Many employees at Automattic were what's called T-shaped, meaning they had one very deep skill set, and a wide range of moderate proficiencies.
Diversity of skill makes people self-sufficient. They didn't need much help to start projects and were unafraid to learn skills to finish them.
They weren't afraid to get their hands dirty in tasks that in a mature engineering company would span the turf of three or four different job titles. That lack of specialization made people better collaborators since there was less turf to fight over. The culture valued results more than process: people were happy to lend expertise they had or teach others what they knew.
There is conflicting advice about the value of specialisation. Specialists are revered when you need one, but often find themselves wedged into a corner and unable to move out of it. Despite their obvious ability to master one topic, many will assume they're incapable of doing anything else.
Generalists are equally misunderstood, seen as the “Jack of all trades, master of none” who is “a mile wide and an inch deep”. As useful as generalists are to have around, many will assume they're incapable of handling a deep or complex matter due to their broad skill set.
When we seek to learn a new skill or move into a new career, the specialist vs generalist dilemma rears its head. We see job titles like “full stack developer” or “infosec guru” with long lists of required skills, and try to tick all those boxes, while at the same time being told to specialise or risk looking like too much of a generalist.
The solution is to aspire to become a T-shaped person. Start by moving across, learning multiple skills to a moderate level of proficiency, then dive deep when the right opportunity is presented.