Hey all. My employer offers many stock benefits through RSU, ESPP, and options. I try to max out my ESPP and as a result my non retirement holdings are heavily skewed towards my employer’s stock. I’m trying to diversify and not worry about timing the market, but what do I need to consider when it comes to timing sales of the stock to avoid wash sales? Currently we are down from the highs a 2 years ago. Should I worry about wash sales relative to timing of various acquisition dates? What am I losing by making a wash sale? Thanks.
I don’t know the rules about wash sales but surely you could just buy S&P 500 index funds to truly diversify. Only thing to consider for ESPP is that you get taxed at the income tax rate (probably higher) if you sell ESPP funds you received within 12 months, and you get taxed as capital gains (probably lower) for anything held longer. So sell the longer-held stock first.