The founder’s dilemma: Structured serendipity
I was sitting in a cafe in Kuala Lumpur recently, sipping an iced mixed coffee with orange, when I realised that the way I organise for trips is exactly how I used to try to “organise” my startup. I was obsessed with the perfect project management software, the flawless internal wiki, and the 18-month roadmap—not […] The post The founder’s dilemma: Structured serendipity appeared first on e27 .
A Kuala Lumpur cafe visit made it clear that the author's method of managing startup projects mirrors their earlier "organising" tendencies for the company. The obsession with perfect project management tools, flawless internal wikis, and a 18-month timeline stemmed from a desire for security, not necessarily the business's need for such rigidity.
Founders often suffer from a "messy organising compulsion," creating unnecessary procedures and SOPs due to fear of the unknown. They want to predict and control every variable, from churn rates to bugs, by organizing them neatly in a Jira board. However, startups are dynamic organisms that thrive on chaos, not static processes.
The sweet spot for a founder lies not in a perfectly planned roadmap, but in "structured serendipity." Founders' obsession with control stems from the "Illusion of Control," a cognitive bias where they overestimate their influence on external factors. Complex systems like startups don't respond well to deterministic management. Instead, founders must adopt "probing, sensing, and responding" to navigate the unpredictability.
Psychologist Dave Snowden's Cynefin framework advises against relying on "best practices" or command-and-control structures in complex environments. The theory of slack, proposed by Tom DeMarco, suggests that companies operating at full capacity have no room for innovation. Leaving white space in the roadmap allows for experimentation and potential pivots when assumptions are proven wrong.
The "rule of scalable slack" advises founders to stop optimizing team capacity to 100% - doing so leaves no room for innovation or market corrections. The "loose-tight framework" suggests that founders should be tight on mission and values, while being loose on the "how." This means building a compass rather than a cage for the team.
Keeping a "security blanket" in the form of redundant systems is acceptable, as redundant systems enhance stability in volatile environments. The "three hour chaos budget" is a weekly time slot dedicated to non-goal-oriented activities such as deep-diving into raw user feedback or exploring random competitor pivots. This is where product-market fit is found.
The ultimate shift for founder leadership is not controlling chaos, but curating an environment for productive chaos. Trust in the built framework to handle disruptions, and let unexpected surprises lead to the next growth spurt.
Written by urgent.news from e27's reporting — not their text. Machine-written — may contain errors; check the original before relying on it.
