[Mook]

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i mean i could have a GREAT month financially (cut spending, invest a ton) and lose money overall or have a HORRIBLE month (spend a ton) and yet make money overall due to variance in the market.

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I assume these assets "in the market" are being held for the long term (i.e. retirement accounts) and not serving as a back-and-forth holding place for your poker bankroll / living expenses. If I'm wrong, get any such $$$ out of index funds immediately and put it in a highly liquid source of funds that will keep up with inflation (ING, money market account, or the like).

Having said that ... You want to set both an income goal and an assets (or net worth) goal - realizing that the former is really just a component of the latter. Tracking your income on a monthly basis makes sense. I assume you have some sort of handle on your monthly expenses, so while I eschew hard-and-fast budgets (life happens, ya know) you should def. know your average monthly "net" (average poker income minus average expenses) and should be targeting this number to invest each month - track this number closely. Know whether you're running ahead or behind "trend" in terms of $$$ invested for the year, and don't let it be influenced by swings in the market itself (that is, don't fall into the trap of thinking, "eh, the S&P's up 12% this month, I could really skip this month's contribution and I'll be all right" - of course, as a pro poker player I'm sure you know about the Kelly criterion, so this is not news to you).

As for your assets, monthly is waaaaay too short a time frame to worry about "coming out ahead" if you're mainly an index-type investor (not trading for a living). The quarterly statements I receive from my 401k / IRA's are plenty good enough for me and even then I realize that I'm going to have 1, and sometimes 2-3, losing quarters a year. Your goal with your assets should be annual organic growth (independent of your contributions) at a rate equal to or better than a broad diversified index such as the Wilshire 5000. (Your total assets will, of course, be growing significantly faster than this, since you're regularly adding to them. Which is the whole point.)

It's true that "you can't eat relative performance", but if these assets are being invested over a 20, 25, 30 year time frame then it doesn't really matter and if you're consistent about moving money from the income side to the assets side (and not the other way around) then 25 years is enough to provide anyone with a 7-figure nest egg. Good luck!

Mook