Two tests for a path: whether it is fun, and whether it is hard

Benioff spent thirteen years at Oracle and became one of its youngest vice presidents. In 1999 he left to start Salesforce in a rented San Francisco apartment, selling business software over the internet at a time when large companies bought it on disks and installed it themselves. By his own account the idea came during a sabbatical he took after deciding the job had stopped being enjoyable.

His two tests work as a pair. Fun is a signal of fit: work that absorbs someone tends to get done well and for longer. Difficulty is a signal of ambition: a path with no rough stretches is probably one many others have already walked. Together they describe work that is engaging and stretching at once.

Salesforce’s early years fit both. The company picked a public fight with the established software vendors, staged protests outside a rival’s conference and gave away its message on buttons that read “No Software”. That was fun in the sense Benioff means: a small team enjoying a contest it had chosen. It was also rocky. Large customers doubted that their sales data would be safe on someone else’s servers, and early outages gave them reasons to keep doubting.

Taken apart, each test misleads. Fun measured week by week is a poor guide, because every worthwhile project has long periods of dull work, such as compliance, bookkeeping or fixing old bugs. Someone who leaves whenever the fun runs low will leave everything. And hardness is not proof of useful risk. A plan can be rocky because it is badly chosen, underfunded or aimed at a market that does not exist.

A better habit is to ask both questions every few months. If the fun and the useful difficulty have both gone, the path may be wrong. If only one has faded, it may be a bad season.

The word “sometimes” is the honest part of the line. A path that is always hard is a warning, and a path that is never hard is probably too safe.