You could try: “If you would succeed at anything, what’s everything that you would do?”

The short summary — boldness seems to be a word attached to something you really don’t have much control over.

Damn fine post GB, and thanks for the serious food for thought and the topic.

But if you need that money to pay your mortgage, betting it all would be foolish.

However, if you could get back 20% in a year by investing in real estate or stocks, perhaps it might be a good gamble. The one who doesn’t will never make that much, while the one who does has a good chance of winning big or winning a little or losing a little or losing big.

Most of the time, I’d say you can still do research around your options to see which ones are a good fit at the time. Its economics to me, evalute the risk, the cost, the opportunity cost, how much you’ll enjoy things, what kind of enjoyment you’re giving up, the percieved risk, stories your friends tell you, posts from someone’s blog etc.

Action talks about these V.C. people who make tons of money etc. But its not like they give it out to anyone who comes up asking for it, you need a biz plan. You need a SOLID biz plan, you need an amazing idea, something that inspires them. Basically, you need to convince them you are a risk worth taking.

Like, here’s a question, being Bold is good right? Well, right now, is anyone willing to take EVERY penny they have and go buy lotto tickets? Or walk into a Casino and bet everything on a single poker hand? I’m gonna guess no (Action might, action is crazy awesome like that). I’m gonna guess its because you guys know the odds, the real chances of success. And if you lose, you’re going to lose all of your money. I would argue likewise you can try to estimate what your risk is.

Sure, sometimes you have to make a choice based on little or no information, like making a new game genre, but that doesn’t mean you have to go full-force into things. What’s the harm in iterating into the risky area until you get a better feel for it?

I think if you look at things this way, you’ll see a lot of “risky” situations really have little loss in them. Like walking up to a cute girl and getting rejected, you’ll feel bad for a bit (or if your drunk you’ll still feel fine) but it doesn’t really cost you anything. Self-esteem and pride are emotions you can rebuild quickly. But when you start venturing into areas of finacial or body-part loss…that’s where things get harder to risk.