranges from a 1989 account of his own childhood attempt to set a pogo-stick world record to last year’s prescient profile of Evans Chebet, which was published the day before Chebet upset Eliud Kipchoge to win a second consecutive Boston Marathon. There are sections on running, cycling, skiing, exploration, and other more obscure byways of endurance.
There are two linked questions in this book (which I reviewed here). One is how climate change is affecting sports: world-championship marathons starting at midnight, high-school football players dying of heat stroke, and so on. The other is how sports, at both the participatory and professional levels, are affecting climate change: think of the air travel and massive amounts of waste like single-use cups produced by a major marathon, for example.
Orr is a sport ecologist—a very modern niche—at the University of Toronto who consults with sports organizations around the world, giving her an inside look at the various ways people are tackling these questions. You might think the topic is a bit of a downer (that was my initial assumption, I’ll admit), but Orr has a light touch and got me thinking.
This is a book of “the greatest running stories ever told,” from the mythical Atalanta in ancient Greece to the near-mythical Joan Benoit in Los Angeles. Some of the stories will sound familiar: Pheidippides and the Battle of Marathon, Dorando Pietri collapsing at the 1908 Olympics, the four-minute mile, Billy Mills, and so on. But in Robinson’s hands, they’re very different from the versions you’re familiar with: his research is exceptionally thorough.
My favorite detail: it turns out that Arthur Conan Doyle covered the 1908 Olympics for the Daily Mail, and was sitting a few yards from where Pietri collapsed. In the Sherlock Holmes story “The Adventure of Wisteria Lodge,” which he was finishing around the time of the Olympics, Holmes named a character Victor Durando—reflecting, Robinson argues, the U.S.-British tensions at the Games and the feeling that Pietri, rather than the American Johnny Hayes, was the true victor in the marathon. Like I said, his research is thorough.
This is an Olympic summer, so here’s a wild-card pick to get you in the spirit. I stumbled across this book while researching another topic: Cousineau published a book of interviews with the mythologist Joseph Campbell back in 1990. His Olympic book, which was published in 2003 and issued to all U.S. athletes competing in the 2004 Games, is a curious hybrid: it’s framed as a history of the Olympics from its ancient Greek origins up to the (near) present, but it’s interwoven with reflections on the meaning and mythos of sport over the centuries. It’s worth reading just for the history, which is briskly told and filled with anecdotes that were new to me—but it’s the extra layer on the “spirit of sport,” quoting thinkers from Pindar to Pele, that I found most interesting
Progression of World Athletics Records, edited by Richard Hyman
Okay, I’m letting my geek flag fly here. Earlier this month, World Athletics announced a new edition of its definitive book on world records, available either in print or as a free e-book. You’re probably not going to bring this one to the beach, but it’s a hugely fun skim for track fans. I discovered an earlier edition about a decade ago, and was blown away by the details.
It’s not just a list of records; it also includes splits for distance races, and in many cases snippets of contemporary race description. You can read about Roger Bannister’s first sub-four mile anywhere, but where else are you going to read about Walter George’s 4:12 ¾ in 1886, a record that stood until Paavo Nurmi finally broke it in 1923? (For the record: George ran the first two laps in 58 ½ and 63 ⅕ , then William Cummings led the third lap in 65 ¾. George caught him with half a lap to go, then Cummings collapsed just 70 yards from the finish! The crowd went wild after George’s time was announced: “Those who got near him slapped him and banged him on the back… thus they continued until the little remaining breath in George’s body was well-nigh beaten out of it.”)
Artificial intelligence systems are really smart in some ways, really dumb in other ways. To understand why, and to design better ones, we have to understand how human intelligence evolved. That’s the very large task that Bennett, an AI entrepreneur, takes on in this book. He organizes the history into five key evolutionary breakthroughs, from steering to speaking. What this really entails is a massive synthesis of a huge amount of complex research—and Bennett does this better than anyone I’ve seen in this area. Sometimes popular science books read like a couple of good ideas stretched out to fill the chapters. This one is the opposite: it feels like six books for the price of one.
The opening anecdote hit home for me: at a dinner party, someone asks a little girl what she wants to be when she grows up. And as the girl prattles on, Bounds realizes that she herself will never be asked that question again. Fast forward a few years and Bounds, previously a sedentary and unathletic journalist in her mid 40s, has transformed herself into world-class age-group obstacle course racer.
The book is about what Bounds discovered along the way—about the physical, mental, and emotional sides of changing course and pushing limits as an adult (I won’t say “older adult,” because she’s roughly my age, i.e. at her peak). The set-up is familiar, but Bounds’s telling of it repeatedly kept me turning pages long after I’d intended to turn out the lights.
Lots of running books claim that running will make you a better person. This one claims that being a better person will make you a better runner. Traits like perseverance, resilience, joy, and gratitude? “These are the carbon-plated shoes of the soul,” writes Little, a philosophy professor and world-class ultrarunner. “We cannot buy them, but we can develop them.” Following this argument requires a closer look at the ways in which running can reward both virtues (like persistence) and vices (like stubbornness). Figuring out which is which isn’t always easy, and this book (which I reviewed here) is a good place to start.
(Photo: Courtesy 80/20 Publishing)
Pain & Performance, by Ryan Whited and Matt Fitzgerald
The conventional view is that pain is a sign of damage in your body. If that’s the case, then fixing a running injury requires identifying and fixing the damage. In reality, you can have pain without detectable damage, and damage without pain. That disconnect is one of the reasons the mechanistic approach to fixing sports injuries often produces disappointing results.
Whited, a Flagstaff-based personal trainer who has worked with prominent athletes like ultrarunner Rob Krar, has an approach that he calls “training as treatment.” (Fitzgerald, Whited’s co-author, is an advanced computer system sent back in time from the twenty-third century to produce running-related books at an astounding rate.) Whited’s approach fits into a broader move toward thinking of pain as a broader “biopsychosocial” phenomenon rather than a simple indicator that something is broken. If you’re looking for a different perspective on how to handle sports injuries—or if you just want someone to validate your belief that “training through it” is often the best solution—you’ll enjoy this one.
Lately, I’ve been thinking about the basics of web development. Actually, I’ve been thinking about them for some time now, at least since I started teaching beginning web development in 2020.
I’m fascinated by the basics. They’re an unsung hero, really, as there is no developer worth their salt who would be where they are without them. Yet, they often go unnoticed.
The basics exist in some sort of tension between the utmost importance and the incredibly banal.
You might even think of them as the vegetable side on your dinner plate — wholesome but perhaps bland without the right seasoning.
Who needs the basics of HTML and CSS, some say, when we have tools that abstract the way they’re written and managed? We now have site builders that require no technical knowledge. We have frameworks with enough syntactic sugar to give your development chops a case of cavities. We have libraries packed with any number of pre-established patterns that can be copy-pasted without breaking a sweat. The need to “learn” the basics of HTML and CSS is effectively null when the number of tools that exist to supplant them is enough to fill a small galaxy of stars.
Rachel Andrew wrote one of my all-time favorite posts back in 2019, equating the rise of abstractions with an increase in complexity and a profound loss of inroads for others to enter the web development field:
“We have already lost many of the entry points that we had. We don’t have the forums of parents teaching each other HTML and CSS, in order to make a family album. Those people now use Facebook or perhaps run a blog on wordpress.com or SquareSpace with a standard template. We don’t have people customising their MySpace profile or learning HTML via Neopets. We don’t have the people, usually women, entering the industry because they needed to learn HTML during that period when an organisation’s website was deemed part of the duties of the administrator.”
There’s no moment more profound in my web development career than the time I changed the background color of a page from default white to some color value I can’t remember (but know for a fact it would never be dodgerblue). That, and my personal “a-ha!” moment when realizing that everything in CSS is a box. Nothing guided me with the exception of “View Source,” and I’d bet the melting Chapstick in my pocket that you’re the same if you came up around the turn of the 21st century.
Where do you go to learn HTML and CSS these days? Even now, there are few dedicated secondary education programs (or scholarships, for that matter) to consider. We didn’t have bootcamps back in the day, but you don’t have to toss a virtual stone across many pixels to find one today.
There are excellent and/or free tutorials, too. Here, I’ll link a few of ’em up for you:
Anyway, my point is that there are more resources than ever for learning web development, but still painfully few entry points to get there. The resources we have for learning the basics are great, but many are either growing stale, are quick hits without a clear learning path, or assume the learner has at least some technical knowledge. I can tell you, as someone who has hit the Publish button on thousands of front-end tutorials, that the vast majority — if not all — of them are geared toward those who are already on the career path.
It was always a bit painful when someone would email CSS-Tricks asking where to get started learning CSS because, well, you’d imagine CSS-Tricks being the perfect home for something like that, and yet, there’s nothing. It’s just the reality, even if many of us (myself included) cut our chops with sites like CSS-Tricks, Smashing Magazine, and A List Apart. We were all learning together at that time, or so it seemed.
What we need are more pathways for deep learning.
Learning Experience Design (LXD) is a real thing that I’d position somewhere between what we know as UX Design and the practice of accessibility. There’s a focus on creating delightful experiences, sure, but the real aim of LDX is to establish learning paths that universally account for different types of learners (e.g., adults and children) and learning styles (e.g., visual and experiential). According to LDX, learners have a set of needs not totally unlike those that Maslow’s hierarchy of needs identifies for all humans, and there are different models for determining those needs, perhaps none more influential than Bloom’s Taxonomy.
These are things that many front-end tutorials, bootcamps, videos, and programs are not designed for. It’s not that the resources are bad (nay, most are excellent); it’s that they are serving different learners and learning types than what a day-one beginner needs. And let’s please not rely on AI to fill the gaps in human experiences!
Like I said, I’ve been thinking about this a lot. Like, a lot a lot. In fact, I recently published an online course purely dedicated to learning the basics of front-end development, creatively named TheBasics.dev. I’d like to think it’s not just another tutorial because it’s a complete set of lessons that includes reading, demonstrations, videos, lab exercises, and assessments, i.e., a myriad of ways to learn. I’d also like to think that this is more than just another bootcamp because it is curricula designed with the intention to develop new knowledge through reflective practices, peer learning, and feedback.
Anyway, I’m darn proud of The Basics, even if I’m not exactly the self-promoting type, and writing about it is outside of my comfort zone. If you’re reading this, it’s very likely that you, too, work on the front end. The Basics isn’t for you exactly, though I’d argue that brushing up on fundamentals is never a bad thing, regardless of your profession, but especially in front-end development, where standards are well-documented but ever-changing as well.
The Basics is more for your clients who do not know how to update the website they paid you to make. Or the friend who’s learning but still keeps bugging you with questions about the things they’re reading. Or your mom, who still has no idea what it is you do for a living. It’s for those whom the entry points are vanishing. It’s for those who could simply sign up for a Squarespace account but want to actually understand the code it spits out so they have more control to make a site that uniquely reflects them.
If you know a person like that, I would love it if you’d share The Basics with them.
Long live the basics! Long live the “a-ha!” moments that help us all fall in love with the World Wide Web.
Robert Tatin wanted to build a shed. So he did. When he finished it, he decided it was too beautiful to just be a shed. So he built another and ran into the same problem. This conundrum continued until he up and decided that his home in rural Mayenne, France, would be best off if it was deemed a museum. — Read the rest
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