Day 112 and Unknowability

Human minds seem to prefer predictably. The back brain craves knowing what is coming even as our flighty consciousness seeks novelty. Talk about a tension that sucks. We’ve all seem just now much this is a recipe for misery when you live in a world with no predictability but easy access to low stakes novelty during the pandemic. We are twitchy, bitchy and miserable as we have no idea what our world will be like but we can dopamine drip our pleasure seekers with social media, food and substances for an enjoyable now.

I’ve written at length in this experiment about my frustrations with unreliability especially when it comes to my own body. It’s one of the hardest aspects of managing a recovery from an autoimmune disease. I need to be mentally strong enough to not let bad days shake my routines so I keep building towards the wider goal. I can’t be distracted by one data point. It’s about movement towards the goal. Ironically this is a skill I learned from startup life.

While the entire planet is getting a crash course in unpredictable futures now, startups are defined by their desire to solve problems that don’t yet have defined solutions. No one in a startup knows if the predictions will be right. If they are working on something that will have the intended outcomes is unclear. You work on faith. You trust that over a longer time frame the daily tasks and routines you push (sometimes we give them dumb names like OKRs to fake a sense of control) will actually get you where your mind’s horizon sees.

I sometimes wonder if those with religious faith would do better on average in startup life. We have some degree of comfort with the inscrutable. Mysteries are sources of joy rather than fear. We trust that there are things beyond our knowing and our control and yet we must live on despite that.

The obsession with data and trend lines and the potential for prediction, surety or knowing amuses me. Sure sometimes you can plan a lot. You should plan. You have some inputs that consistently deliver the predicted outputs. Your best guess are better than other people’s facts (thanks Spock!) But if it were all so neatly defined there would be nothing new to create. We wouldn’t be able to build value. It’s the undiscovered country that we seek.

In faith, in life, and in startups you must manage your squishy human mind that is constantly tortured by its own biology. We want to know and we want it to be predictable. But we also love the tickle of a new experience against our dopamine seeking biology. The spike of pleasure we find pleasure in the newness. That’s why we do it. And it’s on us to balance the tension between our need to predictably build and our addiction to novelty. Manage that and you may get far in your journey. Or it’s a miserable sine-wave that makes you nauseous as you go up and down trying desperately to bring the future forward between impulse and planning. It’s usually both if I’m honest. So if you don’t enjoy roller coasters I wouldn’t get on this ride. But if you do well you just might see God.

Chronic Disease Chronicle

Day 104 and Having HP

When you live with a chronic illness a certain element of unpredictability is always there. As I’m settle into having a case that is under control (what I wouldn’t give for a term like remission but autoimmune doesn’t get terms like that) I find my body is more reliable. More days are good days and bad days can be papered over with drugs. And as an autoimmune case stabilizes you can take more risks to push through bad days without promoting a systems cascade. That means you can take more risks on a good day and have a positive outcome.

Today was a good day. It might sound strange but this was the first noticeable day where I worked a straight workday in over 18 months. I started off before 9am and didn’t wrap until 5:30. I barely broke for lunch. It’s not that I haven’t worked during my sabbatical and recovery months, but typically I try to keep a pattern of rest between work blocks. I doubt anyone feels great at 4pm but in particular I notice all my symptoms are at their worst in the later afternoon. Frankly people are onto something with siestas.

I’m honestly thrilled to have had an extended good day. I didn’t notice any major pain spikes at any point in the day. I can usually tell if I overdo it and need to rest. Sometimes it’s just a pain spike that forces me to lay down. That wasn’t the case today and even more excitingly I don’t think I dipped into any reserves to have a full day. I suspect I’ll feel fine tomorrow.

It’s honestly not that different from using up too much HP or lives in a video game. Sometimes you gotta do it but it’s expensive. And sometimes you go up against a boss and are like oh “huh” guess I’m stronger than I thought. Today I discovered I’ve actually built back up my HP. And I’ve still got all that old XP from years of grinding. It felt like I had misjudged the difficulty of a level I hadn’t played in ages. I was so sure I was going to get beat. But I sailed right though. And I’ve still got plenty of lives for whatever level I’m playing through tomorrow.


Day 100 and Rest Days

When I first set out to write everyday I didn’t set a goal. I think in my mind I meant it as a month long exercise to create more. Now I’ve got no idea what will eventually break the streak. I’m sure when it happens (something is bound to occur) I’ll be frustrated and I will just keep going the next day I hope. I’m trying to remember that Banksy “when you get tired, learn to rest, not quit” graffiti with the little girl sitting staring at a bluebird. I know it’s the stuff of inspiration Instaporn but whatever works right?

I’ve managed to write through a fair amount of awful shit in the last hundred days so it’s not that I’m afraid I’ll quit. I’ve become accustomed to simply opening up the draft space and writing. I just start some days with no particular topic in mind. Its more the knowledge that I am going to need to take breaks. Maybe not from writing but from life.

Today is one of those break days. I can barely tell you what happened today. I’ve got a project with a deadline but as I pushed myself physically yesterday I found that I needed today off. Resting today gives me tomorrow. I know this sounds basic but as a workaholic I’ve not traditionally been good at resting when it’s not been forced on me.

Usually on rest days I’m prone in bed as I’m in too much pain and too exhausted to do anything else. I hid this for so much of my illness and now I’m almost comically transparent about it. You’d think I’d be considered a liability and no one would ever want to work with me (or be friends with me) and yet I’ve found that not to be the case.

The empathy I’ve found in almost everyone makes me wonder if we’ve got our reputation building advice all wrong. I was under the impression I needed to hide my illness and always excuse strength. But the more honest I am about my capacity and my limits the better my work and relationships get. I’m slowly leaving behind the persona of “always on” hustle “I’ll sleep when I’m dead” bullshit of my younger years.

I still have a lot of fear about being perceived as unreliable. There’s not much logic to it. I always meet my commitments head on and when I physically can’t people understand. I work with backups plans and teams so that its never a crisis if I simply need to rest. The work gets done with or without me because my reliability is a function of preparedness and collaboration now instead of will force and midnight marches. If anything I think this makes me a better partner to work with ss instead of relying on my “at any cost” personality you can rely on me simply slowly and with planning getting your further than we could have gone alone.

Chronicle Preparedness

Day 70 and The Joy of Preparing

I’ve found a lot of satisfaction in the feeling of being prepared. And I don’t just mean for the apocalypse. Simple preparation for storms are enjoyable for me. I keep an eye on weather so I don’t find myself at the grocery store among panicked last minute shoppers. I love the run up last minute puttering of battening down the hatches before a snowstorm. I use it as an excuse to do errands or chores I would otherwise find a way to put off.

My usual storm routine is to do all the laundry (including sheets and towels), vacuum, run the dishwasher and take a long shower. This routine comes in quite handy if you lose power as having clean underwear and plenty of dishes is something you will appreciate if you are left without electricity or water.

Storms are a terrific way to force the issue of lingering “to do” lists like go to the hardware for more batteries or run by the pharmacy for more Advil. I personally hate running errands until a hurricane or snowstorm is bearing down on me and then I gleefully tick off chores that have been languish for weeks if not months.

Much of these routines are really about self soothing. The illusion of control calms the mind. I know I have little control about much in life (the pandemic really brought home that point) but by engaging our will we can exert a little pressure on the on the parameters of our world. If we put the intention into our work to prepare, then a few days without power sounds manageable our mind should it come to pass. We’ve already told ourselves this uncomfortable or even dangerous situation is one that we are capable of enduring.

It’s not that I think mind over matter is a plan (it’s not you need a plan for emergencies) it’s that building our capacity for experiencing stress makes actual stress much more manageable. Busting out the generator and the camp stove is fun! I’ve said this so many times to myself I genuinely believe it. A snowstorm is predicted to drop up to two feet in Colorado over the weekend. Lots of breathless coverage is in the local papers and on the weather channels that it could be historic. I’m secretly hoping we lose power for just a little bit. Long enough for me to play with some of my gear.

Chronic Disease Chronicle

Day 58 & The Line Between Progress and Woo

While I spent my childhood deep in the western canon, now I spend my leisure hours reading science fiction. I’m just gaga for space operas, singularity stories, transhumanist breakthroughs and anything else you might put in a paperback to showcase “the future” right around the corner.

I’m what you might call an old fashioned technical progressive. Everything the future brings has a bright side. It’s probably the counter cultural hippie heritage I have. A better life is just around the corner.

Add in the additional nuance of having a chronic autoimmune condition and you can see how the line between science fiction and woo is a little blurry for me. One day a supplement is part of your favorite biohacking routine and the next it’s in the business papers making news as the latest breakthrough for life extension. That’s a real drug by the way. It’s called metformin and I take it every day.

I play around with a lot of weird “science-not-yet” stuff like a pulsed electromagnetic field to produce an analgesic effect in my spine. And I get made fun of pretty regularly by scientific method folks who scoff at basic studies that haven’t fully satisfied their curiosity.

But I honestly don’t care. I want to feel well. I want to thrive. Why wouldn’t I be trying out the latest treatments, supplements and pharmaceuticals? Why wouldn’t I experiment on myself. I don’t want to wait for everything to be double blind studied to death in twenty years. Will it kill me? No. Great let’s go.

We’ve given up on the joy of progress in my generation. We’ve let our imagination sour on the birth right of scientific advancement for the human race. It’s sad we’ve become so cynical. And sure, I often critique predatory health care that sell shame cures to the worried well. But are we confident we understand the line? I’m not. That electromagnetic device I thought was woo? My fancy upper east side New York rheumatologist used to have one in his office but found patients would rather take a drug than spend an hour on a machine even if the efficacy was the same.

Why is it so impossible that I might cure my spinal pain and reset my immune system? Is that crazier than landing Perseverance on Mars? I don’t think so. Sure I don’t like hucksters or charlatans either. And I still think places like Goop prey on desperation. But do I want to believe? Yes! Because progress happens. And it is making our lives better. We can expand our lives. Live better ones. It’s not a hopeless spiral to the destruction of the planet and our species. But if you want to come along for the ride you might have to tolerate me doing some weird shit. Till we prove it of course.

Chronicle Politics

Day 38 and Better Fear Than Anger

Culturally in America we’ve lost touch with the value of fear. Which is a shame as fear is a root emotion (along with sadness and happiness). We’ve became enchanted by anger instead. But anger is not a root fear. Anger is the steam rising off of fear. Cultivate, explore and release your anger and underneath you will find the fear that drives the issue.

We’ve decided we don’t like fear though. We’ve perverted it into a weakness. Especially during the pandemic. Anger on the other hand as won cultural acclaim in America. We use phrases like “right to be angry” and “righteous anger” rather than exhuming a deeper truth that will be more revealing. Fear is good though. It cuts deep. Fear shows us the child that lives in our innermost self, revealing the terrors and traumas children feel from being powerless, abandoned, and small.

Even as we cultivate strong bodies and swift minds as adults, the child who was betrayed by the accidental lapses by our parents remains inside of us. In psychology they call that the inner child. Perhaps your inner child is angry. Mine often feels anger. But at her heart the child is just scared. But rather than answer the questions raised by our fear and overcome it, we are seduced by the power of the anger steaming on top. We cultivate heroics to nurture the anger. Americans craft elaborate myths about the heroic value of anger.

I’m not suggesting you are not angry. Or that your anger has no place. Nor am I invalidating the source of your anger. I am however asking us all to dig deeper. Learn why you are angry. Then go deeper. Find the fear of the child that is inside you.

My fear? That I’ll be abandoned by my people during this pandemic. Just like I was abandoned as a child. I got angry seeing the choices people made. But underneath it was simply the fear that repeated a childhood trauma that I wasn’t important enough for anyone to save me. Knowing that helps me save myself. I take responsibility for my own fear. I can use it as an edge if others don’t work on their anger. But I’d rather we as a nation work through our shit instead.

Chronicle Finance

Day 33 and Psychological Safety

Creativity is scary. Any time you build something new fear lurks around the corner. Because even if it’s not rational, your perception of risk rises when your potential for failure is at its highest. Perhaps this is why when you take a conscious risk you unconsciously try to mitigate any unnecessary additional risks. This has a number of significant consequences for businesses. You want to feel safer when you take risks so you seek out psychological safety from your associates. The principle is simple. You will only take risks if you believe you don’t be punished for it. Psychological safety has been shown to be crucial for teamwork.

I’d wager this is a factor in why startup teams tend to be homogeneous as human nature makes it harder to trust what we don’t know well. Which is fascinating when you consider that diversity is also an important factor in financial performance. And as much as this principle of psychological safety been discussed for team performance, there is one area in startup land where feeling safe is rarely cultivated: venture capital.

Venture’s entire culture is steeped in cliches of competition and combativeness. Which seems odd for a group that theoretically prizes high performance. Wouldn’t they benefit from cultivating psychological safety the most? If entrepreneurs are solving entirely new problems with high chances of failure feeling like they can trust their financial partners should be a top priority. And surely plenty of ink has been spilled on picking good partners in the literature of startup advice. And yet the atmosphere of distrust is pervasive. Venture capitalist and entrepreneur are constantly managing the information flow between each other. Which is exactly the opposite of what creates the necessary safety to take creative risk. So why isn’t this discussed more?

Imagine a fund who instead of poking holes in your data or lobbing grenades in your plans instead showed it was sensitive to the parade of fear and doubt that pervades most decisions. You’d get more done by a mile. Ideas could be refined instead of defended. Plans could be buttressed and shored up rather than rationalized. Having safety will lower the kind of inhibiting social pressures to show “that you are always crushing it” perhaps enough to produce startups that actually do go on to crush it.

This strategy could shift the dynamics of a firm’s competitiveness too. In group dynamics of status and posturing prioritize deal flow among only in group group members which disadvantages everyone by increasing competitive deals and rising prices. Funds who who have psychological safe founder relations will then disproportionately control what deals get done as the creative risk takers will seek them out. That kind of deal flow would be a major leverage point. Rather than getting stuck fighting for the same deals everyone agrees on (which isn’t a sign of quality no matter how much we want it to be so) venture fund that sticks to prioritizing psychological safety will spend more time with productive risk taking that builds the future.

Developing emotional capacity isn’t a platitude. It’s grueling work that takes place over years, sometimes to little effect given our innate resistance to change. But it is truly transformative.


Day 32 and Happiness

While yesterday was the recap of my month of long form writing. I don’t feel entirely done with the experience that is emerging from this practice. The benefits are both much more apparent (and subtle) than simply finishing what I set out to do. So to kick off month 2 and day 32 I want to share a little more about this emerging insight.

I’m just happier than when I started. I feel a sense of joy and playfulness that feels much closer to me than I thought possible. Especially in the shadow of the pandemic and political instability it feels a bit heretical to be rising up. And here I am finding childlike feelings of play in the midst of chaos. But the more I put out these feelings of happiness out into the world the more I get back from friends and family. Writing has turned into a virtuous cycle where I tap into the enchantment and wonder of my own mind. And as I share my feelings and ideas I get back comments, messages, and phone calls with people sharing their own process. It really feels wonderful. We are together making new things from our minds.

Giving each other permission to find joy and excitement in our pursuits seems crucial. If we don’t it’s all too easy to get sucked into the despair of the nothing. You may remember the nothing from childhood. It’s the growing horror that absorbs all creativity and joy in The Neverending Story.

With the narratives of despair (and the terrible realities on which they are based) can consume us like The Nothing. It’s goal was to consume the land of Fantastica. It’s power is disillusionment. And I very much wonder if this constant drumbeat of doom sends us to a similar place. Our very nature as humans who form communities, share insights, be creative, build new things together, all becomes subsumed by consuming horror after horror.

But the nothing was stopped in my life. Even a small gesture like a long form journal brings back the human spirit. We share it and others recognize it in themselves. We connect and share. And in doing so push back the encroachment of the nothing. It’s a battle we can easily win by doing something as simple as being happy sharing our thoughts with each other.

Chronicle Internet Culture

Day 31 and The Goal

I feel a real sense of accomplishment that I did what I set out to do; write one piece of long form content everyday for a month. Now of course having achieved my goal I would like to do it for two months straight but I’ll give myself a moment to enjoy the happy feelings that come from finishing what you set out to do.

On the first day my writing muscles felt atrophied. It has been sometime since I wrote regularly and here I was committing to do it every single night. But I was able to get into the habit and quickly found myself enjoying the routine.

The biggest change I’m noticing is a smoother less disjointed focus in my mental processes. Rather than needing to work myself up to writing or pick a topic and commit to a narrative, I now ease myself into the threads from the day and see where my imagination takes me. This mental fluidity (which requires non judgement which is a struggle sometimes) is slowly improving the quality of my thoughts. I look forwarded getting ideas on paper and tying together disparate thoughts now each day. To seeing what strange new connection might emerge from the day. Like limbic memory and crisis or the power of loosely organized crowds

I’ve also noticed a distinct uptick in the momentum of life. That a daily exercise of writing could push forward my focus shouldn’t be a surprise but nevertheless I’m seeing progress on ideas that may become a reality. Because I’m using this space to think about my investing, finance, and cultural chaos a daily writing habit means I am makings fast progress on a thesis. Writing is an excellent forcing function for seeing ideas more clearly but also for seeing if you may have the seeds for something bigger.

If you are considering a writing exercise like mine I highly recommend doing a month long commitment. Do it in public. You may be surprised by where you end up. I covered a lot of emotional ground which has been a really boost to my spirits.

Chronicle Media

Day 29 and Momentum

I haven’t felt so invigorated by the internet in a long time. I’ve had a week of joyful chaotic fun alongside my virtual friends (which during pandemic times includes my IRL friends too). Without the alt right and their mascot President Trump sucking all the air out of the room I’m seeing a lot of relief. The slight diminishing of the existential threat has lead to a lot of what I can only call silly season.

Just about everyone I’ve encountered has been filled with newfound creativity this week. Stonk mania is really only a piece of the goofy energy. To be sure I’ve been riding high on the wave of GameStop and the other meme stocks (though to be clear we actually made money with a well timed bet on volatility and only bought one share of $GME for the fun). But it’s more than that. The giddiness that comes from any kind of upcrash raises spirits in all adjacent fields.

And as I spend a lot of time in financial and social media circles it’s been a hell of a party. Granted most of us are waiting for a hangover to hit but more than a few of us are wondering if we’ve tilted into an entirely new chapter of chaos as the world grapples with the power of loosely organized crowds.

Whatever comes next a momentum is building from the energy. We’ve seen a possibility that chaos can be fun and not destructive. A sorely lacking feeling in the last few years when memetic armies only fought on one side. Now it’s a free for all. And that is potentially a lot more interesting.