Investing Stages

When I started investing this spring, I already had my financial house with being debt free and plenty of savings. I needed to thaw out my savings from the permafrost of low bank interest rates.  But where to start and how would I go about it? 

This above diagram tries to represent the main stages I am using in establishing my investment portfolio.   You can see this is not a waterfall sequential process but a continuous iterative one that should continue for the rest of my life.   From first hand experience, I find managing one's raw emotions to be the most critical factor to this entire enterprise as Benjamin Graham had advised so long ago.  The stages are divided into the following:
  1. Financial Goals - A mix of concrete and soft goals
    • Concrete goals affixed to dollar amounts and time periods that aid you in achieving your life goals.
    • Softer goals such as learning about different aspects of the market or plans to transition into different strategies
  2. Learning - Attaining a proficient level of financial literacy is probably one of most useful of life skills.  However one can learn only so much via passive book/video/media/talk learning.  The "real tuition" as every investor learns is paid with cash- every market loss will teach you something in a way that book learning cannot.   Investment knowledge was my biggest gap and I spent months learning about different investment strategies. Even if I decided to hand over management to a fiduciary, I needed to know enough to evaluate my advisor. 
  3. Planning - Converting your knowledge, hopes and dreams into an actionable plan.
  4. Execution -  More than account management and making actual trades, this is where money is made and lost.  All the knowledge and planning is useless if you don't act.  Even painstaking weeks and months of planning can go out the window when your emotions take over and you impulsively buy or sell.
  5. Monitoring/Reviewing/Adjusting - While investing is an ongoing process, more studies suggest less shuffling of your investments lead to better returns. Fidelity found portfolios with the highest returns belonged to either deceased or people who have forgotten about the account. 

I filled out the basic subcomponents below with the specific questions I asked myself to formulate this plan below this diagram.


Before I do anything serious and not so serious like cheese selection, I like to brainstorm with questions to make a path for a plan of action. I'll post my answers in a separate series of posts.

1. Drawing Up Financial Goals

  • What do I need money for?
  • How much money do I need for the remaining decades of my life?
    • What's my base minimum expenditure?  
    • Does this account for inflation?
    • What are some unexpected expenses I might need to prepare for?
    • How large should be my cash emergency fund?
  • How does the financial goals support my life goals?
  • What percentage profit do I need to make every year?
  • How much capital am I willing to risk?
    • How much money can I afford to lose?
    • How much money am I willing to lose?
  • What's my time horizon? When do I need the base capital?
  • Are my goals realistic?

2. Understanding One's Self

  • How much time and energy am I willing to expend on investing?
  • Am I truly willing to do the due diligence to DIY invest? 
  • Can I handle the volatility of the current market? Do I have the intestinal fortitude to stick to a consistent rational process in the face of a declining market?
  • Is it better to find a fiduciary to manage my money?
  • What are my biases, weaknesses about investing?
  • What are my fears about money?
  • How can I counter my weaknesses?

3. Learning the Basics of Finances, Investing and Risk Management

These are the meta questions about learning:
  • What do I need to know?
  • How long will it take to learn the basics?  
  • Where do I start?
  • Who or what can help me gain the necessary knowledge?
  • What can be learned from books, web, other static media vs other dynamic means?
  • How can I learn through doing?  How can I simulate investing/trades?
  • How will I know I've learned correctly or deeply enough?
  • What tools can I use?

4. Planning

  • What financial institution should I use for my investing account?
    • What factors should determine which institution to use?
  • What type of accounts(taxable/non-taxable) should I use?
  • What asset allocation is ideal for me?  
    • How can I backtest this plan?
    • What are the pitfalls of backtesting?
  • What investment strategies will I use?
  • Where can I park money safely with high liquidity with the highest possible return?
  • What vehicles/wrapper will I use to full fill the asset allocation?
  • What specific fund or stock will I use?
    • What metrics will I use to judge investment worthiness of an asset?
    • How much money can I lose in the worst cases?
    • What will I do if X goes down 5%,10%,15%,20%,25%...
    • How will I limit a loss and how long will I wait?
    • Is the risk/reward ratio worth it?
    • How does this fit in with overall risks taken in the portfolio? 
  • How will I size and physically execute plan over what time period?  Will I use a lump sum or DCA?
  • What is my process to execute and manage risk?
    • What are my entry prices if any?
    • What is my exit plan?
  • Are there major events or global trends that may impact parts of my plan? 
  • Am I making the most of tax advantages with this plan?
  • What are the risks/weaknesses of this plan? 
  • Is this plan too complicated? 
    • Can I stick to this plan going forward
    • Can my partner understand and carry out this plan if I am not able to do so?

5. Execution 

  • Day-of trade questions
    • Am I well rested and fully alert to successfully execute this plan today? 
    • Is this the right time to buy/sell this asset? 
      • Are the key technical indicators favorable or at least non-favorable?
      • Are there any major world events this month that will impact this plan?
    • What order type, market/limit will I use? 
    • Will I place a protective stop loss order?

6. Monitoring/Refining/Adjusting Plan

  • What tools will I use to monitor and judge performance?
  • How and when will I know I am know my investment thesis is flawed and my plan needs adjustment?
  • How often will I check and make changes?



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