EDUCATION: SYNTHETIC DIVIDEND GENERATION VIA SHORT PUTI think everyone can generally agree that idle cash sitting in your account doesn't earn you much. Here are a couple of methodologies to deploy that capital to emulate dividend generation without being in the stock itself.
For purposes of this exercise, I've chosen HYG, which is not only options liquid, but also has a decent dividend relative to the broader market. Currently, it's 4.92% annually, and its last monthly dividend was .359/share compared to SPY's annual yield of 1.59% and TLT's 1.57%.
In the past, I've used several different methodologies to generate a yield approaching what the underlying is paying annually, depending on how much capital I wanted to or needed to tie up while waiting for opportunities.
(a) The Once a Month/30 Days 'Til Expiry Option: When the next monthly is 30 days until expiry, sell the option paying greater than or equal to the current monthly dividend. Run it until expiry and allow the option to expire worthless and/or take on shares if in-the-money, and sell call against at the same strike as you sold the put. Manage thereafter as you would any ordinary covered call. This is potentially the least buying power intensive setup if you're just selling one contract per month and will necessarily be of short duration.
(b) The Each and Every Weekly 30 Days 'Til Expiry Option: Each week, in the expiry nearest 30 days until expiry, sell the option paying greater than or equal to the current monthly dividend, again allowing each successive weekly option to expire worthless and/or take on shares if in-the-money, selling call against at the same strike as you sold the put, managing it thereafter as a covered call. Naturally, if you want to do something like this each and every week, doing, for example, one contract per week, you'd be tying up greater buying power and/or notional risk to do so. The upside: your longest duration is going to be 30 days.
(c). The Laddering Out in Successive Monthlies Option: Instead of doing just the next monthly at 30 days until expiry, ladder out 30, 60, and 90 days until expiry, selling the put in each successive monthly expiry for an amount greater than or equal to the current monthly dividend. For example, sell the December 18th 83 for .38; the January 15th 80 for .42; and the February 19th 76 for .38. When the front month expires worthless, consider selling a new back month, again for a credit that is equal to or exceeds the monthly dividend. The downside to this methodology is that it is not only buying power intensive, it ties up buying power for greater duration.
Shortput
EDUCATION: EMULATING YIELD VIA SHORT PUTOver time, my basic approach to my IRA has been to acquire shares at substantial discounts over time and to take advantage of "the three legs": (1) short call premium; (2) dividends; and (3) growth, with the eventual goal to be able to solely or predominantly rely on dividends post-retirement, since "growth" can periodically be elusive and short call premium collection on covered calls can vary widely, depending on movement of the underlying, implied volatility, and one's degree of "aggression."*
Typically, this has involved selling puts as an "acquire lower" strategy, followed by share assignment, and then covering. However, as we all know, getting into stock at a particular price results in a less than agile setup. After all -- and regardless of whether you buy stocks outright or are assigned them -- once you're in stock, you're in at the price you bought or were assigned, and there's no amount of magic wand waving that will change the price at which you acquired, even if you shed tears and get buyer's remorse later.
In comparison, staying in options as long as possible affords you greater flexibility as to potential acquisition price since you can roll for credit and therefore cost basis reduction before your getting full on into the shares. Relatedly, you can essentially "manipulate" the potential share price at which you're assigned by rolling the short puts down and out if you become unhappy with the strike at which you sold originally.
All that having been said, what if I want to emulate dividend yield in the shares while I wait to get assigned at a discount? Well, there's a way to do that -- with short puts.
Pictured here is an EEM June 19th '20 36 short put, paying .97 at the mid, with delta/theta metrics of 18/.36. 328 days out in time, it's the expiry nearest 365 days 'til expiry, and the delta'd strike (~18) that will pay something approximating the annualized dividend of $90.** In other words, this isn't the actual trade you'd put on to emulate dividend yield (although absolutely nothing prevents you from doing that), but rather a guide to tell you what delta and/or theta you'd need to sell in shorter duration to emulate the amount of annualized dividend.
In this particular case, selling the September 20th 40 short put*** would potentially fit that bill. Paying a .30 credit, it has delta/theta metrics of 17.29/.69 with a theta burn nearly twice that of the longer-dated 36, with the downside being that the strike is obviously much closer to current price than the 18 delta sold out in time. However, the theta metric makes it conceivable that you could collect what amounts to the annual premium of .90 in three to four expiry cycles as compared to 12, assuming that the underlying goes sideways, up, or even down to a certain degree during your credit collection/divvy generation emulation process.
Post fill, look to roll at extrinsic approaching worthless from the ~18 delta to an ~18 delta strike in an expiry that will pay a credit, aiming to collect at least .25 with any given roll. If you're not able to get at least .25 on a roll to a similarly delta'd strike without going out an absurd amount of time, consider rolling down and out more incrementally.
Naturally, this begs the question of whether and under what circumstances it's worth being in stock versus short puts since you can emulate not only dividends, but also growth with short puts ... . But I'll leave that discussion for another day.
* -- By "aggression," I mean what delta you're willing to sell as cover (i.e., 20 versus 30 versus 40 versus at-the-monied or even monied).
** -- The annual yield in EEM isn't great -- 2.08%, so I'm primarily using it as an example due to its excellent liquidity and market tightness in the off hours.
*** -- Naturally, this is best done on weakness or in a higher implied volatility environment. EEM's at 7/16 here, so you're consequently not getting a ton of juice out of the 18 delta.

