I had two anxieties late last year and earlier this year.
First, since I left MC last year, I had to sell my SARs by Q3 of this year. The SARs represented a material part of my net worth. My strategy was to dollar cost sell, while trying to balance tax implications. I sold in Sept, sold Dec, sold in Jan, and originally planned to sell in June. I accelerated selling in Mar when it was becoming increasingly clear that we were entering a period of high volatility.
Second, how to get back in the market. My original plan was to dollar cost average 10% of the cash based on my AA every month. When the market started sliding, I pinched my nose and started buying when the market dropped 5%, then 10%, then 20%, then 30%, and was planning to buy at 40% (which it never reached). Since then, I am in the process of continuing to purchase 10% monthly.
Overall, this worked out ok. My MC has since recovered and I would have made more if I just sold today, but given the situation, I'm glad that I pulled alot of my chips off the table during the drop. I also used some of my purchases to fund a DAF to mitigate some of the tax obligations this year.
I'm hoping by the end of this year, I could finally have my end state AA and not look at the market. Forced to try to time both the exit of my stock options and reentry into the market were stressful at times, and my preference is not worry about it.