I've only cried literal tears once in the last ten years, over business. Due to inattention while coding during an apartment move, I pushed a change to Appointment Reminder which was poorly considered. It didn't cause any immediate problems and passed my test suites, but the upshot is it was a time bomb that would inevitably bring down the site's queue worker processes and keep them down.
Lesson #1: Don't code when you're distracted.
Some hours later, the problem manifested. The queue workers came down, and AR (which is totally dependent on them for its core functionality) immediately stopped doing the thing customers pay me money to do. My monitoring system picked up on this and attempted to call me -- which would have worked great, except my cell phone was in a box that wasn't unpacked yet.
Lesson #2a: If you're running something mission critical, and your only way to recover from failure means you have to wake up when the phone rings, make sure that phone stays on and by you.
Later that evening I felt a feeling of vague unease about my change earlier and checked my email from my iPad. My inbox was full of furious customers who were observing, correctly, that I was 8 hours into an outage. Oh dear. I ssh'ed in from the iPad, reverted my last commit, and restarted the queue workers. Queues quickly went down to zero. Problem solved right?
Lesson #3: If at all possible, avoid having to resolve problems when exhausted/distracted. If you absolutely must do it, spend ten extra minutes to make sure you actually understand what went wrong, what your recovery plan is, and how that recovery plan will interact with what went wrong first.
AR didn't use idempotent queues (Lesson #4: Always use idempotent queues), so during the outage, every 5 minutes on a cron job every person who was supposed to be contacted that day got one reminder added to the queue. Fortuitously, AR didn't have all that many customers at the time, so only 15 or so people were affected. Less than fortuitously, those 15 folks had 10 to 100 messages queued, each. As soon as I pressed queues.restart() AR delivered all of those phone calls, text messages, and emails. At once.
Very few residential phone systems or cell phones respond in a customer-pleasing manner to 40 simultaneous telephone calls. It was a total DDOS on my customers' customers.
I got that news at 3 AM in the morning Japan time, at my new apartment, which didn't have Internet sufficient to run my laptop and development environment to see e.g. whose phones I had just blown up. Ogaki has neither Internet cafes nor taxis available at 3 AM in the morning. As a result, I had to put my laptop in a bag and walk across town, in the freezing rain, to get back to my old apartment, which still had a working Internet connection.
By the time I had completed the walk of shame I was drenched, miserable, and had magnified the likely impact that this had on customers' customers in my own mind. Then I got to my old apartment and checked email. The first one was, as you might expect, rather irate. And I just lost it. Broke down in tears. Cried for a good ten minutes. Called my father to explain what had happened, because I knew that I had to start making apology calls and wasn't sure prior to talking to him that I'd be able to do it without my voice breaking.
The end result? Lost two customers, regained one because he was impressed by my apology. The end users were mostly satisfied with my apologies. (It took me about two hours on the phone, as many of them had turned off their phones when they blew up.)
You'd need a magnifying glass to detect it ever happened, looking on any chart of interest to me. The software got modestly better after I spent a solid two weeks on improved fault tolerance and monitoring.
Lesson the last: It's just a job/business. The bad days are usually a lot less important in hindsight than they seem in the moment.