Tag: Workaholic

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Finance Internet Culture

Day 1001 and Circumstances Change, People Do Not

“The last sustainable edge in markets is arbitraging human nature.”

I had the good fortune to spend an hour and a half with an iconic Wall Street investor last week. I was invited to be a guest on Jim O’Shaughessy’s podcast Infinite Loops. I felt like the luckiest woman in the world.

I’m blessed to have Jim as one of my “Twitter mutuals” where I’ve come to appreciate his endless curiosity, deep empathy and kind friendship for the players of the “infinite game” of life. Plus he’s got the strongest gif game in the business. You should follow him if you don’t already.

I’ve been privileged to work with Jim and the OSV team as one of my LPs in chaotic.capital. Being entrusted with capital from some of finest minds in investing has been as intimidating as it is inspiring.

My fund is an early stage pre-seed venture fund that backs weirdos. Our thesis is simple. The world is increasingly complex, chaotic if you will, and only the most agile will win. We look for those that have the agency to adapt to the one true constant; change. Circumstances changed by the moment but humans remain reassuringly the same.

Obviously it’s hard to imagine a better LP than OSV for chaotic.capital. We are deeply aligned in our thinking on agency, agility, and adaptability. As much as I’d love to prattle on here, I’d recommend you check out the very wide ranging conversations between Jim and I. We cover a lot of ground practically and philosophically. I hope you enjoy it.

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Chronic Disease Emotional Work

Day 931 and Open Calendar

I am about to sunset a long-standing weekly appointment that has been on my calendar for literally years. And I was surprised to discover how much getting back that time made me happy.

The block on my calendar was for something I very much loved doing and valued highly, so the sheer joy was unexpected. But as it turns out I loathe having a consistent obligation on my time.

This isn’t to say that I don’t like being responsible, reliable, or on time. But rather I like knowing if something comes up that I have some flexibility. And I don’t like to disappoint people by needing flexibility.

My suspicion is that this represents some lingering guilt I have about having a chronic disease. While I rationally know that I did nothing to deserve being sick, I do carry a self limiting belief that being sick is a weakness.

I’ve always prided myself on being a “mind over matter” person. I’ve shown up to countless events, meetings, pitches, and other obligations while in pain. I’ve been known to repeat “Michael Jordan, Game 5” as a mantra to remind myself that I can perform in even the worst physical circumstance.

Michael Jordan famously played and won with the flu. And the logic in my mind was surely I can do the same when something is on the line. So I always have. If someone expects me to show up and perform I do it even if I am struggling.

But as my season of no has begun I think it’s time I stop romanticizing my capacity to work when sick. I love having my time back on my calendar and I love the flexibility that I have to work whenever and wherever I want.

Maybe some people would chose to work less under these conditions. For me though, having more flexibility in when I show up means I’ll find even more time to put into my work. Because I love showing up for me. And sometimes it’s easier for me to show up when it’s not a damn calendar block.

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Biohacking Emotional Work

Day 873 and Commitments

I have two conflicting commitments at the moment. Both are with people who I’d consider intimate relationships with as much access to my inner life as my closest confidants.

I made the decision to show up for both parties last week and this week. And while I don’t regret my decision at all, the choice has had consequences. I am accepting them right now. I’m in bed and in a fun spiral of inflammation. I’m in pain, and even more annoying, I’m fucking itchy as hell. My biometrics are screaming red across every dashboard from Whoop to Welltory.

The irony, of course, is that in being so committed to showing up for others I failed to show up for myself. I didn’t know what I wanted so I did everything I’d obligated myself to do.

I can’t blame it on anyone even though it’s so easy to consider the ways I can rationalize my choices. I’m committed to good and useful things that improve my emotional fluidity and contribute to my personal growth.

Being committed to others means being committed to yourself first. The better I maintain my boundaries, the more I can show up for someone else. Knowing what we want, asking for it clearly, and being accountable for the actions you took is the whole ball game. Everything else is details. And I bet you can manage that.

I am committed to myself as I’ve got to rest and get myself under control or else I’m not being accountable. And I’m not a victim to my circumstances. I chose this.

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Medical Travel

Day 833 and Industrial Romaine

I packed my day a little too full so I found myself ordering a salad from popular New York industrial salad chain Chopt at 8pm right as they closed.

The order was placed on an app so it was a crapshoot and I knew it. And sure enough I got something that wasn’t what I ordered but I’d been running around for 12 straight hours so I just said fuck it I’ll eat this weird burrito of industrial romaine and mayonnaise because I’d really rather be passed out.

Incredibly poor decision making on my part. I was up early and I was up often performing ablutions and praying to the gods of intestinal fortitude that this please pass swiftly.

I appear to have stopped with the worst of it and had about an hour or so before a meeting I really didn’t want to cancel. It’s not as if food poisoning is catching. So I groomed and put on something that would withstand the 88 degree heat of…checks notes… early April in Manhattan? And then I got on the subway.

Shockingly heat and the subway aren’t a great combination, but I was determined to gut it out. I’d left early so I could find my way to a drug store. Naturally nothing was available to purchase without someone unlocking a cabinet. Nothing more humiliating than asking if one could have a key to acquire GasEx, Tums and Imodium. A really stellar look all around.

I’m now comfortably in a lovely office of a venture capitalist hoping it all kicks in before I need to attempt socializing. Naturally I’m taking the time to write about it as I wait as it’s keeping my mind off the discomfort and misery of it all.

This isn’t the first run in I’ve had with agribusiness greens that’s gone awry for me. Many moons ago I got food poisoning from spinach I bought at a Trader Joe’s. A few blocks from where I am now. I had Gucci insurance (literally Gucci the luxury house I do not mean that it was particularly fancy) and spent the night in the emergency room. So maybe this is just a full circle experience. Ashes to ashes romaine lettuce to romaine lettuce to romaine lettuce.

I can feel the drugs kicking in and maybe I’m at the end of it. And hopefully this will just be an amusing anecdote that I recount on why we need to be more careful with food safety and industrial run off. But also I am loathe to cancel a commitment during a business trip. Showing up matters too.

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Emotional Work

Day 775 and In and Out

I am a bit overclocked. I’ve written about it before and the language is useful so I am quoting myself to remind myself what needs to be done.

It will just take some time to let all the cortisol spikes drain out and the other sundry overstimulation issues to get back to baseline.

I am thankfully not experiencing any of the typical anxiety I have felt in the past when overclocked. I just feel tired and shitty and like I need to had off some of inputs to my team.

I’m noting this all here and keeping it short as I need to get in and out so I can get back to the business of recovery as I have so much to take advantage of in my life right now. And the only way I can do that is continuing to maintain the routines and rhythms that got me to this good spot in the first place.

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Emotional Work

Day 707 and Self Discipline

In case it’s not readily apparent from the fact that I’ve written for seven hundred and seven straight days, I am very good at personal discipline. I can will myself to do almost anything. But this gift gets tangled up in negative emotions easily.

Part of this internal sense of discipline is the very clear set of norms I got as part of gendered expectations for good womanhood. You must exert ownership over yourself. Because without doing so, you will be unable to do the work that is expected of women.

You just discipline yourself to serve others. Because women must put other people’s priorities and schedules ahead of their own. Women must be accommodating. Women must be nice. It’s all a very careful training to insure you’d never consider stepping out of line. At it starts at self discipline.

Deviations like weight gain or chronic tardiness or looking unkempt in public were roundly censured in popular culture. I internalized all the ways in which I needed to be constantly improving, fixing, bettering and otherwise making sure I was showing up as others wanted me.

I am slowly unraveling the ways in which this has shown up negatively. Now as I try to unlearn my own obedience I find unproductive ways to rebel.

A small list of the ways this manifests. I hate external deadlines. If someone tells me I must deliver by a specific time I get anxious. If I have a morning appointment r my body wakes regularly through the night to check that I’ve not missed it. Calendars and schedules evoke feelings of despair that go back deep into my childhood. I’ve clearly been learning and unlearning this pattern for sometime.

I am deeply grateful for having discipline as a friend in my life. I have excellent habits in many areas because of it. But making it a true friend will take more time. It’s one of the hardest pieces of shadow work I’ve ever done.

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Emotional Work

Day 703 and Day of Rest

I love a good Sunday. I love a good Sabbath. I love a stolen afternoon away from the demands and observations of the wider world. Getting away from it all, even if it’s a just a few moments stolen away from the world for a private reflection, is in fact a great gift.

I’ve got a tendency to engage in unproductive self talk when it comes to relaxation in particular, but more generally with feeling like I can take time for myself. I’m sure this is a relatable trouble in the hustle bound addiction driven workaholism of startup land.

The guilt I feel about being unproductive overshadows the enjoyment of necessary restorative activities. I’ll “should” on myself. My ego protection insists on it. But I am trying to stay in the adult portion of my mind which can remind my inner child that it’s alright to have a little fun.

And I did have a little fun today. Not because I engages in any hobbies or particularly exciting fun activities. I just took care of myself. I lifted weights. It was leg day so maybe that counts as fun. I took my once a week extended shower where I scrub, exfoliate, shave and condition every applicable inch of my body. Obviously I’m not shaving my head use common sense. Then I spent 90 minutes immobilized a foot masks. No winter feet for me! I meditated. I did some heat therapy. I used the Theragun. I got a little bit high and ate lunch. I took a nap.

I am feeling rested and happy about the entire day. How nice that I was able to enjoy being in my own body. How nice I could take enjoyment from something restorative. Yes I want to justify it with promises of added productivity to come. But it’s ok to just enjoy the pleasure for the thing that it is. Enjoy your life.

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Culture

Day 698 and Looking Ahead

I’ve got the sense that people are writing off big chunks of time. The long now has so thoroughly burned out everyone that who cares about achieving anything in the medium term right? December is a wash. Heck I’m talking to folks who have wrote off all of 2023 and even into 2024. The now and the long term are all that matters.

And I’m actually quite amenable to this viewpoint. I’ve still got to get things done before the end of the year. I’ve got fundraising to do and deals to close. I’m excited for how 2023 will go as a down market is a builder’s market. But I understand the frustration with trying to plan ahead when everything feels like it is crumbling. The medium term feels like a sand trap sucking in your attention and emotional energy.

It takes a guts to walk through a dark valley of despair. And we’ve got a lot to feel despairing about at the moment. But just because it is all doom and gloom doesn’t mean we’ve got no reason for optimism. People are resourceful and humans as a species are shockingly good at problem solving.

So I guess what I’m saying is I’m feeling good about looking ahead. Maybe it all takes longer than I’d like. But maybe it stops me from engaging in brute force efforts that are going to burn me out. We all just need to keep putting one foot in front of the other.

Categories
Startups

Day 688 and Hardcore

My generation of founders came of age during the peak of hustle porn. We were young and dumb, and even without the use of stimulants and nootropics like our Gen Z younger siblings, we got a lot done. Probably because we were well young and dumb. And it’s easier to do things with brute force when you don’t have better tools. Being hardcore made sense for some of us.

Alas if you burn the candle at both ends you may find yourself with an astonishing array of healthcare issues in your thirties. Which is astonishingly common in my cohort. I’m just one of the rare examples that is public about the dangers of overworking yourself. Hustle porn’s legacy is mixed. We lost founders to workaholism and occasionally much worse. A generation learned that mental and emotional health are just as important as physical health.

Hustle culture coincided with a lot amazing companies getting built but it’s not entirely clear to me if being hardcore is the only factor at play. Tempting as it may be to look for simple mono-causal relationships in life, the math of success is never that simple. Life isn’t an engineering problem. And even if life was an engineering problem, applying more force doesn’t solve all problems. It might even make a few worse.

I don’t want to knock hard work obviously. Im a firm believer that the basics never go out of style. Hard work is a given. Most of the greats are working hard because once you discover you have a natural talent then maturity generally encourages you to hone it.

Success is built from many fathers even if it’s mother is hard work. Proper resourcing, adequate incentives, teamwork and an effective hierarchy of respect within it are all factors. And let us not forget just plain old good luck matter just as much as being hardcore.

So tempting as it may be to give in to Twitter discourse narratives don’t get fooled into thinking someone that is successful has it all figured out. You don’t know what it took to get there and who brought it together. Don’t overweight success on its own. Nothing is ever that simple. Expect that the team you want to be a part of will demand that you demonstrate all of the above virtues and along with the necessities of hard work. But if it all comes together it is worth the sacrifice.

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Emotional Work Finance

Day 680 and History Repeating

I found myself crying my eyes out to my therapist this morning. Just full on sobbing. Nothing bad actually even happened to me during this week’s chaos. In fact, I’ve spent the last year or so preparing Alex and I for a downturn. I wouldn’t be much of a doomer if I didn’t swing into this downturn prepared.

It just all felt too familiar. It felt like the worst days of fear and insecurities from my childhood playing out all over again. My family went bankrupt during the great Web 1 unraveling. And I’ve never forgotten it’s lessons.

I remember feeling like I was in a secure situation and then learning in dramatic fashion that it was all gone. That all the hopes, dreams and aspirations that my father had done so much to prepare me to reach for (including a lot of very expensive colleges) would likely be out of reach. We’d be starting from scratch again. I hadn’t really had a lot of time to enjoy being a poor little rich girl. It was over too fast.

My father is a truly entrepreneurial man. When I was born the family lore is that he was pitching a edtech company. We were a startup family. We lived in Fremont which is (was) the shitty poor town. I suspect it was a lot harder than I even remember.

But dad found a way to realize his Silicon Valley dreams. He brought software to millions of people. He really did do the thing. And for a few years during the boom times it felt like we might be wealthy forever.

But finance is tricky. Lock ups can fuck you up. So can leverage. We had both. And then of course regular old fraud happens too. Yay.

But it wasn’t in vain. I learned those lessons well. I swing big and I bet on the future like my dad. I believe in people and in genius. But I also keep a balanced portfolio and back up plans.

I believe in exponential growth. But I also believe in the cost of capital. Sometimes money is cheap. Too cheap. And you need to prepare for when capital is expensive again. Because the laws of physics tell us that energy cannot be created or destroyed. And until someone smarter than me proves the laws of thermodynamics wrong, I will operate based on them.

And I am ready for the dark days. Both because it is literally November but also because I believe we’ve got chaos ahead. And if I’ve learned one thing from my childhood it is that you can survive it. It just takes a little bit of preparation. Which I’ve done. Everything else is just a case of history repeating.