Congratulations.
I know you're thinking about stuff like this, but my not-advice advice to be thinking about:
- in retirement, at least for me, option sales / trading is about generating a dividend-like income. I'm doing a better job, today, about NOT entering positions designed to produce something other than dividend-like income. I've failed on this one badly at the start of the year (and at other times). Maybe this time I've learned the lesson
- how many positions (rather than value) do you need for generating your target level of income. I track positions as the account value of share backed cc's doubles as shares go from 600 to 1200. Same number of cc's, but in one of those, the account value looks a lot better
. For me I'm looking for 12 positions to generate $2/week; about $2500/week and $10k/month. I boost that with a bit of leverage, a bit more risk, and/or more money to support more positions. I'd really rather be at $40k/month. If I consistently find myself in positions designed to beat $40k/month then it'll be time for a leverage and risk review (as in - I need less of both).
- figure out, and know, what constitutes "enough" (both income and value of assets-under-management). I lost track of this at the end of last year and started taking on too much risk and leverage. In my case, "more" = "more to give away while we're alive" rather than a change in lifestyle or what we can leave to our family (no children). Why would I take on extra risk and leverage in order to increase the pile to give away, especially if I risk staying retired? Answer of course - I wouldn't. I forgot this at start of this year.
- watch the leverage. If you feel FOMO coming on, and you need to take on more leverage to really take advantage -- these are the situations where the black swan can send you back into the workforce.
- dividend-like income is as much, MHO, about financial results as it is how you get there. How much effort / energy goes into opening and closing a position? How much stomach acid do positions generate? How closely to you need to follow the share price throughout the day? If you're doing something resembling a job day trading then you've got a much wider range of things you can do. I don't day trade and I need positions to be much more fire-and-forget.
Or in short - I find that being retired on options income is a LOT more about planning for the risks / costs / downsides of any positions, and a lot less about just how big the position can go.
I carry a lot more cash now than I did while working. Like 1/3rd to 1/2 account value in cash (which I use for CSP and buy-writes, but not for very high leverage BPS). Two big reasons - I want 1/2 to 2 years of living expenses in cash (NOT AUM) so I have a lot of flexibility about when to take withdrawals from the investment accounts. EDIT: This is held in my bank account, not in the brokerage.
The other is that I want ups and downs in the share price to have a lesser impact on the account value. I wanted the big swings before I retired - not so much now.
Simplest of all - if you can stand parting with shares as needed, then simple continue buy-n-hold with the plan to sell shares to raise living expenses. This is likely the best overall result over a big enough timeframe. The problem for me is the willingness to sell along with the worry that I'd be selling at a bad time because I needed to.
(And in case it isn't clear - there's a good chance I won't have a tax bill this year; I've had some expensive and valuable lessons)