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Personal Investments • ESPP advice

This forum has been very helpful in answering questions Ive had and im thankful for this community. Recently I have thought about executing a plan in regards to my company's espp. Ive been with this company for my entire 20 year career and have bought shares through the plan offering at different points across those years. I have accumulated a good amount of shares that I am comfortable with in my portfolio. Most all these shares are qualified and have at least 2 year period of holding. The plan offers a 10% discount from either the price of the stock on the first day of the offering period or the last day, which ever is lowest. I have thought about maxing my purchasing opportunity during the next offering period. When those new shares are purchased, I will then sell an equal amount of older qualified shares, effectively locking in a 10% gain(not factoring in the long-term taxable capital gains). I can then distribute the funds from the sale across my diversified portfolios. Does this plan make sense and what am I not seeing or factoring in. Thank you.
May I know with this strategy what kind of returns did you get? Since you did this over 20 years perhaps there was lots of up and downs.

Statistics: Posted by realclemsongrad — Tue Apr 23, 2024 5:59 pm — Replies 21 — Views 1796



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