Categories
Emotional Work

Day 842 and Sucks to Suck

A lot of folks are suffering right now. And I’ve got all the empathy in the world for just how rough it is to live in this modern moment. So I want you to really hear what I’m saying knowing that I do it out of love.

It’s sucks to suck

I’m currently sucking at a bunch of stuff in my life. Because I’m learning new skills and expanding my horizons. I am just sucking big hairy balls as I go about the process of embarrassing myself becoming competent through failure.

Thankfully I am surrounded by a family who loves me and wants me to improve. They don’t mind if I suck because sucking is the first step in success. If I don’t suck at something I’m probably not pushing myself to learn. And just because I’m afraid of sucking is no excuse. Everyone sucks sometimes.

And I get it. It sucks to suck. I hate how uncomfortable it makes me feel to fuck up. I am regularly failing at lots of shit on what feels like a daily basis.

And I do often want to crawl into a hole and stop doing new things so I can enjoy the feelings of power and competence at things I am already successful in.

And yet I don’t want to stay in my comfort zone. Even though I am intimately familiar with how much it sucks to suck. I hate the feeling of having not tried even more. I’d rather shoulder the risk of the fuck ups than live with the crushing anxiety of not shooting my shot.

Because more than it sucks to suck, it really fucking sucks to not even try. It eats away at your soul. You wonder if your life could be better. And I am here to tell you yes it can be. My life is fucking awesome right now. And it’s awesome because I tried. I spent a lot of time being embarrassed.

I didn’t get everything I wanted. But like those damned boomers said, you might find that you get what you need. So go ahead and suck. The path to happiness is on the other side of it. Don’t give up just because it sucks to suck.

Categories
Startups

Day 816 and S Tier

I fancy myself as someone who enjoys playing games. I mostly play the great game but I enjoy a good stupid grinder. Pokémon Go, Duolingo, and Fitocracy all appeal to my sense of hard work mattering.

But, of course, games have exploits. Some of them are significant. Sometimes leveling up is just a matter of getting lucky. A side quest dropped you an s tier item and the game engine smiled on you. Yay!

Silicon Valley mistakes luck for skill pretty regularly. And we don’t take it that well when other people use the same exploits as us because damn it that’s just not fair!

So rules tend to get rewritten and the hacks get patched and the economy in grinder games reliably defaults back to rewarding repetitive work. It’s not that different from the real economy. Gamers want to know clever game play works but not as much as they want to keep the value of what they have earned. It’s a real tension those sunk costs! Even if starting over benefits you the tendency to cling is understandable.

You’ve got to know when to spot when an activity is worth more than the general perception. You used to have to do this sort of work on your own but thanks to the internet we’ve got cheat codes literally everywhere for everything.

Don’t confuse the fact that cheat codes work for the fact that grinding came be the right approach for the game you are playing. Sometimes putting in the work means being a team player is valuable. Sometimes you are the glass cannon. Sometimes your style of play will offend others. Don’t take it all so seriously that you cannot stomach making a move. What’s the worst thing that happens?

Categories
Internet Culture Media Startups

Day 815 and Kayfabe

Here is a mindfuck for you. Pretending works. The mimicry of the thing occasionally, though not mostly, can lead to having the real thing. Fake it till you make it” works if you’ve got a long enough runway to allow for take off. If you’ve judged the resources correctly is more art than science but you should still be able to do the math.

There are, of course, laws of physics to account for in all of this but your reality is more fungible than you realize. I wouldn’t try manifesting a whole fantasy world, but if you are Brandon Sanderson you might have a shot. That guy rocks.

In discussing whether it is better to fire founders or product managers on Twitter today I got to see a lot of the cargo cult culture of Silicon Valley coming off a high. A lot of people can perform innovation and we’ve maybe even got it down to being well liked by financial markets. But sometimes you actually do have to go and do the thing. And you can’t fake it.

If you aren’t familiar with kayfabe, it’s a term used in wrestling. It means you don’t break character loosely. You keep the secret even if everyone is in on it. You can take things a bit too far and the blending of fiction and reality has now given us a reality tv president.

But what happens when you don’t make the jump? Does reality crash in? Will the market punish you for not delivering on a convincing enough value proposition? Do you have to keep your ambition within some scope that can exist in our agreed upon reality? Yes of course. Fuck you it’s called civilization. But every once in a while someone goes from vapor ware to the Revolution. Don’t be so sure you can spot the difference though. Kayfabe doesn’t just fool rubes.

Categories
Emotional Work

Day 809 and Powerful

I’ve been through the gauntlet over the last month. And despite the nauseating rollercoaster of it all, I feel powerful. I am happy that I’ve drawn upon who I am and the boundaries required. It’s been liberating in a professional capacity but I can also see how my personal life got bigger and better as well.

The future is looking as uncertain as a Paul Atreides without the spice. I cannot see how it resolves. I see only hard choices and responsibilities both individual and collective. And I feel ready to hold my ground on what I contribute. But I will be holding others to theirs as well.

We’ve got a long ways to go. Many people do not wish to see things as they are. Issues both material and social are gripping America and by extension the world as the dollar hegemony comes into question over powerful institutional distrust. The power that comes in holding your gaze on what it could all mean and not turning to panic in fear is immense. I am not turning away.

I hold the knowledge that I can do everything right and still fail. I have faced the no win scenario. The Kobeyashi Maru of it all is that sometimes we lose. And we will feel it. And those feelings matter. But then we shoulder the burden and do what needs to be done. The only one who can save you is yourself. And I chose to see the power in the hard choices.

Categories
Aesthetics

Day 793 and Pretty Skills

My mother has always had a gift for aphorisms. I am grateful she has this talent as I’ve been able to simply repackage her wisdom and look much more talented than I actually am at delivering pull quotes. Brevity is the soul of wit and my mother is very witty.

One of the pithy witticisms I believe I learned from her is a classic take on beauty and class being more fungible than we are led to believe.

Pretty is a skill set

Me and/or my mother

If you’ve ever hung out with a bunch of rich girls and wondered why they are all hot consider the dilemma solved. It’s a skill that is cultivated. Like any skill you cultivate or with time but also money. And if you are rich and white the path to beauty is a lot shorter than you might realize. It’s pretty fucked.

I’ve been lucky enough to cultivate this skill set over time. I’ve come to rely on it as part of my arsenal. But I’ve also got a bit of a cranky body so I’ve not always been able to consistently practice the various skills required.

And sometimes life just gets in the way. I look like a fucking mess today. After a week cooped up in an air conditioned room in Mexico with trips outside for slightly traumatic family emotional bonding, I look like shit.

My hair is unsettled and popping off static electricity. I’ve got small pimples all across my forehead. I’ve got patches of eczema on my right chin. I do not appear to have the skill set for pretty today.

Normally I do my best to hide in these circumstances. Especially if I don’t trust someone. I don’t like looking like I lack skill when it comes to presentation. And it is often a sign of respect to look well groomed and beautiful.

In fact, today we’ve got a houseguest that normally I’d feel required to be at full skill set capacity around. And I just didn’t feel like it was necessary. And that’s a skill set worth cultivating too.

Categories
Emotional Work Travel

Day 744 and Nothing

It’s always a toss up as to whether I am going to write beautiful missives showcasing my deepest emotions when traveling or just shit out whatever I can manage. I’ve discovered I’ve got quite a range over the years. And I can almost never predict it.

I assume everyone can relate to this. You can never really predict when your best efforts will yield great results. This is, of course, why I prattle on and on about about practice and habits. If you aren’t forcing yourself to hone a skill set even when you don’t feel like it you won’t ever improve it. If you don’t let yourself fail you never win. You miss all the shots you don’t take.

I totally get why people are obsessed with sports metaphors. I often wonder if athletes use business or war metaphors because otherwise they are stuck with the literalism of being descriptive.

I’ve always hated when business people use war metaphors as it feels a bit offensive (don’t elevate your work to life or death unless it actually is life or death) so I default to sports metaphors.

But mergers, term sheets and deals aren’t as sexy as goals, shots or points so if you are an athlete maybe sticking to literalism is fine? I mean, they are to me, but of course I’m inclined to think my work is hot. You’d be worried if didn’t.

So today I’ll accept that we use the metaphors we have on hand as sometimes we do t have anything else. We’ve got nothing. And you’ve got to work with what you’ve got to make something from nothing.

Categories
Politics

Day 740 and Immigration Failed Us Again

My second attempt at a securing a tourist visa for a friend failed this morning. If you’d have asked me a few years ago if I thought the American immigration basically worked, I would have agreed that, sure I thought it probably worked ok. No reason to think otherwise right? Phew I was wrong.

But after years of being humiliated over and over again by the state department for “the crime” of wanting a family friend to come visit us for vacation, I’ve never felt more ashamed of myself and my country.

I’m ashamed I was such a sucker. I thought we would still do the basic work of being a functional state. I’m ashamed that America treats people who want to visit us this badly.

We have well off, interesting, curious guests that want to explore our culture and spend their time & money seeing our land. We spit on our guests by turning away anyone who isn’t on a Schengen or ESTA waiver. You probably think that includes most people. I did. But we are wrong.

Only 40 of the 195 countries on the planet are granted travel visas without going through the visa embassy approval process. Most people have bad passports. Latin America, Africa, the Balkans, the former Soviet blocks and most of Asia have “bad passports” that require a tourist visa that requires years of waiting for appointments and almost assured disapproval at the Embassy.

I’ve never met a system so broken I couldn’t find a workaround. But here I am at the of my workarounds in tears at how I’ve let down my family and friends. The visa I’ve been helping with was denied a second time today after waiting since March for a second chance to re-apply. That first meeting at which we were also denied also took years of waiting.

And it is getting better. This round after flying to Prague, we got two minutes instead of thirty seconds in Frankfurt. In those minutes they still didn’t look at any of the materials prepared. Just a generic we don’t like the look of your people rejection. We got some boilerplate language about strong ties or weak ties and no we won’t read the 200 pages of supporting documents you brought.

I was a mess yesterday about how afraid I was we’d get down turned down again. But I thought surely I was being too paranoid. The lawyers we paid thought we had a good chance. We’ve brought everything possible for paperwork from mortgages to W2 forms. I’d taken personal financial liability for our friend. I let the government have an invasive look at our finances. I gave the consular offices the deed to my house. I worked for months to get a Congressional letter asking for a fair review of the application. None of it was reviewed.

Now in the aftermath, I’m not even sure if it’s possible to get a consular officer to do a fair review. Our congressional representatives wrote the consular office and they send back boilerplate with no details. No one reads the applications I guess. We can apply again. And again. But would good would it do?

Categories
Travel

Day 735 and Detail Oriented

Packing is one of my most consistent niche subtopics on this experimental “write every single day” habit. I’m fact, I’ve written 23 times about packing over the last seven hundred and some days. It would have been more but the pandemic kept me at home more which also eroded my packing skills.

I’ve written about my recurring packing nightmare in which the anxiety my inner child feels about travel & packing in my childhood looms large. I’ll be trying to locate a key item as a countdown clock ticks down. I never find the item & I miss the trip.

We moved every two years from house to house. We also traveled constantly for my father’s work. The dream so clearly represents abandonment it’s barely worth invoking psychology.

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.

Day 222 and Recurring Nightmares

To overcome this lingering childhood fear, I am a very detail oriented packed. I’ve got lists. I’ve got a whole triage program to be sure I have all of my medicine and vitamins in their original prescription bottles so the security folks don’t fuck me. I do doubles so if I get separated from a bag I can manage 24-48 hours without it. And I never let my core prescriptions leave my backpack which never leaves my sight line.

A grey Muji overhead suitcase and an Aer backpack

I’m a very light packer when it comes to clothing. I’m a two shirts, two pants, one dress and six undergarments type for a two week trip. With some winter sweaters taking too much space. I do them in cubes that zip down for less space and then I label them.

Packing cubes with labels

I try to label everything in my packing cubes and match them back against my master Notion document for packing necessities. I think do another hand written list in my notebook as well.

I have to take a number of medicines and vitamins with me to manage my ankylosis which takes up a third of my suitcase. I could be a much lighter packer if the TSA and other security institutions didn’t insist on me carrying drugs in their original prescription bottle and a file with my prescriptions printed out. I’m not a detail oriented person without focus but nothing forced focused quite like the prospect of falling ill overseas.

Categories
Emotional Work Startups

Day 719 and Step By Step

I was discussing my goals for 2023 with a friend today. They wanted to know if I was planning on making any New Year’s resolutions. I told them that I wasn’t in the habit of using a new calendar year for making big changes.

Generally speaking if I want to do a thing I just start. I honestly feel like it’s far too intimidating to declare yourself to be some kind of fundamentally new person that will, as of a certain arbitrary day, make huge life changes. It’s too much pressure. One of my rules for biohacking is to only change one variable at a time. And I don’t make big changes to it either. 10% a week is good enough for most goals. Anyone familiar with the magic of compounding knows that small changes add up to big numbers.

Which isn’t to say that I haven’t started big life changing projects on January first. If you count back from 719 you will notice I first began writing on January 1st 2021. I did indeed resolve to write every day. But I hadn’t intended it as something I’d keep up for a specific amount of time. I’d hoped I’d practice my writing for thirty days and I allowed myself a little fantasy about how amazing it would be to write for a thousand days.

A thousand days seemed like an impossibility at the time which is why I allowed the fantasizing. My pragmatic side said just get started and see if you can keep going. And I did. I put one foot in front of the proverbial other for two years. Now I’m relatively confident that if I want to do so I’ll make it to a thousand days.

I approach most goals like this. I had a fantasy that I could make it as an investor. I was a founder so I thought let’s wire some small angel checks. We were already committed as a family to being startup operators so why not combine our skin in the game with a little more capital risk with our network.

I never envisioned myself raising a fund and making some big announcement about how I had a venture fund. I just started learning by doing. I cut checks. I ran some special purpose vehicles. And this year I decided to one-step-at-a-time go about raising a rolling fund. I am just doing the thing one day at a time. And it’s going well. Amazing people are coming on board. I am confident I’ll reach my goals just by putting one step in front of the other.

If you’d like to join me my goal is to raise $500K per quarter. I’ve got folks like Joel Spolsky of Stack Overflow and Michael Pryor of Trello so you will be in good company. You can read the fund overview here. Yoican sign up on Angellist through the above link or get on a call with me and we can discuss the fund, our portfolio construction and my thesis. Because I intend to work through the holidays because it remains one day at a time.

Categories
Culture

Day 712 and Effort

One of the biggest mindfucks in life is how little effort and reward are correlated. I spent a bunch of time yesterday trying to write something heartfelt and it just didn’t get there. I spent maybe 2 or 3x the amount of time I normally do writing on this piece and I just couldn’t get it to hit emotionally.

I could feel that I was pushing it too hard. I asked Alex to do an edit and a re-organization of the content. It was a lot more legible but it didn’t have that special sauce. Sometimes working at the problem doesn’t fix it. And because the topic was a little bit too of the moment I had to let it go.

None of which is to suggest that effort isn’t important. You’d be shocked at how showing up and doing the work is rewarded. Putting in a little effort takes you pretty far. And less than you’d imagine so long as you combine that work with social graces. If you are feeling stuck in life go study manners as hard as you can. Then go hang around smart people and watch the work roll in.