@Katers87, I have also gone through a few similar moments.
Like @Chris, I came to a point, a few years after finishing grad school, where I had a choice between large corporations and the startup world. I also chose the startup world, and have been involved with startups non-stop since, that is about 20 years now.
As a single person, until I got married, I had always taken the riskier route. But, at the time, I was married, so this was a decision that my wife and I took together. I think like @Chris I had gotten bored with the large corporate world, and needed more rush into my life. But, in a family, things aren’t so simple. My wife and used some risk mitigation strategy across our two careers: that worked well.
Like @Chris, I have had many ups and downs: lots of startups don’t make it. The stress of no job is tough. The stress or no salary is tough when you startup. The stress of feeling the responsibility for a lot of people’s fates is tough when you are the CEO of a startup, even if it is not the first time, when you are not sure that things will turn out well. So, one part of the response is what @Chris mentioned: how do you deal with stress?
But I think there is also another part of that. To me, life goes in cycles. At some times in your life, you will be ready to take lots of risks. At other times, not so much. It’s like a wave: the peak and the trough. Some of it is driven by the hysteresis of your life (not the hysteria! Or maybe the hysteria too…) for sure, and some by many other factors. So, to me, the other aspect of the question is—what phase of your life are you into? Have you been playing it safe for a few years, and are you ready for adventure again? Or have you been living on the edge for a while, and do you need a bit of a rest from stress?
Finally, I agree with @TiaG on downside management. To me, the best way to deal with it is what she discussed: make lists of downside scenarios with mitigation strategies. If you can identify a good mitigation strategy for each, then you have little downside, and there is really no risk in taking the risky option 
Easy decision then!