Sunday, August 16, 2026

Chapter Twelve: The Path of Radical Repentance

We encountered the idea of repentance early in the book with the parable of the cluttered house.  The householder, collecting one thing after another to impress others, awakens to a recognition of the emptiness of blind acquisition and decides to create a more authentic environment.  Repentance is always the result of awakening:  a powerful emotional awareness of having somehow betrayed our potential.  It is this awakening that moves us beyond ego, renewing our perspectives and our lives, sometimes quite radically.  Let's take a look at how that happens and what that might mean for our trading.  

Sleep and Waking

Gurdjieff, quoted in the previous chapter, viewed the fundamental human challenge as being stuck in slumber.  Moving from thought to thought, activity to activity, we operate as if we were on auto-pilot.  We can speak and act without thinking, reacting rather than truly acting.  Many of the challenges we normally associate with trading psychology--from overtrading to failure to follow trading plans--occur because we are not fully conscious:  we operate in a reactive slumber.  How often have we said, after an errant trade (or something we do to hurt another person),  "What was I thinking?  How could I have done that?"  When we are asleep, Gurdjieff pointed out, we no longer fully consciously guide our activities.



Have you experienced repetitive dreams where the same scenes recur night after night?  Such dreams are important, because they capture a felt reality.  They recur for a reason.

One dream sequence I have encountered over a period of years involves driving a car and realizing that I can no longer see where I am going.  Sometimes I am behind the wheel and have lost my vision.  Sometimes it's as if I'm operating the car by remote control and it has gotten too far ahead of me, out of my sight.  My concern is always that I will crash.  Sometimes, particularly in the remote control dreams, the car does crash.  As I look at the damage of the wreck, I feel tremendous regret.

What's going on here?

When we are fully conscious, we are behind the wheel, determining our course and actively navigating the way.  That is what it means, spiritually, to be awake:  we are self-aware; we are guiding our own life path.

In remote-control mode, we are asleep; we are flying blind.  That is how we live life on automatic pilot:  eating mindlessly, flitting from one self-talk to another, reacting to the next situation that presents itself.  

The dream is about losing control of life, but it is also about regret and repentance.  Surveying the wrecked car, I feel sorry.  I know that I have caused damage.  It is this awakening to the damage we create during un-consciousness that lies at the heart of repentance.


A common theme across spiritual traditions is that we are both physical beings and spiritual beings.  We are souls within bodies.  When we become immersed in our bodies--the material world--we fall asleep in the soul sense.  As in my dream, we become blinded to our larger life path.  Many of life's crashes are the result of our loss of vision.  Through our actions, we seek gain in the world, only to lose our souls.

Renewal occurs, not simply by renouncing the material world, but by placing the physical in the control of the spiritual.  The soul now drives the car, taking us to meaningful destinations.  Many times, as for the householder in our earlier allegory, it takes a painful awakening to turn control of the car over to the soul.  It is the pain of recognizing that one is at a dead end that inspires the search for a new path.

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Trading With the Soul, Not the Ego

Isn't it interesting that we sometimes refer to creative insights as "divine inspiration"?  There is indeed something other-worldly in those flashes of insight and vision.  Anyone who has traded markets knows the difference between forcing a trade--trying to create an opportunity--versus having an opportunity come to us.  Many traders that I work with emphasize the importance of patience.  They know that the best ideas don't come from the need to trade.  They follow from "divine inspiration".

My greatest success as a trader has occurred on short (intraday) time frames, when I can see--and feel--the shifts in flows among buyers and sellers.  The very same skills that enable me to follow the nuances of a conversation during a therapy session sensitize me to the "communications" of markets.  That is a real-time skill:  the ability to detect subtle changes and place them in a meaning-making context.  

At various times, however, I have tried to trade in other ways, and especially on longer time frames.  Often this has occurred for practical reasons:  my work as a psychologist has made it difficult to be in front of screens throughout market hours.  Too, the intraday focus has meant capitalizing on smaller moves and not necessarily participating in larger trends.  Those considerations have led me to move away from what I do best, invariably with poor results.

That is the car crash.  

When I have sought to make trading fit my life, I have placed my needs in the driver's seat.  Which means that the soul is no longer operating the vehicle.  I'm in remote control mode--and my trading results show it.

Conversely, the mindset that has worked best for my trading is amazingly similar to the mindset that I am in when I am engaged in prayer or meditation.  There is no ego/internal chatter, no nagging demands or needs.  The state is one of openness, but also one of connection to something larger.  It is not unusual for me to experience life insights following prayer, immersive study, and the contemplation of nature.  It is also not unusual to experience "divine inspirations" in trading, where ideas fall into place and markets suddenly make sense.

Once, following a particularly large loss that resulted from experimenting with longer-term trading, I found myself saying out loud, "I'm sorry."  I felt deep remorse--just like in the dream of the wrecked car.  I had lost all feel for the market, but even more, I had betrayed my greatest strength.  From that moment, I realigned my trading and followed a much more structured and rigorous form of the short-term trading that had been successful for me.  I let go of the desire to "catch the big moves".  Focusing on what I do best, I felt an inner satisfaction far more powerful than any happiness following a winning trade.

This is the power of repentance:  the awakening to who we really are and what we truly need to do to succeed--in all areas of life.  If I were to impose my needs and feelings onto a therapy client and impair their ability to learn and grow, I would feel tremendous remorse.  That same remorse can power important changes in our trading.
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Let's take a simple example:  drinking alcohol.  We can use alcohol to get drunk, abandon responsibility, and dull our consciousness.  That same alcohol, consumed as part of a wedding ceremony or religious service, can be part of a celebration that inspires us and elevates our spirit.  Similarly, food can be consumed as part of gluttony, harming our health, or it can be part of a meaningful, shared experience and part of living a healthy life.  And money?  It can distort our values and priorities, or it can become a vehicle for noble purposes.  The need to make money can distort my processing of market information, creating losses and pain.  That same money, used as a resource to support my family and contribute to worthy causes, becomes a tool for fulfillment.



When we place the material world in the service of spiritual priorities, we cultivate meaning and purpose.  That is an essential part of renewal.  We are radically renewed when even the most mundane aspects of our lives--from what we drink and eat to how we spend time with family and friends--affirm who we really are.  Each of us has a finite number of talents and opportunities, as Rabbi Menachem Mendel Schneerson (the Rebbe in the Chabad tradition) points out.  Those define our mission in life.  Will we live in a manner true to this mission or suffer the regrets of a life lived in vain? 

As mentioned earlier, the Hebrew word for repentance (teshuvah) also means return.  When we repent, we recognize that we have turned from our life's mission and now need to re-turn.  Across religious traditions, every repentance is a two-fold process:  a recognition of sin and a return to salvation.

An Exercise in Repentance

I recently read a book that addressed the issue of spiritual awakening.  The author suggested a visualization exercise that was especially powerful.  The exercise involved imagining, in vivid detail, being sick and in the hospital.  Your loved ones gather around you and reassure you that all will be well.  You begin to feel better and you look forward to getting out and getting back to your normal life.

Then a setback occurs.  You experience a heart attack.  The physicians are alerted and go into action.  Your family members continue to reassure you, but this feels different.  There is a crushing pressure on your chest and you cannot speak.  You realize that you are dying, that you might not return to normal life--ever.  

You look at the people you love and you realize how much you will miss them.  You think of all the things you wanted to do in life that have passed you by.  You think how wonderful it would be if you could just have another day, another week or month of life.  How special that would be!  You would appreciate every breath knowing now how it feels to scarcely be able to breathe.

But none of that is to be.  Your body is shutting down.  All you can do is shed tears over promise unfulfilled, at the thought of losing everything you have in this world.  Those things that consumed your attention--that promotion you wanted at work, that missed trade, that annoying neighbor--all seem so unimportant now.  How could you have wasted so much of your life on such silliness?

This is more than regret.  It is despair.  It is the realization that you haven't just been doing things wrong; you've been doing the wrong things.  That is what "hitting bottom" is all about for the alcoholic.  

Now visualize that somehow, some way, the physicians bring your heart back to life.  You receive bypass surgery and now, amazingly, you have your life back.  It would be difficult to return to life as usual.  Your perspective would be turned upside down.  Every moment would be precious.  You would be grateful for every sunrise.

That is repentance and the radical change it can bring.  

It begins with consequences, proceeds to pain and regret, and then infuses us with the need, desire, and determination to turn life around.  From the depths of despair, we can reach a point of profound gratitude and transformation.  Someone who has truly repented is no longer the same old person.  They are re-newed.



Let's contrast this dynamic of repentance with what typically happens when traders lose money.  The trader who overtrades and makes silly, impulsive trades is like the person who makes mistakes in life, hurting others, losing opportunities, and wasting time (and life) on petty grievances and superficial priorities.  That can only happen if we believe there will always be a tomorrow.  When we assume immortality, there is never an urgency to change.  The trader who loses money writes in a journal and states an intention to make an improvement, but there is no pain, no deep regret, no urgency behind the need for change.  Without the sense of "sin"--without a painful awareness of the true consequences of our behavior--there is no drive for repentance.
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Taking Each Day as a Lifetime

If we really did believe we could die at any time--and that time could come soon--each day would have a very special quality.  Every morning, upon awakening, we would be thankful for another day in this beautiful world, with all the activities and people that matter to us.  With such a perspective, it would be difficult to waste precious time on trivial worries and concerns.

But, in fact, we can adopt such a perspective.

Suppose we approach each day as a separate lifetime.  We are born as the sun rises, spend a youthful morning on the activities and challenges that matter most to us; connect in the maturity of the afternoon with special people, building what we had started early in the day; and slow down in the evening, celebrating our accomplishments and what we've developed in our relationships.  Then we finish our lifetime peacefully in bed, only to be reincarnated the next morning to live life afresh.

It's a radically different perspective.  Try to place yourself in that mindset.  As I write, it's 2:46 PM on a Friday.  I'm more than halfway through today's lifetime.  How do I want to use the rest of my "life"?  What do I want to experience and accomplish before ending my time?  Every day becomes much more meaningful, much more purposeful--much more consciously lived--if it's approached as our last day, our only day.

Knowing that time is finite pushes us to prioritize, to make the most of what we have.  Waking each morning to a fresh life starts us in a mode of gratitude and excitement.  If we are born again every day, it's tough for life to become boring and routine.
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But this is where the trader's situation may differ from that of the alcoholic or the person who has committed a grievous crime.  If a trader makes poor decisions and fails to live up to his or her intentions, there aren't necessarily huge consequences.  That is why many traders don't sincerely seek changes until they have done real damage to their accounts, perhaps also jeopardizing their finances and the security of their families.  The average person is simply not moved to repentance until they have "hit bottom".  At that point, change becomes a necessity not merely a good intention.

Is it possible to reach a point of radical repentance without blowing up as a trader or causing horrible pain to self or others?  I think there is, but it requires a radical shift of mindset.  If you can make that shift, however, you literally can live your life on a wholly different plane.  

Let's delve into this.

Achieving a New Frame of Reference

We think of repentance as a response to sin.  We do something wrong and we atone.  Repentance, as in my dream, is all about saying, "I'm sorry".  Think about the Catholic person who performs confession each week; the Muslim who fasts and purifies themselves each month of Ramadan; the Jew who fasts and asks for forgiveness each year at the High Holy Days.  Think of the mindset of the Christian who is willing to sacrifice the ego to become reborn with salvation.  Across traditions, the notion of sin is closely aligned with a re-connection to the Divine.   

Suppose, however, you no longer operated from the frame of reference that juxtaposed your "good" self and your "not-good" self.  Suppose your anchor was your great self:  the human being you are meant to be?  Every single day, your challenge, and indeed your mission, is to be your best self, the self you were born to be, the self your Creator meant you to be.  

That is a total and complete game changer.

From this new frame of reference, "sin" is being ordinary, going along with the drift of life without tapping into all of your values, talents, skills, and dreams.  A day lived on auto-pilot is a complete betrayal of who you are and what you can become.  Every day, you are meant to do great things:  learn new, special things; do wonderful things for others; develop yourself in ways that will enrich your life and that of others.  When you feel the specialness of what you're meant to do and who you're meant to be, the idea of living--and trading--on autopilot is unacceptable.  It is such a betrayal that you will do everything in your power to not waste another moment of your potential.


Let's take an example from trading:

You make money at one point in time--one morning or one month--only to become overconfident and give back all the profits and then some.  How do you feel?

Most of us, if we have a reasonable level of achievement motivation and competitive drive, will feel frustrated.  It's one thing to be wrong in markets and lose money--that happens to all of us.  But to succeed, lose focus, become overconfident, and fritter away the profits is something different.

In the big picture, it may feel as though there is nothing to worry about.  We can always come back and make the money back.  Yes, we're frustrated, but our job is to shrug that off and get back to the trading that made us money.  It's an annoyance, but not a crisis.

Many of the successful traders I work with don't easily shrug off those losses.  They are haunted by the feeling that they should have performed better.  Even when they make money, they may say to me, "I underperformed."  They feel genuine remorse over that underperformance.  It doesn't take a blowup to trigger a deep self-appraisal and reform; all it takes is failing to live up to their potential.

Why is this?

It's because they start with the understanding that they are meant to achieve extra-ordinary things.  They don't accept the average.  They expect that they are better than that, and it is that premise that keeps them inspired to live up to their potential.  They hit a point of repentance, not when they blow up, but when they fail to act greatly.

To be sure, this can have a dark side.  Perfectionism can place us in a mode where we feel as though we perpetually fall short.  Radical repentance only works when it is accompanied by radical celebration and appreciation.  In other words, when we make strides in living up to our potential, that can become tremendously inspiring.  We repent precisely because we can do so much more.  We will never be perfect--certainly not in the trading world!--but we can find fulfillment in becoming better and making the most of each day.  I question any trading journal that expresses no joy and no despair.  The paths of joy and repentance are closely intertwined.  Despair brings us the commitment to be true to ourselves; living authentically brings us gratitude and joy.  Trading can either be a means for betraying ourselves or a way of fulfilling the best of ourselves.  



Does our trading draw upon and expand our distinctive strengths, making us better human beings?  If so, those are the greatest profits of all.  If not, that is a great starting point for repentance.

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 Resources

What if trading is the way that you are betraying your gift of life?  What if your talents and opportunities lie elsewhere, hidden by the ego thrills of risk/reward and profits?  I met with a trader who found his greatest success helping others and staying connected to markets for investment purposes.  Even when he was making money day trading, he felt a sense of being incomplete and a vague sense of guilt.  When he reflected on the things that made him happiest and most fulfilled in life, they were all people things.  As this article suggests, our optimal path in life is one that actualizes our potentials.

If we examine the actual practices of spiritual traditions, we find that there are daily and weekly processes designed to achieve repentance.  These occur in special settings, often with distinct rituals.  Think of the Islamic practitioner praying on a special rug, bent over, with the forehead touching the floor.  Think of the piercing sound of the ram's horn (shofar) at Yom Kippur, the day of repentance for Jews.  Repentance is not a one-time, occasional sense of "I'm sorry."  It's a soul-full immersion.  Here's an interesting article on de-cluttering one's life with a mindset of repentance.  The article cites the native Hawaiian tradition of Ho'oponopono, which creates a mantra out of the ideas of "I am sorry; Please forgive me; Thank you; I love you".  It is difficult to act with arrogance and selfishness when we have internalized such a mantra.

In the Hindu tradition, sin is viewed as the result of "desire-ridden actions."  It is interesting to think of trading without desire.  As a psychologist, I am there to listen to my client, make sense of what they are saying, and then offer a framework that can help them process their experience differently and constructively.  The key to helping is listening.  The psychologist cannot be "desire-ridden".  A valuable way to think about trading would be to free one's following of markets from any element of desire and need.  When we are in the ego mode of making market calls, we lead in our dance with markets.  When we rid ourselves of desire, we are free to let the market lead in the dance.  We respond to the motions of the market; we don't expect the market to follow our lead.

Bodhicitta has been described as the development of loving kindness toward others.  The Lama Yeshe from Nepal pointed out that, "If you want to be really, really happy, it's not enough to space out in meditation...bodhicitta energy is alchemical.  It transforms all your ordinary actions of body, speech, and mind--your entire life into positivity and benefit for others."  In his book Training the Mind and Cultivating Loving-Kindness, Chogyam Trungpa describes a twofold process in which, upon arising and again upon going to bed, one vows to "develop a sense of gentleness" toward self and others (p. 192).  The idea is to purify self-centered thoughts that create suffering.  This is repentance in a different sense than we normally think of in the monotheistic religious traditions.  Bodhicitta, Trungpa notes, is a checking of our self-absorption so that we can reach higher levels of acceptance of self and others.  "...The best way to open yourself up," he notes, "is to make friends with yourself and with others" (p. 11).  In all forms of repentance, however, we end up embracing our suffering and being transformed by it.  As Thich Nhat Hanh points out, "Without suffering, you cannot grow.  Without suffering, you cannot get the peace and joy you deserve...Go to the Buddha, sit with him, and show him your pain.  He will look at you with loving-kindness, compassion, and mindfulness, and show you ways to embrace your suffering...The Buddha called suffering a Holy Truth, because your suffering has the capacity of showing us the path to liberation" (p. 121).  

What would a trading process look like that is grounded in self-assessment, repentance, and efforts to "make friends with" markets?  The key idea from Nhat Hanh is that transformation can follow from embracing our suffering.  At some level, what we are repenting for is mindlessness.  Trading with such awareness becomes a path to bodhicitta.
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      Key Takeaways - Anguish can be one of the most powerful catalysts for change.  When we clearly perceive who we are and what we can become, we cannot settle for less:  the average is not good enough.  Energized by the deep sense of repentance, we make fresh efforts and are no longer willing to accept the status quo.  All repentance is a kind of return, from the routine, normal, and everyday to the meaningful and inspiring.  Our challenge is to trade mindfully and consciously, not on auto-pilot.  It is when we lose our self-awareness that we can summon the horror of our self-betrayal and redouble our efforts to stay connected to the hero within.

Practical Exercise - What if, after every trading day, you found one or two things to sincerely and deeply repent for?  Making repentance part of a trading process would mean that you would have to stay emotionally connected to the trader--and person--you're meant to be.  It may well be that goal-setting is a mere paper exercise if it is not undertaken in the spirit of repentance.  

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1 comment:

  1. That's interesting (teshuvah) also means return. I keep a swatch with the Ho'oponopono on it tacked to the bookcase next to my trading desk. When you use it throughout the day (even outside of trading), you can feel your energy return to a more balanced state. I love the paragraph on approaching each day as a separate lifetime. Thing is, you really have to create a shift in perception to live from that space, but once you see it you almost cannot unsee it. Just a matter of continually returning to that consciousness until it becomes your reality. Thanks Dr. B!

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