Buying company stock at discount vs investing in the broader market.

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Do you think it's more sensible to max my buy of the company stock at a discount or push more into market funds? I have about 30-35 years before I retire

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That’s kind of just a judgement call for how you feel about your company and how much of your stock allocation is with your company.
If your plan is like mine, you not only get to buy at a 15% discount, your purchase price ends up being the lowest price over the previous year minus the 15%. It’s hard to justify not buying it, especially if you can sell it right away

Take advantage of the discount. I wouldn't let my holding of company stock get to be more than 10 to 15 % of all of my investments.

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How long do you have to hold before you can sell? To me, that makes all the difference.

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This is the key.

We get a 15% discount on the stock, based on the lower of Jan. 1 or Dec 31 prices. Since it shows up Jan 7th-ish, it’s a guaranteed 15% gain with no obligation to hold. I sell mine immediately with no capital gains impact as well.

If you’re forced to hold for some period of time, I’d have to think hard about the performance of the company and how much of your financial future you want to tie up in the company (salary, benefits, and investments).

I just think the risk is too much for anymore than 3-5% of your portfolio. If the stock does poorly, your job security is also at risk. The added stress of that can lead to bad financial decisions.