Advice on 4000 shares of GOOG
I'm leaving my job soon and will have roughly 4k shares of GOOG. I'm looking to use it to generate income safely, since I'll be mostly retired. But I also want to keep some of it since I do believe in the general direction of Google.
I'm fairly inexperienced with CCs, but here's my general plan:
1k shares selling weeklies at around 0.1 delta. Im estimating this will net somewhere around $800 per week
2k shares selling every ~two weeks at around 0.05 delta. I think this will be around $1000 every two weeks.
Not trading the last 1k shares.
This should roughly put me somewhere around $65k per year. I mostly want the income for general living, we have part time income (~50k) to supplement the rest of our lifestyle. Our spending is generally only around 100k per year so missing some weeks is generally fine. We also have other investments that we could potentially pull from if really needed.
Is this a viable strategy? Would you handle it any differently?
The biggest catch is my basis on these are fairly low, so I'd like to avoid being assigned as much as possible since I'd be taxed pretty heavily. I've rolled some smaller CCs before but nothing of this magnitude. Does the rolling strategy work any differently when trading this many shares?