Looking for the reasons it could work, without ignoring the odds
Asking why something could work is how new options get found. It is a poor way to judge them once found.
You shouldn’t focus on why you can’t do something, which is what most people do. You should focus on why perhaps you can, and be one of the exceptions.
In the mid-1980s the idea that ordinary households would pay a monthly fee to go online looked eccentric. Modems were slow, computers were expensive, and the services that existed catered to hobbyists. Steve Case joined a small company called Quantum Computer Services in 1985, and over the next decade it became America Online, the service that brought millions of Americans onto the internet for the first time. A list of reasons it could not work would have been long and mostly accurate. The company found the few reasons it might work and built on them: simple software, a friendly interface, and a flood of free trial disks.
That is the case for the line. Most people, faced with a new idea, generate objections quickly and stop there. Objections are easy to produce and feel like rigor. Looking for the conditions under which the idea could succeed is harder and rarer, and it is where new options come from. Case’s word “perhaps” matters: he does not claim the reasons are strong, only that they deserve a look.
The line is weaker as a way to evaluate an idea once it has been found. In January 2000 AOL agreed to merge with Time Warner in a deal valued at around $165 billion, justified by a story of why the combination could work: content meets distribution. The reasons it might not work, including culture, the fragility of dial-up and a stock valuation near the top of a bubble, got less attention than they deserved. Within two years the combined company wrote down close to $100 billion, and Case stepped down as chairman in 2003.
The phrase “be one of the exceptions” also deserves a second look. Exceptions exist because most attempts fail. Deciding to be one does not change the base rate, and founders who hear only the encouraging half of the line tend to forget that.
A sensible split is to use the line early and to switch modes later. When sketching options, ask why each might work and give odd ideas room. When committing money or years, turn the question around and write down what would have to be true, then check it. The habit Case describes finds the opportunity. A second, colder habit decides whether to take it.