A simpler way to go about this problem is to use an option backtesting software. For those who are interested in a simpler way to solve the question I asked, you can carry on reading. I carried out multiple backtests in the past 24 hours on 4 uncorrelated stocks/etfs, across multiple timeframes, varying deltas and over 10 years of options data. I came to some conclusions which might be helpful. The conclusions would be stated at the end. I used the edeltapro to backtest(this is not a plug). You can use any options backtesting platform. The keys are: The platform must allow you to exit trade when short strikes are breached. Also your short strikes/barriers should be based on delta. Lastly, should be able to download the backtest report to excel. edeltapro allow me to do all those and the platform is easy for me to understand(again this is not a plug for edeltapro, there are probably better platforms out there). So 2 of the stocks/etfs I backtested and I am going to show here is MSFT and TLT which are both uncorrelated. I have attached the excel sheets below. I used the 16 delta short strangle and monthly expiration over the last 10 years to form my backtest. I exited when either strikes are breached. Those strikes serves as my barriers. After downloading the excel backtest report: Now to calculate the average remaining time after an option strike is hit: First calculate the time remaining(in %)=100-100*(close-open)/(expiration-open). Now you can find the average of time remaining(in %). To account for when barrier is hit you must skip the zero cells. You can use the averageif(column range,”<>0”) function in excel. Msft result in picture below: https://ibb.co/p12ZzML TLT result in picture below: https://ibb.co/fQ7S9gD Conclusion: 1. For a 1 standard deviation(16-delta) short strangle trader on monthly options, you should on average expect your trade to be tested after 2/3 of the time have passed. 2. As can be seen from the pictures above the average is pretty consistent across different assets(with same deltas and time to expiration). So the backtest is not irrelevant/random because the backtest is consistent for multiple uncorrelated assets. 3.Finally, the shorter the time to expiration the lower the average. For example: a 16 delta 5 days short strangle would have it’s average time remaining when the strike is breached somewhere less than 15%. So even though I own a 16 delta short strangle, my strikes would be breached when most of my theta decay have been received for a 5 day option than for a 300 day option. Thanks for reading and I hope it was helpful.