Western capitalism is a tier-based system like every other society in human existence, but its defining feature is that capital is used as the arbiter that allows people to flow from one tier to the next. At the bottom and middle are those who exchange their time and expertise for money. If accumulated and invested in means of production, they become capital and allow those individuals to ascend to the top tier capitalist class, who are able to derive their entire income without giving up their time on a salaried basis.
This is a catch-22 for society as the system requires the majority to be consumers who spend down their would-be capital for goods that instantly depreciate as that spending becomes income for the capitalist class. This is the true inequality as those who do not care for this current consumption can simply invest their way to the top by compounding most of their savings and capital for their lifetime.
But most of us, including me, are somewhere in the middle. This strategy is a systematic way of growing my capital, yet allowing me to at least somewhat enjoy some consumption throughout this journey. This is especially useful for us middle-aged folks in the professional class, who has probably accumulated a bunch of liquid assets and are in their 30s and 40s. They are pulled on one hand by an uneasy sense of scarcity, especially if they compare to peers who always seem to have it a little better, and on the other by wanting to slow down and enjoy a more meaningful lifestyle. This conflict tends to grow as social media highlights the inequality that has always been a part of societies and we become even more alienated from a slower tribal lifestyle that our brains have yet to evolve from.
This strategy therefore needs to make new highs as quickly as possible yet cannot meander around like most low risk bond funds. It also needs to be scalable and easy to implement as I am still a busy professional juggling work and home life. The enemy market regime of such a mindset is not necessarily a brutal bear market like 2008 or 2001, but rather a long stretch of miasma like the French or Japanese stock market. The solution for me is an option selling strategy to continuously lower the break-even point so that when the portfolio is already breaking even when the underlying market is still in drawdown. By the time the market has gotten back to break-even, the portfolio is in healthy profit.
The devil is in the details of course and the best hedge for this strategy is cash assuming the portfolio overall is making enough to cover the inflation drag. If so, that cash can be put to work when markets are down enough where you feel you are getting value. Since I have a macro background, it is easy for me to make that decision.
Putting it all together, I still had to ameliorate the risk of a bad drawdown as psychologically, I do not want to withdraw when there are no profits as a buffer. Based on my analysis, I believe that at worst it will take one year to come out of any drawdown short of total market collapse where guns and canned food become a better investment. Thus, I double that to two years and take half of 2 year rolling average of profits, divide that by 24 and withdraw that amount every month starting in beginning of year 3. Any emergency withdrawal will be subtracted from that 2 year average and following withdrawals will therefore be smaller. If at any point that 2 year average is negative, I simply take a longer average until it is positive again with no withdrawals.
Essentially we are smoothing 2 years of gains in normal circumstances and withdrawing monthly. I suppose my benchmarks should be passive income etf's that focus either on REITs, preferred stock, dividend stocks, MLPs, BDCs, and other option selling strategies. Once I have a year's worth of performance, I will stack my performance against them and see if it has been worth the hassle. We will use sharpe to determine the winner.