Tag: Confidence

Categories
Finance Startups

Day 275 and Manifesting

I had a really terrific September. Everything just started going my way. Projects that I’d been pushing on had significant breakthroughs. My deals got hot. My focus and health improved. Even when I had setbacks and failures I was able to execute on quick recoveries. But mostly I didn’t give in to past bad habits. And all of that happened without any additional effort on my part.

I’ve been making a really conscious effort to stop pushing myself to always be doing more. Either I am able to find elegant solutions or I ask myself to take a step back till I can. Rather than brute forcing everything I am finding ways get where I am going without sacrificing myself to costly bad trades on my time and energy.

I asked for something really significant from one of my investments (an additional allocation for an special purpose vehicle). The second I asked for it I started to panic. I didn’t have an immediate or simple path to deliver on what I asked for from this founder. Even though I was confident I had the money for the deal it out I panicked that maybe I had bitten off more than I could chew. Immediately it started going through my head about how bad I’d feel if failed this founder. I relived the guilt, shame and punishment I had felt in previous failures to deliver for people that trusted me. I hated feeling like I’d failed people.

And I just decided stopped the cycle of worry then. Like turning off a switch. I told myself I could do it, I knew I could do it or I wouldn’t have asked, and that there was simply no way I was going to let down this founder. But this is where I felt the frown Instead of going into overdrive, I stuck by my schedule. I didn’t change anything. I didn’t push myself to a frenzy by adding in calls, pitches & emails. I just put down all the steps I could and would take to make the deal available to the right people and I began.

In the past I would have let that fear drive me. I would have gone into overwork and adding in additional tactics that I didn’t even need to insure I would reach my goal. But here I trusted myself to get the outcome. I didn’t exhaust myself. I took care of myself. And the allocation got filled quickly. I checked the commitments this morning and I’ve only got 15% of the deal left.

Categories
Internet Culture Reading

Day 271 and Correspondence

I love writing to others. I had some pen pals as a child but it wasn’t until as a teenager that the Internet gave me the chance to correspond with practically whomever I liked. And it’s been one of the great joys of my life to reach out to others for conversation.

I developed a habit of writing to journalists, authors and academics whose work I admired. Many of them maintained email addresses and personal websites even back before social media. If you are ever worried that someone will find it odd or unsettling to receive a note from you, don’t fret. I can share that if you are polite and sincere outreach is almost universally appreciated. Most people want to be seen. If you feel you’ve seen someone then you should share it with them. It’s a kindness to you both.

While I particularly like short form correspondence like Twitter, there is no substitute for a more in-depth and layered letter. I’m personally a fan of the threaded twenty response deep email chain. I think of it as like the letter writing of our forefathers. Maybe it’s a bit less satisfying to our heirs than discovering a box of letters but I’ve got a fantasy that the Ken Burns of the future will make excellent use of email and chat logs.

If you aren’t convinced of the benefits of reaching out through writing feel free to test it out on my before you write a letter to your favorite author or thinker. We just might become pen pals.

Categories
Emotional Work

Day 259 and Easing into Habits

Considering I’ve been writing every single day for two hundred and fifty nine straight days you’d think I’d have encountered more writer’s block. But I generally find myself capable of putting the proverbial pen to paper. Well in this case it is thumbs to mobile application layer but that doesn’t sound as evocative.

Even today when I had no discernible topic at the ready I am finding that words will spill out so long as I make the effort to form a thought and codify it to written form. While I had the notion that I had little to say today I am still able to say something. I am saying something about having nothing to say but it’s the act that counts.

It’s not that it’s necessarily a worthy entry, but rather a reminder to myself that the act of doing forces it’s own discipline. It’s practice. I am learning that doing something can be easy as long as I let myself relax into the momentum of doing it without expectations or pressure. This must be what all those sports speeches about practice are on about.

Seeing writing as a habit rather than an inspiration or performance likely helps. I’ve come to view the activity as similar to exercise, taking vitamins or brushing my teeth. Perhaps it’s more cognitively demanding but it’s no less part of the daily rhythm.

I’d like that to be true of more of the activities in my life. Being able to view professional necessities as habits is a sure way to see them not as exhausting “to do” lists but rather enjoyable easy daily practices. Sure it will start out harder but eventually it will become easier.

Categories
Chronicle

Day 257 and Back to School

Today felt like the first day back to school. Everyone has finally returned from their various summer vacations and I mean that mostly mentally. People are back and focused. The whole damn day was nonstop for me. Like a shift happened overnight.

It’s not that everyone I know actually went anywhere this summer, quite the opposite, most people seemed to have stayed home. But there was a kind of mental “out of office” that pervaded. Maybe it was a bit despondency in certain parts of my network that “hot vax summer” never came to pass. August was a frenzy of people canceling shit.

I kept hearing stories of people that were living normally but I honestly didn’t know anyone that didn’t cope with the Delta surge in some capacity (even if it was simply to say fuck it). Everyone I encountered of all persuasions just seemed to be struggling to live through the summer.

And then today all that lethargy felt lifted. None of the basic on the ground aspects had changed. And yet a levity was in every conversation today. People were planning again. Projects were moving forward. Plans were being made. Big school is back in session energy was there.

Categories
Emotional Work

Day 256 and Helplessness

When I was a child I hated being helped. I was a “Mary quite contrary” type except I wasn’t yet in a profession where that was considered a sign of intelligence. I’d ignore the advice, aid and help of teachers. I preferred to figure things out on my own.

A story that I’m sure will eventually turn apocryphal as I get older involved a horse trainer and needing to be left alone. I was was having trouble with a jump in a group less. My horse kept throwing me and ducking the obstacle. My trainer did his best to give me advice on how to keep my posture and encourage my horse. He kept piling on advice and kept his focus on me. And I kept not making it over the jump.

I probably fucked it up over a dozen times. Eventually my trainer gave up and went to help another pupil. Without the glare of a professional, I finally gathered myself up, held the horse firmly in hand and soared over the jump on the first try.

Holy shit was my trainer pissed. “Julie didn’t need my help at all! The second I turned my head she just handled it herself.” From then on my trainer learned that I’d happily internalize his training but if he kept too close of an eye on my I’d develop a kind of learned helplessness. I’d get worse and not better.

I sometimes wonder if this tendency remains a part of me. I like attention so I’ll accept help if someone is willing to give it to me. The upside to this is I am always learning and questioning. But if I’m not careful I’ll just keep enjoying the benefits of helplessness. But I can’t linger there. Because I know moment I’m left to my own devices I’ll gather up the knowledge and willpower and make it over the jump. But it can be temping to wallow in helplessness.

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 Internet Culture

Day 247 and Rooting for You

I watched a viral video of a young white American kid who claims to have quit a 100K job in order to pitch YouTube star Logan Paul for a job. It’s really hard to watch because this poor young man just utterly shits the bed on asking his favorite social celebrity to take a chance on him. He can’t even tell Logan what he is best at. He doesn’t know himself and thus cannot capitalize on his moment in the sun to show his worth. Honestly it will break your heart.

The shitty sad part of watching this kid utterly fail at self advocacy is if you are in a position of power you genuinely want to help people if they are clear about how you can do so. No one wants to say no. We all want to get to yes.

Being asked “what are you good at?” is an empathy driven open ended “get me to yes” kind of question. Logan Paul, never a celebrity I’d have previously associated with emotionally empathic, actually encourages this young fan. Even in a short clip he encourages him.

It breaks my heart a little that this kid doesn’t have anything to say for himself. Even saying something small like “ I’m the best getting groceries quickly” would have given him a chance.

I think the reason this hits me hard is that everyone has emotionally been that young man. Asked someone to help and just utterly bombed. I know I’ve taken a swing and asked powerful connected intelligent people to help me and then subsequently failed to rise to the moment. I carry those emotional failures with me. I think we all do. It’s what drives us to be better. Those moments of defeat can remake us for success. They course correct us. But only if we don’t let don’t let those failures beat us for good. We have to see the patterns that brought it into our life, accept that it’s our failure, and let it improve us.

That’s why it’s so important when you are in a position of saying no to someone to do it with as much grace as Logan Paul. I know it’s a weird sentence to type. We owe it to ourselves to there to hear them at their lowest moment with the hope may eventually become the path to their better self. Because surely someone once did that for you. That’s wisdom.

It’s hard getting a concise answer to “why you” and finding and accepting the truth of what you are truly better than anyone else is at is a lifetime of work. Being able to do it when you are young is what makes for a life that will give you satisfaction instead of disappointment.

I genuinely believe we want to help others get there. I used to hate when someone who turned down one of my pitches would say they “were rooting for me.” I thought it was dismissive. Now I choose to understand that that most people want to help you succeed.

If someone accepts time to talk to you it’s probably because human to human they would like to get to yes. I now take “we’re rooting for you” as sincere. Maybe it’s not in some cases but why not default to good intent first?

Categories
Aesthetics

Day 239 and Missing Vanity

I wasn’t much for makeup or clothing as a teenager, but I fell in love with fashion as I got older. I was swayed by the mysteries of style. The power of being dressed precisely for the occasion was not lost on me. I wanted to command the powers of vanity for myself

But as the pandemic set in I cancelled all my beauty box of the month subscriptions and closed my Rent the Runway account. I didn’t need red lipstick or cocktail dresses. When we summered in the Hudson Valley the first summer of the pandemic, I only brought one suitcase of sweatpants and cotton dresses. I didn’t realize it at the time but I was was leaving behind dozens of vanity rituals.

Like many other people, we decided to move closer to family as the pandemic continued. Going from Manhattan to Boulder isn’t exactly conducive to keeping up with appearances either. I found myself buying hiking pants and wool socks. I had no occasion to dress for anyone but myself.

I’m not sure how much I actually miss getting dressed. At least not for myself. Earlier in May before the Delta variant squashed “hot vax” summer for good, some ink was spilled on the mixed emotions of getting dressed for others after so much time in seclusion.

The pandemic seems to have proven that for me aesthetics are all about the dance with others. The joy of communicating one’s taste and preferences to the outside world is more riveting than playing with my look for an audience of one.

But I do miss that dance. Vanity can be a wonderful motivator to connect and communicate with others. I so badly want someone to see my hair. I haven’t heat styled my hair for well over a year. In fact, I haven’t had it cut for nearly 10 months.

My vanity tells me my hair has never looked better. It cascades down to my mid back without a split end in sight. Just waves. It’s fucking princess hair. My vanity whispers that someone surely would notice how beautiful I look. If they noticed how I look then they must always want me to notice them.

I miss the pleasure of seeing beauty in each other. Sharing a compliment and an appreciation for the little vanities we all keep.

Categories
Emotional Work

Day 231 and Afraid of Feeling Fear

Being sick has left me with some scars that I am working through. Currently I’m afraid of pushing myself to my limits. I don’t know it for a fact but I fear some of the severity of my illness was tied to the overwork that is required when working in startup life. So now I’m afraid of overdoing things physically. I’m struggling to even set the boundaries of what 50% capacity would look like.

This isn’t the first time I’ve struggled with the question of my capacity. I’ve been a fan of what I call the “Gattaca” method since I was a child. “Never save anything for the swim back.” But now having experienced the worst case scenario of being unable to work for two years I’m gun shy. That common knowledge says failure “is never as bad as you imagine” is bullshit. Losing two years of my life was fucking awful. What if next time I give my all and I lose more than two years? I’m running myself in circles with this fear without any indication that it will become reality.

When I was a teenager I rode horses. I liked cross country eventing where you jump over obstacles on an open field. It’s a bit dangerous. That’s how Christopher Reeves got hurt. I had plenty of spills but it never really upset me. I always got back on the horse. I wanted to become more competitive so bought a thoroughbred who was being retrained from being a racehorse. I thought I was a talented enough rider for the job. I wasn’t.

He was a high strung panicky creature and threw me into a wall. I cracked my helmet, blacked out briefly and was diagnosed with a concussion the next day. Despite the severity of the fall, I got back on the horse immediately. I was afraid of being scared. So I pushed through.

Turns out I should have just felt the fear. I should have gone to the doctor, allowed myself to recover and not pushed through it. I never fully recovered my nerve about that concussion. I just slowly circled the drain emotionally and my fear won over my enthusiasm for rising. I never went back to competing in eventing. Instead of working through my fear I chose to ignore it. That turned out to be a sure fire way to let fear win in the end.

I don’t want to be afraid of being scared. I want to embrace my feelings and their origins. I want to come to terms with them. Because unlike horseback riding, I intend to keep working.

Categories
Internet Culture

Day 212 and Notes for A Unified Theory of Shitposting

Yesterday I was fucking around on Twitter, as I am prone to doing. I made a barely sit-com worthy joke about divorced guy energy.

You ever notice how women thrive in the aftermath of divorce but men implode? Why is that?

My husband Alex replied with a searing burn “don’t worry, I’ll be fine” response and we were off to the races with all our mutuals dunking. I was howling with laughter. The two of us were trading zingers and watching the DMs roll in from friends.

Obviously the undercurrent of any thread on social media got dark very fast. So quickly I ended up putting out resources for men who were struggling in the replies. The amount of pain on display was enough to make you want to donate to the first domestic abuse charity I could find.

So why is it that I can shitpost about a topic and come away unscathed, indeed it was a fun and entertaining night for both myself and Alex, but others melted down? I think it might be about class and social signaling. It takes a lot of social capital to shitpost. And those that shitpost on the most socially contentious topics are demonstrating their social capacity to discuss whatever they want without consequences. I can shitpost because I’ve got enough social capital to do so.

One theory I’ve got is that shitposting is a backlash to Ted Talks, super serious reverential coverage in glossy business magazines, and the proliferation of HBS style “business” books. We’ve had an saturation in performative professionalism.

Once it became unclear that every self seriousness biography or magazine puff piece was placed by professionals to make their clients look like geniuses (visible effort undermines certain kinds of status) the savvy social seeker knew they needed a more authentic way to telegraph in-group power. The next logical step was demonstrating that you were so smart, so powerful and so connected you didn’t even need to demonstrate it. Hence the shitpost.

The weirdest part of “shitposting” being an actual status symbol in venture capital is that a couple of billionaires are going to see me and Alex making jokes about divorced guy energy and this will only increase our status. Which is ludicrous on its face ans yet absolutely true.

This isn’t even a flex on my part (though it obviously is a flex) as it is now accepted that having a following for saying whatever you like gives you a leg up in startups. A friend likened it to “dressing down” or the practice of wearing causal clothing even in formal settings. It shows you are so powerful and wealthy you don’t need to give a fuck about manners. Shitposting on Twitter is like wearing ripped jeans at the country club.

I want to explore this topic in more depth so this post is just some sketch notes. But I wanted to get it down and organized so I hope it’s alright to have some half baked ideas. It’s my blog so I figure it’s fine b