Categories
Emotional Work

Day 494 and A Place to Stand

It took me a long time to come to terms with the idea of investing in a home. I’ve moved 38 times over the course of my life. The constant instability in my childhood gave me the capacity to tolerate a lot of uncertainty. It’s an incredible piece of leverage for living life. But it’s a super power born out of trauma.

Give me a place to stand, a lever long enough and a fulcrum and I can move the Earth

Archimedes

When your normal is starting over again and again, eventually you become comfortable living in chaos. I can achieve a lot things fall apart and life starts anew. It’s why I work with early stage startups. The current market and the volatility inherent in the chaos makes me feel safe.

But there are limits to chaos. I can’t live in it perpetually and make gains without some kind of safe harbor. Otherwise it’s just a repeat of my childhood and I’ll constantly be starting from zero. What I really want is a safe home so I can take advantage of the chaos around me. I want a place to stand so I can move the world. While everyone else is out surviving the chaos I want to have a firm ground under my feet.

The world is going through massive changes and constant upheaval. That’s an opportunity of a lifetime. All of those moves I made prepared me to shine during this moment. But if I cannot have some about of safety, the land on which to stand, then I’ll merely be surviving yet another move. And I’m over that. This time the world moves for me.

Categories
Emotional Work Preparedness

Day 422 and Very Good Care

I’ve been bouncing around a little in the zeitgeist and media frenzy of last few days. I’ve not done a great job of processing the Russian war in Ukraine. I’ve got ambient stresses related to the generally chaotic moment so the acceleration of conflict felt both inevitable and unnerving. And yet we might outrun the apocalypse yet. Doomer optimism has never seemed so apt a term.

I am going to take care of myself during this tumult. This year of self love and affirmation means thriving in the worse situations. Because I take responsibility for myself. I am a victim to no person or circumstance. I control my response to any situation. That is the freedom to live.

But that thriving only occurs when I prioritize myself first. If I can’t parent my inner child through her fears and reactions, than how can anyone else trust that I will come through for them? Mutual trust comes from understanding the motivations in our relationships and what we get from each other. And that starts with being an adult to ourselves.

This idea of emotional responsibility is a simple concept that is surprisingly hard for people. I work on it every week in therapy. Feeling our emotions (often driven by our childhood experiences) gives the capacity to interact with others as an adult. It’s a step beyond professionalism. I’ve found it’s what separates those who are good at the work they do versus being truly great at their profession. The great are present in who they are.

So don’t be afraid to become truly ok. Thrive. Love yourself and your life even when it feels pointless. Even when the world feels crazy. Especially then. You have no need to attack yourself. Remove the self as an attack vector. We do not harm ourselves. The world is hard enough as it is that it needs no help from us. Now is the time to take care good care of yourself.

Categories
Emotional Work Startups

Day 383 and Good at What I Am

Startups are a privilege. You meet people who are exceptional at what they do. Brilliant qualified people who are so capable you could spend your whole life working and only achieve 10% of their innate capacity by natural talent. But the real differentiator is never the talent. It’s the acceptance of who you are. You can’t just be good at what you do. You have to be good at being yourself.

Be good at what you do. Then be good at what you are. Startups require both.

I struggle with this and watch many others who struggle as well. I am brilliant at connecting and amplification but terrible at details and logistics. I used to hate this about myself. I’d beat myself up when I’d get performance reviews that said I wasn’t detail oriented. I thought it was a moral failing. But guess what? It’s just a regular failing. I doubt I’d be great at my actual natural talents if I also had to be good at my failures. Accepting your light means accepting what cast shadows equally.

It’s hard to do. Our coping mechanisms praise us for our good traits and claim full responsibility for achieving them on our own merits. Equally we disown and assume divine intervention or forces outside our control drive our vices. We cannot be responsible for our failures. We only like to take responsibility for our wins.

And I get it. Accepting your shadows is hard. Our parents and our social circles show us who we are supposed to be. Show us what to strive for in the good life. If we are loud we are told to shush. If we are shy we are urged to socialize. Acceptance oh who we are isn’t encouraged. And for good reason. We must push to grow. To become an adult requires effort and work. But we must always remember the ultimate goal in becoming an adult is to become who you are. If you never accept yourself you will never be truly great. And the road is long so start getting good at being who you are.

Categories
Finance Internet Culture

Day 371 and Never Work A Day In Your Life

I had almost nothing on my calendar today I didn’t want to do. I had small administrative things that took up maybe two hours and that’s excessive by my standards. It’s rare I ever have more than half an hour of genuine obligations. Mostly I just go where I feel like on any given day. I lay in bed on my phone and I move the world with strangers on the internet.

I’m not sure how I optimized for this kind of idyllic work life. I certainly didn’t used to live this way. When I was a founder I was constantly at the mercy of meetings I didn’t want and obligations I wanted to shirk. I always felt put upon. I never felt more like hustle culture owned my life than during my founding years. I was constantly optimizing and I felt like I never had any relief.

Maybe it’s the pandemic. Once we stopped with offices and workdays and all their attendant events and activities, life got a lot better. Everyone kind of settled into routines that made space for what mattered most to them. We no longer had cocktail parties or conferences. Thought leadership stopped being keynote speeches and started being shitposts on Twitter.

I don’t know what the fuck I did it exactly to free myself from that over scheduled fate. I’m so much happier and more efficient. I get shit done and I am less stressed and working fewer unnecessary hours.

Maybe part of it is that I might be a better investor than I was a founder. I could spend the whole day skipping through direct messages and sharing insights in Telegram group chats or having product breaksdowns in Notion. I’m actually good at what I do now. I bring more value and I do it more quickly. Maybe this is what real optimized work is like. You are so good it’s easy.

I’m so fucking happy right now. Over the last hour I’ve done more to advance my deals, connect my community and dig into shit that I genuinely passionately love than I thought I could do in an week. It’s like winning the lottery. I cannot believe I make money doing this.

I basically gossip all day with super smart people and then trade a bunch of densely coded social signals. Those all translate into money. I plot elaborate stories with fellow degenerates with deep aesthetics and then we send it into media zeitgeist. It’s like I work in fashion but the pay is much much better. So I guess it is true what they say. Do what you love and you never work a day I’m your life.

Categories
Background

Day 363 and Best Of 21

One of the unexpected benefits of writing every single day has been the accumulation of reference material. I can send folks a synopsis rather than retyping a topic that I get asked about a lot. So if you want to know how I get healthy, or how I invest, or even how I think about aesthetics this page will serve as a reference for year 1.

Health & Wellness

Biohacking 101 Guide

Supplements for Beginners

Self Care & Pacing and Recovery Protocols

How To Communicate with Me

Why I Prefer Asynchronous Communication

Why I Dislike Phone Calls (Or DM Me First)

Getting To Know Me for Founders Seeking Investment

Investment Thesis Thoughts

Empathy Investing

Chaotic Labor Markets

Chaotic Families

Request for Founders

Psychological Safety

Mental Flexibility

Bias Towards Fuckaround

What Don’t I Know?

Why I Don’t Like to Invest In Retail Anymore

Aesthetics

Fashion Week Back in The Aughts

The Thursday Styles Problem

Swag (Or My Facebook Hoodie)

A General Theory of Shitposting

Cultural Hegemony and Internet Citizenship

A Short Guide to Becoming an Edgelord

Advice for Startups

Above All Else Fun

Inertia

Rooting For You

Stress, Luck & Startup Families

The Emotion of A Big Exit (or Stack Overflow Sold)

Show Me Anything

Just Make Stuff

Optimizing For The Right Outcome

How To Work With A Startup

Emotional Growth

3 People Inside You

Punishment

Forgiveness and Failure

Easy for You (Not For Everyone)

Superpowers

My Addiction to Work

Categories
Emotional Work

Day 345 and Trust

I’ve not always been accepting of my own weaknesses. Instead of focusing on how well I can hone my super powers, I’ve occasionally fixated on where I lack innate talent. I’m not particularly adapt at operations or logistics but I feel bad about it. I am however genuinely top tier when it comes to narrative & attention. Somehow I don’t feel equally good about this.

I’ve tried to work in teams where my talents & weaknesses are balanced out by others. I like teamwork now in a way I didn’t fully appreciate when I was younger. I’ve learned to trust my own value. And I am able to emotionally trust the people around me.

The psychological safety that comes from trusting yourself and others is a lifelong process. Even a few years ago I’d struggle to not compulsively overwork to overcome my weaknesses. When I should have been honing my unique talents.

I’ve got an opportunity over the next few days to really trust one of my teams. We’ve got a deliverable that isn’t in my area but I’d crucial to success. I could spend my extra energy worrying over it and making an attempt to contribute just so I felt useful. Or I can emotionally let go and appreciate the trust I have in others.

Categories
Emotional Work Internet Culture

Day 208 and Boundaries

It’s fairly common to struggle with boundaries. The desire to come through for everyone is strong, but not half so strong as the fear that if you set a firm boundary, then no one will accept you for where you are and what you want. What if love is only ever available on someone else’s term? This is a terrible fear straight from our inner child.

We’ve turned loyalty into a obligation test. But how perverse is that? “If you love them, set it free” is a culturally touchstone for a reason. We want the freedom of choosing our the loyalty that works for us. And we know each demonstration of loyalty means nothing if it wasn’t in consideration of the other person’s boundaries, needs and desires.

I suppose this hit me today because I’ve been astonished to see athletes like Naomi Osaka and Simone Biles holding their boundaries firm. They loyalty to sports, their countries and to us as fans only matters if it’s given freely and with joy. They owe us nothing, so when they do perform as their most elite selves, it’s what’s most beautiful and courageous thing. It’s a feat without ego. Those victories come in freedom.

Prioritizing one’s boundaries and well-being doesn’t need any apology or explanations or attempts to change yourself to fit another, if someone requires obligation on their terms it’s natural to feel invaded.

It’s the most loving thing in the world to set out what you actually want and need. It’s always the right thing to do. We don’t own each other. We each get to choose what’s best for us. And that fear we won’t be loved if we stand firm? Let it go. We always feel safest and most cared for when we know what we are offering is genuinely wanted.

Categories
Emotional Work Startups

Day 174 and Easy for You

I’m not normally the type that reads business books. I’m pretty disinterested in management techniques and organizational structures because I suck at it. And I bring up sucking at MBA style topics because as I was doomscrolling I came across an older article from the Harvard Business Review. The headline was “why do talented people not play to their strengths?” I clicked.

It begins with fairly standard case study chit chat about the NFL and I’ll admit my eyes glazed over. Why had I bothered to click when I’m so not the business school type. And then I spotted a nugget that rang so true I swear I’ve got a little tinnitus from the “ding ding ding” bell that rang in my head.

We often undervalue what we inherently do well.

I’ve written in the past about my struggle to accept things that come easy to me. I have had a self limiting belief about the necessity of struggle and it’s inherent morality. Maybe I’m rationalizing pain and hardship because emotionally I need there to be a “why” for having fought through a chronic illness. Surely suffering through and taming a spinal disease has made me a better person right? Or maybe shit just happens.

And maybe I’ve been downplaying all of the many super power and talents I have. I’ve spent so much time grieving the loss of the hard things like working long hours and always hustling that I’ve been ignoring that i can win doing things that feel easy. Because they might just be easy for me but not easy for everyone. Quoting the article.

Often our “superpowers” are things we do effortlessly, almost reflexively, like breathing. When a boss identifies these talents and asks you to do something that uses your superpower, you may think, “But that’s so easy. It’s too easy.” It may feel that your boss doesn’t trust you to take on a more challenging assignment or otherwise doesn’t value you — because you don’t value your innate talents as much as you do the skills that have been hard-won.

Working long hours were always hard for me. I fought to stay up late because I would find myself fatigued and in pain. I really valued that because it hurt me. It was hard for me. Whereas I never valued being at being ahead on news and trends, or my facility at gaining media coverage, or how easy I found it to spot when the market was going to move. I distrust the skills I can do effortlessly.

But I realize now that those are valuable skills. It makes me a good investor, especially in private markets where seeing where the market is going and alerting people to potential is very well remunerated. So next time you scoff at a compliment from somewhere on you work ask yourself if what you did is easy or just easy for you. You might be surprised to find you have a superpower you never noticed.

Categories
Aesthetics Chronicle

Day 116 and Taking Up Space

I take up a lot of space. I spend time on social media because there is so much space you can literally be the President or a celebrity billionaire industrialist and there are still corners of the web you don’t penetrate. There is a lot of room for loudmouths, so much so that even someone like me still has plenty of room. I barely rate on the Elon Musk attention scale. Even when I’m screaming at best I crack into D-list zeitgeist. It’s like the privacy that comes with living in New York City. You can have some notoriety but the web doesn’t care. I like how you can feel alone.

The irony of course is that I think no one is paying attention to me. I think I’m an average Joe nobody that no one ever notices. This despite the fact that I am paid to be an expert in getting attention. No literally I cost a fortune (I’m worth every penny) but I’m somehow convinced I’m invisible personally. I can feel lost in a lonely world where I’m not even sure the people that love me the most can see me. I’m stuck in some lonely portion of my childhood where I felt abandoned so I’m replaying it out now as an adult. It’s not great but I get something from it.

Except this is a fantasy that is not true. I’m not that child anymore and I know how to get attention. I’m not alone. Even when I’m not consciously drawing energy to myself, people do see me. I can simply be myself and be seen. I command attention. It’s who I am.

You always think as a kid you will get some cool superpower like laser eyes or flying but nope you are going to get a super power like public relations or brand marketing. And honestly, when I’m not a self pitying victim I know those to be awesome super powers. You can make money and direct business and politics with those super powers. I just though I’d get something a little more aesthetic you know? It’s dope but also like adult superpowers are a letdown for your inner child.

I just need to remind adult me that I am seen. That even my normal personality not exerting her will force onto the universe is actually still quite visible. I can just exist and I’ll be holding space for myself. And it’s a good space with plenty of room for all of me. And still intimate enough to feel the love around me.