What was the worst time of your life as an indie Game Dev? This could be writing complex code, designing levels, characters, etc
Worst time of your life as an indie
I think "worst" isn't really the right word for what you're going for. Work is work and sometimes it goes well and sometimes it doesn't.
Probably a significant instance of a project not going well for me was having spent several months working solo on a game that was meant to be played online to find that I was not able to work out a solution for a lobby to connect players. Money ran out so development stopped and since then I just haven't gone back to it.
The worst time for me is when I don't get to make progress on the game. Making a game is so time consuming that losing even a single day can be really demoralizing.
Even when I know the weekend will allow me to makeup for lost hours, it still feels like any day not working on the game is a day I can't get back.
I shifted from making a game to making a tool for gaming (not an engine), so my worst moment(s) is the feelings that I've taken on more than I can chew. Many at times I feel so overwhelmed with TO DOs that i kind of shout out internally HELP!!
The other thing is getting stranded for too long with some bugs and over-running my estimated time for that section of the project. When this happens back to back (and it usually does) I get pissed.
Having income streams dry up faster than anticipated and subsequently life savings disappear quicker than you thought and credit cards go from being well managed to maxed out, rent payments bouncing, bills being months late, driving an unregistered car, just waiting to be pulled over by a cop and slapped with another $800 fine on top of the $400 registration that you couldn't afford, wondering how this happened all so quickly and feeling like a failure who is going to doom their family to eviction and poverty because they thought they could work independently, having the weight of this so physically crippling that sometimes you can't get up off the floor of the shower even though the hot water has long run out, the weight so emotionally crippling that sometimes you just have to cry in the bathroom for no specific reason, it just being another bodily function now like sleeping, which you can only do by taking large doses of melatonin because otherwise you'll be up all night honestly wondering if you're strong enough to make sure that your infant son will grow up having a father.
How about you?
Looking at a sea of scowling faces waiting to tell me which of their day's inconveniences are my fault while at my day job and realizing "these are the people that I'm sacrificing my free time to attempt to bring joy to."
Worst time was getting trolled. Game dev is easy compared to firing up your computer of a morning and have Internet Explorer abuse all hell out of you.
I soon learned what accounts I had though, thanks to one troll in particular. As a result I have ditched virtually all forms of social media, very few online accounts still remain.
4 hours ago, grumpyOldDude said:Lol @Hodgman I'm quietly hoping you are exaggerating X 3 over, to inject some humour.
A deliberately dramatic reading, for effect, sure, but 100% legit. That's my worst indie dev story, as requested. Another: at a dinner party with other indie devs recently, we realised that we were all on prescriptions for anti-anxiety medications... Something about entrepreneurial risk taking personality types, maybe.
Indie dev is a dumb thing to do. Stick to hobby dev! 
Also, watch 'Indie game: The movie' (and the Indie game: The movie Epilogues) and try to spot which devs aren't struggling with an overload of stress and/or other kinds of mental health deterioration.
Worst time of your (my) life as an indie game dev (full-time): When I'm out of money, the world ends.
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