Jairus Joer Senior Developer and Designer

The Sisyphean Struggle for Simplicity

A personal reflection on the pursuit of simplicity; setting boundaries, resisting endless refinement, and accepting "good enough" after struggling to balance clarity with hidden complexity.

The second part of ‘Migrating the Monolith’ was scheduled for release, but it has been postponed due to scheduling conflicts. In the meantime, enjoy this article, which focuses on my personal quest for simplicity and how I came to terms with it.

Recently I somewhat randomly watched Behind The Scenes Of Notion’s INSANE Design (w. Notion Team), a video on Notion’s design psychology and their endless pursuit of simplicity in the user experience of their product, which led me to this week’s topic: the Sisyphean struggle behind it all.


The Essence in itself

When viewed through a narrow lens, simplicity appears to be as ambiguous a term as clean when it comes to its pure definition. Yet it emerges with distinct characteristics that elevate its status as a desirable yet ephemeral goal in both design and development.

In our individual work and lives, we strive for simplicity, somewhat unknowingly forming a consensus on its characteristics. A distilled, essential idea; reduced complexity revealing clarity; shaped by purpose and elegance – yet elusive through relentless reduction and refinement.

We encapsulate the essence of simplicity in definitions of boundaries, which we designed to contain and prevent the spiral of relentless reduction and refinement inherent in simplicity. This allows us to converge on a tangible subset of qualities that we might strive for in our process.


Where simplicity begins

Simplicity begins with the finalization of an initially complex design. Once these boundaries have been established, the process of reduction and refinement can begin. However, this introduces an additional hidden layer of complexity that users must remain unaware of.

Although this additional hidden layer of complexity introduces costs, we can rely on our boundaries to limit overreach and focus on the process. For now, these boundaries are providing guidance for the initial reduction and refinement process.

The initial stages of the reduction process promise a vision of a simpler, more refined experience that will delight designers, developers and users alike. While the previous boundaries remain intact, the outcome is more with less on the surface – a promise sure to be broken.


Expanding the boundaries

In the name of simplicity and everything simple, the design should feel simple to the user. But what makes a design feel simple? At some point set boundaries begin to dissolve for the sake of more simplicity – more reduction and refinement for a yet simpler experience to possibly delight in.

Expanding boundaries can be a healthy step towards improved designs and implementations. However, if we rely too heavily on expansion, it can undermine the very thing we are trying to improve, resulting in the process itself becoming self-destructive, like the Ouroboros.

Yet the outcome so far has been promising. There are plenty of ideas on how to optimize, expand, simplify and strive for even more excellence. It seems that we are now on the verge of breaking free from the vicious cycle of relentless reduction and refinement. Just one more refinement is needed.


Where simplicity never ends

What seems simple is often the most difficult. At some point, considerations outweigh the possibilities of implementation, and layers of complexity become increasingly apparent and intertwined. At one point, a complete rewrite might even be considered, starting from a clean slate.

However, a clean slate won’t stop the relentlessness in its tracks. The only way to leave this cycle is to compromise, accepting that good might just have to be good enough, and that the excellence we so nobly strove for is as unobtainable as it is absurd.

This compromise rarely provides relief, as we know that we could have achieved so much more. However, the relentless and elusive nature of the Sisyphean struggle can overcome even the strongest-willed designers and developers. This is a fate that should never be ordained.


When good surpasses excellence

Accepting healthy boundaries when striving for simplicity has in my own experience become essential to the process itself. I’ve learned this the hard way by indulging in my own Sisyphean struggle – my personal website, which, despite its simplicity, took years to release to the public.

Ironically, the recent sources I sought inspiration from provided me with the epiphany I needed to stop my metaphorical rock. The pages I frequented were dead simple in design and reflected my ideal of simplicity. Yet they were crafted using the most complex tools to enable obsolete behavior.

This obsolescence revealed to me the futility of my effort and allowed me to finally draft a version that satisfied not only the essentials but also me. It took me a little under a week to implement and publish what once was my Sisyphean struggle. Good finally proved itself excellent enough.


What it took to be good

In order to succeed, I had to abandon many details that I had previously held dear. Overreaching ambitions caused me to neglect the essential scope of an initially simple design, leading me to focus on parts that would be considered supplementary rather than reductive in nature.

Taking a lesson from Progressive Enhancement, I provided a simpler but still usable experience at the core, and crafted satellite features limited in scope to accommodate additional functionalities that would enhance the core rather than sideline it eventually.

This focus on a robust core enabled me to iterate with greater elegance and speed than I had desired before. Satellite features were swappable, easy to add or remove at will and did not hinder the fundamental implementation behind them, but rather embraced and enhanced it.


To conclude it all

In the end, the pursuit of simplicity is less about achieving a final, flawless state and more about embracing the journey itself. Simplicity is not a finish line to cross, but rather a direction to aim for. This requires honesty, restraint and, above all, acceptance of imperfection.

By setting clear boundaries, focusing on the essentials and resisting the urge for endless refinement, we can create work that is functional, elegant and genuinely meaningful. The struggle may be Sisyphean, but it is the lessons learned along the way that make the effort worthwhile.

The true reward does not lie in achieving perfect simplicity, but in the clarity and confidence gained from grappling with complexity. Every attempt, whether successful or not, shapes our intuition of what truly matters. In this way, the struggle itself becomes a source of growth and creativity.