The path isn’t always planned—but the work reveals the way.
Introduction
In What I Worked On, technologist and writer Paul Graham shares a personal narrative of how his career unfolded—often not through careful planning, but through a series of motivated shifts, creative side projects, and decisions to leave one path in favour of another. The result is a body of work that spans software, art, startups, and essays, unified not by discipline but by an underlying approach to learning and making.
Rather than a how-to guide, the essay offers something more reflective: a look at what it means to follow internal direction rather than external structure. It invites a few questions: What if meaningful work emerges less from strategic goals and more from what draws our attention? And how might a non-linear path turn out to be the most coherent one in the long run?

1. Moving Beyond the Straight Line:
Progress rarely moves in straight lines.
The conventional view of a successful career often assumes gradual ascent within a chosen field. But some careers form through pivots and tangents that appear disconnected until viewed with distance:
Different phases may look unrelated, yet contribute to a coherent skillset or worldview over time: what appears inconsistent at first often reveals continuity in intent or method.
A decision to change direction can be driven by evolution rather than dissatisfaction: leaving one area does not imply failure, but a shift in relevance.
What feels like a detour may later prove essential: work set aside can return with new purpose in unexpected contexts.
This way of navigating change provides the groundwork for following internal signals rather than external expectations.
2. Following What Draws You:
You don’t need a map if you trust your compass.
When energy leads, insight often follows. Projects started out of interest or frustration tend to create deeper engagement than those born of strategy alone:
Working on something because it feels necessary creates momentum: tasks rooted in genuine curiosity often bypass the need for motivation.
Initial side interests may grow into central work: writing, building, or experimenting without a clear goal can later shape one’s core contributions.
A small internal pull is sometimes more accurate than a well-developed plan: instincts can notice gaps and potentials before logic catches up.
This responsiveness to curiosity often results in creating new tools or systems—ones better suited to emerging needs.
3. Making the Tools You Need:
Tools are not just utilities—they’re amplifiers of thought.
Rather than accept the limitations of existing systems, one response is to build alternatives—tailored environments that make better work possible:
Tools built for personal use often reflect clarity and necessity: solving one’s own problems can yield broadly useful solutions.
Platforms or products created with others in mind often stem from something first felt individually: making something one needed five years ago can serve many who need it now.
Creating tools reshapes future thinking: once a better system exists, it changes not only what is possible, but what becomes imaginable.
Building tools leads naturally to questions about how time and focus are managed to use them well.
4. Protecting the Space to Focus:
Attention is a zero-sum game.
Important work competes with everything else for attention. Protecting space to think, build, or write may be the most strategic decision in any project:
Deciding not to pursue something can be an active creative act: it frees time, energy, and mental bandwidth for deeper work.
Spreading energy too thin can quietly undermine quality: even promising projects suffer if attention is divided across too many fronts.
Focus often requires structural support, not just discipline: environments that reduce friction make concentration sustainable.
Protecting this focus sometimes means ending a project—not due to failure, but to make space for what comes next.
5. Knowing When to Move On:
Leaving something good can lead to something better.
Endings are not always about dissatisfaction; they can reflect recognition that a phase has completed its purpose:
Letting go of a role or project can be a sign of creative timing: something may no longer demand your best energy, even if it still works.
Successful work may outlive its usefulness to its creator: contribution and personal direction aren’t always aligned indefinitely.
Moving on can allow others to take things further: stepping back can create room for others to lead and evolve what’s been built.
These transitions are not disruptions, but part of an ongoing process of alignment between work and attention.
Conclusion
This approach to working life—curious, iterative, and periodically redirected—doesn’t rely on consistent progress or long-term prediction. Instead, it values responsiveness, focus, and trust in what feels engaging. Rather than committing to a single track, it makes space for continual adaptation and unexpected coherence.
The result is not always a clearly mapped career, but a layered one—made up of moments where interest met timing, where tools were built from necessity, and where endings allowed new beginnings to take shape.
Sometimes the side quest becomes the story.
Afterthought: When Straight Lines Stop Leading Anywhere
“You don’t always need to change direction—just to notice you’re no longer moving.”
Lately I’m a desperate believer,
but I’m walking in a straight line…
Sparks ignite and trade ’em for thought…
Set me on fire in the evenin’,
everything’ll be fine.
— Silverchair, “Straight Lines”*
These lines suggest a tension between persistence and purpose—between the drive to keep moving forward and the quiet need to pause, recalibrate, or reconnect. Sometimes the difficulty isn’t the absence of direction, but the insistence on staying on course when the energy or sense of meaning has shifted. The lyric points to a kind of emotional autopilot: forward motion that may not yet reflect actual change or improvement. Yet within that are sparks—small signals of unrest or reflection—that can become a way back to deeper creative paths. There’s something quietly hopeful in the idea that what looks like stillness or struggle can be the early sign of something beginning to shift.