Have you ever stopped to think about whether it really makes sense to buy more of your own company’s stock through the employee stock purchase program? On one hand, that 10–20% discount is hard to turn down. It’s basically free money and part of our compensation. But then again, it feels a little risky having both your income and your investments depend on the same company. Do you go all in to take advantage of the discount, or keep it light to avoid putting too many eggs in one basket?

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I have it setup to be the full 15% contribution to ESPP and then quick sell at the end of every period. My company is only a 5% discount but after taxes every quarter it’s about a 3.6% return (ish) which isn’t much but is definitely more than if I didn’t do the ESPP. My risk appetite is too low to hold that much stock in my company long-term.

That’s a smart approach. I used to do the same, but the short-term tax hit started to bug me. Still, it’s hard to pass up that easy return!

That is a very good point. I always try to diversify, but when there is an overall downturn, it impacts everything anyway.

So true. Diversification helps, but when the whole market dips, there’s no real escape.

If you see yourself as being there long term and able to impact the bottom line and you're still decades away from retirement, I think a healthy amount of buying is in order. It shouldn't be your only investment though.

True, if you’re there long term it can make sense to buy in. Though honestly, I’m not sure how much one person can really move the bottom line - that seems more like exec territory 😅

I sell the day it hits my account. 25% arbitrage

Haha can’t argue with that! Even after taxes, a 25% return is still pretty sweet.

Depends

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