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Eight episodes in and I\’ve loved every single moment of Andor. It\’s so refreshing to have a show without space wizards that all are one degree from separation of the same family. Diego Luna all the things!

Three years at Webflow

Today marks my three-year anniversary at Webflow. It feels like yesterday when I was returning to work after a short sabbatical after my tenure at One Medical. My desire was to take a longer sabbatical to explore what a “Product Me Fit” would look like. I didn’t want any product and design role, but one where I would love the product’s mission the the people working towards it. In all the best ways possible, Webflow cut the sabbatical short, and I found a place with purpose and intention.

In my 20s, I explored a lot of different jobs and roles, as I think one should. Aside from starting my own product studio and running that for five years with my co-founder, I was never at a company for longer than two years. I’m now in a different arc of my career odyssey, and find myself at two companies for the last seven years: One Medical and Webflow—a stark contrast of my early career.

Approaching the forth year at a company might have felt closer to the end in the early arc of my career, but now it feels like the beginning. A mentor of mine once told me that as a leader, it takes year-over-year effort to see the desired outcomes of your work come to fruition, and I see what she means. The senior designers on my team at One Medical are now Staff Product Designers or Product Design Managers either still at the company or at new opportunities. Products I thought that would never see the light of day have now shipped.

I would be lying if I told you there were no hard moments. Hyper-growth is hard and there are many lessons I learned that required taking a hard look in the mirror and facing reality. Our team comprises of 25+ incredible Product Designers and Content Designers, almost twice the size of the team of Product Design, Brand Design, and User Research that I started in the first year.

I’m grateful to work with all the incredibly talented people here—current team members and alumni. You all are such a joy and the reason I am bullish that Webflow’s Product Design org can become the team of the decade with the most thriving alumni group.

Thoughts on the Light and Magic documentary

I spent last night binge watching the new documentary Light & Magic on Disney+. It’s a six-episode series on the story of Industrial Light & Magic (ILM), the company filmmaker George Lucas founded. Along with the General Magic documentary, I love hearing stories about creatives and innovators. Light & Magic is a great documentary and I’ll bet you learn something new even if you’re familiar with the story.

*Spoilers..? I’m not sure if you’d consider if you can spoil a documentary, but if you’re not familiar with ILM the a documentary*

Reflections

Proof of concepts are very lean

One of my favorite moments in Episode 6 is when they were talking about how the team was approaching the first Jurassic Park, which was a blend of Computer Generated Images (CGI) and practical effects. For obvious reasons, the team did not have reference photos of how Apatosaurus dinosaurs stampede. The crew decided to set up props in the back of the studio and filmed themselves running to get more references. It also resulted in one of the team members falling and breaking their arm, hence the name of the episode: No More Pretending Your Dinosaurs.

Even when you have incredible technology, ideation starts by storyboarding, body-storming, and conveying the concept. In Star Wars, Lucas put together stunt reals from other films to put together the story (Lucas is not known for originality).

Work with multi-disciplinary people who push you

A studio is one of the most sacred places in the world to me. ILM was comprised of incredibly talented people who push themselves. There was autonomy to go work on other departments: sound, writing, second unit direction, film editing, etc. ILM created an amazing alumni group and people who directed films in their own right. When Joe Johnston was going to quit ILM after burnout, Lucas offered to send him to USC and work part-time so he could go to film school. Johnston ended up being a director in his own right, including titles such as Honey, I Shrunk the Kids, The Rocketeer, and Captain America: The First Avenger.

Effects serve the storytelling

I loved the details of effects to tell a wonderful story. The effects should serve the storytelling, and not technology for the sake of technology. As much as we make fun of the Star Wars prequels, Lucas was pushing the technology to tell stories at such a higher scale.

Imagination pushes technology

Okay, so the Star Wars prequels weren’t great. I remember seeing The Phantom Menace in high school and was so disappointed. What I did not realize is this movie that introduced Jar Jar Binks was the reason theaters started switching over to Texas Instruments’ DLP projectors. This kicked off the revolution of movie theaters and evolving the industry to digital. As much as I appreciate a movie in film, digital let’s people see movies at a broader scale and more accessible.

It’s incredible to think a company like ILM helped inspire innovations to spin out Pixar as its own animation studio and John Knoll creating Photoshop for The Abyss and Terminator 2.

Industry methods will evolve, and you need to

This one is top of mind for me as we think about how AI and ML is going to exponentially evolve the way Product Design is done. Computer graphics accelerated the industry: from The Abyss, to Terminator 2, to Jurassic Park, and beyond. Inevitably the model shop was shut down in order to move towards a new paradigms.

Notes

Below are some unstructured notes of what resonated with me:

Light & Magic is available on Disney+ and highly recommend watching it!

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I loved the new Predator movie, “Prey.” Hope they continue funding this as a series at a higher budget. I would absolutely watch an Anthology of Predator period pieces where they hunt and wreck colonizers from world history.

Treat Life Like a Video Game

I recently had a conversation with my friend Leslie about a professional decision that had to be made. One thing in question was that I would have to live in two cities. Leslie is a talented art director from Toronto, and she also lives in New York City part time. I asked her to share her experiences. She said she loves it because there is “always has a deadline”, whether it is personal or professional. She constantly has a friend to see, a project to finish, or a plane to catch. It is exhilarating to her to always have something to accomplish like this. She then gave me some wonderful advice:”Treat life like a video game.”I initially was a bit confused about what she meant, but after pondering about it more, that saying made total sense. In a book or movie (I like books and movies, so this isn’t to bring them down), you are being told the narrative in a very linear fashion and the result is already determined for you. You are consuming vs. interacting. In a video game, you have to make decisions and figure out ways to achieve your goals in the game.As an avid video game player, I understood it. Surely Leslie didn’t mean treat life like Call of Duty or a third person shooter, but any game with an open world environment.Definition of an open world game on Wikipedia:

“An open world is a type of video game level design where a player can roam freely through a virtual world and is given considerable freedom in choosing how or when to approach objectives. The term “free roam” is also used, as is “sandbox” and “free-roaming”.

Some of my favorite open world games: Far Cry, Fallout 3, Saints Row, Grand Theft Auto, Wing Commander: Privateer, and Borderlands. Note that Skyrim isn’t on there because I have not played it yet. (I know, I know)Here are some aspects of video games (particularly open world games) that translate well into life:

Persistent Effort After Failure

I don’t think there is anything I fail more constantly in and continue to try to achieve a goal than in a video game. If you play games, you have been through that part of the game where you are stuck and fail 100 times. Yet, for some reason, you keep trying, even sometimes almost peeing your pants because you won’t go run to the bathroom until you beat this part.(Number of times I’ve actually peed my pants while playing video games: zero)Why is this? It is because a challenge has been set and it is something you have to do in order to beat the game. In contrast, people often seem to give up on dating or looking for a new job after a few failures, or sometimes, one. Why don’t we put that same effort in life that we do in video games? We should.The way we learn how to beat that aspect of the game is to remember what we did before that did not work and adjust accordingly. That, or we just use sheer will to overcome it.

Level Up

In a lot of open world games, your character (which you often customize) starts with a limited skill set. After achieving a set amount of goals and gaining experience points (XP), a player will be able to level up their character, usually with improvements on certain skills, unlocking new skills, or the ability to access more areas on the map.This is life. You don’t start playing Diablo and go straight to the boss when you’re a Level 1 Warrior. You have to gain the skills and prove your ability to accomplish such a thing before. Take this to the workplace. You’re a junior designer and have the goal of being a creative director someday. What you have to do is figure out what skills you’ll need to level up in and how to go about getting those experience points.Let me take a moment to remember how traumatized I was from that Speeder Bike level from Battle Toads.

Interact And Get Invested With Characters

I often feel I am more invested in video game characters than in a movie. For me, it’s the direct experience the character (you) and others around him or her. I can’t tell you how many times it has made me truly sad when a character dies in a game. Hopefully without giving anything away, Metal Gear Solid is a prime example of that.In a lot of open world video games, there are characters that you interact with that help you or stop you from beating the game. You quickly find out who is a positive experience for you and negative experience for you.Yet, in real life, we often hear people complain about having toxic people in their life. In a video game, these people would appear as a red dot on the map and you are told to avoid them.

Explore The Open World

When I moved to New York City two years ago, I did not know the area at all. However, I actually recalled certain general areas because of playing Grand Theft Auto, which takes place in the fictional version of New York—Liberty City.Remember that exploring can lead to achievement points or new characters in the game.In fact, that is how I met Leslie. She was visiting a friend at the co-working space I was at and we started talking and exchanged contact information. We have kept in touch since. I would never have guessed she would inspire me to make a significant decision in my life a year later upon meeting. I walked up to her and pushed the X button to interact.

Conclusion

The key to life is participation. You can engage and interact with it as much or as little as you want. Treat life like a video game. You can either treat it like a movie where someone is telling the story for you or you can grab that controller that’s called Life and start playing! Remember, there is no reset button though so live life like it is Nightmare Mode on Diablo.P.S. Don’t cheat.P.P.S. I wish money worked the same way in video games as it did in real life.

Lessons learned from writing 100 newsletter issues

This month, I hit an unexpected milestone—100 issues of my newsletter, Proof of Concept, celebrating with 100 – The 100th issue. Like many things in my life, it was serendipitous and unplanned.

How it started

I started my newsletter in December of 2019, and after eight months, I only wrote three issues. I did not have the discipline to be consistent. I was frustrated with myself not following through with all the projects I’ve wanted to do. Serendipitously, a friend of mine shared with me a writing fellowship called On Deck.

I enrolled in On Deck’s Writing fellowship, a spark that led me to become a program partner several months later. On Deck Writing (ODW) was exactly what I needed. There are a lot of great writing courses out there (some very expensive) and what I was seeking—community accountability and a place to learn and grow. In addition to peer group writing sessions, some of the best writers joined for fireside chats to share their wisdom. One of the guests was Polina Marinova, author and founder of The Profile—one of my favorite newsletters.

Marinova dropped some knowledge bombs in her fireside chat. She said these words that I’ll never forget: “consistency builds trust.” Those three words were exactly what I needed to hear with my writing habits. The main piece I wrote during the 8-week fellowship at ODW was Jodorowsky’s product roadmap, I wrote issues of my newsletter weekly as a way to practice. Fast forward to today, and I have not missed a Sunday writing the newsletter. I’m not sure if I’m planning to have a Cal Ripken-type iron man streak. If  the streak breaks, it breaks. However, writing has become a passion accompanied by discipline. 100 issues celebrates consistency.

Why a newsletter? To focus on community. The word “community” is used as a catch-all these days. I don’t see writing a newsletter as a replacement for blogging, and I plan to blog more frequently now that I have a rhythm with the newsletter. The newsletter isn’t a replacement for Twitter or other channels. When I started building Proof of Concept, I wanted something unique delivered to people’s inbox or RSS. I was looking for a smaller connection.

Sharing lessons learned

I’ve learned a lot throughout the past three years maintaining the newsletter. It’s not only writing. You have to think about content generation, making visuals, and running it like a product. There are hundreds of lessons and I’ll focus on the first five that come to mind.

1. Write drafts, lots of them

When creating a newsletter, you’re on the hook with a certain cadence, so that means deadlines. There is no worst feeling for me to sit in front of a computer and have no idea what to write about. Art school taught me to fill the canvas quickly to allow refinement. In the beginning of Proof of Concept, I was frantically spending nearly an entire day going through the entire content creation process: ideation, writing, editing, creative, and publishing.

The most helpful tool I added was writing Morning Pages and using 750words.com as a morning practice. Instead of waiting until Saturday, I spend every morning during my morning coffee to write. To be honest, most of what I write is horrible, but that’s the point. The idea is to get a high volume of writing done so you can be and editor and curate. There are certainly some days when I’m writing on Saturday, though those are rare. My Saturday mornings is more focused on editing, refining, and publishing from a backlog of ideas. Don’t get stuck in front of a blank screen.

2. Ship it,  avoid perfectionism

On Saturdays, I schedule the newsletter regardless if I’m finished with it or not. It’s a forcing function for me to have a sense of urgency to get it done and out there. Yes, it’s backfired, and there have been a few instances where I sent a newsletter with grammatical errors. Would I prefer catching that? Of course. Is it the end of the world? No.

I stumbled upon this tweet and it’s too real.

One of the main reasons that prevent people from writing is not because nobody will read it. It’s because you made something tangible to the world for people to see and react to. It’s a scary thing to do, and takes a lot of courage to put yourself out there. The fortunate part is digital work has the luxury of making quick fixes and improvements.

3. Solicit feedback early and often

Early readers have been my largest source of inspiration. Get feedback and ideas from them. The earlier you receive feedback, the faster you can refine the trajectory of your desired outcomes. In the first 10 issues, I renamed the newsletter to, “The Creative Odyssey.” People hated it, and honestly, I realized I did too. Proof of Concept resonated more and was relevant to the theme of the content. I’m thick-skinned when it comes to feedback. I studied studio art and built mobile apps for the App Store—you’re used to criticism.

Share the early drafts with people who will be critical. I recommend avoiding sharing with friends and family because most of them will tell you its great. Naturally, they want to support you, and people broader in your network will give more critical feedback.

4. Storytelling with words and visuals is my preference

Don’t expect to smash that like button or support me on Patreon any time soon. I have no desire to become a creator and want to focus on building tools for creators. This newsletter is a way for me to dog food the workflow. I’ve learned writing and making visuals is my preferred way of storytelling. I have heaps of respect for YouTubers, Podcasters, and various creators. However, I don’t have the time to spend on high production content like that. The production cycle in writing is more rapid.

5. Keep a physical notebook

I love software and truly believe it can change the world. I also believe in making computation humane and using it as a tool. The irony of a digital publication is I spend 80% of my time writing and drawing on pen and paper.

The computer is my assembly line. When I sit down in front of my purple iMac, it’s processing. Pen and paper is the ultimate tools for thought. My LEUCHTTURM1917 dot grid A5 notebook has been my notebook of choice for the past decade.

What’s next

It’s been a wild ride, and I’m going to keep it going. I am a huge advocate of side projects as the learnings are applied to your daily work. Proof of Concept has been a tiny corner of the internet I get to spend to express ideas, thoughts, and strive to improve. I enjoy the intimacy of a newsletter instead of blasting threads on Twitter. I’m excited to see what the next hundred issues might look like. But first, I’ll focus on issue 101.