I was CTO of a company that had a two-week outage due to technical debt. I didn't sleep much for any of it. We fixed it, and we'd lost about 30% of our subscriber base in that period. The company took on new funding to survive, invested that in a new set of products, and shuttered the old stuff just to stay afloat. I am currently working in a business where there is a nearly 8-year old Rails app (600+ models, 250+ co…
And that wasn't a stressful place to work with insane deadlines - it was fairly relaxed for the most part.