I was recently in the same or similar position (partial buy-back) and opted to sell. Tax concerns aside, your essentially betting that the stock will do better

I was recently in the same or similar position (partial buy-back) and opted to sell. Tax concerns aside, your essentially betting that the stock will do better than an alternative investment. That might be the case, but taking the money and then reinvesting it is also a valid “I don’t need this money right now” option. There’s also the factor that you’re more “eggs in one basket” if you keep the stock. I personally pulled mine out to donate it, as it is potentially life-changing money in other people’s hands.