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I'm a Rails core member too, and Eileen is my colleague... You are interpreting both links you gave in terrible ways.

• stevebmark 3y ago
  I’m quoting, not interpreting. What am I missing? It sounds like you’re seeing the pain GitHub suffered through rose colored glasses. The talks about GitHub Rails upgrades say it took years and caused burnout.
  • byroot 3y ago
    You are quoting out of context, losing the meaning of the quotes. The conclusion of Eileen's talk is that by not following with upgrade and essentially forking Rails 2.3 they painted themselves in a corner. They took short term gains, and produced longs term losses. It's a self induced problem. In the end they upgraded and are now tracking the main branch, so the problem wasn't Rails.