"Move fast and break things". "He who treads softly travels a thousand miles". Two philosophies, one destination. Which should you live by?
It's a bit like choosing a pension plan. You can either play it safe and invest your savings in index trackers and government bonds, or take out a high risk strategy by investing in stocks. Whatever your decision is, you've based it on the same goal: You want a comfortable retirement. Which will get you more? That's unknown, that's the risk.
What about in everyday life: You can either walk slowly and reach your destination in one piece; or run fast, break a leg and get there sooner. I believe it should be a mix of both, depending upon your circumstances.
In your business or job, as I've discovered with London Startups, those that succeed in the early stages tend to be the ones who stick their necks out and run. Those that walk at the beginning, or swim in the shallow-end get overtaken, leap-frogged and left behind.
But as you grow and mature, you shouldn't run so fast. The branches that you trip over hurt more than before. You start to get attacked from more sides and have to take more care in your defence. This is when it makes sense to tread softly (with foresight).
The depending factors are time, resources and tolerance. If you (or your company) are young, then you have more time to recover if something goes wrong. If you're rich then you have more to solve the problem with (note - this could be rich in terms of many things). And if you can tolerate high-levels of pain, then you can survive and come back. I would also add a final factor: Your ability to learn (see People Who Refuse To Surrender Are Stupid).
Of course, in the modern world that we now live in, we don't just have one direction that we head for, we have many: Careers, aspirations and families to name a few. Where I might be more willing to take risks in the former, I'm less willing to take risks in the latter. For that reason, there are moments where a compromise has to be made - work too hard, or for too long, and the quality of your family life diminishes.
If you see others that take more risks and say to yourself, "I wish I could be more like them", stop and ask yourself why not. How many years do you have to recover? How much money, friends and support do you have? How much pain, anguish or poverty can you take (multiply your answer by one hundred)? And how quickly do you learn from mistakes?
Answer these questions comprehensively, and you can start to take intelligent risks.