Hindsight is 20/20, but people seem too often to forget that foresight can go a long way towards saving you from having to stare backwards at a disaster. Hopefully the OP learns from this and makes his future failures (because we all fail, and just doing it once would be an incredibly rare feat) more palatable to himself and his family.
It's never possible to eliminate all risk. However, there's a difference between taking a calculated risk, and being reckless -- and reckless people more often than not believe they were taking a calculated risk. This is especially true of people with gambler personality.
(Not making an opinion about original poster - I have no info to base an opinion on. Making a general statement)
It's also perhaps worth noting that yeah, I'm also not making any value judgements on the OP, except to say that sometimes, even calculated risks are subject to sheer and utter failure, and that even playing things extremely safe, unless one has piles and piles of money, could easily lead to bankruptcy-worthy situations.
Just quoting this because it deserves to be read twice.
But I find people who know what it means to be irrational are far more interesting.
On a tangentially related note, what is the moral philosophy around having children? I'm not familiar with this area at all. Is having children generally considered a (or close to) a human right? Because it seems a lot of discussion about social policy (especially minimum wage) revolves around the assumption of supporting more than just oneself.
I want my kids to take risks. I want them to challenge the status quo. I want them to think for themselves. I want them to appreciate the irrational.
I don't care if they get an xbox for Christmas.