Time to update my strategy. Again. I know it sounds weird but yes, I need to update my strategy, because the one I wanted to use showed up to be a dead end.

I was trading naked puts at some point against dividend stocks but later I turned into spreads. When analyzing why I found out that I started losing money as soon as I deviated from my strategy. The biggest issue was that I started trading stocks I didn’t want to own, so I started defending my trades, rolling them converting them, doing whatever I could to avoid assignment.

So I turned into spreads against SPX hoping that that would be the right strategy to make tons of money and not to worry about being assigned. Of course, SPX cannot be assigned, right?

I was losing money even faster and I couldn’t stop it.

It is time to go back to basics and start with what originally worked well, but this time stick to the plan.

I will be trading options against dividend stocks as of now only putting the SPX spreads aside for the time being.

 

 · Accounts

 

First, let’s review what I am doing and that I am not that crazy as you may think when reading about my gambling with options.
I use several account and my options trading was just a small part of the entire investing empire I have.

 
TD trading account
 

This account is reported on this blog This is my trading account I use primarily for trading options. I will not be buying and holding stocks in this account unless necessary as part of my trading strategy. This account’s purpose will be generating income to be invested in my other accounts and abridge my early retirement income before my 401k and ROTH kicks in.

 
401 k account
 

This account is not reported on this blog I invest in a 401k retirement account. As of today I contribute 7% of my income and every year when I receive an increase I increase my contribution by 1%. I also get 3% employer match. Choosing investment vehicles in this account is limited but I could choose funds which pay large distributions or dividends (as much as I could) which can be reinvested. I rebalance this account every 6 months.

 
ROTH IRA account
 

This account is reported on this blog This is my dividend growth investing account. I primarily invest into dividend growth stocks and reinvest dividends. I will also use options strategy but not as my primary goal.

 
Scottrade account
 

This account is not reported on this blog I opened this account because I loved the FRIP program. It is not my primary investing vehicle, but I really love to play with the FRIP. It is a play money account. I invest into dividend stocks and use FRIP to be buying new shares and new stocks. I am just curious how this account would build up overtime as I am not contributing any money to it. I just deposited $600 dollars starting money in it about two years ago and let’s see how this works out 20 years from now.

 
Motif investing account
 

This account is not reported on this blog This is yet another pet account to me. It is not a primary investing account but I loved the concept of creating my own mutual fund and let that fund play out on its own. It is an excellent idea utilizing fractional investing. There are many stocks I always wanted but couldn’t afford to buy them or didn’t want to spend $50 dollars only in a regular account (like ROTH) due to high commissions and fees. Motif allowed me to buy those stocks and now they are growing and generating income.

 

 · Put selling strategy

 

The strategy is very simple. I am selling naked puts against dividend paying stocks.

 
You must trade this strategy only against stocks you are willing to own.

1) Sell puts against dividend stocks as long as you get assigned.
2) If you get assigned, keep the stock and sell calls against the stock
3) Sell calls against the stock as long as you get assigned
4) While waiting for assignment collect dividends.

 
 
In my TD account when I get assigned to the dividend paying stock, that will be the only time I end up holding that stock in the trading account. I will only hold it as long as I get the stock called away from me when selling calls against that stock.

I will use this strategy in my ROTH IRA account. The only difference is that I will be selling calls only against shares acquired through the put selling strategy.

For example, if I hold 100 shares of an XYZ stock as my core holding and I sell a naked put against that stock and get assigned I will end up holding 200 shares of that stock.

All dividends from that stock will be automatically reinvested into my core holding (increasing my core holding) and I will be selling calls only against the acquired 100 shares, so if I get called away, I still keep my core holding (possibly increased by dividends reinvesting program).

 

 · Dividend Growth Strategy

 

I will search and invest into dividend growth stocks and reinvest dividends primarily in my ROTH IRA account. I will be buying these stocks and hold them forever (if possible).

To purchase new shares I will use an OTO strategy (contingency order or “one triggers other”) which trails the price of the stock. This technique allows me to buy the stock cheaper.

During my accumulation phase when my account is small and generating less than $1,000 dollars per month in dividends I will use DRIP program for reinvesting dividends.

After my account grows larger and I start earning more than $1,000 in dividends I will stop DRIP program and start using dividend for selective re-investing.

The reason for $1,000 limit is commissions and fees. Unless you can buy shares for free, it is better to buy with $1,000 or more. If you use less, it becomes expensive.

To choose a dividend stock I want to invest in I created a screener which selects the most undervalued stocks for me.

 

Of course, this screener is not necessarily a buy list I will be blindly investing into stocks which are listed as “buy”. I will use those stocks for further evaluation.

 

 · Money distribution

 

After I grow my accounts enough to start distributing money I will use the following rules for money withdrawal or reinvestment.

 
In my TD account:
 

For every $1,000 monthly income I withdraw $200 for my own use and spending (paying bills, debt, vacation, but also buying dividend stocks for example in Scottrade account, or saving to my ROTH IRA account). After I reach $10,000 monthly income, I will take out 50% for my own use. The rest will be left for taxes and account growth.
Still long way to go!

 
In my ROTH IRA:
 

After I reach $2,000 monthly income I invest 50% of that income into dividend growth stocks. The rest will be used to grow my options trading portion of the account.

 

 · Conclusion

 

I have a lot of work in front of me to reach my goals and I hope this strategy of put selling against dividend stocks will help me to reach those goals and I finally will use it right. If I will manage to make it right this time, I should soon recover my account, preserve my money, and grow them enough to reach a comfortable retirement.

Bear with me, follow me and see how good or bad I will be in my effort. If I am successful in this, you will have an example to follow.