If You’re in a Rule-free Job, You Still Need Rules
Though this be madness, yet there is method in it.
- Shakespeare
Rules aren’t cool. Nobody gets excited by them. Beethoven didn’t compose Ode to Rules. Rules often lead to worse products being shipped, more slowly. In the process, team members’ spirit gets stifled. Smart and ambitious people often leave, or refocus from doing good work to getting promoted.
But the other side of the coin is that rules (and processes and cultural expectations, which I’ll collectively refer to as rules) define how work is to be done. They guide us: “Do this, then that, then check if A happened.” “If X happens, do Y.” These provide a template for how to get work done. In the absence of rules, people wouldn’t know how to get work done. The opposite of rules is not freedom, but chaos. If you think rules don’t result in productive work — chaos doesn’t, either. When people don’t know how to go about doing something, how will they be productive?
Emotionally, rules provide grounding. If you think that rules are stifling, chaos is disorienting. It makes people feel lost, which is scary.
When we play sports in a field that doesn’t have a fence, we feel uncomfortable. When we switch to one with a fence, we feel at ease.
So the choice you need to make is not rules or no rules; it’s who makes the rules:
One option is to work in an organisation that already has strong rules in place: big companies, universities, government, the military. In such places, trying to set your own rules is like trying to build a house on top of another house. If you choose this career path, understand what rules different organisations have, and pick one whose rules work for you. Choose poorly, and you’ll be unhappy.
The alternative career path is to work in an unstructured environment. I worked as a solopreneur, ran a startup, ran a dev agency, worked as a CTO of a startup, and for the past few years I’ve been working as a Tech Advisor to CXOs. None of these environments come with built-in rules. Since there’s a rule vacuum, we need to define our own.
Let’s take prioritisation as an example. How should a company decide what to work on? Here’s the system I’ve evolved over the years:
Prioritise outcomes (“Our stack can scale by 20%”), not activities (“Migrate the database”).
Prioritisation is in the order (“A, B, C, D”), not in labels (“A is High Priority, B and C are Medium, and D is Low”).
Two things can’t have the same priority. If they do, pick one — doesn’t matter which — and put it above the other.
This is similar to the system a company may have in place, but at a personal level. Over the years, you need to evolve such principles1, rules, checklists, processes, all combining to form a personal approach to work2.
Choosing to work in an unstructured environment and not creating structure is like buying a plot of land and living on it without building a house.
Structured and unstructured work environments have different failure modes: the former are often stifling, and the latter chaotic and disorienting.
In summary: rules are necessary. There are two different career paths you can take: You can either choose a structured path, in which case your job is to pick an organisation with clear rules that work for you. Or you can choose an unstructured path (like an advisor, consultant, founder, owner of a dev agency, or solopreneur), in which case you need to evolve your own rules.
e.g., If you increase the scope of the project, it will take longer.
You should reject work practices, people and and organisations incompatible with your personal rules. For example, when a startup isn’t working out, I understand root causes before fixing anything. Some impatient founders want to see action immediately, and I reject those engagements.
Rules without enforcement are not rules. Sometimes people say, “I believe in A and B”. But they still work with organisations that violate both. When pushed, they make excuses. They’re only kidding themselves. Maybe they don’t have the self-confidence to fully believe in their personal approach.