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.











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