Good morning, my chronically employed friend. This week in the make work suck less group chat...

👏 One good thing. Standard Chartered is facing scrutiny from regulators in Singapore and Hong Kong after CEO's absolutely bottom-of-the-barrel remarks about replacing "lower value human capital" with AI this week. Love that for them.

📮State of the business. It started as a question that kept popping up everywhere. On LinkedIn. In group chats. In conversations with friends navigating layoffs, burnout, and career pivots. Are careers dead? That was the premise of a recent conversation I had with Hebba Youssef on her podcast I Hate It Here. We were talking about the future of work, and somewhere along the way the question emerged: if the traditional career ladder feels increasingly unstable—or irrelevant—what comes next?

But before we can answer that, what did we mean by “career” in the first place?

🍽️ The evolution of work from survival to identity One of the things I keep coming back to is how much the concept of work has evolved over time. We started as hunters and gatherers. Then farmers. Then tradespeople. Then industrial workers. Now many of us are knowledge workers navigating an economy increasingly shaped by technology and AI. Each stage changed how we thought about work. At different times, we’ve said: I have a trade. I have an occupation. I have a profession. I have a career.

Even the language tells a story. The word career comes from the Latin word for chariot—something moving quickly along a defined path. A job comes from an Old English word meaning a mouthful, a piece of work done for pay. And business comes from a Middle English word that literally meant anxiety.

Over time, work became more than survival. It became identity. Pride. Status. Growth. And eventually, something we expected to follow a steady upward trajectory.

🪜 The career ladder was built for a different world The modern idea of a career—stable, linear, predictable—took shape in the 19th and 20th centuries. You joined a company. You stayed there. You moved up the ladder. But that model depended on a set of conditions that don’t really exist anymore.

It depended on long-term institutional stability. It depended on pensions and predictable advancement. And it depended on an entire layer of invisible labor at home. The 40-hour work week only works when someone else (usually a wife) is handling everything outside of work. Childcare. Groceries. Doctor appointments. School pick-ups. Sick days.

That model never worked particularly well for women. And it certainly doesn’t work for many working parents today. By the time we started using terms like “working mom” in the 1980s—and eventually “career mom”—we were already trying to retrofit our lives into a system that had never been designed with us in mind.

♻️ The faded promise of stability For decades, the social contract of work felt relatively clear: loyalty and hard work would be rewarded with stability. But that contract has been eroding for years. Layoff cycles are now a regular part of corporate life. Entire industries shift quickly in response to technology and global markets. Pensions have largely disappeared. Many workers are classified as contractors rather than employees. Deloitte just took away benefits from their admin team.

In 2025 alone, more than 1.17 million layoffs occurred in the United States, including over 120,000 in tech and 180,000 federal workers.

These weren’t necessarily people doing poor work. Many were high performers who simply found themselves on the wrong side of a restructuring in the name of "efficiency." When the systems around work change this dramatically, it’s natural that our definition of career changes with them.

🔍 What do we mean when we say, “careers are dead” When people say careers are dead, what they’re usually reacting to is the collapse of the traditional career ladder. The idea that there’s a single path. That loyalty guarantees security. That advancement happens in predictable steps. That version of a career is becoming harder to find. In its place, we’re seeing something more fluid.

Some people are combining consulting, fractional roles, side projects, or entrepreneurship. Others are intentionally moving between industries or roles as their interests evolve. In the HR world, we see this with the rise of fractional leadership roles. Across industries, we see experienced professionals leaving corporate jobs to start consultancies or build businesses of their own.

None of this is entirely new. People have always worked multiple jobs to make ends meet. What’s different now is that these shifts are happening across the white-collar workforce, and they’re often motivated not just by necessity—but by a search for flexibility, autonomy, and alignment.

🧬 How do we define our relationship with work? For a long time, work and identity were tightly intertwined. Your title, your company, your tenure—these things told the story of who you were. But as the structures around work shift, many people are rethinking that relationship.

Instead of asking: What ladder am I climbing?

We’re starting to ask: What kind of life do I want to build—and what role should work play in it?

🏆 Redefining success A career used to imply stability, loyalty, and steady progression. But the future of work looks less like a ladder and more like a portfolio—a collection of experiences, skills, and opportunities that evolve over time. For some people, that means entrepreneurship. For others, it means a mix of full-time roles, consulting, creative projects, or periods of transition.

The point isn’t that the idea of a career has disappeared. It’s that the definition is changing. It's not necessarily a crisis. It could be an opportunity. An opportunity to design work that better reflects our values, our priorities, and the realities of the world we’re living in now.

🎙️ The Conversation Continues If this question—Are careers dead?—has been bouncing around in your own head lately, you’re not alone. Hebba and I dig into this conversation in much more detail in her podcast. We talk about the history of careers, the structural shifts happening in the workforce, what it might mean to rethink our relationship with work entirely, and how we're talking to our Gen Alpha kids about what they can be when they grow up. Because maybe careers aren’t dead. But the way we think about them? That's due for a reset.

🎧 Listen to the full episode here: S11 E3: R.I.P. to Traditional Careers as We Know Them on I Hate It Here

💬 Coffee break gossip. Some news to share over an iced Dunkin coffee this week:

1. Last fall, California Governor Gavin Newsom vetoed the No Robo Bosses Act to stop employers from using AI in firing decisions. Now, after another round of Meta layoffs this week (and threatened support to his 2028 presidential campaign), he's motivated enough to sign an executive order to prevent AI from taking human jobs.
2. Pizza Hut's AI delivery system (Dragontail... lol what?) managed to double delivery times and Starbucks' AI inventory tool was just making sh!t up in the stockroom. Woopsie.
3. I just discovered the Corporate Gossip podcast (highly recommend). But even better is the co-host reciting the entire dating history of Google co-founder Sergey Brin FROM MEMORY. Excellent.

Do me a favor - if you enjoyed this Saturday morning drop in your inbox, forward it to a few friends.

Until next Saturday, you got this.
Cassandra

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