Career Advice part 1: Risk

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I'm often asked for career advice. I take this very seriously, because each time, this is someone's life we're talking about. Giving the wrong advice could mess someone up for years.
So, before we even get into it, let me share this disclaimer:
***Do what I say, not what I've done (or continue to do).***
Sounds a bit backwards, huh? Sure. But let me explain: I have taken more career missteps since college than most ten people will ever take. Oops! I'm like a career crash test dummy. Learn from my mistakes, please!
All right. With my disclaimer clearly in your head as you continue, here goes nothin':
1. Weigh your tolerance for risk.
I put this first on purpose, because everything else you do hinges on this one issue, and no one knows the answer but you. How much economic uncertainty can you stomach? Personally, I hate being broke. Hate it. But quite a few times I've literally been without money to pay the electric bill or even to gas up the car because I have this penchant for taking the main chance, for betting it all on one more roll of the dice.
To me, the risk of being financially middle class for life is much more distasteful than the risk of being dirt poor for a short time before I build a fortune. Key words: To me. This is one aspect of my personality that leads me toward entrepreneurialism. By far, most people are not cut out to run their own companies, and this is one big reason why.
Can you stomach losing it all? Only you can answer that one.
2. Weigh your situation's tolerance for risk.
Are you a kid just out of college, who can move back in with Mom and Dad for a while if things don't work out? If so, you can probably afford to make some mistakes and gamble on your future a bit. Are you a bread-winner with kids to care for, a mortgage, car payments, and all that other good stuff? Do you have employees to look out for, too? Only you can decide what's best for you and yours, but I urge you to think twice before betting the farm.
I'm a Dad now, and the sole breadwinner in our family. My situation is not the same as it was ten years ago. I'm in a different place in my life. How about you?
3. Weigh your spouse's tolerance for risk.
Two things lead to more divorce than anything else: (a) one or both people are selfish jerks, and the couple shouldn't be together anyway, or (b) financial stress. Never mind (a), but (b) is something you have to take sober-minded stock in before you proceed. In all seriousness, you may have to decide between your spouse and a risky career move. Don't kid yourself on this. I don't know which is more important for you. Only you know that.
Taking me as an example again, I decided one hell of a long time ago that Jane is more important to me than anything else in this world. The thing is, she is one of the most risk-averse people I've ever met. If we weren't so in love, we wouldn't be together still - I took risks with our business and my career than she just didn't deserve. So eventually we had it out, and I'm more careful now. No more betting the entire farm.
...Which doesn't mean no more adventure for me - far from it! I just have to be careful that we have a safety net. I'm more of a grown-up now, and it's a good thing. Jane isn't slowing me down at all, she's just inspired me to direct my energies differently than ten years ago, when we both worked and had no kids and lower bills.
These three considerations, all centered around risk (and of course opportunity), are not the full story, but I don't want to overwhelm you right now. In a future post we'll talk about career moves, including what you should do when you're hot to trot in a company that's not.
Tell me what you think so far? After all, this is just one man's advice.