Tag: Psychological Safety

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Emotional Work

Day 329 and Thanksgiving

I have so much to be thankful for this year. I don’t have a lot of poetic thoughts on it, though I have written extensively about my feelings on some of the bigger moments of the year. So click those if you want essays as this is going to be mostly a list.

I’m grateful to have recovered my health in 2021. I’m equally grateful I had the money, support and willpower to achieve it.

I’m grateful I have a husband who understands me and gives me the love, support and freedom to be me.

I’m grateful for having a space to share my thoughts daily, and rather than be punished for speaking my mind, I am rewarded for it. That includes WordPress, Twitter and all the people who made the internet possible.

I’m grateful I can live in Colorado and still do the same work I previously thought I would only do in New York or San Francisco.

I’m grateful my mother sent me to Waldorf school. I’m grateful I have a father who supported my development as a full human being.

I’m grateful I can afford to buy whatever dumb shit I like for my hobbies which range from expensive skincare to preparedness.

I’m grateful I can consider buying a home that will have the capacity to provide safety even as the world around me has risks.

I’m grateful to have business partners who share my vision for investing and founders and entrepreneurs who allow me to help them.

I’m grateful I never have to worry if there is enough money in the bank to buy a book.

I’m grateful that the supply chains have held so that I have an apple pie that I ordered online the day before the biggest holiday of the year which I picked up in my car that I was able to buy even as global trade was strained and our currency was inflated.

I’m grateful for the time to pursue emotional capacity and the money to pay for it.

I’m grateful for chemistry and the wide variety of pharmaceuticals and supplements that I take every day.

I’m grateful for my iPhone, it’s applications and games I use daily on it that have connected me to a world of people virtually that I love as truly as the people I interact with physically.

I’m grateful for shitposting.

I’m grateful William Gibson still writes. And I’m grateful that Twitter has let me interact with my favorite writers.

I’m grateful for West End BBQ and Spruce Confections.

I’m grateful for my raw milk dairy cooperative and it’s farmer Daphne.

I’m grateful for sunscreen and for apple cider vinegar.

I’m grateful for Costco.

I’m grateful for my parents making good decisions when I was younger that have compounded into incredible luck and prosperity for me.

I’m grateful to be American and I’d like that to remain a thing for which I am grateful.

I’m grateful for democracy, the enlightenment, free elections, a free press and liberalism.

Categories
Startups

Day 305 and Request for Founder

I was having an emotional conversation with a friend. They were giving me a piece of feedback that was truthful but hurt me. Because I feel psychologically safe with them, I was able to take the feedback in a receptive and open manner. I could incorporate it into my mental framework immediately because I trusted my friend. And I knew that their feedback was important and accurate.

One of the traits that I feel is most central to success in founding a company is the ability to process feedback effectively. Founders are constantly getting feedback. An average day might include angry customers with product complaints, a venture capitalist with heartfelt but partially useless advice, an unproductive strategy meeting where no one can seem to align, and a bunch of smart ass shitposters on social media with job advice for you.

A startup CEO gets a lot of feedback. Every day is a deluge of the stuff. And founders have to be gracious about it. Even when a lot of the feedback is useless, or even occasionally downright bad. You as a founder have to decide what to take and what to ignore. Because learning how to synthesize and integrate feedback; positive, negative or even profoundly unhelpful, is in fact your job. Being good at it matters. It’s the closest thing I have to a litmus test as an investor.

This is a trait I prioritize highly in founders. If you yourself are a founder that is working on improving your capacity for feedback processing, I want to hear from you. That mental flexibility is one of the core criteria I look for when I decide on an investment. Do I think you will be able to intake enough information about their market to get to product market fit? Will you be able to adjust your mindset and mental models quickly enough to outrun inertia? How emotionally strong are they that there can hear constant negative input and still hold their positive vision? But equally can you adjust that positive vision when negative feedback that actually matters presents itself.

These are the questions you need to have answers to for yourself. If you can drop me a line on Twitter DM. I’ve got an entire primer on now I like to get to know founders.

Categories
Startups

Day 298 and What You Don’t Know

I work with a lot of first time founders as a seed stage investor. Or rather I enjoy working with first time founders so I slowly became a seed stage investor as moving from advisor to angel investor. When you are a founder yourself, as I once was, you get a lot of inbound from others in the startup ecosystem as the bias has been that “only other operators can ever understand” so it breed insularity.

This has generally meant that there is a significant body of knowledge on best practices in startups that doesn’t get codified in writing it’s passed on as an oral history from one founder to the next. Maybe if someone published their Gchats and emails public we’d have a searchable wiki. But even with the trend towards startup communities, explainer Substacks and operator podcasts there is still a substantial portion of unspoken knowledge that no one will tell you. You literally don’t know what you don’t know. And the people that know have forgotten what it’s like not to know.

It’s easy to forget this as you assimilate norms and conventions over the years. I have been working with a portfolio company’s CEO to prepare some press and go to market work recently. Something I take completely for granted about media outreach wasn’t in fact obvious or intuitive.

But it was so obvious to me I never thought to mention the detail that tripped us up. And of course, the founder being a first timer didn’t know what they didn’t know. Why would they! That’s why they work with more experienced investors and advisors. It was my fault. I knew the thing but in my “water is wet” mindset didn’t even consider that the founder might not realize they were swimming in water yet. And that was entirely on me.

I find it somewhat comforting that startups are constantly introducing new founders who don’t know what they don’t know. Because maybe they will be the one to discover a new way of knowing that changed it for all of us.

The best is old timers can do is pass on what we think we know and the newbies can assess that using their fresh eyes. Sometimes (ok probably most times) we save you from making dumb mistakes that we once made. But maybe what I think I know for sure is just me not realizing I’m a fish in water. You can learn that from experience sure but also from having a totally new lens.

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Emotional Work Internet Culture

Day 293 and A Good Cry

I’m a cryer. I hear the swell of trumpet from the Star Trek theme song and I’ll start welling up. I’ll read a poignant passage in a cheesy airplane novel and my chest will tighten with emotion. My eyes will tear up when I tell a friend that I’m proud of them. I’ve found myself sniffling over a set of emotional text messages. I love a good cry.

I think I’m a cryer because I bottle up my emotions otherwise. I’ll share feelings in public but the real deep down core emotions are harder for me to express openly. The fear and hurt and sadness that make up the core of my emotional unconscious take some coaxing and a lot of psychological safety to get out into the open.

One of the reasons I find social media so much fun is it is a cesspool of emotions. Much of shitposting is just rage and anger expressed with a joke. And the shitposts that are sad are often told with a kind of vulnerability that I more commonly associate with 12 step meetings or group therapy. Internet culture has become an escape valve for emotions we didn’t know we even had.

The more I see the negatives that comes with keeping emotions bottled up the more I appreciate ways to let them out. If it is a good cry then I’ll take whatever brings it on. If you need something stronger than I highly recommend a light dose of Internet emotions. Just don’t let it overwhelm. Ease into the shallow end with an anonymous shitposting account first.

Categories
Emotional Work

Day 291 and Self Control

Self control is a form of self abuse for me. Early in life I learned that I could control others by controlling my emotions. Instead of showing my feelings, I’d distort my emotions into whatever got me attention from adults. That’s pretty clever for a child, but is the road to misery once you’ve grown up.

Alas I’ve kept up the habit of self control. It might not look like it from social media or press narratives, but I self censor a lot. I’m often conscious of what others will like or dislike and I will edit my feelings if I feel it isn’t to my benefit. What can I say, I am still hurting from feeling like I wasn’t loved as a child by my father. Same old story that everyone has in their lives (well maybe for you it was your mother but same idea).

But it hurts to keep your emotions inside. Eventually it will turn into pain or sickness. Not that I’m saying all pain or illness is caused by emotions (that’s some bullshit) but the mind body connection is real. The point is it’s only hurting myself to exert so much control over my emotions.

I need to get more comfortable with being uncomfortable with other people and how they feel about me. The control I have is largely a fantasy. It’s not that it’s not possible to change how others perceive you. Hell I’ve picked professions where that’s practically the main skill set. I love the perception game. Public relations, fashion, even venture capital are all games you win by building a good reputation.

Having a good reputation doesn’t mean turning off honesty. If anything reputations are built on being trustworthy. And that generally means saying what you mean and meaning what you say. So I’ve got to stop abusing myself by choking off emotions I don’t think others will like. Maybe it’s a gender thing. I learned pretty quickly no one likes an angry woman. But sometimes I get angry. Whatever excuse I’m using for hiding unpleasant emotions has got to go.

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Media

Day 281 and Villains

This is a post that will have spoilers about the end of the second season of Ted Lasso. Do not read any further if you have not seen it. I’ll put an extra paragraph to keep it from your eyes and we can meet again tomorrow.

SPOILERS BELOW

The first season of Ted Lasso may be one of the most perfect seasons of television ever made. It’s like being inside the best session of therapy you’ve ever had. The kind where you have a breakthrough so profound that the hurt and agony of your worst childhood trauma suddenly feels not only bearable but also the reason to fully love yourself. It’s just that good on the emotional truth scale. The warmth and safety and growth is beautiful.

But season two leans into tropes and villainy where it used to rely on nuance and kindness. Rather than feeling the pride and hope of emotional truth that has been hard gotten (the truth will set you free but first it will piss you off), we are given the obvious end of Nate betraying Ted and Rebecca by going to coach for Rupert’s new team West Ham.

Nate makes a massive accusation that Ted abandoned Nate emotionally but we are given roughly thirty seconds to wrack our brains for these betrayals before it is revealed that Nate has chosen to abandon Ted. How do we feel about this? Wouldn’t we normally explore how both people contributed to the feeling? But nope it’s send Nate right into insecure narcissistic reactivity rather than mine for the potential nuance.

We could have been given a story where we see Nate and Ted equally participating in the traumas they each carry and how it affects their relationship. Ted with his fear of abandonment brought on by his father’s suicide very well may play out that pattern of abandonment on Nate. But that’s left largely unexplored. Perhaps it could have shown us how Nate intuitively sees that because of Ted’s unresolved pain with his father, Ted in fact isn’t fully there for Nate in his new role as a surrogate father figure coach.

The struggles of a young man coping with a new position and unexpected authority granted by father figure like Ted juxtaposed against Nate’s own issue with his father who doesn’t show him respect would have been an empathetic story in the hands of this show.

There was so much fertile ground for how each character could trigger emotions in the other and for how they could own and resolve these feelings. But instead it’s straight to villain don’t pass to don’t collect 200 dollars. By the end I wasn’t even sad about the loss. I’d resigned myself to the conclusion. But they could have done so much better by everyone. Even if Nate must experience his darker impulses we would have been wiling to see the full journey of how he arrived there and the pain other’s traumas has inadvertently wrecked on Nate.

I guess I’m not sad. I’m just disappointed. And that’s how you know it really mattered to me.

Categories
Emotional Work

Day 269 and Pacing

I’m very defensive of my time. While I work at curtailing reactivity in my emotional growth, it’s still easy for me to feel invaded by obligations to others. Taking video or meeting in person was among my least favorite activities even before the pandemic. That’s one reason I’ve written extensively on how to communicate with me asynchronously. But another deeper reason is my fear of misusing my time. And tempting as it may be to project it onto others, I know that this fear is entirely about me.

I am very fearful of anyone needing things from me. I don’t mean things like money, favors or advice; though it is harder to say no than you’d think. My fear is deeper. I’m afraid friends and family will start to count on me for their emotional needs when I’m still figuring out how to be present for my own. I’ll deliberately put distance between myself and others to avoid feeling needed.

So what does this have to do with pacing? I’m not very good at giving myself enough space to be challenged and recovery. And when every encounter with another person is an emotional challenge, I need to be careful about pacing myself.

Maybe there is some latent autistic spectrum issues or maybe I have more trauma than I can consciously dig up but it’s a rare human that doesn’t make me anxious about the energy required for maintaining my own boundaries. It’s not about other people to be clear. It’s about me and my fears of being emotionally invaded.

As I build up more systems and accommodations to allow me to work effectively I need to figure out better pacing. How do I connect with others without emotional fear while still respecting my needs for down time and rest? Giving myself enough recovery has been an ongoing challenge that I write about extensively. But putting it into writing also serves as a valuable reminder to course correct before a crisis emerges.

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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.