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I'm not quite sure how to balance the investments between my 401k and my individual investment account. Should I be striving for some overall plan between both or really consider them disjoint and invest each of them independant of each other?

Strive for an overall plan that incorporates both accounts. It's best to look at allocation percentages over the entire portfolio, not by account. I do this on a spreadsheet, where I classify each holding (i.e. Large-cap value, small-cap growth), and then total each category and chart it. I have to use a spreadsheet because many of my holdings don't have public tickers, but if all of yours do, you might be able to find a website that can do it once you've input all the data.

I've been following this one--Fidelity Overseas Fund (in one of its various flavors/tickers)--for a number of years, and IMHO think it's a dog, trailing it's class and benchmark. You might want to move your dollars to ING International Value CL I (NIIVX), which performs slightly better, even with a slightly higher ER. It appears these two are the only international funds offered in your 401K.

My individual investment portfolio is a complete anomoly and goes against my better judgement really. I have too much tied up in that one engineering/transportation company, but they are a startup and I have made a whack of cash off of it. THey are poised to continue to grow at an exponential rate.

As long as you understand that this is more like 'gambling' money than 'investing' money, and that you currently have over 30% of your portfolio at risk in it.

I am planning on selling off about 50% of my holdings to diversify more.

That's not a bad idea. Ask yourself this, if you didn't own this stock today, and you got a $23,000 bonus (after-tax), would you invest it all in this stock? If not, how much would you invest in it? (Be honest)

I think I may be investing in too many funds in my 401k and want to figure out if I should just make things simpler, and put 75% in 1 or 2 index funds (the vanguards) and split the other 25% in a mix of others.

I think your first step should be to formulate an asset allocation plan. Decide what percentage of your port you want in each asset category and class, then adjust your portfolio (all holdings) accordingly. IMHO, part of your plan can include a 'gambling' percentage, I use about 10%, but you'll have to decide this yourself. A book that might be useful to read to formulate such a plan would be William Bernstein's 'Four Pillars of Investing'. You might also peruse

The point is not 'how many funds' you're invested in, but are your dollars invested in such a way as to afford you the best shot at long-term growth while avoiding a level of risk that you find unacceptable? Once you have formulated those portfolio parameters which comprise your goal, then allocate among available funds in a way which best suits it--always with an eye toward fund cost and ease of management for you.

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