Eric referred to aggression level being a predictor of landout probability.

It is possibly semantics but to me aggression equates to pushing the limits
without consideration. An approach that generally results in running out of
height and ideas at some point. Even in a contest you have to finish tasks if
you want to score well, so there is a careful cognitive process of assessment of
conditions, personal and equipment performance and acceptable risk of landout to
determine how hard you push. When racing I generally have little to lose so I
can take risks - the top positions in the pack will be more averse to a landout,
because that will demote them. The winning by not losing idea of George Moffatt.

Same applies to personal flying. We should be balancing risk and goals
analytically.

My club is averse to XC flying, it is very hard to get anyone to retrieve you.
Since not getting retrieved is at best inconvenient and could be bad for your
health, I have to fly conservatively most of the time.

74 flights and 145 hours in my Std Cirrus - 1:37 on a GOOOD day. One land out,
at another airfield. With a nearly two hour average - including the winch
launches at sunset for a hangar landing, you can see I am generally flying in XC
weather. But the conservative flying style means I have only a couple of 300+ km
flights. We have pilots who own 1:29 performance ships that have never landed
out in 10 years of flying. Clearly glider performance is not a predictor of
landout probability.

Conversely, flying in regional contests I can (and do) take a lot more risk in
terms of land out. My flying has improved, as a result. I really believe that
glider pilots should be encouraged to explore the performance capabilities of
their aircraft. I disagree with the aggressive word though, to me this is all
about developing judgement. In this context aggression would be referring to
Instrumental aggression (aggression directed towards obtaining some goal,
considered to be a learned response to a situation - care of wikipedia.)
I would prefer to think of setting a risk level - What is possible today, and
what risk of landout can I accept? As a measure - I tend to be below the half
way position in contests. With my conservative flying meaning I fail to exploit
the conditions and capabilities fully. I generally share this area with the
other mis-judgers, either too conservative or trying too hard. (aggressive if
you like)

Now. I know Eric is a very experienced XC pilot so some opinions please.

Should we be landing out frequently enough to account for luck only, or more?
Should we ever intentionally fly aggressively as per the definition of aggression?