What is the biggest financial risk you've taken?

[greentea]

This question comes from a comment in another thread where I asked about debt. What is the biggest financial risk you have ever taken? Did it work out well or badly? What lead you to take the risk even though you knew it was risky? Did you learn anything from doing it?

[97guns]

the biggest risk i took was in 2009 unloading my entire net worth into 4 single family homes. i had cold feet when i did it, the amount of foreclosures was staggering, for sale signs on seemingly every other house. the real estate market was still declining from the housing bubble and i had a hard time renting my first unit, i was really scared at this point.

come to find out 6 years later as the market worked itself out that i bought at the absolute bottom in 2009 and its all gravy now but still my riskiest move

[ua_guy]

We completed a home purchase/sale last year that still makes me wonder if it was real. We risked to lose everything, but, we took a chance, many chances, actually, ended up beating the odds, and came out on top. Things you would not believe. We sold the old house free and clear and are happy and healthy, and enjoying the new place very much.

[Miz Pat]

Greatest Financial Risk

Getting Married!!

What a risk and how divorce can screw your plans.

[scfr]

My husband quitting his salaried job to start his own business. It meant not only the loss of his income and benefits, but we also had to save up what to us was a substantial amount of money and then risk losing it all.

Yes, it paid off.

Decided to take the risk because my husband is an entrepreneur at heart and I would not hold him back from following his dream, I trust my husband, I knew the business really well (actually I knew some aspects better than he did) so didn't feel I was going in to anything blind, DH was willing to make sacrifices to get there (we both were), he consulted me every step of the way, and he told me he wouldn't do it unless I gave him the go-ahead. In a nutshell, I did it because I'm a supportive partner. (I know that may sound arrogant, but it's true. And I must add that he is supportive of me too. Our marriage is a real partnership.)

[Nika]

Besides buying a co-op apt? Exercising an expiring Apple option 2 days prior to the earnings call, on borrowed money, no less. And this was before the stock split!

[midlifefinance]

This question comes from a comment in another thread where I asked about debt. What is the biggest financial risk you have ever taken? Did it work out well or badly? What lead you to take the risk even though you knew it was risky? Did you learn anything from doing it?

One of the biggest financial risk I have taken is switching from a full time office job to a full time freelancing career without an assurance if I will become successful in the said field. I learned a lot things doing it, dealing with clients and I gained a lot of new skills that I haven't learned in a an office job setting.

[elessar78]

Proposing to my wife.

[cypher1]

Dropping out of college to work full time in IT, which lead me to a career path I continue to enjoy doing. Coming up on 14 years soon. Folks were not too happy with that decision for some time.