Most people wouldn't, psychologists have found.
Irrational it may be, but only professional gamblers and particularly cold-blooded financiers make these decisions on the basis of probability and expected value alone.
The rest of us make them emotionally, and the fact is that for most people the pain of losing £100 counts for more than the pleasure of winning £180.
The malign consequences of this psychological asymmetry are not difficult to spot.
If we spend too long in rotten jobs, poor relationships and unfulfilling lives, it's not because we don't believe in the possibility of better. We get stuck because, although we do believe in the possibility of better, it is psychologically outweighed by the risk of worse if we attempt the change.
It's the same in organisations, fear of failure is more powerful than the prospect of success. Promising projects take forever to get started while we obsessively plan every last detail. Failing projects are kept alive long after they should have been put out of their misery.
'Become more comfortable with the idea of failure!' we exhort ourselves (or others), but this is a doomed idea. We can no more make an intellectual decision to feel differently than we can solve a quadratic equation with our emotional intelligence.
So what to do? Psychotherapy may be one answer, but first try this thought experiment, for which I am indebted to the great Daniel Kahneman.
He asks us to imagine a company with 25 divisions, each worth £100m. Each division has the option of a project that could either double its value to £200m or halve it to £50m, with equal probability.
None of the divisional CEOs would take the risk - the consequences of failure far outweigh the rewards of success. The group CEO, however, would love all the divisions to take the risk.
This gives us the clue. To overcome the fear of failure, broaden your frame of vision. Look at weeks, not days. Years, not months. A portfolio, not an individual investment. Not one year, but a lifetime. Then perhaps the ratio of risk to reward starts to look more attractive.
Alastair Dryburgh is chief contrarian at Akenhurst Consultants and author of Everything You Know About Business is Wrong (Headline, £13.99). More at www.alastairdryburgh.com.