I think it depends on the quality of the funds in your 401k, plus the fees associated with them. Paying the $100 per year in brokerage fees is the equivalent of an extra 1% expenses at your current 401k amounts, which is ridiculous. In addition, since the trading commissions are quite high at the brokerage window the break even would depend greatly on how often you will be making trades.
Without seeing your 401k fund choices it isn't possible to evaluate the choice on the numbers, but my gut tells me you would be better off avoiding the brokerage window at this point.
Once you reach a larger level in your 401k, I would also not suggest you buy individual stocks, but rather low cost mutual funds. With $20 commissions you are going to have a tough time getting good diversification cheaply. You would be better off going with a taxable account if you truly want to play the market.
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