tl;dr - don't freak when things don't go as planned. Plan on it, instead.
I think my career path may be taking another turn. It amazes me how truly far off I am from what I thought I wanted when I was in graduate school. I had the husband, two-income household, house, kid, and degree. I didn't have the job, but I was in a city I loved.
The city changed and became unbearable, so I moved. The marriage is over, but I have another dude who is wonderful. The house was sold long ago and a duplex I can barely afford has taken its place. I still don't have the job I want and we're at about slightly less than 1.5 income household. The kid is awesome and growing up.
I couldn't possibly describe myself as unhappy. I don't know where I heard this, but someone remarked that people generally want a good job, relationship and place to live, but you don't get to have all three at once. Relationships in general are the most important part of my life and I'm pretty good there. The living situation is ok and the job is pretty left of center, but I'm in decent shape overall.
I may have figured out how to fix the job situation. I have a doctorate in psychology, but have not been able to afford the hoops to become licensed and now my job may be at stake. This has been absolutely agonizing and the main black cloud in my life since I graduated SEVEN years ago. I won't even discuss it with people at this point because I don't like to think about it. It's wrapped up in anger, shame, sadness, and fear.
After years of this fight and a recent horrible experience with a professional board I'm starting to wonder if I want to go all the way with the doctorate-level license. This is HUGE. It's all I've wanted for years, but when I look at what I enjoy about what I do it seems like a master's-level license might be enough. I wouldn't be able to make much money, but I'm not making much right now and have pretty much no control over my career (I can't compete in my field without a license). It feels like an expensive step back and I'm not even sure it's feasible, but I don't know what to do any more. It's also always been obvious that I don't fit in with the doctorate-having folks. So many of them take themselves VRY SRSLY and I just can't with that. My life isn't tidy, "The best-laid schemes of mice and men often go awry" seems to be the story of my life, and I don't pretend this isn't true. Awry doesn't scare me as much as it used to. It doesn't mean GAME OVER.
What career risks have you taken that paid off? Not necessarily made you a millionaire, but helped you find peace.