The Recursive Why Principle

In America, there’s a strong narrative about not just being another cog in the machine but understanding and shaping the bigger picture. In contrast, philosophies like those in the Bhagavad Gita, which I’ve seen reflected in some Indian and Chinese colleagues, emphasize doing your duty well without attachment to the outcome. These perspectives influence how we view our work and our roles within larger systems.

Who Needs the Big Picture?

In places like Ethiopia, where there’s a stronger emphasis on social harmony, I’ve noticed how these ideas play out. In Addis Ababa, for example, labor is abundant, and roles become highly specialized. There’s even a person whose job is to sit in an elevator, press the buttons for you, and prevent wear and tear on the panel. If a job like that exists, the cost-benefit must be worth it—this illustrates how specialization is prioritized and valued in that context.

I had this realization while watching a traffic cop in Addis meticulously fine a driver for a missing sticker. The city has different kinds of police—city cops, federal officers, regional police—all with distinct uniforms. But only traffic police handle traffic violations. If there’s an accident, traffic stops entirely until a traffic cop evaluates the scene.

It struck me how this kind of overspecialized system works in harmony, and not everyone needs to question the deeper ‘why’ of their roles. For some, knowing what the task is and doing it well is enough.

But for others, particularly those driven by a desire to understand the broader impact, simply doing a job isn’t enough. We need to know how our roles fit into the larger scheme, and when we can’t see that connection, dissatisfaction sets in.

My Individualist Perspective

As someone raised in the U.S., I lean toward individualism. It shapes how I approach my work in tech. I believe we should optimize how we spend our time to align with our values, not just for the paycheck but for meaning. This means reducing blind obedience and avoiding inauthenticity, instead seeking out roles that allow us to question, understand, and influence our work environments.

From Management to Individual Contributor

In 2021, I stepped down from my role as Head of Engineering and took a year-long sabbatical. When I returned in 2022 as a Staff Software Engineer, I found myself grappling with layers of management that kept me from the strategic decisions I craved. The most frustrating part? Getting unsatisfactory answers to my ‘why’ questions—answers that seemed to dodge deeper engagement.

The Hierarchy of Whys

I’ve come to believe that your rank in an organization should correlate with your ability to understand and articulate the ‘whys’ behind your responsibilities. If you hit a ‘why’ ceiling—where you stop caring or stop trying to understand—that’s probably where your growth in that role ends.

Asking ‘why’ can be uncomfortable. You might find out:

• Your job isn’t as important as you thought—it’s redundant.
• Your great work is part of a mediocre project.
• The incentive structures are distractions, and the team is spinning its wheels.
• Leadership is just winging it.

But here’s the thing: the people who care enough to ask these questions? They’re usually the ones capable of stepping into leadership. It’s the quiet engineer who attends meetings they don’t have to, the one who treats code debt like personal financial debt. That instinct to take ownership is a natural leadership trait.

Understanding the Levels

I see four levels of understanding when it comes to work:

1. Task-Level Understanding: You know how to do your job well but might not question its broader significance. Think of the traffic cop who fines drivers for missing stickers without considering the larger implications of traffic flow.

2. Project-Level Insight: You understand not just the task but how it fits into the project’s goals. A software engineer who not only writes code but grasps how it impacts the product roadmap is operating at this level.

3. Organizational Understanding: You see how your work fits into the company’s larger strategies and goals. A manager who understands how their team’s work contributes to the company’s market position is at this level.

4. Existential Understanding: At the deepest level, the company’s goals align with your personal values and sense of purpose. You understand how your work contributes to your life’s meaning, and you can clearly see the costs and benefits of your professional choices. Sacrifices and compromises become transparent, allowing for fully informed decisions about your career path.

Testing Depth with Everyday Encounters

Think about an Uber driver. If their understanding stops at daily operations, they’re at the task level. If they’re thinking about automation and its effect on their future, they’ve reached project-level insight. If they understand Uber’s strategy and market position, they’re at the organizational level. And if they see their role as part of a mission to transform transportation, aligning with personal values of sustainability or community, they’ve reached the existential level.

I’ve realized that to feel truly fulfilled, roles need to provide more than just task execution or even alignment with organizational goals. They need to connect with something deeper—your sense of purpose. As I navigate the shift from leadership back to individual contributor, I find myself searching for that deeper integration, where my work resonates with both the company’s objectives and my own values.

How Deep Do Your ‘Whys’ Go?

Are the answers to your ‘whys’ satisfying, or are they leaving you seeking more? And if you’re not satisfied, are you ready to take a leap to find that deeper meaning and purpose in your work?