Knowing When to Hold and When to Fold

Hassan Karimi
4 min readJan 19, 2024

1. Separate the artist from the art

“Murder your darlings,” Sir Arthur Quiller-Couch, a revered British writer, would advise. His point? As creators, we must distance ourselves from our work, making choices that serve the larger narrative, even if it means discarding parts we love.

Consider the vast drafts of renowned authors, where cherished paragraphs-sometimes entire chapters-are axed for the story’s greater good. This ability to view one’s work from a detached perspective transforms good work into exceptional work.

This principle underscores the importance of evaluating one’s work without the cloud of personal attachment, enabling more objective judgments.

2. The beautiful dance with failure

President of Pixar, Ed Catmull’s insight from “Creativity, Inc.” is profound: “Failure isn’t a necessary evil. In fact, it isn’t evil at all. It is a necessary consequence of doing something new.”

At Pixar, early drafts of stories were downright bad. When it’s understood that failure is part of the process, crude and unrefined ideas are not immediately discarded. Teams dig in, they separate the diamonds from the rough, and they press on. This refinement process led to works like Toy Story and Finding Nemo.

3. Beware of ‘False Fails’

In Safi Bahcall’s “Loonshots”, he describes ‘False Fails’- A mistake attributed to the idea, but actually a flaw in the test.

Akira Endo’s mevastatin, a cholesterol combatant, initially showed no promise in rat tests. Instead of conceding to failure, Endo’s curiosity led him to question the result. He theorized and tested on chickens, revealing a stark difference: unlike rats, chickens, like humans, have both good and bad cholesterol. The drug’s potential was illuminated.

Similarly, Facebook’s early days were marred by skepticism. Investors saw social networks as unstable, noting users jumping ship from platforms like Friendster and MySpace. Peter Thiel dug deeper and acted on an alternative hypothesis. He realized the problem wasn’t in the very idea of social networking; instead, it was Friendster’s unstable servers letting users down.

Drawing from military wisdom, Bahcall emphasizes the principle of “Listen to the Suck with Curiosity” in his book. It’s not just about acknowledging challenges or criticisms but delving deep into them with genuine interest. Both Endo and Thiel exemplify this mindset, leaning into apparent failures with curiosity rather than defensiveness. By doing so, they uncovered hidden truths and turned potential setbacks into groundbreaking successes.

4. The wisdom in decisiveness.

Jeff Bezos, the mastermind behind Amazon, speaks to a dilemma every creator grapples with: when to be firm in your convictions and when more deliberation is necessary. He frames this in terms of decisions — one-way door decisions or two-way door decisions.

In a shareholder letter, Bezos wrote:

Some decisions are consequential and irreversible or nearly irreversible — one-way doors — and these decisions must be made methodically, carefully, slowly, with great deliberation and consultation. If you walk through and don’t like what you see on the other side, you can’t get back to where you were before. We can call these Type 1 decisions. But most decisions aren’t like that — they are changeable, reversible — they’re two-way doors. If you’ve made a suboptimal Type 2 decision, you don’t have to live with the consequences for that long. You can reopen the door and go back through. Type 2 decisions can and should be made quickly by high judgment individuals or small groups.

As organizations get larger, there seems to be a tendency to use the heavy-weight Type 1 decision-making process on most decisions, including many Type 2 decisions. The end result of this is slowness, unthoughtful risk aversion, failure to experiment sufficiently, and consequently diminished invention. We’ll have to figure out how to fight that tendency.

5. Iterative innovation

Eric Ries, in The Lean Startup, champions a potent mantra: “Build-Measure-Learn”. It underscores the essence of rapid prototyping, immediate feedback, and swift iteration.

Consider the early days of Dropbox. They began not with an elaborate product, but a simple video demonstrating its potential use. This approach enabled them to gauge user interest and gather feedback without investing heavily in development. Once they confirmed the demand, they proceeded with building a more refined product.

The lesson? By embracing a cycle of creation, measurement, and learning, creators can validate ideas swiftly, refine them based on genuine demand, and reduce the risk of extensive efforts on unproven concepts.

6. The idea refinement arc

Legendary designer Charles Eames once remarked, “The details are not the details. They make the design.” This captures the essence of an idea’s evolution: it starts simply, morphs into a complex form as it’s fleshed out, and then, with refinement, returns to a more profound simplicity.

Apple’s iPhone serves as a textbook illustration. Its initial idea was simple: a device that combined an iPod, a phone, and an Internet communicator. Yet, the development process was anything but straightforward. It involved intricate design choices, engineering challenges, and countless iterations. But the end result? A product hailed for its simplicity, intuitiveness, and elegance. The iPhone’s journey mirrored the arc from a basic concept, through the quagmire of complexity, and finally to a polished simplicity.

The road from inception to perfection isn’t linear. It meanders through the dense forests of complexity before emerging into the clear meadows of refined simplicity.

Originally published at on September 22, 2023.



Hassan Karimi

UX/ product former architectural designer writing about building a creative practice in modern times