Why would you even want to attempt to change your risk-tolerance? Frankly keeping all the fortune-cookie BS aside, to quote you:
here's the problem. I'm not learning
from my mistakes. Years and years into
this, I still find myself doing this,
yet I can't stop. I'm "pretty certain"
of things, yet want to wait until
things are "all but guaranteed"before
moving on them.
So looking at that I am guessing you have already gone through all the self-help sections in libraries and bookstores, already fantasized about the potential profits and the major fictitious losses due to opportunity costs, i.e. regretted not being able to earn those awesome profits that you could have earned in an ideal world.
Perhaps the biggest and most futile risk you will ever take is trying to change yourself, as it will take years to achieve (the years you may have already spent are just the beginning), if the probabilities play in your favor and you manage to make the ranks of 0.01% of people who actually change you will be left with two problems:
You have absolutely no idea how this
is going to affect your business,
you may be able to take more risk,
but are you sure your edge is
not being risk-averse. Being
risk-averse can be an asset.
Unfortunately, I think you dont even know what your actual risk tolerance levels are; the all but guaranteed in your statement has a high likelihood to be an outcome of a lack of a guaranteed max level of loss aka a Stop Loss!
I believe John MacIntyre came the closest to this point so far, and he does have some great point but to elaborate on what he was saying, plus argue a few points.
- If the risk is too high, its not
worth it! A partner may reduce the $
figure share on the risk, but it
will also reduce the % share of
profits, AND it will still not be
- Risk Analysis is awesome, but for
the most part for most people
include way too many variables that
are out of our control, hence making
it a quasi-luck analysis, hence
- I do not mean that you should not do
Risk Analysis, but rather that you
will need to eliminate all variables
that are not in your control, most
likely you will be left with the $
value of the maximum loss as the
only variable(along with the
projected time to achieve ROI).
Avoid basing any analysis on "Opportunity Costs" instead go for "Stop loss vs ROI analysis" while these sound exactly the same, and in theory are the same in practicality, opportunity costs will always be lagging indicators that are an outcome of a beautiful mix, of seeing someone else be successful doing the same thing or regret! it will always push you towards the direction of recklessness due the innate quality contained in the word "opportunity" to make us believe that opportunities have a very short expiry date thus helping induce recklessness!
The fact of the matter is among early adopters of technologies and ideas the probability of a high ultimate (not immediate) success of an individuals and organizations are usually an anomaly!
That said, I usually allocate funds(the $ value of my stop loss) for each business plan, trade, or any kind of investment, and aim for a maximum of a 100% loss on the downside, not a penny more.
Through the years I have found that explicitly spelling out how much I'm prepared to lose on an idea and then staying focused on that scenario forces me to accept the possibility of loss rather than fight it, or second guess my decisions. It a psychological trick that helps me see my idea through while ensuring that I remain emotionally detached from my idea.
So essentially while on one side I can get classified as a very high-risk taker the fact is my risk is always very controlled and usually depends on a single variable (the $ value) hence making me less reckless and risk-averse in a sense! So my counter question to you is:
Are you sure your problem is not being
able to take risks? or is it rather not knowing how much risk you are taking? Cause they are very different...