Newsletter #17: The Gen-X career meltdown, Careless People review, and when AI starts replacing us
Stories, books, and articles that made me pay attention.
Just when they should be at their peak, experienced workers in creative fields find that their skills are all but obsolete. – Steven Kurutz for The New York Times
Yes, I was born in the 1970s. This makes me a Gen-Xer. Why is this important and worth your time? First, I read a great story by Steven Kurutz in The New York Times with curiosity. Apart from the excellent visual presentation, the story touched on some truths about creatives who belong to this generation.
Gen X refers to people born between 1960 and 1980, who experienced significant economic, political, social, and technological changes. I was born a year after martial law was declared in the Philippines and raised in the country's summer capital.
So, imagine life back then. The Americans built the city where I grew up. Since it’s way up in the mountains, the Americans decided it was a perfect spot for R&R for their troops visiting the country. I consumed a lot of free TV content from several local channels. Cable TV was expensive. The government controlled at least three channels. Community newspapers were available, but what caught my interest were American comics featuring Superman, Batman, and other DC characters. At the American Air Base, known as John Hay, I watched the Far East Network Philippines broadcast, a network of radio and TV operated by the US military. Then, there was the Voice of America, which I listened to through a transistor radio. At midnight, the station played rock and roll music, a break from all the foreign medley of disco music played on the FM radio.
Our generation grew up watching Sesame Street and later MTV, as television and music merged and cable TV became more affordable. I learned my English watching the Muppets Show, Bert and Ernie argue, and other Sesame Street characters talk and sing. Pepe and Pilar were two childhood characters I’ve come to know. They were the main characters of the books we were taught to read in grade school. Then, we read Bible stories every night before I went to sleep. These were all in English.
TV became my obsession, my “go-to” medium for entertainment. From this boob tube, I got immersed in Japanese cartoons, which was later called Anime. I also remember watching Japanese TV shows, featuring a team of superhumans identified by their “Star.” For example, Star 1 was the leader, and you had Star 2, and so on. I was introduced to Godzilla, Voltes V, Daimos, Mazinger Z, and Battlestar Galactica – all Mechs or robots that battled other robots. Voltes V became an obsession. We drew Voltes V whenever we could, and imagined ourselves as members of this elite human team, which battled aliens wanting to take over Earth.
Then came the Betamax and later the VHS, portable video machines that allowed you to watch movies at the convenience of your own home. Yes, movie theaters were nice, but these little, nifty video players provided a steady stream of content at the price of a decent meal. Video rental stores popped up like mushrooms, and of course, illegal movies and pirated content abound. Years later, these video rentals switched to CDs and higher-resolution DVDs. With these advancements, TV technology improved, featuring high-definition screens, stereo sound, and richer, more vibrant colors.
That was a long story for several points I’m making about the New York Times article:
Gen X is the generation that experienced life before the Internet and eventually migrated to digital. We were not digital natives.
Our skill set were a mix of both analog and digital, plus you throw in some creative juices there to make you stand out from the crowd. (A wise man once told me that originality is no longer relevant these days; creativity is).
As a former journalist, I have made several “lateral movements” to new jobs, which in turn, landed me in different roles – so far removed from the creative job that I was doing when I started working.
Digital technology, the Internet, and smartphones have changed our lives as we know them. We, Gen X, somehow adopted this and found ourselves doing things that may be out of our comfort zones.
Because of technology and innovations like AI, we’ve experienced the so-called Peter Principle, where we reach the ceiling of our ability to go higher on the proverbial ladder. In organizational speak, this principle means that individuals in hierarchical organizations tend to be promoted until they reach a level where they are no longer effective or competent. They are then stuck at that level of incompetence.
TL;DR: I don’t wholly agree with this New York Times article because I have somehow evaded being “stuck at the level of incompetence.” I’ve found ways to keep learning new skills, failing in many, but moving forward and striving to be useful in my current job or chosen career. Confession: I still think I was an accidental journalist, and I still consider myself an accidental digital marketer today, in my current job description.
Have we sold out as Gen-Xers? No way, but we all need to feed our families, pay our bills and mortgages, and secure the future of our children. So, if life hands you lemons, you turn them into lemonade and sell them for profit of at least 20% with good branding and packaging.
“It wasn’t the things they did; it was the things they didn’t do.”
Careless People: A Cautionary Tale of Power, Greed, and Lost Idealism, a memoir by Sarah Wynn-Williams, is a sharp and candid memoir that exposed the inner workings of Facebook (Meta). Wynn-Williams is an insider, in fact, a senior executive at Facebook's global policy, who mainly dealt with governments outside the US, as the company was focused on pursuing growth.
A Kiwi, Wynn-Williams fell in love with the idea of how Facebook could change the world and saw herself at the center of this technological revolution that would connect the world’s billions of people. This was until she was on the ground dealing with ethical issues, as well as governments wanting to use Facebook to silence critics, control the narrative through misinformation, win votes by targeting fringe voters, and even allegedly allowing government to “spy” on citizens.
Her memoir puts her in the middle of major global initiatives, including reopening Facebook in Myanmmar and introducing Facebook in China. She dealt with Mark Zuckerberg and Sheryl Sandberg, both of whom had allegedly turned out to be “careless people” who were after expansion no matter the price.
Memoirs are a “historical account or biography written from personal knowledge or special sources.” This is Wynn-Williams account of what happened to Facebook when she was hired and eventually fired because she raised serious accusastions of a toxic workplace culture that ignored instances of misogyny, double standards, sexual misconduct, and marganilization of dissenting voices.
As a lawyer, she helped negotiate and push policies within Facebook on how to deal with misinformation, including Facebook’s role in events like the Rohingya genocide in Myanmar, where she claimed that the world’s largest social network failed to implement adequate safeguards against hate speech and misinformation.
“Myanmar would’ve been far better off if Facebook had never arrived there,” she wrote after seeing how Facebook has become a tool to spread fear, hate, and misinformation in this Southeast Asian country.
She witnessed how Facebook faced moral dilemmas of balancing growth with global responsibility. The company’s mantra of “moving fast and breaking things” would always win over ethical responsibility, she said.
Wynn-Williams’s memoir is not the usual tech memoir. It reads more like a warning, as she reflects on how technology and companies like Facebook are becoming too large and too powerful—powerful enough to influence elections.
She thought she had a dream job: shaping global policy for one of the world's most powerful companies. It turned out that her idealism got swallowed by scale, and good intentions collapsed under the weight of “move fast and break things.”
This book reminds me that tech doesn’t just fail because it moves fast. It fails when it stops caring. And often, it doesn’t even realize it has.
Wynn-Williams wrote with restraint. No exposé-style drama. Just quiet frustration at how people in power—especially at Meta—allegedly chose growth over accountability. Her reflections on leadership, ethics, and the silencing of women in the workplace is painfully honest. “It wasn’t the things they did; it was the things they didn’t do,” she wrote.
AI will replace us
“Before asking for more Headcount and resources, teams must demonstrate why they cannot get what they want done using AI.”
This was one of the central messages from Shopify’s CEO to its employees recently, in a leaked memo, stressing the idea that AI will soon replace jobs within the e-commerce company.
He wanted everyone in his company to be proficient with AI, indicating that knowing how to use AI is an essential skill, just as knowing how to type or use the Internet.
“Reflexive AI usage is now a baseline expectation at Shopify,” he wrote in X, soon after his memo got leaked.
“Maybe you are already there and find this memo puzzling. In that case you already use AI as a thought partner, deep researcher, critic, tutor, or pair programmer. I use it all the time, but even I feel I'm only scratching the surface. It’s the most rapid shift to how work is done that I’ve seen in my career and I’ve been pretty clear about my enthusiasm for it: you've heard me talk about AI in weekly videos, podcasts, town halls, and…Summit! Last summer, I used agents to create my talk and presented about it. I did this as a call to action and invitation for everyone to tinker with AI, to dispel any scepticism or confusion that this matters at all levels. Many of you took up the call, and all of us who did have been in absolute awe of the new capabilities and tools that AI can deliver to augment our skills, crafts, and fill in our gaps.”
Here’s a summary of Shopify CEO Tobi Lütke’s memo:
AI is now a baseline expectation for all Shopify employees.
Before hiring, teams must first prove why AI can’t do the job.
AI usage will be evaluated in both performance reviews and peer reviews, including those of executives.
Lütke calls AI the most significant shift in workplace productivity he has seen in his career.
Staff are encouraged to think of their role alongside AI agents, like adding a new teammate.
The goal: faster execution, fewer meetings, and a leaner org — driven by AI.
Older millennial here - we're the generation that had computer classes in high school and populated mIRC and ICQ chat rooms through prepaid internet 🙃 We did experience analog life, but could also be considered digital natives in a way.
I've tried going off Facebook before, but was forced back into it by an MFA professor who used it for class notices. If the local fountain pen community and marketplace aren't on Facebook, I'd ditch it again. Considered leaving Threads and Instagram too, but right now Bluesky and Mastodon are too Global North-heavy and Pixelfed's got low uptake
I thought Careless People was great. It’s making me consider deleting all the Meta products I use.