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Usually the problem is something to do with self-worth, like feeling you deserve the money (which is a lot to do with if you accept and love yourself, if you received love as a child or this love was absent or conditional), or to do with money itself, if you think its scarce or evil etc etc. As you say he is having trouble following through with the method which indicates some sort of subconscious sabotage. if you want to get to specific causes hypnotherapy is a good idea because it puts the mind into a deep state of relaxation where the conscious is shut off, and where memory recall is made a lot easier (see George's post, he also gives a few more solutions), usually reliving that cause will eliminate the issue. I don't really think its him not trusting a younger mentor. Our beliefs will fractal out into everything we do pretty much, so general negative beliefs about money will mean you will have trouble with it in your life, regardless of what specific actions or situation you get into to solve your financial problems (you have to get your thinking right before you can take effective action, as action stems first from thought, and our habitual thinking is largely based on subconscious beliefs). The methods I suggested are focused on embedding new positive beliefs into the subconscious, overwriting older "programs" as you can't hold contradictory beliefs.
Understanding yourself is just as important as understanding markets.
I pondered my original hypothesis that he was having trouble with following my lead and decided you are probably correct. Its not an age gap, something else is blocking him. Chrometophobia? is not an issue here (he has the same view as I, money is just the concentrated time of others ) I think however fear of error itself is close to the mark and needs some time.
I had a good think about it I also traced through his trades. I have decided to do an eye-tracker & biofeedback survey to evaluate how he is processing the information in front of him. I suspect a part of his issue is he is not parsing the data efficiently in his mind. I'll see if the key information layout can be improved, it is very often counter intuitive. His career experience had lead him to work in a very specific manner. We need to work with his existing neuron training, not fight it.
I think you are aside from the main point in reframing your boat of beliefs to boat of a system with an edge. Many expert traders have posted that they can teach a proven profitable system to a group and they will lose money with it. If you have a proven profitable system then you can hire traders teach them and they will print money for you and you will soon own most of the world's money.
On the other hand if you have you have a sound supportive belief boat - you believe you will succeed, you deserve to succeed, success WILL happen it is INEVITABLE, then you will soon bring to you the resources you need (readings, actions, teachings etc) that are needed and do the work needed, to fulfill your belief of ASSURED VICTORY. In short you will build a solid system with a clear edge because it is needed for your success. Your Boat of Successful Beliefs will cause you to create a system with an edge.
A system with a proven edge without a Strong Boat of Beliefs
is like having a Massororti (sp?) and not knowing how to drive or even that being able to drive is a feat possible for you.
In reading your post I was wondering why have you not asked him about the dilemma? -that is you saying
"What I see is ..... solid system ... appear to not following .... don't come to ask when - roadblocks.
How do you see the situation?
How can I help you better?
From your viewpoint are the system and steps clear?
Do you see blocks to implementing the system? If yes what do you see as blocks?
That is don't assume xyz is a block (e.g age differential etc) ask him.
He would be used to learning a series of procedures that is what air traffic controller is all about.
I doubt its "old-lion". Actually assuming that may be a block in your truly listening to him. If it were old-lion he would not have agreed to try your system.
Have you actually typed out the steps of your "system"?
This is important. If you can't clearly type them out perhaps you are trading things that you aren't aware of. You may think you have described it accurately but haven't. When he asked about situations did you reply:
"It's so simple you do this and this."
If you haven't typed out your system but only described it in a verbal and fragmented way with examples then you need to be honest with yourself. Why have you not bothered?
I think your student has proven from his career, he has the ability to follow clear procedures and to follow them under pressure and exercise good judgement.
Because "you knock it out of the park" - is not proof you have a clear solid system.
We all agree on this point. But a system with proven edge will not stop the "boat" from sinking when you have subconscious beliefs that are blocking you. If you cant execute a system properly you cant extract its edge. You need both.
Understanding yourself is just as important as understanding markets.
Is the problem one of subconscious beliefs or is it a discipline problem.
Believing you are going to be successful won't make it necessarily so. Believing in your system or your systems edge may enable you to trade with the discipline necessary to make it successful.
"The days when I keep my gratitude higher than my expectations, I have really good days" RW Hubbard
Naturally having a system with an edge is a requirement. But is a second level requirement.
You must have the foundation of a house well-built and solid before erecting the structure. No one believes a house is complete with only a solid foundation.
However many people erect a structure, patch it, repair it and all for not. They fiddle and tweak endlessly without recognizing the root problem - they have no foundation and it is built on sand.
I wanted to highlight that if you have a strong belief foundation you will seek out the resources you need to build your system with the edge. You will read the right books and more importantly extract the key points. You will meet and engage with others who are positive and believe in success.
Many people can read a book on trading or a thread on a trading forum, perhaps understand on an intellectual level.
And only a few extract the key lesson and more importantly weave it into a knowing-understanding that strengthens and empowers their trading (and on trading system).