For risk, what really taught me how to deal with risk was playing Freecell. The short time span and the ability to play a game and if I lose replay it, and see where my playing was risky and where risks paid off really helped me, especially in business.

I started riding bikes in heavy traffic at age 8. What did I know?

It's simple, Gee...
High Risk = Higher Danger and Higher Reward
Low Risk = Lower Danger and Lower Reward

I could ride my road bike only on the sidewalk and risk minor collisions with pedestrians and kids on a tricycle -- boring! I'll take my chances on the road where the reward (and risks) are much greater. I guess my signature below tells you that I am comfortable with a fair amount of risk in my life -- not the "let's go poke a grizzly bear and see what he does" type, but a risk-taker nonetheless!

There are some great responses above. Thank you all!

I've been playing with some ideas from James Neill, a professor at the University of Canberra. He talks about two kinds of risk: R- and R+. R-, or negative risk, is whatever strategies we use to minimize risk of loss to maintain status quo. For example, (if I understand him) we might wear helmets to minimize the chance of cracking our noggins. On the other hand, R+ is risk for gain -- when we engage in a risk for growth or gain. Choosing to bike on the road, as some have mentioned, offers a significant positive experience that outweighs (in our minds) the risk of being doored or sideswiped or whatever.

R- philosophy is "risk aversity", e.g. insurance, law, etc.

R+ philosophy is "risk engagement" e.. exploration, sport, etc.

He talks about Outward Bound programs as opportunities to embrace the value of risk as a means of education and self-discovery. Sounds a lot like some of our reasons to cycle, no?

He discusses risk education as well: R- is education about how to manage negative risks (e.g. safe sex class) , and R+ is education about how to manage positive risks (kama sutra workshop).

The goal of R- is to avoid negative consequences, and the goal of R+ is to obtain positive consequences.
Obviously, in cycling we all probably have a combination of risk strategies, from avoiding falling and cracking our heads open, to experiencing the thrill of speed, riding down mountains, etc.

He also believes, as do I, that society has swung the pendulum towards risk aversity and away from risk embracing. Look how we treat our kids nowadays in terms of "keeping them safe."

Anyway, I find the topic fascinating. . .

I think that for some people taking risks is an adrenalin rush that they get addicted to. This can be very risky behavior like base jumping, adultery or leveraging your company to the hilt and buying new businesses. It is a behavior that is tied to a persons, for lack of a better work personality. Then there are those who are completely risk adverse who always play it safe. I don't think either of these are very healthy and the majority of people fall in the middle and weight the benefits and negatives of the risks they take and go with the one they feel provide the most benefit at the least risk. I also think that the majority of people tend toward less risky than more risky behavior and that taking more risks can make large improvements in both your personal and business life.

I used to get allegories all the time but then I got shots for it and they all went away.

A very interesting thread.

My tuppence worth

One day workshop, four themes, 2 hours per theme, in each using bicycling as a metaphor for commercial decisions involving risk

1 Calculation. R+ and R-, risk and reward, making a decision to operate only in the zone of potential gain. Don't do anything you can't do. Don't ride bikes unlit in Manhattan, don't do a ride in Arizona summer without planned water stops, understand your present strength and fitness, don't borrow at 8% to open 5% roi businesses. Do the sums, honestly and accurately.

2 Anticipation. Understand traffic patterns on your route, don't ride on the school run or commuter traffic, don't ride (here in August in Bahrain) after 8.00 am, don't ride at sundown into the sun when traffic from behind will be dazzled by low sun in front. The Motorcycle Safety Foundation advises "Think 6 seconds ahead - and think six seconds ahead for everyone you can see, who aren't thinking 6 seconds ahead". Avoid routes (or commercial ventures) where the biggest risks (semi trucks, cash rich competitors) might prowl.

These two themes are about "Is it worth it". The next two are about "How to do it".

3 Mitigation. Tool kit and the ability to use it? Water stops, food stops, power bars, cell phones, loved ones warned and agreeing to be a sag wagon? Planned "quit" decision points? Go/no go points within the commercial project plan? Sponsor agreement to each of these "Continue/Quit" milestones?

4 Preparation. Have you gained the required levels of skill, commitment and fitness? Have your companions (staff)? Are you planning something that your necessary collaborators (staff, financial backers, technical and financial collaborators) consider daft? Does your sag wagon driver have a liking for a frothy one after 5.00 pm, when you're going to be out after 8.00? Have you done this before? Have you benchmarked the skills and endurance required against others who have?

Hey, sorry but I got interested!

>>> a workshop on risk-taking for the executive team in an organization

My Inner Uber Cybic trembles at the thought of taking on such a project. Any 'team' with sufficiently low time stress to attend a seminar is by definition not about to take the slightest risk. Risk-taking is borne of desperation. In addition, executives do not retain 'execution' privilege past the point of their first failure . .implicit in the risk concept.

Cycling implications? If executive's advancement** were contingent on the risks associated with cycling, they'd contract it off-shore.

** - The only significant metric you're dealing with here and the only one you can use to keep them awake.

Many people who are adverse to risk have difficulty managing more than one plan at a time. Good risk takers have alternative actions planned in advance for when a less than optimum plan must be abandoned.

For example, the military trains for many eventualities because theirs is a risky business. The ability to shift into an alternate path is a necessity.

Most of inhabitants of "cubical land" that I observe have only one plan. If and when it goes bad they have inadequate fall back routes prepaired for use.

Whe you approach an intersection on your bike where you have the right of way do you have an alternate plan for what to do when that car at the stopsign ignores you and pulls out anyway. Most of us have learned to deal with physical problems like this almost automatically. Alternate plans are a good survival trait and minimize the bad side of risk.

Risk taking in the business world however is not something we practice every day while just walking around breathing. Plans for how to deal with the upside or downside of risk need to be put in place alongside the original plans to ensure best results.

Risk is the area that makes the successful what they are. If you do what everyone else does, you will always be like everyone else. The "trick" is knowing when to take risk and having the forsight to plan for the outcome.