Generalist Engineers and the Rise of "Side Quests" in Anthropic Hiring

The definition of a capable software developer is undergoing a radical shift in 2025. For years, the industry pushed specialized depth—backend wizards, frontend gurus, and data pipeline architects. Now, a different signal is cutting through the noise. Boris Cherny, the creator of Claude Code at Anthropic, has explicitly stated a preference for hiring generalist engineers who bring something specific to the table: "side quests."

These aren't necessarily GitHub repositories filled with open-source contributions. They are manifestations of curiosity, ranging from complex home automation systems to brewing kombucha. This hiring philosophy suggests that the era of strict "swim lanes" is ending. Companies like Anthropic are looking for generalist engineers who use tools to solve problems across the stack, rather than employees who stay strictly within a single job description.

Real-World Generalist Engineers: Transforming Workflow with AI

Before dissecting the corporate philosophy, we need to look at what this looks like on the ground. The most compelling arguments for the rise of generalist engineers come from the practitioners themselves who have adapted their workflows to the AI era.

In the past, setting up a monitoring stack involving Grafana, Prometheus, Loki, and ArgoCD was a multi-day ordeal requiring specialized DevOps knowledge. Today, a single developer with a generalist mindset can deploy that entire infrastructure in under an hour. By leveraging tools like Claude Code or Copilot, the role changes. The engineer stops being a line-by-line executor and becomes an architect.

This shift creates a "superpower" effect. Developers who previously felt locked out of complex domains like Kubernetes or advanced security configurations are now bridging those gaps. They treat AI as a pair programmer that handles the boilerplate implementation while they direct the strategy.

This is the exact profile Anthropic hiring teams are hunting for. It is the "Linux Admin" who didn't ace the standard technical interview but landed the job because they spent twenty minutes passionately explaining their DIY plotter or their Raspberry Pi home server. That specific drive—the itch to make something work simply because it’s interesting—is a better predictor of success in an AI-native environment than rote memorization of algorithms.

The "side quest" indicates a person who runs into a wall and figures out how to climb it, dig under it, or blow it up. In a startup environment or an AI lab, where the roadmap changes weekly, that resourcefulness is the only currency that matters.

Why Anthropic Hiring Favors "Side Quests" Over LeetCode

The logic driving this new Anthropic hiring standard is that real-world engineering problems rarely fit into the neat boxes found in university textbooks or coding bootcamps. Boris Cherny’s focus on generalist engineers stems from the belief that specialization is often "artificial."

Generalist Engineers Bring Curiosity, Not Just Code

A "side quest" serves as a proxy for curiosity. When a candidate spends their weekend figuring out the fermentation chemistry for kombucha or woodworking a custom desk, they demonstrate a pattern of learning that transcends software.

Cherny and other industry leaders, including Figma’s Dylan Field, are betting that the future belongs to "product builders" rather than code specialists. A Code-focused role at Anthropic now sees Product Managers and User Researchers writing production code. The barriers are dissolving.

For generalist engineers, this is validation. The ability to wear multiple hats—formerly seen as a lack of focus—is now an asset. The logic follows that if you have the drive to build something from scratch in your spare time, you possess the agency required to navigate undefined problems at work. You don't wait for a ticket to be assigned; you see a gap and fill it.

The Death of "Swim Lanes" for Generalist Engineers

Large tech companies have historically organized generalist engineers into rigid silos. You are a Level 4 Backend Engineer; you do not touch the CSS. You do not touch the database config.

Anthropic hiring signals a move away from this factory-line model. The creation of Claude Code itself was designed to empower individuals to handle 60% of their daily tasks faster, freeing them up to work on broader, more complex systems. When the tool can handle the syntax, the human needs to handle the system design.

An engineer confined to a swim lane is less valuable in this context. If an AI can write the React component and the Python API endpoint, the human value add is understanding how those two things talk to the database and the user simultaneously. This requires a generalist view, often cultivated through the messy, unstructured nature of personal weekend projects.

Navigating the Disconnect: Generalist Engineers vs. Modern Interviews

While the philosophy is sound, the reality of the market often lags behind the vision. There is a palpable tension between the stated desire for creative generalist engineers and the actual mechanics of getting hired.

When Generalist Engineers Face Legacy Hiring Gates

A significant point of friction arises when a company advertises for curious, project-driven generalist engineers but retains a hiring pipeline designed for specialists. Candidates report being courted for their "side quest" mentality, only to be thrown into five rounds of generic LeetCode grinding.

This disconnect damages the brand. If Anthropic hiring—or any tech hiring—claims to value the "maker" spirit, the interview process must reflect that. Testing a builder on their ability to reverse a binary tree on a whiteboard ignores the very skills the company claims to want: the ability to integrate disparate tools, deploy real systems, and solve novel problems.

Furthermore, there is a demographic reality to the "weekend project" requirement. Experienced generalist engineers often have families, aging parents, and health commitments. The assumption that a top-tier engineer must spend their Saturday coding implies a specific, often younger, demographic.

If companies want the wisdom that comes with experience, they have to accept that for many senior generalist engineers, the "side quest" happened ten years ago, or it currently looks like raising children. Excellence during working hours should not be devalued because a candidate prioritizes rest during the weekend.

The Compensation Expectation for Generalist Engineers

Demanding a lifestyle where work and hobbies blend into a continuous stream of productivity raises the stakes for compensation. If Anthropic hiring is targeting people who live and breathe their craft—people whose identity is tied to building and creating—the market demands top-tier remuneration.

Expectations of "changing the world" and "all-in" dedication are viable only when matched with equity and salaries that reflect that intensity. Generalist engineers capable of acting as entire departments—building the product, managing the infrastructure, and handling the data—are effectively doing the work of three traditional employees.

The Future of the Technical Portfolio

The industry is inching toward a new equilibrium. Anthropic hiring has already updated its policies to allow the use of AI in job applications, recognizing that using tools like Claude is a practical skill, not cheating. This pragmatism is a positive sign for generalist engineers.

The future portfolio might not be a list of languages learned, but a gallery of problems solved. Whether that problem was optimizing a data pipeline or automating a greenhouse, the core competency is the same. As AI tools lower the barrier to entry for coding, the ceiling for value creation rises.

Generalist engineers are uniquely positioned to hit that ceiling. They understand that code is just a lever. The "side quest" isn't about the code; it's about the leverage. As we move deeper into 2025, the engineers who thrive won't be the ones who memorized the textbook, but the ones who wrote their own chapter because they wanted to see how the story ended.

FAQ: Anthropic Hiring and Generalist Engineering

What does Anthropic mean by "side quests" in their hiring process?

"Side quests" refer to personal passion projects, which don't necessarily have to involve coding. Anthropic values hobbies like brewing, woodworking, or hardware hacking because they demonstrate curiosity, agency, and a natural drive to solve problems without external direction.

Do Generalist Engineers need to know every coding language?

No, a modern generalist engineer doesn't need to memorize syntax for every language but must understand system architecture and how to connect different technologies. The focus is on adaptability and using AI tools to bridge gaps in specific language knowledge to build complete products.

Has Anthropic changed its policy on using AI for job applications?

Yes, as of July 2025, Anthropic updated its policy to allow candidates to use AI tools like Claude Code during the application process. This aligns with their pragmatic view that effective engineers use the best available tools to communicate and work efficiently.

Why are companies shifting away from specialized roles?

AI tools are automating many of the repetitive, specialized tasks that used to define specific roles. Companies now prefer generalists who can oversee the entire lifecycle of a feature—from backend to frontend—allowing for smaller, faster, and more autonomous teams.

Is it a requirement to have a weekend project to get hired at top AI firms?

While not always a hard requirement, having active personal projects is heavily weighed as a differentiator. It signals to hiring managers that the candidate possesses an intrinsic "itch" to build and learn, which is crucial in fast-paced research and development environments.