07 // Inside and Out: A Brief Review of an Excruciating Year

What if an Annual Letter to Shareholders and a sonnet had a child that was this email?

I hope you are getting some time to recharge, reset, eat food, and just generally not do things. Doing less right now is your job. Please take it seriously. This is a long long read. If you feel so compelled to share it, please do that. Or simply screenshot and add your own annotations. That’s what it’s here for.

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‘Tis the seasons of vision boarding, reflection posts, and assessments. It’s the time of year that I unsubscribe ruthlessly, unfollow judiciously, and generally clear the clutter that has amassed in my own mental attic. There is much to be grateful for because there was so much I cried over. The rejections brought a more sustainable sense of patience because they were mine.

I am limping into 2020. Not running, flying, skipping, or jogging. ACL tear energy with twice a day rehab and intensive training is more my current speed. I’m not embarrassed by it, but that in itself was more recent. I did, however, struggle with how low the lows were, and how the highs weren’t what I expected. 2019 was what it needed to be, even if I barely made it through. Courage quietly manifested in the private moments. It was a year in which I lost performance as a metric of a life well-lived. I prefer the stretching of a student. I forgot what freshman year can be. 2019 reminded me in detail. Frankly, I’m happy I didn’t get things I wanted this year. I would have mismanaged them.

There were moments where I wondered about the importance of a year like this. It most certainly was not one of the outputs. I felt the build of creative energy in my mind, but there were blockages to bringing things to fruition. I did not produce at the level I wanted, and I encountered a drought that was pervasive and visceral. Felt love I couldn’t speak on, then realized I was the issue I had been protecting myself from. I was afraid to be creative, unsure about my own skills, and happier to be hidden. I didn’t want to write, but I wanted to be held like a book you love; close and every page brings you deeper. And I made ribs in my Instapot and they were phenomenal. Really.

I made a credo that governs the exercise below, to ensure that it is meaningful and not just a rhetorical symphony of noise. Three rules govern my process of self-inquiry at the end of the year. I miss the mark, but they provide the buffers I need for this to be actionable and :

Waste no words. Hide no fears. Force no resolutions.


Questions That Don’t Need Answers

For longevity, I discovered its more beneficial for me to understand the reason than the outcome. Having a list of questions is a forcing function for me because I can come back to them with new eyes. They are individually helpful but collectively transformative as the parts of something deeper. The six that have made me pause:

  1. Do I need to be remembered as the person who did ______, or am I, okay being the person who still did _____ and never saw it come to the fruition I wanted, in my lifetime?

  2. Am I open to learning that will require me to assume and embrace the role of a novice, or am I opting out of this experience to fortify the perception of mastery?

  3. Am I labeling the discomfort of this growth as unnecessary, because I do not think I am worth what this growth will reveal about what I am not?

  4. If nothing in my life ever changed, and today was the peak, how would I pursue joy?

  5. If I got everything I desired today, what would change about me as a person?

  6. What am I not owed?


General Learnings (read: stuff I saw that made me think )

  1. Oversimplification of the wrong things is a trap that eliminates any opportunity for learning.

    The older I get, the more I respect how much genius it requires to make things simple. There is an art to distilling. But there is another side to that. The hot take becomes the cold serving much faster than expected. Avoiding these traps is a healthy way to not lose your time in reductive contests of signaling. Who really wins when we try to shame people who get bi-weekly paychecks? There is a difference between simplifying something to understand it, and minimizing it so you can appear more informed. Stupid games always have stupid prizes.

  2. Unspoken expectations are the Theranos’ of any relationship. Don’t do it.
    Fraudulent, overhyped, and unsustainable. Empathy is not mind reading, and what someone else did because they knew you, is not what someone who is getting to know you will automatically understand. Using your words can be difficult if you never had the language, but learning how and then working through it is table stakes.

  3. Know your code, and frequently interrogate it.
    Influence is silent because it does not need a podium. It instead can secret into the mundane, and gain control through activities that don’t appear linked, until you find that your entire framework for why you do something has shifted, slowly. And questions remain:

    a. What would I rather die for than betray?
    b. What would you give your life over?
    c. How am I going to live, and why?

  4. Don’t confuse the vehicle with the mission.

    Succession plans > talking about how successful the things you’ll always be doing will be. Sometimes, you have to get out of what you are driving in, so you can get a better view. Getting to that view though might make you get out of a very nice vehicle you like, so you can get a better vantage point for what you are trying to do. The mission requires what other things will ask you to deny.

  5. You don’t fully encounter the beginning of what you have faith in until you begin to engage with the paradoxes that influence it.

    The paradoxes are what lead to deeper questions. Avoidance is what makes it feel like you can’t ask the questions your heart needs too, so you vacuum seal them and freeze them. The question isn’t the answer, but it’s impossible to start without it.

  6. To do requires action. “To be” requires transformation.

    The productivity industrial complex would have us believe that, if we were just doing the right things more often, and had sharper goals, we’d be where we needed to be. Aside from providing no nuance (see #1), it leaves a crucial step on the table: you the right things right now, will change tactically and specifically, at different points in your life. I am not speaking about principles, but

  7. To continually cancel appointments with yourself is to make a clear and everpresent statement about what you think you are worth, then announce it from a megaphone.

    It’s not about your calendar. It’s about how you honor what you said you would do for you, just because it’s you. PERIODT (as the kids say).

  8. Explicating where you feel pain, is not analogous to being ‘negative’. We treat specific emotions with disdain because they are wildly unpopular, and less easily sedated. They are immovable from our experience.

    There are negative things. There are people whose center of gravity can revolve around believing that things cannot happen. Protecting your space in that regard is important. But sometimes it is not that. It is lament, sadness, and grief that echoes in spaces because the acoustics are there and it needs space for the reverb to do its job. Space to call things what they are, and to be still, with those unspeakable and untenable things, is needed.

  9. We build monuments to everything that we refuse to let go of.

    Never intentionally, we’re too smart for that. We just rename it.

  10. Freedom from something is different than freedom for something.

    Freedom from is how the idea of entrepreneurship has become much more like a cult than an opportunity matrix. The way it’s described as a zero-sum equation: If you aren’t doing it, you’ll never experience freedom. But that’s what’s so elusive abut the definition. If it is, then it must also be freedom for something. What do we use what we so desperately want, to do?



    Things I Learned About Myself (read: have applied and/or still grappling with)

  1. I have a preoccupation with silencing my own needs while disguising it as “service.”

    The role I have in my family is not the role I have in other people’s lives. I understood this on an intellectual level, but interpersonally I still may have wanted to be more than I should. I also realized how much of that as true when others did it to me, inadvertently. Conversational narcissism is not confined to making an exchange all about yourself; it is also about trying to solve an empathy gap you may have because you don’t want to appear insensitive the moment you hear something you haven’t experienced. It’s like walking through a cancer ward with a broken arm, announcing that “you too feel pain” to all the patients and the attending nurses. I am guilty on both accounts, for accepting and displaying that.

  2. My biggest vice has been perfectionism as an identity marker.

It’s a tough pill to communicate that what you do has nothing to do with how you feel. It is entirely different to wonder if there is something wrong. When I under-perform to my own standards, it can become crippling because of how I dissect what happened and slows down my ability to move towards a solution. I missed my own targets this year in almost every facet of my life. That felt like a failure, which is actually what learning feels like. Then there was the personal reckoning with that which I couldn’t control. Both hurt, but one leaves scars.

  1. Space is a love language of mine that is hard to articulate and difficult for many not to take personally.

People vary tremendously in what they need, how they need it communicated, and their current level of capacity to receive that which they say they need (assuming they were able to find the words to use to tell you). NEEDS. A fascinating context in a zeitgeist obsessed with independence as a marker of strength. Sometimes, I have too many tabs open and have to sort through the pages, get what I need from the information presented, then close them so I can get more of my personal memory bank. The speed at which I can stop communicating and go directly into my mind for prolonged periods of time is jarring for anyone who comes in contact with it. It can, without proper explanation when required, feel intimate and personal. It may also seem unbelievable given the public nature of what I have done revolves around a high level of communication. How do you negotiate the feeling of distance, with a need to express space as actually a language of love that has nothing to do with the person being a problem? I am naturally distant as a core function of my personality, not as a response to people. That perspective leads to insensitivity if I can never see outside of it though. So I had to decide whether I wanted to be “right” and alone with my pride to keep me warm, or lay that down and start to hear what it was I refused too.

This process continues to be arduous, but it is a core part of who I am. I have done a poor job of telling people this for two reasons: (1) I internalized earlier experiences of not always believing I deserved the space I needed (2) it triggers a feeling of remorse that is projected back into our relationship in a way that requires more management. I anticipated the guilt even when there was nothing to be guilty about so much, I made it into an unconscious reality. I know my friends love me deeply, I’m just not always sure how to check in on them when I feel like I have nothing to give (see #1) which feels like I am a failure. None of that is true, but I have not solved this issue, but knowledge of what role I play in it, has helped me become more proactive. There is much at risk conversations about this, so learning how to be more exploratory and less accusatory has led to deeper insights and a more amicable process of letting go of what no longer is, or welcoming what could be the beginning of a fruitful relationship, platonic or otherwise.

  1. Grieving for the living is a pain unto itself.


    I had to create some eulogies for the time that passed between myself and others. Getting urgent emails while walking someone into urgent care is all you need to reevaluate what words mean, and how they. To remember death is a consistent way to honor the life I have. I never thought I’d live forever, but that hasn’t made learning how to live, in the fullness thereof, any easier.

  2. I am a good communicator. I am also a bad communicator. I am both.

    I suck at communicating with anyone I haven’t asked how they would like to be communicated with. All the EQ in the world still means I will misstep if I don’t ask questions to learn what I could never know on my own.

  3. The healing hit different when I stopped obsessing over how long it might take to feel better.

    Healing is kind of like hot yoga; at a certain point, you realize that the only way you are going to make it out of that room without melting into your mat, is by focusing on what you need to be doing. Everyone is sweating, but you are not everyone, and that backbend is not going to do itself. That’s why its called a practice and not an achievement.

  4. I find no value in achievement and my ambitions are being updated to reflect where I am trying to go, instead of what I want to appear to be.

    This terrifies me. Saying it feels like a betrayal of the highest order. It feels like a violation of some code that I held, that no longer exists is deeply concerning to me. Not because of achievement per se, but because it makes me wonder about the drive that I so diligently protected, and I attributed to my ability to get me here, wherever that may be. The things I’ve done or maybe known for, mean much more to people around me than they do to me personally. I enjoy seeing them move forward, but I not sure the same fuel I used to push myself here, is renewable. I don’t want much of anything I see. The byproducts are nice, but they do not match up to what I see.

    But if I’m not ambitious the way I was, who am I? What am I worth out here? Will I still be a meaningful contributor to the culture? Will, as Money Mitch mused, the game still loves me? Why do I care so much if it does? Have I conflated legacy with being a monument to other people? Why do I think that’s all I have to give? How did I learn how to limit myself this way? If all I measure is outcomes, didn’t I miss the point?

  5. I do not have friends with the expectation they will simply resolve situations for me. I have friends because people have chosen of their own volition to bare witness to the realities of my life.

    The distinction has helped me deepen existing bonds, and let go of spaces where others may want to solve problems that I do not require. Sometimes that’s bumped into their issues of self-worth relative to what people expect of them that they have yet to push back on. The demands of my life are becoming more extreme. Some things I can speak on, others I cannot. My village has moved with me to both scenarios. They held me accountable to loving myself. Every time I forgot, they got creative.

  6. I have the occasional urge to slap fire out of my peers for lying to the people we say we want to help. I expect the same from them if I do it.

    We do a tragic disservice when we chose to wax poetic when we could have said: “I don’t know”. There is a lot of false flagging disguised as cosigns because we’d rather sit next to people instead of holding them accountable. Here’s the problem though: people really believe you once you cross a threshold of where they may want to be. The speed of trust accelerates, and you get to make a decision. You can act like you have no influence and that you are just “doing you”, or you can believe you do whether you want it or not, and chose how you will act.

    Less capping, and more talking about what these cap tables mean. If I can’t teach what I learn, I don’t know it well enough. “I don’t know” is beautiful.

  7. A damaged inner child has resulted in me crafting a silent monster that comes alive whenever there appears to be a threat to the safety of little Jonathan.

    Right now, I’d rather be a hero to a younger version of myself, than an expert to anyone else. If the byproduct is that I am somehow, then so be it, but I’ve stopped confusing the byproduct ith the focus. I spend much more time with that part of myself, and it’s helpful.

  8. I did not spend enough time developing platonic intimacy with other men in my life until 2019.

    A much longer and more necessary written exploration is forthcoming, but there was, until very recently a large gap in how I engage with other men my age, and how we structurally relate to each other. I have found so much joy and excitement in these bonds, which is a wonder why it took me so long to fashion them. Now, I can’t imagine my life with that connectivity.

  9. My brokenness offended people. The way they told me this was by offering help I didn’t ask for or assuming I wasn’t caring for myself.

    I was upset for a long time over this. Resentful too. Then, as I had less time to spend seething, I was able to see that, I was better for these new pieces of information about how people regarded me when I struggled. Pettythan, my less attractive and more vindictive alter ego, thought about maybe gifting all the people who ask ‘are you in therapy’ their own therapy sessions since it became immediately clear they thought I could be Amazon Priming my way to wellness.

  10. Family dynamics may never adjust to what I would like, but I also have the opportunity (and if I so choose the responsibility) to challenge the norms I disagree with in healthy ways.

    They do not have to be loud, overbearing, or even targeted adaptations. That could mean I simply just don’t do things in my life, that I was shown. I can be delicate, thoughtful, and firm. It’s taken me some trial and error in how to do that, but it is possible and necessary. Maybe we spend less time talking about who doesn’t trust who, and explaining what a living trust can do.

  11. I decided that I am interested in being a partner to someone, but had never considered how much work learning to receive was going to be.

    I also realized I had to learn this entire part of life that I had never known existed. It was as if, there was a complete section of my emotional library that had no books in it, and I had “made it” this far without it. It was embarrassing at first, but over time I wanted to explore this. If I can learn this, then there’s an entire world I get to explore that I thought I’d never had access too by virtue of never seeing it practiced.

  12. I will risk (almost) anything to put myself in a position to learn.

    I regained the confidence I thought I lost when I realized that I was betting on myself in major ways, it just wasn’t affirmed publicly. That’s when I stopped looking outside of myself for confirmation that I was moving in the right direction. I think I wanted more support at first, but I have come to see that I didn’t think I deserved the places I arrived at, which made me seek confirmation that doesn’t mean anything. I’ll do this for the rest of my life. Things that take time away from exploration feel crippling. It has become apparent that I learn in places some might not see as tenable. That may never stop, but the support I need will have to change so I can continue along that path.

  13. Most “wrongs,” I think should be righted, have more to do with a narcissism stemming from what I think I am owed because of the offense.

    That is not to say anything about justice in a structural sense, but on a personal level, I can easily project what I think I should get because of whatever series of reasons baked carefully into a narrative and warmed at the temperature of my pride.

  14. Parenting other people is a role that doesn’t have to define me, and shouldn’t set the context for where I find value.

    All that responsibility is exhausting, until I chose to reframe it, and stop trying to be a hero. No capes over here.

  15. My 20s have been jampacked of a subtle objectification based on my intelligence, but the care never extended to who I was as a person. I believed, internalized, and acted that I was only as good as what I could talk about.

    I stopped speaking almost entirely because I never felt like I was doing anything other than being ogled. I gained much more value being in my apartment reading than being outside. I swung the pendulum too far in one direction though, so I have been slowly working to find ways of better energy management. I cannot avoid who I am, but I also don’t have to leave other things unexplored.

    I’m grateful to be regarded as a thinker and a doer. I am perplexed by how much of that encompasses all of who I am in public. My private life is much more interesting because it’s mine. The tension between the two still rages, but my ability to manage it(or just not mismanage it), has grown.

  16. Craft > work.

    There are always things. Deadlines, places, meetings, and yes, more meetings. But none of that is more important than the space I need to do none of them, so I can sit with what I need. I’ve been learning that ‘craft’ is more important than simply talk through what I ‘work’ on. When I say ‘work’, more often than not I mean learning and application, confusion, editing, and the repetition that comes from immediately putting things down and into the constant conversation.

    I punished myself for not making things, by not honoring the space I was in. I didn’t have it, and that was because I did not allow myself the slowness it takes to not rush things, or the deliberate effort that comes with refusing the inspiration industrial complex. A portfolio is what I am after. One where you can flip through the pages and they are worn but filled. Some are tattered, bent, ripped. Others have annotations top to bottom. But anywhere you open it, it tells the same story: I left nothing in this life.

    Excellence isn’t always the most important thing. Sometimes, good enough is good enough. The things I don’t delegate are more about my pride than whether or not someone else can do it. I do not want to chase the wrong things with the right ferocity. I’m working to connect things that don’t always speak to each other, so it makes sense I’ve struggled with it. I don’t want a house for my work. I want a power grid that lights up anything that comes near it. No one evicts you from the land they didn’t find value in. Excellence will always be a synonym for perfection if I do not define it.

  17. My perspective is more powerful than my perseverance.

    I spent a tremendous amount of time asking why. Perhaps too much. There are some questions in my life, that will not get answered on this side of it, no matter how earnest my pleas, or honest my behavior. I am not owed that. But what did give me space and margin to explore things, was when I worked to reconfigure the vantage point. None of my circumstances changed in 2019. Problems I had, got worse. Cancers came out of remission, pressure intensified. But what did change was a discovery of how I could make the most out of what I have. What will I do next in spite of everything I am seeing? It is a much more empowering way for me to walk, run, crawl, and sometimes inch forward.

  18. I grew my hair out because it was the only thing I felt wasn’t dying around me.

    Conditioning and moisturizing my hair have been the most critical action of loving myself in 2019. I had to teach myself how to do it, and once I developed a routine, it spilled into other parts of my life. Now my apartment looks like I’ve been on a string of beauty supply robberies and I run my cash-only braiding cartel out of my kitchen. This is 4C.

  19. Reflection without action is poisonous to me.

    Because I am prone to deep swaths of inner dialogue if I reflect on something, I have to give it away, or I tend to revisit it. There’s comfort in some of the spaces, even if they are no longer good for me. Questions are sacred because they allow me to clear space. I spend time asking them so I do not begin to worship them.


    A Thank You

    I appreciate you welcoming me into your inbox, and engaging with my creative missives, as I’ve worked to find a voice that is both all my own, and focused on creating more knowledge at the edge of my own skillset. It is a privilege to be here, with you right now. In 2020, I'll be delivering more originals, more writing at the edge of what I know, an updated cadence, and some special surprises.

    Here’s to a new year and more opportunities for us to explore what we don’t know and expand on what we do.











06 // A Most Delicate Instrument

If the power of the mind isn't a joke, why do we play with it so much?

You ache with the need to convince yourself that you do exist in the real world, that you're a part of all the sound and anguish, and you strike out with your fists, you curse and you swear to make them recognize you. And, alas, it's seldom successful.

 - Richard Wright, Invisible Man

 ‘Mental Health’ is the new ‘Hustle’

The phrase ‘mental health’ is overwhelmingly broad and verbose. You can use it as a blanket for anything. In fact, putting it in front of, in the middle, or  

Mental health is super important. Definitely not something to neglect.

I think these days, it’s critical that mental health comes first, for anyone with a high-stress job look after themselves.

The mental health of the  *insert well-funded entity* team is a top priority which is why we give * BIG PERK* to all our employees. We want you to not just work, but live.

If you say something enough, it begins to mean whatever you say it does. If you’re looking to try this out for yourself, here are a few test words The specific becomes subjective with unprecedented velocity.

It h has become a garnish; sprinkled across, under, and through things to soften their bite and satiate cultural correctness in large part caused by the changing dynamics of work environments. A new generation simply won’t tolerate the norm, so friction ensues. That is more a population story than a discussion about the hysteria we encounter in our lives. It’s pretty hard to care for yourself, all things considered. You don’t even have to do work to talk about how important it is; you just need to read about stress and the terrors it causes, and share about how you would never that become your life.

But for all the talking, sharing, and caping that comes with mental health, I’ve noticed the glaring and persistent gap in the discourse continues to widen; little to nothing is said daily hygiene that keeps most of us intact or, without it, shattered. PTSD is no respecter of persons or environment., yet we somehow still want proof. That’s the paradox sight; we need to see it too believe it, but we can still invent things that aren’t true to satisfy what we want to see come to life. What a time to be conflicted.

The remedy is not the prescription

My mom is a board-certified Registered Nurse, If you ask her, she will tell you that she is a “medical professional”, because it more fully encapsulates her skillset, and she does what she wants.  It’s true. She gets recertified every year in multiple states so she can continue practicing her chosen vocation. She’s been a trauma nurse, home health and hospice, pediatric, outpatient, and ICU. There are few situations she hasn’t seen, and her grasp of what you may need for what ailments persist is astounding. She really knows things.  

Yet, with all that, she will still ask me, the same question about me, every winter, any time I develop a cold:

“Have you rubbed yourself with Watkins yet?!”

If you are unfamiliar with Watkins, let me get you in the mix:

It’s the older, more oval cousin of Vicks, and sits squarely in the West Indian mom starter kit for all ailments, across from Apple Cider Vinegar (add some water, gargle twice, and swallow the third time) and right underneath prayer. A LIKKLE dash (which is an important measuring standard), is all that is required when sickness comes for you on that flight, in seat 12B, when another grown adult showcases their inability to cover their mouth when they couch all over the handrest.

Even with her training, she will prioritize remedies that are natural along with ‘modern medicine’. She is by no means an anti-vaxxer or one who shuns regular check-ups. On the contrary, she is vigilant about them. But she has somehow encoded the same amount of space for but she also knows that medicine is in the eye of the person prescribing things to you. It would offend people’s sensibilities if you have no context for where she grew up and what “care” looked like. That might be why I grew up knowing what Echinacea was before I knew that people took Tylenol. As I’ve thought about it, it may have been an exercise in centering culture while being mindful of advancements that enhance, but never cancel out remedies. It’s the reason she never let doctors overprescribe me (because the easiest way to label a child is to say they need something they don’t, you know like  Ritalin in the 90s)

We know the burnout hits differently, its just hard to discuss the what, the how, and the cost of surviving both. This time of year, everything gets exposed. There is no hiding in Q4. Only unearthing.

Counting the Unfamiliar

I spoke to a neurologist recently, who helped me reframe my entire view of illness and its relationship to our minds. Simply:  

How many steps go into making a cup of coffee? How about ordering one?

 You do not think about it normally, because it is an unconscious function. That’s the point. You only become aware of the complexity when you are forced too, either through experience or visibility. You do not know how many steps go into making a cup of coffee, until you can't remember how to do it.  Everything is simple when you do not have to realize you had to learn it to begin with. The mind works similarly. You take for granted how much processing you do, about everything and everyone, until there is a gap, and you are forced to recognize it. We speak of the brain, but its complexities still confound us. I think that’s the point. To speak of something, but not fully know it, is the height of willful ignorance.

That’s why hobbies are more important than side hustles. In all this conversation of multiple streams, somehow, we forget that there is value in just having things that give yourself room to breathe. A byproduct is how these actions steel you for the environments where you have to make difficult decisions with limited information in adverse conditions. To not cultivate things for yourself is to simple do because you enjoy them, is to slowly starve yourself and intentionally keep the most important parts of you malnourished.

In fact, that simple cultivation of a  increases your ability to apply new insights into the things that make you money. The higher the pressure of the environment, the deeper the need to step away and craft a space that doesn’t echo.

But instead, we wax poetic about multiple streams of income, and never multiple streams of rest. The latter has an exponential impact on your ability to generate whatever idea of “more” that you have for yourself. Our addiction to self-improvement doesn’t actually solve the main focus of the hyperbole; to be is to decide what you won’t be doing, because you do not have time to be anything other than what you decide.

20mg of Peace

There was a day, not too long ago, when I realized that my dog and I had the same anxiety medication. His name is Tank, and he is gluten free. My mother, the medical professional referenced above, affectionally calls him her  “grand puppy”. He is 12 years old. I have already said more than necessary about the situation.

Due to an incessant travel schedule, our family dog developed a fairly severe case of anxiety, which manifested in random bouts of peeing in the house, destroying every single bed he has ever been given, eating specific shoes of people he didn’t like, and altogether doing anything for attention to make sure we knew he was there. When my brother would return, he would be fine, then once another business trip beckoned him onto another plane, the cycle would repeat.

This particular day, I was getting ready to give him his daily water and realized that one of the bottles that his meds were in was eerily similar to the same one I had on my nightstand for most of college: 20mg of Citalopram.

Citalopram is known as a selective serotonin reuptake inhibitor (SSRI).  Simply, it works to help restore balance to a natural substance found in your body and nervous system (serotonin). Things like cognition, memory, learning, and a bunch of other physiological processes are tied into that neurotransmitter. I know this because when you lose a part of your brain functioning as I did, you are forced to learn more about how it works than you ever thought. That’s another newsletter though. Simply, that pill bottle helped me navigate a significant portion of my undergraduate studies, in a space that was so viscerally destructive, reflecting on it gives me pause. Nothing profound there, just more space worth exploring.

My vice of choice is perfection. I just spent time calling it execution and making excuses for why building things never left me feeling better than before.  My coping mechanisms were, until very recently, staying as close to everything I mastered so as to avoid the discomfort of radical change. The most dangerous orientation for someone like me is not the pressures of work, failure, financial insecurity, or even extreme pain. It is the overwhelming feeling that I have to prove something to someone, somewhere, and that if I don’t do it, all the things I think might go wrong, will come true.

05// Economies of Influence Part 4: The good that hide young

If you have 'it', do yu need to talk about it so they know you got it?

This is part four of a four part series on influence. What it does, how we use it, and what it does and what that means. Part 1,  Part 2, and Part 3,  might be interesting for someone who doesn't get this newsletter yet. Screenshot away. This is the overdue finale.


I had a strong plan for this newsletter, which should have happened two weeks ago. It was fuego. Research is an art that allows distance because you can sift through reams of information and pick out what you are looking for. With practice and precision, you elucidate thoughts clearly and deliberately. I enjoy that process immensely. It’s what made me almost complete several PhD applications many moons ago. Almost. That ceases to be possible when you become the research you're doing. It's me. I’m the footnote.


I took a new job in a new place and I'm still figuring it out. As part of that job, I have to do more public things in a more pronounced way, more consistently, than I have had to do. 

So I sent a tweet out because I had a new job, I have to hire across 2020, and I actually would only be telling the facts about what it is that I am doing. Light work. Until it wasn’t. Immediately following what was a simple and standard internet activity.

I was bedridden for 24 hours following my own announcement. The last time I was rendered that immovable I had UPN was dominating the ratings, and Sega Dreamcast was the pinnacle of technological advancement. I thought I was having an allergic reaction, to something. I was, except the something was myself. Rather, this new reality that I had sequestered myself from.

1. What is my own relationship with influence (the kind I have and what it means)?

  1. Why do I like thinking about influence, but shy away from managing my own? 
    3. What was my mind doing to make me think this was protecting me?

    We’ll focus on the first two because the 3rd is another email for another time.

    Perhaps, the most dangerous thing you might face as a polymath doesn’t happen until you start getting appreciated for one of the multitudes you have. The trap that I have been unsuccessful at avoiding is the assertion that being noticed for your intelligence is the same thing as being seen as equal because of it. That’s why we hide. The fear of being seeing for the immensity outweighs the ease of just exhibiting a small portion that you can control.

Most people with a public persona tell you that the downsides outweigh the upsides. They have a target on their back from critics. They have less creative freedom. They feel irresponsible when they turn down opportunities because they know other people would kill for the chance. It’s not all bad of course, but there are real problems that go along with fame and fortune.

- Ryan Holiday

If your reason for being quiet is simply not to be like them, you are living a lie of convenience. Worse, it is an insidious kind of selfishness. I know, because I have embraced it much longer than anyone I know. People who do deep work often spend time avoiding who they don't want to be, and don't necessarily work on more of who they are trying to become. Both are important models, but they work in conjunction. If you lean too heavily on one side, you can become obsessive without direction. The same intensity that can create a space for you, can also hollow you out. 


The moment your status changes in any visible capacity, friction enters the equation. You aren’t simply just doing your work; you are managing the external reality that was previously only internal. Your velocity outpaces everything around you, because you are breaking free. It's exhilarating and terrifying. I tended to focus on terror because I often think I can solve it more easily than anything else. If not solve, at least survive it long enough to find a makeshift operating structure that allows me to get by. The issue is that it followed me for so long, I befriended it. It helped me cope with the survivorship bias; the weighted blanket forced upon you when you "make it". That is to say, ascend past the mean, and arrive at a place that's wholly unfamiliar to you, and seemingly aspirational to others. It’s kind of like the Delta lounge; you didn't do something extraordinary to get in, but since you're there, you can investigate the assorted dips, and use the less terrible.


Accountability acts as a lubricant; it allows things that would normally be at odds to engage with each other. It is a lie to believe influence escapes you because you do not want it. For some, it is not a choice they had to make. You can very well be born into a space that has it built-in. Other times you amass it slowly for what you say and what you. Sometimes, it is just you doing the things that you do, and the dubious recognition of being the only one hangs ever-present. 

I do not mean that there should not incorporate silence, periods of focus, research, and unmitigated glee. On the contrary. I am actively looking to find more as they are necessary for life. We bribe our inner child with the distraction of safety, and stunt their creative growth. Then, we have the nerve to shame them for not being more “productive”. We’d rather silence them than let them play, then wonder why they don’t want to come outside anymore. Growing up isn’t the worst thing; finding reasons to not see the world with childlike wonder is far more dangerous I wonder if its arrogance or pure fantasy that creates the false equivalency that I don't have to share what I'm doing and that people will simply just find it anyway. How would they know what to look for? Why would I make them?



But the biggest failures aren’t things you did. They’re things you didn’t do. Playing it safe is one of the biggest failures possible.

 Ramit Sethi 


As the complexity increases, a peer set becomes harder to find. Not simply people who think like you, but those who willingly choose to think, regardless of. 
The conundrum of choosing to remain curious is that you create much more distance for yourself to do the work you want to do because you aren't consumed by simply doing what has already been done. It's no surprise that it happens until it happens to you. 


Exposure left me traumatized, the same way unprocessed film exposed to undue heat becomes perishable. With too much of it, the latent image erodes, and the color balance erodes. .I needed a darkroom for myself, so I built one. Then I decided to never leave.  That's why I don't like looking back at the reference points other people have for me. They see what they are able to. Most of what they see clearly about me is blurry to myself. I thought this was an issue of confidence, but it is much deeper than that. It is not so much that I do not think I can't be what they assume I am; it's more that I know the very real costs of what that means and have spent time not trying to ever be in that conversation, you are placed there anyway.

The Fear of Expansion


Or maybe you know you're good, you just don't think you can do this thing in front of those people and be consistent for that long. You play the background because you know the pieces of the puzzle, but not where they all go. We keep things close to our chest, not because we don't want to share. But because we want what we do to start close to our hearts, then expand. As it grows, the heartbeat never changes. We know it’s alive because you held it before it grew the strength to walk. That’s why the project you don’t let go of, is the one that haunts you in your mind before you let it go on paper.

The more you love your art/calling/enterprise, the more important its accomplishment is to the evolution of your soul, the more you will fear it and the more Resistance you will experience facing it. 
- Steven Pressfield, The War of Art 


I don't want to be seen. I want to be felt. But the latter is sometimes a pathway to the former. It doesn't cancel you out. It is not as zero-sum as we can make it.  Disquieting and uncomfortable, it often bears resemblance to the other things that help enable growth. If you do have influence, and you know it, you are also aware that awareness about you isn't about control. It is about what you decide to push forward because you have the leverage to do so.


The most dangerous space for me is to noodle in the abstract as an excuse to not be grounded in the present. There is no way for me to predict or place sound judgment on what I might like. I've wordsmithed myself out of my own work, then found reasons why it isn’t up to par. It’s not imposter syndrome if you know you are that person. It’s actually just avoidance because it’s easier to try and get to it another time.


It was never just about being private for the sake of avoidance. It can start off that way, but it usually morphs into the need that is universal; to be seen outside of the image that might be cast and understood in spite of everything around you that says otherwise. The paradox for me has been that I might believe my surroundings because I am most susceptible to the  It is often about maintaining space for the sacred, whatever that may be, and for whatever reason. The quirky, the unseen, the divergent, and the weird are the prized frameworks to someone who has more in them than they might know but needs time to see it come to fruition. 

I still have aims on being notoriously private about a select number of things, but not everything. Perhaps that's a more useful pursuit than expending energy trying to simply remain fully invisible. The right things should be in plain view. Those can double as things that also stand the test of time. 

04 // Economies of Influence Part 3: The Immediacy of Expertise

I can sort of teach it, so how do I sell it?

This is part three of a four part series on influence. What it does, how we use it, and what it does and what that means. Part 1 and Part 2 might be interesting for a friend or an enemy. Either works.

This should have been in your inbox on Sunday, but it didn’t contain the nuance necessary. I apologize. You’ll get a double filling next week.


There is always an overabundance of information about the things that we need intrinsically: safety, relationships, growth. Most of my close friends who have partners, generally both work. Some have corporate roles and so does their beau. Others are artists. Some are more blended. Regardless, their advice is always nuanced. It’s even become culturally relevant enough to craft robust data sets to help explain how people are doing it. It’s personal and specific to how we navigate life. So why is it still distilled down into some of the least functional advice possible? I have a theory.

Manipulate Me Zaddy

At the top of the food chain in this digital wasteland of conjecture, more apparent than inside of what I’ve deemed the Relationship Industrial Complex. Simply, it is the persistent flood of information about what you should be doing to secure the person you deserve and live the life you dream of. In a newsletter I used to write that wasn’t as good as this one, I described those who perpetuate this framework. They respond to many names, but they occupy a singular title; that of the perpetual Guru Zaddy:

The guru zaddy is any person(s) (zaddies for the plural), that thrives off of the assumption of their expertise, without checks or balances about what they are in fact an expert of or in.

You can generally recognize them in a few distinct ways:

1.    They rarely admit they have any form of coaching or assistance in growing into where they are

1.2      They rarely discuss things with contemporaries who could challenge them or push their thinking

1.3      Being wrong is never an option. Much easier to invent haters than realize you may need to reassess your position

1.4       They can never give credit to the source of something. Instead, they just use TinyShot to put it against a colorful background, and reap the social capital of never having to attribute anything

1.5      it's been a while since they've been a practitioner, so just trust them on what they are talking about because YOU LOVE AND NEED IT

I’d summarize some of the most egregious forms, but you know where they are, and how they move. It’s embedded into how we trade on influence as capital. You probably skipped past a few today.

Deep(est) Work or whateva

Malcolm Gladwell created an entire cultural firefight after Outliers, by summarizing the work of K.Anders Ericcson. The 10,000 hour rule as he called it, described how you can gain mastery by the accumulation of hours put into your chosen task. You can’t open Instagram with out a declaration of how many hours people are NOT counting. The only equation more in

. First, Ericsson was studying violinists. Anyone who has played an instrument can attest to this idea; you suck at something, then you progressively suck less. Instrumental practice requires a focus that you can’t always maintain past a certain point, because your mind or your body deals with consistent exhaustion. Second, the 10,000 hours he described for that study, was entirely arbitrary. Not every violinist he studied had reached the number of hours that could extrapolate into success.

Third. the phrase that delineates the kind of practice that he suggested led to mastery ( deliberate practice ) was in the name of his groundbreaking study. It’s actually the title: The Role of Deliberate Practice in the Acquisition of Expert Performance. But it’s much easier if you can attach a number to something, because, if someone has tens of thousands of people that engage with them, they must be right about something. That came out in 1993. Outliers came out in 2008. We’ve spent a decade nestling the idea of 10,000 hours with it being fully out of context unless you wanted to find the source material.

Being deliberate is what separates you. It is, specific, focused, and exhausting. You have to rest so you can return to it. You know its happening because you are teetering on the edge of your experience and on the precipice of everything you haven’t experienced yet. It’s brutal. You shoulder weight of a beginner by choice. Then you learn. There are a plethora of errors that say everything about your progress and nothing about your worth. All of the

You can be at the tippity top of your field and not be close to an expert. Just go to a conference about anything and look for the headliner, and ask what they are struggling to understand. Big cricket energy. You can also be the best at what you do and only be celebrated posthumously. Zora Neal Hurston sold more units after she died. That’s unconscionable, preventable, and commonplace. Funny thing about genius; it’s easier to engage with as a perspective than a person. We love to find manuscripts, but never ask why we have to dig for what’s already in front of us. It shouldn’t be archeology every time we need to surface something that moves us.

Is this your (expert) King!?

We are all closer to cryptomnesia than we care to admit; the generating of an idea you think is yours, but was created by someone else. It’s often psychologically unintentional, which does nothing to lessen the impact when it isn’t actively confronted. Or, they just steal it. Why give credit when you can just pretend you had the idea first anyway?

 Perhaps that’s why the Alex’s among us are more often hidden in public until they aren’t. Fighting for your own space is to acknowledge that you need more of it in the first place. In a world full of noise, quiet becomes uncomfortable. Untenable. Unbearable for longer. If you aren’t saying enough, how can you prove you’re doing it!? The paradox of being an original, is that you surrender to doing it on a timetable that confounds public perception. Compound interest is a great concept to visualize, but it’s not exciting to experience. But it’s what you need to expand you ability to learn across and through things.

The charade of expertise isn’t just in the presentation, it is in the delivery. It’s not next level thinking because we haven't seen it. If everyone is an expert, who is doing all the learning? Raising your credit score 100 points in a year doesn’t make you a financial expert. It could simply mean you decreased your credit utilization rate. Or you opened enough Or you leveraged your DUNS number effectively. Or there’s a credit union near you that offers lower rates because it’s community-owned. Inspiration is cool and its helpful; it does not a curriculum make nor a CFP create.

We run a deep risk of creating more sycophants and less contemporaries. We don't see each other, because no one wants to be a novice long enough. I’ve never met an expert who is truly afraid of being wrong. In fact, most of them aren’t always convinced they are right. They are convicted that they must do something though.

So Prolific, So Gifted

Frederick Douglass was the most popular man in America at the turn of the century. He had to find balance between silence, environment, responsibility, and his ethics, in the midst of great turmoil. Perhaps, that tension is best explained through a letter, he wrote to the slave owner who refused to let him free his sisters:

I will now bring this letter to a close, you shall hear from me again unless you let me hear from you. I intend to make use of you as a weapon with which to assail the system of slavery—as a means of concentrating public attention on the system, and deepening their horror of trafficking in the souls and bodies of men. I shall make use of you as a means of exposing the character of the American church and clergy—and as a means of bringing this guilty nation with yourself to repentance. In doing this I entertain no malice towards you personally. There is no roof under which you would be more safe than mine, and there is nothing in my house which you might need for your comfort, which I would not readily grant. Indeed, I should esteem it a privilege, to set you an example as to how mankind ought to treat each other.

I am your fellow man, but not your slave.

A brother trying to free his sisters, in the midst of shouldering the responsibility of articulating why humanity was a birthright. The turning of a nation inside of itself with ha pen, a voice, and an elite blowout. The instruments change, but their effectiveness doesn’t if you know that it’s in you and not on you. I can’t imagine that pressure, but I can identify with the intent.

There is tremendous latency whenever you attempt original thought. It is isolating and can drive you into the inner caverns of your mind as you work to sort through what only you can see. It takes years, and even then, you get much closer to realizing that much of your work, will remain unfinished. It doesn’t diminish the need to do it, it increases it. The shortness of life has the tendency to do that.

Too often we let people without the range tell us where to aim.

You can’t summarize your own genius if you want to make an opus that sounds like you. But if you want to just be out here, there’s a blueprint for that too. Just make sure you have your course ready for pre-sale.

03// Economies of Influence Part 2: Visibility, Influence and the Grand Strategy of Optics

If they don't see you, are you doing it right?

This is part two of a four part series on influence. What it does, how we use it, and what it does and what that means.

In case you missed it, Endeavor IPO is in limbo. The game is not based on sympathy and 32 pages of risk factors isn’t going to go away.


Katie Couric is very, very short. It’s not something you’d think about unless you were sitting next to her, and you saw how her feet dangled so high above the floor, you didn’t really think it was possible. It can be a shock to see someone you’ve seen for the first time, and realize that the camera angle adds a cool 6 inches to their stature. I met her wearing what I’ll describe as a luxe pair of Air Mom ‘93s, which makes sense for someone who spends a lot of time behind a desk, and deserves to have their arches supported. She was friendly, engaging, and funny. You love to experience it.

In 2014, Ms. Couric signed a  behemoth deal with Yahoo, to usher in a new phase of her career, as their inaugural ‘Global Anchor’. The idea was that as more people continue to engage digitally, she would able to capture their attention via a permanent slot on the homepage, the same way you’d expect to Few people have the kind of track record that Mrs. Couric has, or the consistency to reinvent yourself on-air. NBC, ABC, and CBS was nothing to trifle with at the time. In a chess move of epic proportions, she also negotiated to keep a role at ABC as a special contributor, executive produced things you watched and probably had no idea about and kept her rights to continue building Katie Couric Media. She left that deal in 2017, and re-upped with her current podcast situation. Levels.

On this particular day in 2016 however, the energy was at an all time high. No one had any idea what the results would be of the 2016 election. I was there, because a booker for the show had slid in my inbox at the time, asking for a “black millennial perspective given the nature of this election”, was an interesting ask, and led to a few phone calls, scheduling, and the biggest speaking opportunity of my life. “Speaking opportunity” is ironic, because I didn’t do that much of it. Halfway through the interview, Ohio flipped, and the rest, is our current environment. I'm not here to talk about that. I am here to tell you that it was everything and nothing I thought.

The footage never came out, I never spoke about it, and I’ve largely forgot this happened to me. I didn’t care, and on some level, I was embarrassed. I’m usually embarrassed by this level of exposure (we’ll get to that part 4), but this was something else entirely. I felt guilty for not talking about it, saying yes to it, and somehw still thinking I under performed while it was happening. The lights weren’t blinding. The sense of fulfillment was. I was guilty for not feeling more excited about what this actually was.

Adjacency is not power. It isn’t even access. It’s bottle service that you didn’t pay for, in a club you do not own, standing next to people you don’t know. Pour up if you so choose.

You see me onstage though

Perhaps the greatest adjacent activity right now, is Yes friends, I am talking about panels.  The forty-five minute group think activity that has taken every professional identity by storm and used to

THE PANEL TALK.

Let’s paint a scenario: You get invited to a housewarming. There are only 6 people there ,and five of them are friends for a decade with the host, which is why they got there early. You are the new-ish, having known the host for less than a year (give or take), but you wanted to be courteous so you got some wine (not too expensive, no need to flex) and actually got to their apartment on time? Now, you have to ease into a conversation or risk the socially abhorrent activity of just standing awkwardly, somewhere between the living room and the kitchen, cuddling your cup and just nodding to how much you too like Lizzo, but desperately looking for something else to talk about, until the other thirty people who confirmed the e-vite show up, a smooth forty minutes later, which you had planned to do until you decided to be a hero and be early. No? Cool, just me then.

I don’t know why they upset me so much. Maybe it’s because I have seen people I admire say what they think people want to hear, because they are next to someone who they want to like them, more than they want to say I don’t know. Maybe it’s because I have close confidantes who think that if they could just get to this stage everything will change, no knowing that the stage is in fact, an invention.

I like my ideas like I like my gumbo: seasoned, mixed, freshly stirred, and left to simmer and steep. But that is not what we are getting served. We get spoon-fed under- cooked oatmeal with imitation fruit on the top. The unmitigated gall to not even try for real blueberries or raspberries or even a dash of brown sugar? It’s hate incarnate.

There’s a moment in most panels where you can feel the beginning of the end. It’s usually thirteen minutes before the Q&A is meant to start, and someone has launched into a personal soliloquy about a topic that they want you to know about, that may or may not be even loosely related to the reason the other one hundred or so people are in the room. They finish a tough landing along the lines of:

“…I ‘d like to piggyback on that…”

OR

“ I echo everything they are saying, and to add…”

There is no issue with being entertained, inspired, or stimulated. I’d just argue that a panel isn’t the best place for that as a focus, but is actually a byproduct of a well structured conversation. If the point was just too pontificate endlessly, couldn’t we just do Zoom calls? Voice notes? There is a false equivalency between saying you know something and actually knowing it.

“…All we need is names”

But what’s more costly than the reputational damage, is the disgrace that it causes. You can put a price on it, because there is an industry constructed to help manage it. Scandal was a good show, but Judy Smith has spent a quarter century being on call for the oil spills of people’s personal lives. Some things are unavoidable and others aren’t. Anything can cause a crisis

In an ideal scenario, alignment produces exponential results. Morgan Stanley told the world that Steph Curry was worth $14B to Under Armour based on his endorsement deal. When his signature shoe dropped, he increased their shoe sales 350%, across the business. Whether this was causation or correlation we may never know. What we do know, is that it was beneficial for both parties.

But what if that proximity isn’t positive, you need to reverse out of the relationship while still protecting your investment and reputation? Hopefully you planned for it, and got disgrace insurance. A little known public product, it falls under the purview of contingency insurance, which helps an insured party, reclaim damages

TL;DR - if you violate me, you are liable for that violation because I have coverage that insures me against your poor choices.

I recently met a founder who flipped this model on its head, via her company Spotted. She saw a gap in the archaic claims process, which often requires you to prove that there was a “disgrace” and that it caused you a specific type of damage. So instead of trying to build a different product entirely, she just optimized an existing one:

That’s why a well kept dataset gives you infinite leverage; it’s not just about who you know, and how you know them; anyone can make a rolodex. What makes data such a precious commodity, is how you can organize it to elucidate what appears to be a jumble of information. The numbers do not make it intellectual property; how you chose to display them and create a framework around those activities, does.

If you take the assumption that you are your most valuable asset, you also assume that you can be your own downfall. The risk isn’t external. IT YOU. YOU ARE THE RISK. The ability to self assess and be ruthlessly honest about that is one thing, but acting on that assessment is not for the faint of heart. That’s why scandals don’t stop

Assuming someone doesn’t have it because you haven’t seen it match the pattern you expect, doesn't change the fact that they might in fact, have it. This kind of misjudgment has gotten people punched in their face since the beginning of recorded history.

Who gets defined as “risky” is all about a reputation that gets made by what can be linked to you, and referenced from what you appear to have done. Protecting an investment isn’t a static process. It’s a dynamic one, especially if I have the means to protect myself against you, reap the benefits if nothing goes wrong, while mitigating the risk if it does.

They might not tell you you’re a risk. Someone might just take steps to insure you have no ability to cost them more than they paid you.

Value Decommissioning

After the election results, I left the Yahoo set, and walked through Times Square, before finding a cab back to Harlem. It was terrifying, because of the deafening silence. I had time to myself to think, and what I couldn’t comprehend, was how everyone in the green room who was equally as surprised to be there. It was one of the worst nights of my life, and I couldn’t understand why. I felt like a failure twice over: I hadn’t found the right strategy for capitalizing on a huge media frenzy, and I was scared to admit I wanted nothing to do with it ever again. A rock and an exceedingly hard place.

We all yearn to protect ourselves, but sometimes it’s not clear from whom, or against what, especially when the optics look perfect. Being in the wrong fight is more dangerous than losing a round in the right one.

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