The Messy Middle

Into the Mind of Serg.AI v001

Sergey Piterman
Tomorrow People

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“Draw me a picture of what it looks like in my mind based on what you know about me from our previous conversations.”

“Here’s an image that reflects a blend of your interests and thoughts based on our previous conversations. It combines elements of technology, history, nature, and a hint of the futuristic, creating a vibrant landscape.” — Chat GPT

I thought I’d write a quick post with a few of the things I’ve been thinking about lately just to get the creative juices flowing again. Who knows, maybe I’ll turn this into a series.

For some reason, I felt very flattered by what Chat GPT came up with for what it looks like in my mind. It reminds me a little bit of Lake Merrit in Oakland almost, with a splash of Dubai and Blade Runner mixed in. I liked the motifs of green spaces mixed into the bustling metropolis with glass high rises and futuristic lighting and technology. It does capture the essence of what I hope the future looks like, a place where nature and technology can come together and work well seamlessly.

I’ve been feeling a little bit stuck with a video series that I’ve been thinking about for some time. I think what’s been challenging about it is that I normally don’t do much planning when it comes to my videos but for these, there’s a strong need to. I’ve been finding myself avoiding working on the idea, doing anything and everything, both productive and unproductive, to distract myself.

It reminds me of this quote I heard from Chris Williamson:

“The magic you are looking for is in the work you are avoiding”

In a way even this blog post is me avoiding the other work. Although I suppose there’s a silver lining to procrastination if it gets you to work on other projects that you’ve been procrastinating on. You just end up doing the things that are lower priority or at least feel less good to procrastinate on. It’s a really weird dopamine maximization strategy.

Anyway, a theme that’s been popping up for me lately is the power of unknown unknowns and how sometimes they are worth leaning into, even if it’s a little scary. Because if you’re not doing something that’s at least a little uncomfortable then you’re not stretching yourself and not growing.

See lately I’ve felt like I’ve had a good routine but I’ve been feeling a little burnt out and in need of some deeper motivation. It feels like a time of personal transformation for me and I’m not certain what my life will look like 6 months or a year from now, which is both a bit exciting and a bit scary.

It’s a bit like the mid-game in chess, where there are a ton of ways things can go and it’s hard to see very far ahead. In the early game, there’s more structure that develops out of standard openers, and later in the game, there are fewer pieces and more forced moves based on positioning and constraints. The middle though is where the key decisions and blunders are made that aren’t always obvious until way later down the line.

Generally, when you’re young you aren’t really in control of a lot in your life, you go to school, do as your parents say, and progress through pretty standardized paths that tend only to diverge from your peers once you get to high school. And then when you’re old you start losing things, like your health and people around you until an illness or accident finally gets you. Because in the end, the game ends the same way for us all.

The tricky part is the middle because there are many options, and it’s hard to see very far ahead. You’re walking the line between order and chaos, where you need the predictability and structure of good routines and habits but you also need variety and novelty. They just have to be the right amount and the right kind to introduce new ideas and possibilities into your life.

To that end, I decided to sign up for a mastermind retreat in Switzerland with a group of young entrepreneurs and creators.

I’m at this point of tremendous growth in my life where I feel like I’m struggling to find a good community of people to push me in the right direction and figured I’d roll the dice on this because it was personally recommended to me by a good friend.

I had some apprehensions about it because I wasn’t looking for some bougie party up in the Alps for a week, that’s not where my mind is at. But after talking to the founder and doing a bit more research on my own and getting my ducks in a row I think it could be beneficial and help me connect with the right people.

It’s a pricey trip, but it was honestly pretty crazy to contemplate that I could afford it. And I think that’s the part of leveling up that I want to intentionally work, which is the mindset. I know on an intuitive level that I have so much more to offer to the world and that I can create an amazing life for myself and the people around me. It’s just a question of overcoming my fears and limitations. And the worst case it’s just an expensive lesson because as one of my close friends pointed out correctly, the real work lies in the daily choices we make.

I also wanted to share some quick ideas that I’ve been pondering lately that are more or less related to the Tomorrow People.

A Third Place

First, and I think I’ve talked about this before, but one of the main goals of the Tomorrow People is to open up a Third Place of some kind.

I’ve been brainstorming what the business model for such a place would look like, what the inspiration would be behind it, and how it would work. It’s some combination of a gym/country club style space mixed with a coworking/workshop mixed with an interactive museum/university/tech campus. It’s broad at the moment and needs refinement but the plan I have is to run experiments to see what works. I want it to be a space where people can come together and learn about important things but also socialize organically. Sometimes you don’t need much structure but I do think to take the idea above and beyond just a social club more structure is necessary.

Show and Teach

To that end, I think hosting a show and tell or teaching session would be an awesome way to make this experience of coming together in a Third Place unique. I always loved doing hands-on learning as a kid and I don’t know how much of that we do regularly anymore once we leave college.

Something I liked from Mark Robers's online engineering course was having an “order list” of what materials you would need to bring to participate. He gave Amazon links to all the tools and things you would need to make the builds he was demonstrating so that could be a good way of making it interactive ahead of time. And then you could record the session, and make a video about it at the end and post it on Youtube.

Teaching is an awesome way to learn material on a deeper level because you’re forced to recite it and you can’t do that properly if you don’t understand it yourself. Sure you might be able to get up and deliver a pre-written lecture, but if it’s interactive and you don’t know what questions will come your way you need to understand the material on a deep level. One of the main ways I developed my algorithm skills was by teaching the material over and over to other engineers.

I like this too because I can host things at my place or in the common area of my building to test out and refine this idea first before getting a permanent space. But I do like the concept of people volunteering their time to share their skills or give talks about subjects they know a lot about.

Interventionism is Generally Bad

I finally saw “The Marvels” movie, and even though I heard it got pretty bad reviews I generally enjoyed the experience even if I’m starting to feel like I’m aging out of these movies a little. I won’t get into too much of a review of the whole movie but mild spoilers ahead.

One aspect I liked was how it showed that interventionism can create more problems than it solves. This is especially true if you’re going in with incomplete information, or if it’s coming from a place of needing to solve some deep emotional problem rather than a well-thought-out logical place.

So in the movie, Captain Marvel destroys the Supreme Intelligence, which is this AI that governs an alien civilization called the Kree. She does this thinking that it will free the Kree people, and also as retaliation for manipulating and brainwashing her for years.

But after destroying the AI, the Kree end up in disarray because of the power vacuum that’s left behind and this leads to all kinds of messy collateral damage.

Aside from the theme of having a centralized intelligence in charge of your civilization, which I think is an endlessly interesting science-fiction plot point that we seem to be heading towards more and more daily, I like that this movie deals with the idea of unintended consequences and how it can be dangerous to act alone and in a vacuum

Creative destruction is something that I think deserves a fair amount of thought in how we engage in it. On the one hand, it’s often important to tear down the old to make way for the new, especially in the case of oppressive systems. But that destruction can lead to a lot of side effects that need to be either mitigated or accounted for. This is why it’s so important to collaborate effectively and get lots of different perspectives and input, although at some point you need to balance deliberation with action. It’s tricky and I don’t think there’s a general solution to this problem other than trying to cultivate good judgment.

Politician Influencers

After the Kansas City Chiefs won the Super Bowl Joe Biden’s official Instagram account posted this picture. Basically, they were making fun of all the conspiracies of the NFL rigging the games to try to maximize viewership.

I thought it was pretty funny, but it made me reflect on how deeply intertwined social media is now in our politics. Being able to get your message out effectively has always been key to any politician's success, and mastery over the relevant technology of the times is key to that effectiveness. Just look at the famous Kennedy vs. Nixon debate that swung the election in Kennedy’s favor since he had been preparing to master the new visual medium that television offered.

But just as old movies looked and felt a lot more like theater plays than modern movies do because plays were the closest analogs early movies had and people hadn’t experimented much with cinematography yet, I think politicians in the future will feel a lot more like social media influencers.

Most current politicians on social media feel like politicians who just moved their platforms online, but I’m interested to see what will happen when we start getting more politicians who build their platforms and followings online and then move into politics later. It could be a great way of showing consistency and evolution in their views over time, answering common questions they get, building a catalog of fleshed-out policy ideas, and interacting with their constituents and supporters in a scaled way.

Multiversal Video Games

I’ve grown up playing a lot of video games and still use them as a way to keep in touch with my cousins and friends who live far away.

It’s fun to reflect on how much gaming has evolved over the years and think about what themes or strategies seem to work to keep things fresh and entertaining. On the one hand, you need a consistent, balanced experience, especially in PvP (player vs player) scenarios, but you also need variety and have to mix things up. This is all while sticking to a core game loop/strategy and not trying to water down gameplay with too many mechanics. You also need difficulty scaling to appeal to a broader audience and create room for progression. It’s very tricky to get it right, and no matter what you do the game will never be perfect and there will always be complainers.

Personally, I like the way Destiny 2 solves a lot of these problems by having daily, weekly, and seasonal “loops”/challenges that help corral players into certain content and activities, as well as by sunsetting certain content after a set amount of time. It’s also a game with some incredibly deep lore and philosophy with themes like dualism, order vs chaos, and information theory, just to name a few. Part of what also makes it so fun is that at the highest levels, you really need good communication with your team and defined roles kind of like football and it’s gratifying when it all comes together and you end up making hero plays with your boys.

One trope that seems to be popping up more and more frequently in media and seems to be getting explored more is the multiverse and alternate timelines. This could be interesting for games to explore more in the future, where the outcome of encounters is determined or heavily influenced by previous choices you made. One game that did that pretty well (at least until the ending) was the original Mass Effect trilogy.

I could see this being something that gets explored more in future games, especially if there’s a seasonal release component to them where maybe the number of enemies you have to fight depends on how many you cleared out beforehand or which sidequests you accomplished or how many allies you saved or how much you upgraded them.

I could also see this being something that works with games with seasonal releases where maybe only the most popular plot directions get built out based on the collective choices/achievements of the community or have them vote on how they want the story to play out.

Redemption Arcs

I was reflecting on some of my past mistakes recently and it’s funny how painfully vivid those memories can be sometimes. Fortunately, I don’t think I’ve made any irredeemable mistakes but I do think there needs to be a broader conversation culturally about forgiveness, atonement, and giving ourselves and others room to grow and make mistakes. I think the desire to punish ourselves and others is deeply intertwined in a lot of the social and political tensions we’re seeing, things like the drug and mental health crises and the prison industrial complex.

All of those are too big for me to solve individually but I did come to the conclusion that as far as I’ve come, and as much as I’ve grown, evolved, and improved, I can always try to show up even better for myself and the people I care about and love. It reminded me of this fun show from a few years back:

A Serendipitous Mess

It’s so funny because as I was in the messy middle of this blog post (that for some odd reason I thought would be a quick one) I was sitting in on Creator Now’s weekly kick-off call and Kate, one of the founders, brought up exactly what I was writing about independently.

It’s pretty crazy how often they’ll bring up subjects or questions that I’ve been struggling with recently and it just goes to show how deeply they are tuned into the creator community and the challenges the people in it face.

She brought up some great points about how often we learn more in the middle of the process than in the ideation phase itself and that sometimes the most magical things happen when you do go off script and have a sense of openness. You’ll see this a lot of times in movies where a famous line was improvised and something about it just feels right and organic.

By definition you can’t premeditate spontaneity, you can only be lucky enough to capture it.

But there are challenges to being in the messy middle. There’s a lot of ambiguity in what you’re doing and you risk losing yourself in the work. If you’re iterating on something, you risk losing your mind if you never actually complete it. While it’s true that often you need to backtrack to ultimately move forward, you also need to strike that balance with actually completing projects and moving on. It’s the parable of the pottery class.

I like what Chris Williamson has to say about this, where people tend to get caught up in optimizing rather than maximizing, and I think that’s a trap I fall into quite often. Sometimes you just need to brute force a solution and optimize later, rather than using optimization as an excuse for inaction.

Exploration is important to rule out the bad ideas and discover the good ones, but at some point of diminishing returns, you need to ask yourself if you’re just adding additional work.

Because ultimately the edit is never finished and you just put it out.

Just like this blog post.

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Sergey Piterman
Tomorrow People

Technical Solutions Consultant @Google. Software Engineer @Outco. Content Creator. Youtube @ bit.ly/sergey-youtube. IG: @sergey.piterman. Linkedin: @spiterman