Month-to-date Progress:
I was kind of scratching my head earlier and couldn't figure out how far along I was towards getting my new tech toy. Rather than wonder I decided that a well timed mid-month update would settle the matter.
Originally posted by datsmahname
October Goals
[4k] Play 13k hands
[3k] 10k hands at 1/2 (20K/50k for 2011 Milestone)
[x] Calculate the risk of ruin for moving up to 2/4, Evaluate options. 
[x] 2+ Gold Articles
[x] 4+ Session Reviews
[x] 2+ Coaching Sessions
[3] 9+ HU SNGs (play 3 per HU session)
[~200] 500+ PokerStrategy Points, Gold Status
[x] Find suitable Rewards for completing these tasks.
In every area I'm doing great except one: volume. I'm only filling 80% of my hand volume "quota". Its roughly the same story with PS points and HU SNGs(~80% and 66% respectively).
Now, I'm sure I could come up with some kind of excuses about why this is the case: sleeping during peak hours, playing 1-3 tables max... but this theme has recurred for such a long time (and increasingly so) that I'm forced to consider a much more general explanation.
Fear of failure. I think that a part of my tendency to study like a mad man but play so infrequently is that I'm afraid of not playing really well, but I don't think this considers the big picture.

Naturally, a quick google search returns your 7 step guide to overcoming the fear of failure. Its actually a good read.
The cost of doing nothing:
First, my risk aversion towards game conditions is almost certainly costing me money because of the number of profitable opportunities that I am missing. Sure, I seat select and game select well (bum hunt)... I only play when I'm awake and comfortable, when I'm confident and in the right mind... but my "meta-nit" style actually costs me money.
So while my image at the tables is certainly LAG (or almost spewy) my approach to the game away from the tables is REALLY nitty. My opponents gain from my tendency to avoid marginal playing conditions.
How can I overcome this?
Do the research:
It seems the best thing to do is to educate myself. What are the possible outcomes associated with playing in tougher games? What are the probabilities associated with each outcome? What are the risks, and conversely what are the gains?
Playing against tougher opponents at my current stakes may mean playing in games where I do not have an edge. How can I evaluate my edge in that game under more marginal situations? This seems like a tough question to answer from my perspective. Simply put, I need more information on my opponents. This brings me back to a goal from last month that I did not achieve, once again a clearly important goal.
Originally posted by datsmahname
September Goals
[ ] Get Stats (invest in some 1/2 hands)
Evaluate the worst case scenario
Intuitively it seems like the worst case scenario is that my winrate decreases. This implies that the swings associated with playing will tend to involve more running losses (or downswongs). I would be statistically more likely to endure a +300BB downswing... but is that so bad?
Even with a 0.5 BB/100 winrate (very conservative estimation) I'd lose 500BB or 1K in less than 5% of all cases (a 2 outer). This is the worst case scenario: a more than 95% favorite to maintain a healthy bankroll even after a BIG downswing and a significantly smaller winrate. Not to shabby.
Losing $1K or $1.2K seems pretty bad, but thats why I've developed a nice big roll. Even after such a brutal run I would still have a good BR for my current stakes. My conservative Bank Roll Management is designed specifically to let me play in a wide range of game conditions.
What are the benefits of failing?
Well, playing in tougher games will certainly tend to improve my game. It will give me the much desired experience that I want before considering another move to higher stakes. I will also be far more likely to reach my hand volume goals. While 10K hands of 1/2 is somewhat arbitrary, those arbitrary markers are nevertheless rewarding to achieve.
Plan for the worst:
A number of good articles have been written on dealing with tough runs. I have a well developed plan for these swings and I've posted it once in this blog already. My BRM is part of this plan as well. Having a healthy roll after a brutal run. [x] planned.
Take Action
This relates back to all of my hard work & study. I meet almost weekly with intelligent regs that play at my stakes. I review hands regularly, participate in coaching sessions, read articles... and I absolutely love this aspect of poker. The intellectual challenge of studying poker, understanding my opponents thought process, my image... these challenges are really interesting.
Burn the Boats
How do I leave myself stranded with no other option but to proceed as planned?
A prop bet would help here. Some commitment to other people would help... I've tried this before but my odds were 1:1 and for that reason I think I was never going to get action.
This is something for me to work on next.