Tag: Psychological Safety

Categories
Aesthetics Internet Culture

Day 264 and Shiner

I’ve been eyeing the full recline zero gravity chairs and desk combinations for a while. Because of a spinal condition sitting upright at a regular desk is tiring for me. It seemed like an extravagant purchase as they are well over $4000 at a base model but being able to spend a full work day in comfort reclining seemed worth the investment.

The Altwork chair and reclining desk

Last week I finally decided to pull the trigger and buy the chair on the advice of executive performance coach Dr. Julie Gurner who helped me see that investing in an environment that accommodates my physical needs is worthwhile.

Today was set to be the big set up and reveal day but in the excitement Alex was trying to take a picture of me laying flat while working and he dropped my phone form about three feet over my head onto my right ocular bone. It hit so hard it formed a blood bruise immediately. It was such a shock I didn’t even yell. So rather than playing with my new desk I’m icing my face.

Blood bruise from a phone hitting my face while photographing my new chair.

It hurts like hell. My face is swelling and I’ve got that jumpy nerves thing that comes from a physical trauma you didn’t see coming. So tomorrow I’ll finish setting up my new workstation. Right now I’ve got to stave off a shiner.

Categories
Startups

Day 250 and Getting to Know You

I don’t really like musical theater (it’s the people sorry) but I’ve been humming a tune from The King and I called “Getting to Know You” as I codify my process for meeting founders and startups. It turns out Julie Andrews through Rogers and Hammerstein lyrics may be a viable strategy for finding out if someone is a fit for Chaotic.Capital. The actual play is racist, colonial nonsense but you know take art for art’s sake.

Getting to know you

Getting to feel free and easy

When I am with you

Getting to know what to say

Haven’t you noticed

Suddenly I’m bright and breezy?

Because of all the beautiful and new

Things I’m learning about you

Day by day

She’s talking about being a teacher and getting to know her pupils but it’s also maybe about falling in love, but I like the sentiment that learning “beautiful and new” things “day by day” feels bright, breezy, free and easy. That’s a good template for relationships of all kinds.

Pitching is none of those things. It’s practiced, formal, and exhausting. It may be a necessary evil for founders as you need concise and clear communications about what you are doing and why it requires capital. But I don’t think it’s the best way to get to know people. Getting to know someone should feel easy.

I like to get to know someone over the course of conversations. My preference is through asynchronous communication mediums like chat, direct message or email. There is something about the volleying back and forth of information that helps me more. I like a back and forth that is informed by revealing thought process but also context and background. I’ll chat with virtually anyone and keep my direct messages open on Twitter because I value conversation so much.

I generally don’t feel that phone or video calls are that helpful to me in getting to know someone initially. I don’t mind short 10 minute bursts. What I do dislike is the planned hour long call for an initial conversation. Rarely am I able to be emotionally and physically present for something like that if I am not already interested or invested in story.

But if we’ve had conversations through Twitter, direct message or email where I have more context and connection then it’s possible I can be present for you. But I wouldn’t recommend asking for an hour synchronous medium as your first interaction with me. I’ll do it as a favor to someone now and again but I almost always resent it.

I’d rather get to know you over time before I’m trapped in a room for an hour to put it bluntly. I promise this is for both of our benefit. You wouldn’t take someone on a two week vacation for a second date so why would you hinge your chance to work or get investment from someone by insistence on spending an hour together right off the bat. Let it simmer a bit. Give me an appetite for wanting to help you. Then you won’t be able to get me off the phone or Signal. I will be your most available investor if you take the time to show me who you are.

So go ahead. Message me. Message a bunch. Send an email. If you don’t hear from me message some more. If I’m being evasive tell me straight me. But the end goal should be that getting to know you is free and easy. And you will be able to tell if I’m excited. Don’t give up. Just keep the conversation flowing like Julie Andrew’s did.

Categories
Emotional Work

Day 228 and Recurring Nightmares

Chances are you have some kind of recurring nightmare that your subconscious tosses up for processing regularly. Some blend of math tests or being naked at a big meeting seems pretty popular. I used to regularly have a dream where I was told I wouldn’t graduate from university as I had forgotten to take some core requirement. But by far the most consistent and upsetting nightmare I have is packing.

I moved a lot as a child. A fun (sad) fact about me is I changed schools every two years for my entire tenure as a student. These moves were generally coupled with moving homes while some just were just me moving by myself. I did first and second grade in Orange County in California, 3rd and 4th in Sacramento, 5th and 6th in Niwot Colorado, 7th grade I was homeschooled (somewhere in there my parents got divorced so my mom and I moved out), 8th was a prep school outside of Boulder, 9th grade was boarding school in Connecticut, 10th was half at prep school and half in France, 11th grade I dropped out and took classes in Manhattan, then for 12th I was back to Colorado and remote classes and prep school. The first and only time I had a consistent schooling experience was at University of Chicago. I did it in three and a half years to save money.

Just writing it out makes me anxious and sad. I wish I could condense it for purposes of the narrative. It feels too long reading it over. It wasn’t just moving schools and houses. It’s actually worse than I’m letting on. My father loves travel. I was put on an airplane at six weeks old for a flight to Hawaii. Many of my childhood memories are of airplanes and cruise ships and motor homes. You name a form of traveling and we did it. We were always going somewhere. I fucking hated it.

Now as an an adult I loathe packing. It brings back all my childhood memories of never feeling stable. Boxes and suitcases take me back. And I don’t just dislike it, I loathe it so much I dedicated several years of my life to making it more convenient to carry your cosmetics with you. I called the line Stowaway. It was all travel sized. I hate packing so much I went to years of trouble to make one core routine easier to take with you. I wanted one thing about travel to be less scary. Less overwhelming. One less thing you leave behind. Childhood trauma sticks.

Maybe only people who love travel should try to improve the experience. Working from a place of childhood trauma is often the road to riches. I guess it worked out fine for me. But I don’t have the fondness for travel that many millennials of my generation have. I only have nightmares. Maybe if I had realized that before I started it would have gone better.

A common theme in my recurring nightmare is trying to find all the basics I will need for some trip. I’ll be searching for underwear or prescription medication. As the dream unfolds I’ll find a key item only to have it disappear. There is always a countdown. Some reminder that a flight is taking off soon. But it’s usually much more dramatic than that. It’s often some kind of unspoken crisis. I won’t remember it when I wake up. Maybe it’s apocalyptic. But it’s rarely a go bag or a bug out situation in my nightmares. It’s just a suitcase or a box or a bag never being filled up.

I never leave on the trip. The dream never lets me finish packing. I guess my unconscious hasn’t figured out how to proceed that it wasn’t the packing that scared me, it was leaving behind the life that I thought was safe. Maybe I’ll get there eventually. I don’t want to be stuck in a nightmare, packing up my life, being afraid of being dragged someplace I don’t want to go.

Categories
Startups

Day 190 and Neutrality

One of the more influential pieces of art on my worldview is the science fiction comedy Men in Black. Yes you read that right. My philosophy is underpinned by a speech by Tommy Lee Jones.

1500 years ago everybody knew the Earth was the center of the Universe. 500 years ago everybody knew the Earth was flat and 15 minutes ago you knew people were alone on this planet. Imagine what you’ll know tomorrow

I don’t really know shit. I know enough to know I don’t know shit. My mother had a favorite bumper sticker “ask your teenager while they still know everything” which at the time as a teen I found a bit insulting and now as an adult think was quite astute. The more I know the less I know for sure.

Because I’ve slowly come to realize that knowing can be a crap shoot I keep odd company. Arguably bad company. I follow some truly outrageous people on Twitter. I follow hard right partisans and tankie left wing socialists. I follow folks with deep convictions on the irredeemable evils of technology and the most ebullient techno-optimists. It’s hard to talk me into not keeping an eye on all view points. Sure I think some folks are dead wrong but how do I know I’m not one of them?

Not knowing things for certain as saved my life. Medicine has a tendency to interpret data as absolute. Biometric markers and test results can for some doctors have as much authority as a papal decree. Anyone who has been told “well your test results are normal” while still feeling like absolute shit will know how frustrating this can be. Plenty of data points look absolutely normal before a system cascades into failure.

We don’t know as much as we need to believe we know. Our craving for certainty as humans is a significant weakness. The venture capitalist who insists that some metric will determine a crucial outcome is a favorite trope of mine. As if favorable CAC/LTV ratio functions as a warding spell or an attractive margin structure offers protection against a changing consumer preferences. Knowledge isn’t magic. Superstition can just as easily apply to P&Ls as poltergeists.

I find it best to remind myself to take a neutral when approaching entrepreneurs. Maybe I don’t know. Maybe everything I’ve ever known was particular to my circumstances, bias, education quirks or just plain randomness. Maybe one small insight will shift the grounds underneath me and reveal entirely new frameworks for interpreting reality. The unknown unknowns have a habit of springing themselves when you least expect.

It’s often tempting to throw opposing viewpoints into buckets that are easy to dismiss. Venture investors are notorious for this. We dismiss folks for any error we spot. We deride their data. We applaud ourselves for spotting cracks in their plans. Resist this tendency. We must always retain the neutrality of perspective that allows us to change our mental models. What we know to be true might be a lie. We may lack a key piece of context that would unlock a cascade of understanding that changes our entire perspective.

This is why the adage “strong beliefs weakly held” can be so key to success. Changing our minds is a strength. It’s hard to admit to ourselves we’ve gotten something wrong especially if we sunk a lot of time, money and reputation into it. But would you rather be right or successful? Feeling superior can be a delight but not if it gets in the way of what we want in life.

Categories
Emotional Work Startups

Day 166 and Safe Advice

Mistakes are expensive in the moment but priceless long term. This is why failed founders are so respected and sought after in the startup ecosystem. Their advice is the best money cannot buy. Money literally cannot buy the experience that comes from having utterly fucked yourself.

Sure maybe you lost a couple million bucks but you will never make the same mistake again. And because it hurts so god damn bad you will go out of your way to help others to avoid your fate. I’ve found that founders with failures are generous. They have seen the ways even the best laid plans can implode and want to help you from doing the same.

This is why it’s all the more frustrating for these operators watch a startup struggle to take advice. Speaking as a founder with failures, I know when someone else is about to make the mistakes I’ve made. I feel it in my bones. But it’s not always easy to help people help themselves.

Getting someone to an emotional place where they can hear that they too are about to fuck up their professional life takes love. Psychological safety is crucial to hearing someone else.

I have a theory that it feels safer to hear a hard piece of advice when it comes from someone you know is delivering it without ego. Someone who never seems to have struggled a day in their life tends to evoke our own feelings of inadequacy. Their advice could never work for us because we aren’t as smart, rich, connected or sexy as they are. But someone with scars? Sure maybe they get why this is so hard for us.

Categories
Emotional Work

Day 148 and Ted Lasso

As I’ve written about before, I like shibboleths and secret codes. And Ted Lasso is my go to show for the language of emotional empathy.

It’s touched a nerve for a certain corner of the internet. The folks yearning for positivity. It shouldn’t have worked. And yet the show’s curiosity opens up your heart. It was a tonic for a tough year. So much of its magic is about learning to accept others as they are and love yourself for you.

Jamie Tartt: “Coach, I’m me. Why would I want to be anything else?”
Ted Lasso: “I’m not sure you realize how psychologically that is

I’ve written about the concept of psychological safety in building partnerships, most recently in venture capital. If you have a desire to improve your bonds with others try Ted Lasso. It will teach you much about feelings you never knew you had.

Whenever someone special is going through something in their life or if I just really love them I’ll rewatch Ted Lasso. I’m having an afternoon off and doing just that.

Categories
Finance Startups

Day 146 and Gossip

Gossip drive the world. The stories we tell about other people reflect a lot. Even if we claim we don’t care what others think what others think moves the world around us. And I would posit that this actually isn’t a bad thing. It can drive closer bonds and increased connection.

There is a concept in evolutionary psychology called indirect reciprocity. Natural selection favors strategies that base the decision to help on the reputation of the recipient. Social interactions in which one actor helps another and is then benefited by a third party are key to cooperative reputations.

This isn’t just a systemic population level issue either. People who are more helpful are more likely to receive help. It’s uneven obviously and people can obscure their reputation. Depending on if you are up or downstream of helping or being helped, you make different calculations. Some people help more but they feel it’s worth the cost. They are downstream. Others accept more help because they are upstream. We are all making trades based on our position and arguably they are fair market trades.

How we decide to cooperate and with whom is driven considerably by reputations and shared value beliefs. Relaying reputation signals to bolster your capacity to connect to others is actually a key part of empathy. We need to establish psychological safety to partner with each other. Gossip helps us find suitable relationships. This is especially true in disciplines which require creativity. Quoting myself on the topic of psychological safety in venture capital.

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. Yet the atmosphere of distrust is pervasive. Venture capitalist and entrepreneur are constantly managing the information flow between each other.

Managing the information flow is a key component of gossip. Showing you understand their context, their fears and their reputations concerns helps you. An act we denigrate in popular culture actually helps you to deepen the relationships as each signifier breaks down space between two people and builds trust. So don’t knock gossip. It has evolutionary, societal and individual benefit. Just remember the ultimate outcome is about bringing people closer.

Categories
Emotional Work

Day 137 and Feeling Invaded

The line between feeling abandonment and invaded is thin for me. Being a child that often felt abandoned by my successful but distant father ingrained in me a fascinating pattern as an adult. I fear that I won’t be chosen, but when someone does choose me I easily tip right over into feeling invaded. I suspect this is a pattern many others will recognize.

There is a deep yearning to be the priority. My desire to be the one that gets picked is so strong. Such is the lingering fear of abandonment on the inner child. But because I have more comfort and recognition in the feeling of abandonment, when someone shows up for me it’s a swift inversion to the feeling of being invaded.

How dare this person who I so desperately wished would choose me then actually choose me! I will then become shy, distant, evasive and cold as the feeling that someone has overstepped their boundaries (which they haven’t) makes me retreat. For anyone who has ever been so sure that someone gave them all the signals of desire only to have it feel as if it was yanked away, this is the pattern your desired may be reenacting.

Because the consequence of being wanted is, well, being wanted. They desire something of me. I don’t even just mean this of friends or sexual partners. I can be thrilled that someone has chosen to work or collaborate with me and then when they approach me as if I have committed to them I will seize up with anxiety. The agony I feel at someone wanting something from me even when I gave them every indication that I want to give that thing to them is intense. My chronic fear of calendars is a deeply comical manifestation of this fear. I’ll spend an entire day agonizing over one short phone call in an otherwise empty day.

I doubt I’m special in this pattern of yearning and retreat. One of the most quoted lines from Star Trek is Spock noting “After a time, you may find that ‘having’ is not so pleasing a thing after all as ‘wanting. ‘ It is not logical, but it is often true.” For me it is often true and it is a pattern I wish to break. For when I reach out and offer my time and emotions to others I do mean it. The fear of invasion and patterns of retreat are simply a reactive pattern from my childhood. It is protective, and even in the mind of a child, logical. But children’s logic can only take you so far in life. As an adult I take responsibility for my emotions and through mindfulness can move beyond it.

Categories
Chronicle Internet Culture

Day 108 and Energy Vampires

Recently I’ve been watching a mockumentary about vampires living in Staten Island called What We Do in The Shadows. It’s surprisingly funny for what you’d imagine is a set of basic gags. My favorite running joke is a type of vampire called an Energy Vampire. Everyone in the house is your standard drinks blood loved forever vampire except “Colin Robinson” who is an energy vampire. He lives forever by draining the life force out of people. It’s the most common type of vampire.

As you probably guessed Colin Robinson is meant to remind you of vampires you probably have in your own life. The show runs heavily off “boring” jokes but the real kicker is how energy vampires are perpetual victims. Colin Robinson is always sucking you in with pity and apathy. Energy vampires prey on your emotions.

As you might expect they have an episode about social media and Colin Robinson gluts himself on the low quality but copious amounts of energy available. There is also a troll joke. It’s pretty funny because it rings true. One accidentally viral tweet and suddenly your energy is being sapped by a crowd of vampires. The extremely online eventually pick up some Van Helsing skills to keep their energy from being drained. I like to think I rarely spend time online without my garlic, holy zingers and reply through the heart stakes.

The real issue is when you discover you’ve got an energy vampire in your real life. I recently realized someone was draining my life force. I thought they were a friend but a set of misunderstandings I finally realized they’ve been sucking me dry for years. They are pretty good energy vampires as I actually thought I liked them quite a bit. It took one overdrawing of my energy to wake me up to the reality that their tactics exhaust me. With the energy vampire metaphor you can enjoy a laugh as to whether this behavior is malicious or not. Energy vampires need to feed! But the end result is you feeling shitty.

As much as Colin Robinson jokes amuse me I do think I need to keep my energy vampire away. Their last feeding left me feeling tired and obsessive. I let the shitty feeling they induced in me upset other people close to me. And that’s just fucked up. Then energy vampires get even more energy. So I’m going to try to keep them at bay. I don’t need to prolong the life of someone feeding on me and I certainly don’t need to waste my boy immortal life as someone else’s emotional food.

Categories
Chronicle Internet Culture

Day 67 and Virality

There are few more satisfying feelings in the world than seeing your emotions mirrored back to you. It’s what makes us fall in love, form communities, build anything that takes the work of more than one person. I’m not sure that anything matters more to humans than feeling seen.

Feeling seen is valuable. Finance knows it, marketers know it, fashion designers know it and the algorithms really know it. A switch flips when the outside world mirrors us back. The cold reality of being atomistic individuals dissolves just a little with the prospect that the other might not be so far away after all

This is why going viral on social media is such an ecstatic feeling for people. Being mirrored at mass scale is beyond pleasure and pain. Virality is existential. This fact is not lost on Silicon Valley and various expatriates of the culture and even current citizens question the morality. Creating virtual existential experiences feels wrong to us. And I can’t argue that the consequences of virality hasn’t done significant damage to the fabric of civilization. Facebook has more blood on its hands than a small government. But I’m not sold that synthetic experiences are morally worth less than natural ones. Social media replicates religious and cultural experiences but whether it’s “worse” than the other existential experiences is a bit like questioning if opium or fentanyl is worse because plants are morally superior to chemistry labs. The effect is the same more or less. Sure the dosing is what gets you but arguing scale gets you into a “good of the many or good of the one” debates and I’m not the crew of the Enterprise or Spock.

I can tell you that it’s probably best to be cautious about anything that can get you hooked if you know you are an addict. I’ve gone viral on Twitter several times in the past week and probably going on double digits now in the last year. Each time I get a new appreciation for how much it can feel like a god has messed with your reality. If it goes poorly you feel like you got hit by a bolt from the blue. Even if it goes well you worry if maybe Aries has decided to make you his tool. I’m a Christian so I’m no stranger to the feeling of surrender to a higher power, but watching a machine algorithm play like the left hand of God in your life is fucking weird.

By Silicon Valley standards I’m a minor clerical authority in some backwater. I’ve been initiated into the rights but I’m not close to the Vatican or Mecca. Being swept up in the miracle of virality makes some amount of sense to me and I appreciate the benefits of status that it confers. But I know it’s a ritualized way of bringing us closer to the divine that’s not about the individual and is ultimately about the institution. Fortunately I’m also a Calvinist so I have very few illusions about my place in the experience. I’m still a sinner and whether I’m damned or not hasn’t got much to do with human rituals. But I’m not immune to the awesome either.

So if you are inclined to use social media be careful what weight you assign to your actions and words. At any moment a miracle facilitated by the rites of machines can and will occur. I made a stupid joke about a monarchy in decline and a television show about a witch in a massive universe of superheroes. But 31,000 accounts decided to like it and a million discrete instances of it were produced to “others” willing to mirror it back to me. Which is about as stupid a thing as I can imagine happening and also as close to the random miraculously nature of God as I can possibly imagine. Just don’t read too much into it or your faith might have an existential crisis as well.