I was reading a great Quartz piece by Camille Ricketts, How this booming startup invented its own flat hierarchy, about Gumroad’s new way of working. One quote about tools caught my eye:
Fewer tools means that people need to be more resourceful, and this is a quality Gumroad hires for aggressively. “One of our core values is that you have to be comfortable with being uncomfortable,” [Gumroad founder Sahil] Lavingia says. “Employees are told upfront, during the interview process even, that they should expect to be outside their comfort zone on a weekly if not daily basis.” This is how Gumroad determines if candidates are built for their way of thinking. Some people get really excited about this, and that’s exactly who the company is looking for.
This is working in the whitespace, way past the security and cover of the org chart. Out where there are no rules, and authority is unclear.
You have to be comfortable with being uncomfortable, in a sparse business.