Planning and Re-Planning for Long-Term Success in Trading and Investing

Introduction: Regular planning and re-planning is the ONLY way to long-term success in trading and/or investing. Objective/Subjective review is a very important key to improvement.


There are periods of time when things go: very well, ok, and could have gone much better.

It is a good idea to objectively review one’s condition regularly, or at least at key intervals. By observing your results as if you were looking at someone else’s, you will tend to see things that your ego or emotions may have hidden.

Equally (or more) important is to subjectively assess your enjoyment of your financial approaches and how they may impact the other things you wish to do in your life.  It isn’t all about making money after all, but also your mental well-being and happiness.

Below we will summarize some considerations for assessing and making improvements in your trading life.


1 – Ideas to assess your situation:

Assess at regular intervals (Monthly, Quarterly, Yearly).

It is best to assess your situation from various directions.  Don’t wait for a “crisis”.  The end of year is a great time.

Always maintain a list or document with the activities you plan to do each day/week/month.

This will allow review and to not forget key things that are important to you.  Ideas and thoughts come and go, but the good ones, you don’t want to lose. It also is a great way to “see” your progress as it happens.

Start with interviewing yourself a bit by asking yourself the following questions — and don’t cheat yourself with the answers.  Be honest and thorough in your assessments. There are other questions you could ask yourself, but these are a big starting point.


2 – The Questions to ask yourself (primer-as how you initiate your own change can vary)

(The technique to do this is to write everything down and keep it handy. If you do not have your plans written down, you can’t change them.  If you don’t have your issues down, you can’t remember them, and if you don’t have your actions down, you can’t keep yourself accountable to execute them consistently.)


Q1 – Am I a better trader than I was (3 months) ago?  (Note: This has nothing to do with money results, but whether you are properly trading). This is a very important question, because your techniques should ALWAYS be getting better (independent of financial results), especially for the strategies that are most important to you.  You must do this for all strategies and techniques you are currently executing and planning on implementing.


  1. If “NO” – Make the list where you need improvement. Follow up this list by honestly assessing the “Why” you need improvement. We don’t need to get into that here – you know if you have been paying attention.
  2. Brainstorm and prioritize a list of what you are planning to improve. Follow each up with actions to address them. For example, what materials to review, what classes or instructions to take, etc. Brainstorming is a skill where you don’t filter before you dump out the ideas.  It may not be easy for some, but just put all the ideas out there,while being fully aware you will assess them for cost and practicality afterwards.  Then review the list and sort for what you can get to in the next period, and what you need to put off for whatever reason. The key is to not overwhelm yourself with too much change at once. KEEP THE FULL LIST.
  3. If you have a coach or trading/investment “Buddy” share this with them. Four eyes are sixteen times better than two when dealing with complex things – like your trading plans, strategies, and measurements.


Q2 – Am I happy with how things are going in my financial strategies? (NOTE: Assess and evaluate your financial expectations and results for each of your accounts and strategies first)


  1. If “NO” – First forgive yourself immediately and relax. Be honest with yourself and document all the issues you fell short on. Take the time to do this right. Engage all resources that you think can provide input to you on this for discussion of the issue, and/or possible actions and solutions.
  2. For each of the issues – create an action plan. If any action plan is not realistic, use that fact to possibly re-prioritize what you are doing.  It is always healthy to identify what has less chance of success to possibly cut it out of your efforts (and time spent) and focus on your best opportunity for success.
  3. Often, unrealistic expectations take a little work and internal reflection to surface to action. If you find one of those, don’t rush with the action and make sure you are in the right “place” mentally to change major direction or strategy.
  4. If you need to re-allocate your resources, this is where to do that.
  5. Ask yourself – do I need help or someone to review my plans with?


Q3 – Am I spending my desired amount of time trading and investing?


  1. It is very important for your health, life, and your success to have strategies and plans that fit your life needs beyond the keyboard.
  2. As you are making your trading strategic adjustments, always consider the impact regarding your time commitments for trading and personal life.
  3. Trading should be in the range of boring to fun, and make sure you are planning for that. Whichever it is, you should like what you are doing, and not see it as a burden, overly stressful, or otherwise distasteful.
  4. Oftentimes, these considerations will move traders from being day-traders to swing traders or vis-versa for time. Go to where you feel you need to be for the next period. If you have the trading stills, how you do it becomes less of an issue.


Conclusion: This article was intended to point out some general actions and techniques for tracking, reviewing, and improving your condition.   In no way is this a complete detailed list of what to do to improve. This list is here to offer key items that one may consider for regular review.  Look to any resources that may help you expand your efforts in these areas, and most importantly, do so regularly, to keep apprised of your situation and move forward with a positive attitude. 




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