Tag: Work

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Emotional Work

Day 310 and Short Burnouts

Is it possible to have brief periods of burnout? I’d always associated it with the years on the other side of a startup. If you’ve put in long hours for an extended period it makes sense to have a year or more of recovering from dipping into reserves for too long. But I wonder if it might be possible to have a week of burnout from a couple intense months.

I wrapped a few big projects last week. It was easier than anticipated and I felt a real sense of joy and accomplishment. But then this week I was a bit of a mess. I had several days of terrible sleep. Then I burned my hand making breakfast. Fun fact blisters are a form of burn, which finally made sense once I experienced a real burn as it’s healing looked exactly like a blister you get from a hiking boot. I’m feeling a sense of overwhelm with the drumbeat of preventative care and appointments that comes from 20 months off from things like dentists. I just felt like I got nothing done that was important to me this week. It was one thing after another. And it seems like others are feeling the stress as well.

Maybe it’s alright to have a week of feeling unproductive. I was very on for all of September and October and then I wrapped some stuff so it’s possibly normal to feel like all focus and willpower has gone out the window. But the temptation to force a fix on it is quite strong.

I’ve got a habit of turning everything into an opportunity for self improvement. I’ve been concerned about my capacity for using self control as a way to abuse myself. It’s been a running theme that I find myself concerned about the work that goes into keeping myself productive and healthy. So maybe it’s just par for the course. But I’m already worried about next week as I’ve got 4 fucking doctors appointment including one that involves a long drive. Maybe there is never a world where productivity is easy to come by and I should let go of the worry. The days are short but the years are long. And progress compounds over time.

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Emotional Work Politics Reading

Day 306 and Shortcuts

I never really thought of myself as a perfectionist. But I have impossibly high standards for myself that may be unproductive.

While I’m sure some of it innate, some of it is nurture. I went to a school system called Waldorf Schools that didn’t have grades. Every child was evaluated against their individual performance and each class was deliberately taught to the best student in the class not to some perceived middle. That’s left me with a habit of always believing I can improve and also the expectation that our average performance must be comparable to the best.

Of course this is unrealistic if one continues to climb up social, economic, intellectual and cultural ladders. I kept looking for my limit and then finding a new mountain to climb. Know I know there will always be mountains. And that perhaps it’s ok to take some shortcuts on your journey.

I really struggle with shortcuts. So am forcing myself into taking some so I can let go of some of my impossible standards.

I don’t scan books. I read them. So I bought a really bad prepper novel and am forcing myself to take shortcuts in pacing and focus. It’s so bad I don’t have a choice. I have to skip a lot or else I just wouldn’t finish.

I had to go to an appointment today. Normally I’d be sure to shower and wash my hair if I need to be in polite company. I showered yesterday but I just didn’t feel like going to the trouble two days in a row. So I put dry shampoo in my hair and opened up weight wipes for my nether regions. I doubt anyone would have noticed but a shortcut in my grooming routine was pretty liberating.

Today is also Election Day. My hometown has a bunch of local ordnance changes and some important bond related measures. It’s also city council elections. I’ve been following all the ballot issues but I just couldn’t find any city council people I liked. I read all the local papers and they all suck. None of them remotely come into my preference wet. So I took a shortcut. I voted on all the ballot issues and left the city council blank. I just wasn’t going to spend any more time picking lesser evil candidates.

These may seem like pretty different issues and maybe I’m also not fully committed to my civic duty (I’d argue as a democracy it’s a right to abstain from a vote if your conscience cannot condone it). But the point is that instead of getting bogged down in every unrealistic expectation I had of myself I could just take a shortcut.

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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.

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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 Politics

Day 294 and Allowing Help

I’m extremely uncomfortable having help with my home life. I’d say this is the surest sign that I wasn’t raised in the upper class, but I did have a nanny when the first tech boom hit so I can’t claim it’s a new experience. It’s not as if I’m adapting to having the money to hire help for things like cleaning, cooking or household help. Twelve year old Julie had a lot of privilege.

In fact, I think it’s a great use of resources to have someone who is adept at these tasks do them instead of me. Everyone has different skills and abilities and mine are not logistics. People should absolutely trade their time in the ways that they prefer. Capitalism gave us labor specialization and I love the benefits. You wouldn’t want me running operations for anything.

No, the thing that troubles me about hiring out for help in the home is that I’m uncomfortable around other human beings for long hours. I know this sounds like some sensitive white lady shit. You can peg me for that. But it’s more than just being a soft bitch. I’m genuinely nervous around people in a way that I don’t think I’d normal.

Too much time socializing stresses me out. If I have to smile, make small talk, and be conscious of my interactions I find it draining. You’ll see it in my biometrics too. On a day where I go to a doctor or have an extended period where I am one-on-one with another person my resting heart rate goes up and my HRV goes down. My Whoop records a higher strain score. I want to blame this on the rational concern for physical health as I have an autoimmune condition that puts me at higher risk. But I think I’m just less capable with people than others.

This has made me reconsider the calculus of whether it’s always logical to outsource tasks to make time for work whose time value is dramatically better. That logic makes it clear that all activities can arbitraged for more value. But what if some things you suck at make you happy? What if some things you are bad at are less stressful than things you are good at. Some people move to cook but have no talent. Some people are amazing at jobs they hate. If I really find that people around people is using up valuable energy maybe I should do it myself.

I think it’s possible we might have so thoroughly skewed our human values to economic gain we aren’t even sure where to spend time for joy. Which I realize is a really ponderous way to look at paying someone to clean the kitchen. But aren’t we all reconsidering what valuable in our lives?

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Biohacking Emotional Work

290 and Self Care

I’ve feel like I should have an entire category on the blog dedicated to “maintenance” as I’ve got loads of posts on my struggles to balance the activities of staying alive with well, the rest of my life.

All of the activities that go into keeping a human alive and functional are so damn time consuming. How does anyone ever get anything done when so much of life is dedicated to keeping our meat sacks from spiraling out? I’m pretty sure these are the things that actually make up life and I’m supposed to treasure this time in my body. But until I become as enlightened as the Buddha, I feel like this whole embodiment thing is just getting in the way of what I should be doing. My therapist likes to call this “human doing” instead of “human being” and I don’t love the joke.

I had a terrific day of doing things this Sunday. I woke up at 7am and didn’t finish all of the various routines and self care activities till 1pm. I went for an hour long walk (which is pleasurable since sunshine and mountain air but also low impact cardiovascular activity) I lifted weights (alright fine, I love squats). I meditated (mindfulness doesn’t count when you quantify it). I showered, shaved & washed my hair. I did the grocery shopping and meal planning for the week. I did three loads of laundry. I made lunch. I cleaned up. I juggled supplements (I’ve got a spreadsheet to track them all with 8am, 10am & 11am slots) which are completely separate from my medications (I have 7am and noon spots for those). And only then at 1pm did I finally get a chance to settle into work. There was so much work just to get to work.

And while I know all of those things that keep me balanced and healthy are the stuff of life, I also resent their necessity. I have elaborate fantasies about what other people get done with their time. Other people don’t need to exercise, meditate, take vitamins, or watch their nutrition right? Well alright I said it was a fantasy. If you also spent your Sunday doing chores and self care it would make me feel better to know that.

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Internet Culture Politics Preparedness

289 and Apocalyptic Aging

Millennials are aging, but that doesn’t seem to have kicked off the midlife crisis handwringing of popular culture yesteryears. The first millennial are edging towards 40 but it feels like no one is a day over thirty on social media. Maybe because it’s hard to feel like you’ve hit midlife when the traditional markers of stability like children and mortgages feel more like luxury status symbols.

Maybe no one is craving red sports cars and the open road because no one has the security of a home life from which to break free. A midlife crisis seems like an almost comically indulgent thing that our boomer parents did. Imagine having kids and a home and thinking that you wanted to go back to the insecurity of your twenties? And boomers have the balls to call millennials spoiled. You had to have have stability to throw it away first.

I’m an elder millennial and a reasonably comfortable even wealthy one at that. But I don’t have kids or own a house. I frozen my eggs when it seemed like having kids wasn’t financially feasible. My husband and I lived in Manhattan at the time and we both had early stage startups. It seemed like a wise idea to put off the decision at the time. And we never even considered buying an apartment. Tying up all that wealth into a one bedroom apartment was for trust funders not the professional class.

Now it’s clear we can afford children and a mortgage on a house, but it seems crazy to commit to either. No one has a clue what life is going to be like in ten years so why would you anchor yourself and innocent progeny? It almost feels immoral to consider.

I don’t really understand how one can age gracefully when so much of life feels casually apocalyptic. Maybe millennials aren’t acknowledging aging because we live in the stasis of the long now. If there is no future then we aren’t moving into it. Each passing year is just a lucky bonus when nothing builds towards stability.

Not being able to afford children and houses is a blessing if you don’t believe in the future will be better. We’ve rationalized that the basics of the American are luxuries only for the wealthy. The wealthy can afford to live with rising tides and six figure college tuitions. Everyone else is thrilled to have enough cash to buy prepper supplies and pay their health insurance deductible.

And in some horrifying sense it is rational. I don’t trust the political system in America. Which means I don’t trust we can solve pressing issues like climate change or rising debt. So when new and exciting issues like the pandemic destabilize life even further it makes committing to a future even less appealing. There is absolutely a part of me that stopped believing in the future sometime in 2016. Everything went Hobbesian. Millennials are aging but we aren’t growing into a future.

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Internet Culture Startups

Day 282 and Stop & Go

I wasn’t born until after stagflation so I can’t tell you what America or Britain felt like in the 70’s but the chattering classes seem to enjoy bringing up the comparison. But there does seem to be a bit of “stop & go” energy in the air. Everyone is raring to go but the energy cannot quite flow freely as we smack into obstacle after obstacle. Demand is pent up but the reality of supply is uglier.

Obviously this perspective of excitement and demand is colored by working in startups where the bias is always towards the excitement of building new things. Crypto is burning with the fire of millions of zealots, all of whom are confident we are building the infrastructure for a better future. Everyone feels like it’s worth investing and higher prices are a good sign. There is more go than stop here.

Of course, I am one of those zealots. I’ve got the optimism of someone who saw how fast previous waves of web1 and web2 changed my entire world. Wealth and creativity was unleashed twice over for the elder millennials who were lucky enough to witness the dot com boom as children and the social media era as their first jobs.

There were massive crashes and financial implosions too. Stop more than go. More of us got hurt than got wealthy. But we saw the possibility even as failure engulfed most of us. So we believe we might be the lucky ones this time. That we might be the ones to win the game. “Red light, green light” seems fun if you can make up ground when everyone is running. Just don’t get hurt too bad.

I feel this energy in my own body. I am excited to push into everything. My portfolio companies are all riding high. There is no way I can do it all in any given day. So when the go energy pushes me sometimes I find myself leaning into stop and simply taking a nap in the middle of the day. It makes me a little jittery to feel the push-me-pull-me of demand grind up against the limited supply of energy and focus. I’d like to feel fully unleashed but I know somehow there are moments where it’s best to stop before I go.

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Emotional Work

Day 278 and Overshooting

I have been feeling terrific. That means I’ve been able to do a lot more. But it’s also one of my tendencies to overshoot my capacity. Workaholism, like any addiction, is something I’ll have for the rest of my life. Being in recovery for it means recognizing I could relapse.

I feel a bit of that overextended twitchy feeling at the moment. That jittery adrenaline fueled vibe that proceeds a crash isn’t something I’ve allowed myself to feel for several years as frankly I was worried I’d go on a bender. A bender for me is perceived as societally approved. Look at that work ethic!

So this is me recognizing that I feel like I could go over the edge and I’m not going to do it. The temptation I had to find something to prolong the adrenaline of my winning work streak is heavy. I have a number of topics I’d like to write about today. I’ve got to do lists with tempting targets. But I’m not going to overshoot. I’ve written my paragraphs. I’ll tag it. I’ll send it out into social media and then I’m going to watch some trashy tv. Hold

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.