Retired, 450k fun money, lets see what happens - SPY Options

Will I be successful and outperform the S&P 500?


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If you are going to be doing SPY options, you might as well doing SPX options. Higher premiums, no pin risk, no assignment risk. Everything cash settlement, what you win/lose is what you get.

If you are assigned to turn the wheel and sell calls.
 
If you are assigned to turn the wheel and sell calls.

What if the wheel turns again and your short calls start to get ITM? Worse, with differences larger than what your long position(s) can cover? Better to take/fork over the money and start anew.
 
What if the wheel turns again and your short calls start to get ITM? Worse, with differences larger than what your long position(s) can cover? Better to take/fork over the money and start anew.

They are not short calls but covered calls if you have been assigned on the short puts. Then turn the wheel and sell puts if you are bullish. You need to join the theta gang. Www.Reddit.com/r/thetagang
 
I threw in the towel to enjoy retirement. I've got a nice 450k saved in my roth 401k that is being rolled into a roth ira to mess around with. I'm okay with direct market exposure as I have more than enough savings and passive income from real estate to pay my bills.
I don’t get it, your idea of enjoying retirement is to actively manage money? Why not just buy and hold?
 
I don’t get it, your idea of enjoying retirement is to actively manage money? Why not just buy and hold?
Buy and hold is for the young, we do not have the time to wait for some bear market to recover. Plus this is a reason to get out of bed, I do not golf...
 
Discussion
The “Wheel” is a three-part option strategy that involves:

  1. Selling cash-secured puts on an underlying.
  2. If/when one gets put shares, hold the long shares, and sell covered calls against them.
  3. If/when one’s shares get called away, return to selling cash-secured puts.
Often dubbed as the “triple income” strategy, the idea is that a trader receives income from the short put premium, experiences capital appreciation and/or receipt of dividends on the long underlying, and receives income from the short call premium.

Despite the promise of three revenue streams and the promise of lower volatility associated with options strategies, not a single strategy outperformed the “single income” strategy of buy/hold on either a total or risk-adjusted return perspective. In fact, one strategy even went negative! Let’s take a look under the hood to see what’s happening.
https://spintwig.com/spy-wheel-45-dte-cash-secured-options-backtest/#Days_Till_Expiration
 
To clear things up - my goal is to be invested in the market and get a little premium on the side. If the market tanks, my account will tank with it. I'm bullish on the market and want correlated exposure to it.

My plan with this account is a bit different from the traditional way of running the wheel. I'm going to sell very short term premium at close to the money levels that I would want to enter if the market dipped a little bit. Once that dip happens and I get assigned, I'll sell covered calls where I want to take profits, expecting the market to bounce back up. If the market continues to fall and I can no longer sell covered calls above my strike price, I wait it out. If it doesn't recover right away, I'll be happily sitting on a beach, drinking beer and fishing.

I don’t get it, your idea of enjoying retirement is to actively manage money? Why not just buy and hold?

I'm no stranger to markets and managing money. Having a goal of building wealth has always been a personal challenge of mine that I find exciting.
 
I've been waiting for this day for a long time. After 40 years work, I threw in the towel to enjoy retirement. I've got a nice 450k saved in my roth 401k that is being rolled into a roth ira to mess around with. I'm okay with direct market exposure as I have more than enough savings and passive income from real estate to pay my bills.

As soon as the funds clear, I'll be running the wheel on SPY. I've never made one of these journals before... hell I've never even traded this strategy before but my goal is to outperform the S&P 500. I'll be selling very short term premium at a specified price hoping for an assignment.

Funds are set to clear next week. More soon to come...

How about you just burn it man.
 
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