How my spiritual confidence is born of pain & suffering

This is a long post I wrote this morning…so set aside 10-15 minutes to read it.

I have been sharing a lot of content that I’m sure many people feel is shamelessly self-promoting, arrogantly over-confident and an unreal farce for deep insecurity and unresolved shadow.

In this post, I will share many of the incredibly challenging experiences that enabled me to reach my current perch of unshakeable confidence.

Hopefully you will understand more about how the times of my greatest weakness, ultimately became the fuel for my greatest strength. And that my posts of strength rest on substantive foundations rather than air.

“The strongest steel is forged by the fires of hell. It is pounded and struck repeatedly before it’s plunged back into the molten fire. The fire gives it power and flexibility, and the blows give it strength. Those two things make the metal pliable and able to withstand every battle it’s called upon to fight.”

I have been through a lot of struggle in my life to get where I am today.

• I have struggled with social alienation, with both men and women, for most of my life.
• I have dealt with the intense Autoimmune illnesses of Leaky Gut, hyper-allergic-sensitivity to foods and Multiple Chemical Sensitivity.
• I have been through 4 episodes of Major Depression.
• I have been a part of many gut wrenching business failures, co-founder divorces and legal warfare.

My strength comes from the conquest of my adversity.

A) Social Alienation:

I have felt socially alienated for most of my life.

I didn’t have a close friend who I could truly discuss my true feelings about myself and the world until I was a sophomore in high school.

Instead of relationships founded on depth and connection, I derived my confidence and social self-worth from my athletic abilities.

As an athletic kid and teenager, when I was healthy, I was in the top 1% of my age group.

When I was 13, I started experiencing chronic back and ankle injuries that kept me perpetually in athletic purgatory. I was healthy enough to play, but never healthy enough to play to my potential or my peak abilities for very long.

From this place I was no longer a leader on my sports teams and the bond of masculine brotherhood was no longer there in the same way. Competing from an often injured place, I was now more burden than value.

I couldn’t find anyone who met me intellectually and spiritually, so now with my primary modality of social-connectedness gone, I felt completely alone.

While injured, I felt my social stature amongst men decrease. So did my self-confidence and it was harder to defend myself from the typical teenage jockeying for status. My social life was full of intentional emotional bullies, unsympathetic classmates, and little camaraderie on any level.

I also felt unattractive and undesirable to women. I was rejected by women I was sexually attracted to hundreds of times. I was rejected by women I loved many times. After high school, most of these interactions were with women 5-10 years older than me. Since I dropped out of college almost immediately to enter the technology world of Silicon Valley, these were the women in my community (if women were around much at all, in the 90/10 gender ratio waters I often swam in).

I was often told implicitly or explicitly by women that our connection was real, but that they couldn’t commit to a deeper physical connection because of our age difference. I was left to dwell in the feelings of unrealized possibility and unrequited love.

I endured the societal pressure, pain and loneliness of not losing my virginity until my early 20s. I didn’t have a girlfriend until I was 25. After all of these experiences, I couldn’t help but wonder whether there was something fundamentally wrong or unloveable about me, despite a deep sense of self-worth ready to rush back to the surface at the first sign of external validation.

(An Aside: I feel so fortunate that my first imprint of committed partnership in this life has been with Tara. Where I have felt fully loved, seen, appreciated and directly experienced the power of a securely attached romantic bond. I feel so grateful for being part of an enduring relationship, that has been so transformative in how we have offered each other mutual support towards evolving into greater versions of ourselves.)

B) Entrepreneurial Hardship

When I was working on the early ideas behind the Startup Genome I was told by entrepreneurs that I respected that I was delusional and that I should give up and go back to school.

Even after my work started getting traction in the world, I was still told by some of those same people that my work on the Startup Genome was worthless, harmful to entrepreneurs, and that I should quit and go back to the safety of a conventional life path by getting an undergraduate degree at Stanford or working at a well funded tech startup.

I have been rejected by people in the business world hundreds of times.I have attempted dozens of business ideas with friends that have failed at various stages of development.I have been forced out of a company I co-founded, that I put the entire force of my being, vitality, and life mission behind.

I have had some of my closest mentors abruptly disown and abandon me, presumably because they were afraid of my fire — and have had them never truly engage with me again.I have been in legal warfare with my best friend and become good friends again years later. I have been completely broke where I also felt too ashamed to ask family for help.

I have felt incredibly excited to collaborate on a business with one of my spiritual teachers, only to find his own self-worthlessness come out in equity discussions, and when we couldn’t come to agreement, have him threaten to sue me if I worked with anyone on similar concept. At this point, I couldn’t help but wonder if I was destined to simply repeat the pattern of seeing the potential for beautiful, transformational tech companies that would continually be undermined by the lack of enduring alignment with my business partners.

C) Biological Illness

I have been diagnosed with Leaky Gut, toxic mold poisoning, heavy metal poisoning and Multiple Chemical Sensitivity.

Worse still, before I found conformational diagnoses with cutting edge autoimmune based lab testing, close people in my life believed I was a Hypochondriac or at the least, almost all my symptoms were Psychological rather than Biological.

When I first learned about Multiple Chemical Sensitivity, I read that it was a lifetime illness that could only be managed not cured. I read dozens of stories from people on forums on the internet, who validated that the lifetime incurable nature of the condition. Their lives seemed miserable and full of unfulfilling, meaningless struggle.

Initially, my family had a lot of resistance to getting me the medical support I needed to investigate this Autoimmune disorder, as the tests costed thousands of dollars, and the actions to take as a result were not necessarily going to be clear.

My condition of Multiple Chemical Sensitivity was still very much a part of my life. Even though I had a proper diagnosis, the healing road was long and uncertain.

Living with MCS, the world outside my home was always dangerous and unsafe. Everywhere I went, harmful invisible, small chemical particles lurked. I couldn’t go to any social or professional event without fear that I might have to leave. And when I would insist that I couldn’t be in a space due to MCS, many people wouldn’t understand why and also believe there was something psychologically wrong with me.

To a person without Multiple Chemical Sensitivity the effect of these particles is a minor stressor that is unnoticeable to most in their conscious awareness and is easily processed by the Liver.

To me however, small quantities of these harmful, airborne particles would trigger a debilitating Autoimmune reaction leaving me to feel inflamed, fatigued and mentally foggy like I had 3 glasses of wine.

Sometimes, when I felt comfortable enough with the people I was with and there was low grade mold or VOCs in the space I was in, I would put on one of those high tech respirators that bikers in China wear to protect themselves from air pollution.

But I still I felt like one of those strange feeble looking women you see in the airport with the medical masks over their face — instead of being the strong, masculine leader I saw myself on the trajectory of becoming.

Most old buildings have some quantity of mold and most new buildings have off-gassing Volatile Organic Chemicals (VOCs) primarily from building materials, furniture and poor air quality due to the of circulation of fresh, oxygenated outdoor air.

At times, I felt completely debilitated, cognitively incapacitated, and energetically drained from my biological and psychological illnesses.

Without my abilities, and without a prognosis that included hope for making a full recovery I often felt completely worthless and that life was not worth living.

D) Psychological Illness

I have been through 4 episodes of Major Depression.

I have experienced the Dark Night of the Soul not just once, but multiple times.

I have met with many therapists who made my depression worse, reflecting back a set of life possibilities for myself that felt like Spiritual Suicide.

I have been completely crushed by the Simultaneity of my problems:

All at the same time, I was kicked out the company I co-founded, I lost my sense of life purpose and direction, could check nearly all the boxes on the Quarter Life Crisis checklist, I had toxic mold in my living situation and experienced constant low grade inflammation, brain fog, chronic fatigue and sensorial tingling that left me with little capacity to dig myself out of the hole I was in.

I had almost no money. The rest was being drained by poor quality lawyers who failed to translate my case into a viable strategy and led me down a legal dead-end, where they were simply wasting tens of thousands of dollars my and my family’s money. I had no ability to get or work at a job. And no ability to create a new healthy living situation for myself.

I would talk with friends and family about my situation and almost always came away feeling misunderstood and more depressed due to lack of resonance and the additive feeling of a vulnerability hangover and the effect it would have on my reputation if I ever did find a way to get better again.

I thought, “who would support me in being an entrepreneur again, as a co-founder, employee or investor, if they’ve seen me like this?”

Friends and family felt helpless in knowing how to support me and I had to endure the inaccuracy of their projections.

One of the biggest areas of dissonance when I would share what I was feeling with my friends and family, is that their message would roughly be along the lines of, “it’s okay if you don’t achieve your ambitions…they were naíve or misguided ambitions in some ways, and the lesson to learn from these hard times that have sent you into depression is that you need to take less risk and be more realistic.”

I didn’t accept that, even when I was depressed.

I wanted a path to get better and to make another attempt at my life goals — from a new angle, with new learnings and new depth alive inside me.

I never wanted to give up. I merely felt lost without a viable path forward toward recovery and re-emergence.

Even when I fell low enough, for long enough, that friends finally were able to provide me with the support I needed to form a foundation for my life from which I could rebuild, my outlook was still very bleak.

How could I ever feel satisfied living such a humble life as a result of my biological and psychological illnesses when all the meaning I found in my life was from the Existential Hero’s Journey of grand contribution that I felt I was on since I was a young boy.

I felt that everything I wanted to do with my life was now longer possible.

I wanted to die and start over.

I thought either I have a soul and I will get another shot or that is it and the pain will be over.

If there’s no path out from where I am, either option is better than this debilitating purgatory. But I can endure for a long time before I’m ready to take my own life.

I felt ashamed for thinking this way. And that I couldn’t share this logic with anyone lest they try to hospitalize me or put me on medication, or some other conventional medical intervention, coming from a place of fear rather than understanding and love.

I felt ashamed that I wasn’t able to hold many of my Spiritual Realizations through experiences of Depression. But I also felt the boldness of my soul’s mission was also a Spiritual Truth that many traditions Spiritually Bypass by skipping straight from the Relative self to the Absolute God.

I had a Major Depressive Episode go from bad to worse when the 2nd night of an Ayahuasca Ceremony completely overwhelmed me with feelings that the Life Story and Hero’s Journey I worked so hard to construct for myself was a complete lie, and that I should just kill myself now.

I was left feeling utterly flattened into a pit of despair and hopelessness for nearly 7 months towards the end of 2014 into 2015.

It’s possible I shouldn’t have been doing Ayahuasca, as it can often accelerate the emotional amplitude of those who experience both intense depression and hypomania. However, I would still like to engage the medicine again when I am more in the middle of my emotional spectrum, as I have so many friends who have received so much value from this work.

I have endured the exhausting never ending background noise of Suicidal Ideation for months at a time.

I have imagined that the most my life would be worth to society would be as a “Cautionary Tale of Ambition gone Wrong”. A modern day Icarus.

I was too ashamed to see friends.

I couldn’t work. I couldn’t think. I couldn’t feel.

To beat the suicidal ideation, I resolved to simply let the world do whatever it wanted with me.

And to see how society would treat “a failed, debilitated, formerly intelligent, ambitious, middle class white male”.

Unable to see a path out of my situation, I played chess and online poker for 12 hours a day to numb the pain.

It may not always be easy to tell that I am a highly emotional person, since in any personality system I am one of the most cognitive types. But the intensity with which I feel is what drives the bipolarity of my emotions. And I see this as an immense strength and gift that I must learn to harness rather than illness.

In my most recent depression, I completely surrendered what I once believed to be my Purpose and Destiny.

I completely gave up on my dreams and my identity.

I gave up all that I am to the Sublime Powers beyond me.

And I rested in the faith of their plan for me.

I rested in the truth of Being and Becoming.

Of relative perfection and that whatever happens from here on out is perfect. Is beautiful. Is art.

I chose to source my identity not from anything I did in this world.

But from the depth of my Soul.

And the Oneness of my Spirit.

Suffice to say,

Spirit has trained me well.

And what my pain and suffering have done is burn away all that is not me,

Leaving only,

Who I Truly Am



I have been reflecting on how I’ve handled my experiences of pain, suffering and hardship in life and what lessons I would like to offer to others:

1) Feel your feelings. Do not numb yourself to your emotions. Let them move through you. Work on you. Shape you.

See depression as a cleanse. See failures as temporary mistakes on your quest in learning how to enable your Soul to Soar and your Heart to Sing.

“Pain is temporary. It may last a minute, or an hour, or a day, or a year, but eventually it will subside and something else will take its place. If I quit, however, it lasts forever.” ― Eric Thomas

2) Don’t let the pain of your disappointments lower your standards or ambitions. Your deepest desires are unshakably true. Never give up on pursuing their fulfillment.

“True desire in the heart for anything good is God’s proof to you sent beforehand to indicate that it’s yours already,” – Denzel Washington

3) Practice Self-Responsibility, Forgiveness and Compassion.

Self-Responsibility. When things go wrong in your life, start by looking at yourself and inquiring into what you could have done better. Don’t be a victim. At a fundamental level almost anyone who harmed you, you let them in your life. And if there was a fundamental misalignment between the two of you, you only chose that person because you hadn’t yet sufficiently learned that lesson.

Forgiveness. Holding onto resentment and anger is an emotional poison that only hurts yourself.

“Holding on to anger is like grasping a hot coal with the intent of throwing it at someone else; you are the one who gets burned – Gautama Buddha

Compassion. Understand that people aren’t evil. They have their own traumas and deficiencies, and most people really are trying to do the best they can. Do not morally vilify people for their incapacity. But do raise your standards. And even if you are hurt by people, you can still unconditionally love them through their own growth experience. All human Souls are evolving back up towards the Divine Light of God. But sometimes some of them get stuck, and forget who they are and forget that we are all Ultimately One. Help them remember. Even when they hurt you.

4) Fear is an illusion

“There is nothing to fear but fear itself.” – Franklin Delanor Roosevelt

Fear fundamentally arises from a false illusion of separateness from the totality of being.
Death is an illusion. The personality dies but the soul lives on and is always learning, growing and progressing. Learning to rewire your identity to the whole of the cosmos and your agency to the timeless depth of your soul is one of the most powerful spiritual transformations you can have.

5) Pain is Inevitable in Life but Suffering is a Choice.

Whether life phenomena are experienced as mere pain sensation arising in the field of awareness, or instead as unbearable suffering is a matter of learnable perspective.

In essence, this is a summary of the 4 Noble Truths of Buddhism.

I’ve seen them well summarized like this:
i. Suffering, unsatisfactoriness, dissatisfaction, disappointment, illusion and confusion are an inescapable part of life.
ii. There is a root cause for these.
iii. There is a way to work with and eventually remove this cause.
iv. There is a practical method for doing so accessible to anyone willing to apply themselves.

Every human can find their own meditative path of Awakening, if they would like to be free of suffering, experience Ultimate Liberation, the flourishing of all positive states and an inextricable feeling of meaning, purpose and connectedness.

If you have had glimpses of these Higher States of Consciousness, which almost everyone has, know that they are Real. Have faith that you can access them all the time. And that if you find the right teacher and set of practices and lineages aligned for your personality and soul, you can have access to these deeper truths of Reality all the time.

The Great Spiritual Saints, Sages and Mystics of Human History are not wrong.

In fact, they are more right than the small you could ever know.

Also published on Medium.