Thinking like a CEO: Getting into my 8 step Option Trading mindset

I borrowed some “Planning and strategy” habits from my Business Analysis profession and corporate CEOs and tried to implement those on my option trading practice. I used eight planning components to build an option trading plan. Hence, the heading: “Thinking like a CEO: Getting into my 8 step Option Trading mindset.”

Step by Step Options Trading Plan

Components of my option Plan

This plan that you are studying is a plan tailored my “environment” of risk tolerance, age, capital, trading experience, trading objectives and many other things that I intend to execute. Also identify possible potential scenarios can threaten the achievement of my objectives. Check out what you can pick and what you need to change here in this plan.

  1. Vision and Mission: My dream of becoming a successful trader. Mission is the objective, the goal
  2. Developing strategic mindset
  3. Identify targets, the watchlist of the Underlying I want to engage.
  4. Outline my quality control criteria. The justification for accepting or rejecting a trade idea from the watchlist.
  5. Identify tactics: the most appropriate option strategy that I will use.
  6. Setup tactical deployment, a.k.a. risk management
  7. Outlines my trade management plan: How I will manage my trade after the execution?
  8. Exit Plan
Only set SMART goals!

Every trader has a vision(dream), motivation or intensified desire to achieve some goal or be someone. And, every trader has a mission, this mission must include an objective(s) and a plan to achieve these objectives. Make sure your objectives are S.M.A.R.T. (Specific, Measurable, Achievable, Realistic, and Timely) 

This plan is outlined exactly, the way I will accomplish each of my objective. In option trading plan I have defined tactical mindset, targets (potential trade candidates), quality controls (my accept or reject decision), the tactic (options strategy to use out of many) to achieve objectives.

My trade setup, that is tactical deployment method to mitigate potential risks. Then comes the post trade guidance, called trade management: it is course of action that follow after executing the trade.

Last step of this plan includes, the contingency plan for exiting trade prematurely.

Why? Because, trade did not go exactly as I have planned and I have to cut my loses, for that this exit plan is precise, and clear.

Defining a Plan: a series of steps to achieve an objective of my an(y) option trade.

TRADING PLAN

QuestionWhy bother to plan options trading?

Short answer: an option trade plan is the only tool to keep being a disciplined a trader. It helps me to keep my fear and greed emotions at bay. An options trade plan is solid foundation for disciplined execution of trade.

More reasons to plan your options trading:

Having a plan fosters trading discipline. A plan also defines upper limit for the amount I am ready to lose, if things did not work out, in ‘Risk

Management plan’. Planning process layout the minimum knowledge I must have to open an option trade.

mission1. Mission: The ‘purpose’ to trade options

I am a professional trader, trading options, stocks, commodities, bonds and Forex. My objective as traders is universal, that is “to make money, not to lose it!”. I have listed my three objectives as below:

  1. Income generation: Use Options to potentially generate income on stocks I own or want to own.
  2. Hedging: Options to minimize the risk on an existing stock position in my portfolio.
  3. Speculation: Options trading helps take a speculative market position using leverage. Surprisingly, I can even take a position that can profits if the market stays neutral.

Every trade plan I outline must supports these objectives.

P LAY 
I Non-Directional Strategies 
2 Anchor Trades(Hedeed Portfolio) 
3 Collateralized (Cash Secured) Put writing 
Simple Spread trades 
S PORTFOLIO linked Futures Trading 
MAX TRACES 
15-20 
TARGET 
Positive annual return 
go 100% 
Target PUT INÜLXcquaI or aLm'eIO% 
15 
TBA
S.M.A.R.T. Objectives are must; quantify your goals.

The fact is, I am not going ‘win’ all trades, therefore, If, I am wrong about my trade, I want to get out of that trade with minimal loses and keep my capital to trade another better trade at some other time!

This is universal objective and guiding commandment for my option trading. I don’t need to write it down every time.

It uses to take about 20 to 30 minutes in past when I was not using this plan. But now the planning process is understood, I hardly take more than 10 minutes to execute a trade.

  1. Strategic Option Mindset

Strategic options mindset is intentional and rational thought process of ‘option trading’ decision making process. It focuses on the analysis of Options pricing model, critical factors and the Greek variables that will influence the long-term success of an options trader.

 2. The Strategy: creating mindset for trading options

I have been trading options, only for 3 years now, there was lot of cognitive dissonance about some options trading terms, that obscured my understanding about options. I needed “some streamlined thinking process” and some “critical success factors to master”. I picked up some of important terms (shown in thinking icon) critical to success from Option Pricing Model. Some of the concepts I consider as ‘rule of the thumb’ in options trading are shown with rule of thumb’ icon. Both ‘mind set’ and ‘rule of concepts’ are subject to change in future, as I go along with the suggestions and critiques of veteran traders. Make sure you visit this page in future to check some updates. Following terms were most difficult for me to wrap my head around:

MindsetImplied Volatility Rank (IV Rank):

IV rank can be compared to P/E ratio for a stock. If above AFL stock is trading around $50 per share, that is absolutely meaningless, without additional information. Is there is any way from price per share to figure out Aflac Incorporated (AFL)’s EPS (earnings per share)?

However, P/E ratio is 7.71 tells me the earnings yield is 7.71%, similarly we can compare P/E ratio of comparable companies in Financial Services sector. (AFL is in life Insurance business) and general market.

rule-of-thunbRule of thumb #1: IV rank provides context.

I took following real examples from yahoo to show option’s trading example. The stock I am citing in this example is:

Underlying stock: Aflac Incorporated (AFL), listed in NYSE and Nasdaq, on April 1, 2021 closing.

AFL’s Current stock price: $50 (actual $51.42, but nearest whole number is good for simplicity’s sake and to explain math)

Implied Volatility (IV): 22.8%

Implied Volatility (IV) example trade: scenario low volatility ranking

Implied Volatility (IV) is 22.8% (for simplicity’s sake let’s make IV=20%), that is annually stock will fluctuate +$10 to -$10, that is $40 to $60

This means, 68% chances that price will stay between $40-60.

Aflac Incorporated (AFL) 
NYSE - Nasdaq Real Time Price. Currency in USD 
51.42 
+0.24 (+0.47%) 
Add to watchlist 
At close: April 1 4:00PM EDT 
Summary Chart Conversations 
Statistics 
Historical Data 
35.356B 
0.98 
6.67 
Apr. 27, 2021 • 
May 03, 2021 
1.32 (2.57%) 
Feb. 16, 2021 
Profile 
ID SD 
Financials 
1M 6M 
Analysis 
YTD IY 
12 p.m. 
Options 
5Y Max 
02 p.m. 
Holders 
Previous Close 
Open 
Bid 
Ask 
Days Range 
52 week Range 
Volume 
Avg. Volume 
51.18 Market cap 
Beta (5Y 
50.96 
Monthly) 
51.40 x 80 
51.41 x 800 
50.88 51.47 
30.32 - 52.78 
3,864,004 
EPS (TTM) 
Earnings Date 
Forward 
Dividend & Yield 
Ex-Dividend Date 
ly Target Est 
Sustainability 
Full screen 
51.60 
51.42 
51,33 
51.18 
51.07 
04 p.m. 
10 a_m_ 
49.20 
Trade prices are not sourced from all markets
Aflac Incorporated (AFL) 
NYSE - Nasdaq Real Tame price, Currency in USO 
51.42 
+0.24 (+0.47%) 
4:00PM EDT 
Summary Chart Conversations Statistics 
to watcWiSt 
Data 
profile 
0.00 
0.05 
Financials 
Analysis 
Options 
Holde rs 
ShOW•_ LBt 
for January 21.2022 
Strike v Last Price 
Option Lookup 
Cm nge 
AFL220121cooorsooo 
AFL 2201211200070000 
AFL 220121C0006sooo 
Last Trade Date 
2021-03-24 9:30AM EDT 
2021-03-23 2:00PM EDT 
2021-03-26 2:28PM EDT 
Ask 
0.20 
0.40 
0,50 
Cha 
0.00 
000 
0.00 
Open 
7500 
70.00 
65.00 
0.15 
0.25 
0.45 
inability 
Vea 
23.68% 
2346% 
2039%

MindsetOption trade thinking:

That is, at the end of the year, if the price of AFL stock is above my $70 strike, then I can make money.

Should I purchase an AFL $70 strike call option that expires one year from today?

Now, million-dollar question, how much premium should I pay for AFL $70 strike call option contract?

AFL’s historically, moving maybe 22.7% per year on average. Can we expect AFL to move about same 20%?

$60 
16% 
$50 
68% 
16%
50.88-51.48 
Option urn e 832 
30.32-52.78 
Volu me: 
vwA2 
22M 
51.24 
30-Day IV: 
IV30 % Ran 
IV30 
22.802 
Subdued 
35.2 a 
Marke2 
P/E Ratim 
P/salu: 
P/800k value: 
Dividend: 18-May So.33 (Est.) 
Div Yield: 
Eam•ngs: 
2.6% 
28-Apr (Est.)

I can see, that the $70 strike call option is probably not worth much. In (OPM) Option Pricing Model likelihood of price moving to $70 is only 16% that is, chances of profit are small.

I can see from IV of 20%, that probability price move above $60 is 16%. What is the probability of price moving from $50 to $70? An eyeball rough guess, is about 8%. This probability of moving is 2X the normal $10 move is apparently, even lower, than crossing $60 price level by next year.

IF. PROBABILITY OF ABOVE 
THEN. WHAT IS THE PROBABILITY OF MOVING ABOVE 
20% IV MEANS 
$40 TO SO MOVE 
16% 
50 
68% 
CURRENT PRICE $50 
OOS 
$60 
$70

My decision to reject this trade idea: Consider this trade a lottery ticket!

This option contract costs $0.25 and probability of success is 8%. Can I go ahead and say, “this is less of trade and more a gamble?” Hallmark of a lottery ticket is cheap price and probability of winning, very low.

Now let’s see another example, but this time high volatility is crazy high! I took this example from underlying stock CDTX, on Friday April 1,2021 from Yahoo as below:

underlying stock: Cidara Therapeutics Inc. (CDTX) listed at Nasdaq GM

Price per share: $2.70

Option play: September 17, 2021 $7.50 call strike costing %0.35 with IV 190%

Sector: Healthcare

Industry: Biotechnology

Implied Volatility (IV) trade: scenario high volatility ranking

This stock is a small biotechnology company, moving as much as 180% per year. Therefore, market might expect the same type of volatility in the future.  The expected range over the next year is $5.13 up or down.

That means there is a 68% chance the stock trades between -$2.43 ($0.0) and $7.83 before its expiration on September 17,2021. There is high probability that CDTX stock has potential to move In the money at expiration.

Cidara Therapeutics, Inc. (CDTX) 
NasdaqGM - NasdaqGM Real Time Price. Currency in USD 
2.7000 
+0.0400 (+1.50%) 
At close: April 1 4:00PM EDT 
Summary 
Previous Close 
Open 
Bid 
Ask 
Day's Range 
52 Week Range 
Volume 
Avg. Volume 
Chart Conversations 
Statistics 
Add to watchlist 
Historical Data 
129.716M 
1.47 
N/A 
-1.8020 
Feb. 25, 2021 
N/A (N/A) 
6.83 
Profile 
ID 
Jam 4, 21 
Financials 
Analysis 
YTD 
Options 
Max 
Holders 
2.6600 
2.6600 
2.7300 x 3200 
2.7300 x 900 
2.6100 2.7700 
1.8200 - 4.4500 
689,039 
917,169 
Market Cap 
Beta (5Y 
Monthly) 
PE Ratio (TTM) 
EPS (TTM) 
Earnings Date 
Forward 
Dividend a Yield 
Ex-Dividend Date 
ly Target Est 
1M 
6M 
Sustainability 
Full screen 
3.4000 
2.8667 
2.3333 
1.8000 
Feb. 16, 21 
Trade prices are not sourced from all markets
CDTX, Stock related information
Cidara Therapeutics, Inc. (CDTX) 
NasdaqGM - NasdaqGM Real Time Price Currency in USD 
2.7000 
+0.0400 (+1.50%) 
Add to watchlist 
At close: April 1 4:00PM EDT 
Summary Chart Conversations 
Statistics 
Historical Data 
Profile 
Financials 
Analysis 
Options 
Holders 
Sustainability 
In The Money 
Show: 
Calls for September 17, 2021 
List 
Straddle 
Strike A Last Price 
2.50 
0.95 
5.00 
0.40 
7.50 
0.35 
Option Lookup 
Contract Name 
CDTX210917C00002500 
CDTX210917C00005000 
CDTX210917C00007500 
917,169 Est 
Last Trade Date 
2021-04-01 3:23PM EDT 
2021-03-29 9:31AM EDT 
2021-03-24 3:58PM EDT 
Bid 
0.85 
0.30 
0.30 
Ask 
1.25 
1.10 
1.00 
Change 
*0.10 
0.00 
0.00 
% Change 
*11.76% 
Volume 
10 
Open Interest 
91 
533 
60 
Implied Volatility 
139.65% 
166.02% 
193.36% 
Avg.
CDTD, Option chain information, we are looking at Sept 17,2021 $7.50 strike

If the stock is expected to swing wildly in future than the premium value of puss and calls options, would be higher, because traders expect a higher chance of making money

rule-of-thunbRule of thumb 2#: Relationship between implied volatility and an option’s price (other things being equal) is as under:

(1) When implied volatility or market expectations increase, then option’s premium price also increases.

(2) When implied volatility or market expectations decrease, then option’s price decreases.

Rule of thumb#3: When selling a PUT look at the delta value, which corresponds roughly with the OTM probability at expiration. For example, If you pick the strike at 15 Delta, then your probability of being OTM is 85%

 3. Qualified Watchlist: Narrow down potential trade ideas (targets).

Sector Analysis for market assessment

GoalIdentify the best-performing underlying’s/stocks in outperforming or underperforming sectors.

Market Analysis

I start with generic my watchlist and filter that though global financial situation, sector wise analysis, broad markets, specific sectors and VIX then drill down to stocks and underlying’s within a sector using chart, fundamental, macroeconomic and technical analysis.

I like to use this top-down analysis approach, starting with a quick look at the ‘broad market segments’ performance, then sequentially drill down to ‘sector analyses for granular level of the markets. I narrow down what are the current session’s high-performing and worst-performing sectors. There is sector-rotation approach too, used by some traders.

Step one, is find the hottest sectors in today’s markets, then step two: to find top and bottom ten to fifteen trade candidates to build or populate my watchlists. Did you notice I have multiple watchlists!

Sector analysis examples from stockchart.com and barcharts.comBloomberg also has very clean sector-analysis page.

00 
INTREST RATES 
COMM oomEs 
MIII 
INCOME opn0NS
My six asset classes that I trade
These 11 sectors are key to watch for opportunities

My generic watchlist of underlying assets, that are potential trade candidates for option trading positions. I will focus on eight asset classes, that is defined my Strategic Mindset. Sector’s trading gain exposure to a specific area of the economy, for example the ‘oil sector’ and trader get a basket of related stocks, from the same index and industry. Trader can also go long or short on the sector as a whole without buying and selling companies’ individual shares.

The key to the ‘Sector Analysis’ is check on macro economy indicators and spot opportunities in a specific industry – opposed to a specific stock or index.

I have added Crypto currencies this year, after much debating. Previously, I did not touch Cryptos because trading community I follow, does not trade it, my background is economics and cryptos are created out of thin-air with no anchoring with any central bank or GDP. Lastly, cryptos are way too volatile for my appetite.

My trading platform does not allow me trade options on Cryptos (yet).

Baseline Assertion 
of m v of market analysis 
1. Bullish 
2, Bearish 
3. Volatile 
4.
Baseline Assertion

Baseline Assertion depends on analysis of the current situation to create a ‘Target Qualified watchlist’ which we narrow down to find potential trading ideas. These potential trading ideas guides are considered for Tactical selection to fit appropriate option strategy. Strategic Mindset way of market analysis is one the ‘Baseline Assertion’ to take, on underlying asset or the market from four categories:

Depending upon my baseline assumption of being bullish, bearish, volatile or neutral, I like to filter my watchlist for potential trade ideas based on market action, volatility, earnings, and income-based pre planned strategies.

 4. QA- Quality Control

Market-analysis results in my market-view and ‘Qualified Watchlist’ that facilitate most of trading decisions like:

  1. To analyze potential option trade positions
  2. Appropriate bias for the current market.
  3. Baseline assertions from market-view
  4. Qualifying potential trade ideas before finalizing them.
  5. Analyzing all potential Trade ideas through Probability, assess the potential risk, reward, and pricing scenarios of a trade before deciding to take a trade

Quality control is a “elimination Process of qualified watchlist” that will result in justification for fila trade candidates.

Why I decided to trade or reject an underlying asset.

Quality Control: Justification to accept or reject a trade idee!

 5. TACTICAL DEPLOYMENT: my action plan

After my ‘Qualified Watchlist’ is narrowed down with ‘Quality control’ parameters, I end up having final list of trade candidates. Here, I Identify ‘my action plan’ from the ‘Options Strategies Toolbox’. It is doing, detailed and step by step part telling me ‘How’. You have to build your own detailed decision-making process tree.

MindsetPicking up a most appropriate option strategy is rather a “process of elimination” than selection process. Tactics Tool box, helps me to shortlist most appropriate option strategy from my 20 strategies to deploy for desired position that I am planning to opening.

Many option traders deploy more than 30 strategies, but I am contended with the 20 options strategies in my tool box. How many ‘options strategies’ you have mastered and use in your options trading?

Example of tactical tool box with 5 strategies:

Objective Baseline assertion(Tactics) Strategy Description
Income generation Neutral to bullish Covered Call Sell a call against an existing stock position 
Income generation Neutral to bullish Cash-Secured Equity PutSell a put, secured by cash set aside in case of assignment
Hedging  Neutral to bearish Protective PutBuy a put on an existing stock position

Speculation  
Either direction StraddleBuy a call and a put at the same strike 
Speculation  Either direction Debit SpreadBuy and sell a call at the same time, or buy and sell a put at the same time 

Build your toolbox of strategies like shown in this table

Risk-management6. Tactical Employment: RISK MANAGEMENT PLAN

My Pre-Trade Planning, KPIs, Performance and answer to an important question, “What I’m getting into with this particular trade?”

Tactical deployment is the set up for our option position. It outlines tactical what we are getting into, when we enter a trade.

I think of tactical deployment as performance monitoring of trade parameters, the good, the bad and the ugly. My trade can fall into any of these parameters.

Risk Management

Risk management is integrated into the option trading plan, as risk parameters are defined below:

  1. I know exactly when to get out
  2. how much is my maximum acceptable loss is for the trade
  3. How I will exit or adjust the trade position to save profits or limit losses.

Defining these parameters beforehand will prevent me from getting into mental-landmines (emotions such as greed, fear, attachment to a trade etc.) to take bad decision making.

7. Trade Management plan

In the following illustration, I am using ‘The Rocket Ship Launch’ analogy to compare to each of my trade launch scenarios. I am using ten steps ‘count-down’ in my every trade. Step 0 is kind of semi-permanent, I update annually, as my situation changes. Once the trade is executed: trade management kicks in.

Meteorite threats to success of my trade, are occurrences that can negatively affect our position during the life cycle of the trade. An example of a threat to our success: We were bullish and then implied volatility increased unexpectedly due to a negative economic report.

Trade plan analogy: ‘launching rocket’ to be send to ‘planet profit’

Contingency planning is simply having a basic game plan if our trade is not going per design: do we roll up, roll down or get out? Our Eject Criteria are our ―no questions asked, I will just get out of this trade.

In my ‘Vertical Bull Put Spread’ from Option Strategy Toolbox; exit criteria includes rule: “Exit this Vertical spread in any of following condition occurs first”:

  1. Exit with profit of 50% (of width of spread) maximum gain is achieved.
  2. Exit with lose of 100% (of width of spread) maximum gain.
  3. Exit with 21 DTE, or roll into next month.

 8. Exit Plan

The Exit Plan is how we are going to get out of a trade. We never get into a fight unless we know exactly how we intend to exit. Factors for planning an exit include: a sound reason for exit, layout our closing trade set up, whether we are exiting prior to expiration or taking it all the way to expiration.

It is important to know exactly how you are going to exit a trade before the volatility of the markets get the better of you.

Passive Exit when:

1. my initial stop-loss is hit

2. When my target-profit is hit

3. When trade parameters no longer valid

Active Exit when:

4. My trailing-stop is hit

5. When trade parameters no longer valid

6. Volatility based Exit approach using (ATR)

7.Roll into next contract

That’s my plan and mindset for trading option. Have you noticed; this is nothing but a logical sequence to steps trade options?

You can take this idea make your own plan that suits your needs, how find best candidates, verify them, what suitable strategy to use , then how will you enter and exit. Don’t trade without plan.