The purpose of Proof of Concept is fostering creative experimentation for designers, builders, and entrepreneurs. This includes my own personal growth. When I started this newsletter, there was no expectation of hitting 200 issues and writing them consecutively without missing a week—even when I didn’t have the motivation.

Today we celebrate Issue 200 by reflecting on the 100 Series (101 to 199) like I did with the 000 Series (0-99). To celebrate, the one-year subscription of the newsletter is 25% off until June 30. Please consider sharing this offer with people—appreciate it!

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Personal lessons

I learned a lot writing 200 posts; what works and what does not. The biggest lesson is it is difficult to keep content fresh after writing for so long. I now understand why television shows have fillers like how The Simpsons would do clip shows. Creativity sticking to a schedule is a challenge! My commitment was shipping every week, even during the weeks I didn’t feel motivated. There were issues that were a big hit and some were duds. Here are reflections on what I thought worked well and where I want to improve:

What worked

Interview format: I did a spotlight interview with Brooke Clifton. Not only did I receive great feedback about her story, doing this post helped me learn more about her personally. I get why people do podcasts because they get to chat with interesting people as part of their job.

Inspiration notes: A concept where I share open notes about a piece of media that inspired me. I shared notes on one a talk that inspires me deeply, Hideo Kojima's Making The Impossible Possible.

Launched the paid subscriptions: In the 100 Series I decided to make a component of the newsletter paid as a way of patronage. I have a day job and not looking to heavily market the newsletter, but incentives motivate people. It means so much people support this financially—thank you.

Speculative writing: I started writing about speculative ideas and where I see things going. Dynamic Interfaces was not only the most popular posts in the 100 Series, but of all-time thus far!

What didn't work

Weekday email deliveries: I ran a test experimenting sending the newsletter on a weekday. It didn't make a material difference in terms of increased click throughs or views. A concern I had was since this newsletter is focused a lot on work that Sunday emails would invoke the Sunday Scaries for them. From a few readers, I was told that was not the case.

Deep cuts can be too deep: I love obscure cultural references. However, it can be confusing for people who don’t have the context, such as sports references if people don’t follow it. My goal is to reduce them when necessary but also do a better job of writing about the context as a way to story tell.

Themes looking back

It was clear looking back there were themes top of mind for me. I re-read previous issues and identified the following themes and included a few select articles that received positive feedback or high readership.

Craft and interfaces

I started my career as a UI Designer and crafting interfaces will always have a special place in my heart. I wrote about Dynamic Interfaces, a new way I believe interfaces will work with AI. In the mobile era of design, it wasn’t until Loren Brichter created pull-to-refresh on Tweetie for Mac that we saw interfaces break out of the shell of previous eras. In addition to predictions, I wrote about how we can make taste as objective as possible and what good looks like for interface quality.

Selected issues:

• Dynamic Interfaces

• Enter Dynamic Island, a major hint at Apple’s Extended Reality (XR) strategy

• Waiting for AI's pull-to-refresh moment

• The role of taste (and what it means)

• Signals of interface quality

Trends and predictions

I try to avoid anything that feels like thought leadership, but a mentor once told me that part of your job leading is sharing your thoughts. You don’t have to be a digital prophet and proclaim something is definitely going to happen, but sharing your point of view and what you care about is important.

The time issues 101 to 199 were written was when it felt like a Factory Reset moment in tech—loads of layoffs, tech vets starting companies, and the continued speculation of when Software as a Service (SaaS) might finally die.

Selected issues:

• Tech is going through its factory reset moment

• The four types of software in the future

• Bring your own abstraction

• The future of PLG is Design

• IDDE

Careers and the evolution of roles

One of the joys in my career is helping others with their careers and how roles might evolve. I encourage people not to focus too much on achievement unlocked—focus on the fundamentals the score will take care of itself. That said, I write about career navigation because it gives people a data input.

Selected issues:

• Choosing a company

• The rise of the design founder

• Design Engineering

• Why brand designers make great product designers

• Wearing the number one headband

Operating

I’m an investor, writer, but most importantly, and operator. Practicing my craft is the most important thing in my career.

Selected issues:

• On leading Marketing and Design

• How experienced managers should think about career opportunities

• My five favorite books on leadership

• The oil and water problem

• Early company building

Personal best practices

This is my Behind the Scenes (BTS) where I share how I do things as an operator. There are tons of tutorials on how to use a web framework or using Figma, but not as much for how to do things operationally. I wrote a few issues sharing my personal tactics in hopes it inspires you to develop your own methods.

Selected issues:

• Writing a POV doc

• Concept to keynote with Figma and Google Docs

• My product prioritization framework

• Managing towards outcomes

• Individual point of view and collaboration

Words of “advice”

Many people write to me asking for advice about how to get started with writing. Long-time readers know I don’t like giving advice but will share a few thoughts if writing more is your goal:

People often worry about what people will think about their writing. I have good news for you: nobody is going to care for a while. I published for two years before reaching 1,000 subscribers and grateful for the early readers. Shipping your writing allows feedback loops to iterate. I highly recommend Steven Pressfield’s book, "Nobody Wants to Read Your Sh*t."

Your point of view is what makes you unique. The internet is a crowded place. Don't let it intimidate you. Your perspective and experiences is the unique viewpoint you bring to the table

Time is made, not found. I always romanticize about renting a cozy cabin for weeks to write the next great American novel. The reality is I don’t have time for that. Between balancing my personal life, work as an operator and investor, and resting, time is not a luxury I have. Instead, my writing looks more like 20 minutes every morning with my coffee, writing on my phone while waiting for a friend or handwriting in my notebook. Polina Pompliano talks about finding “the pockets of time” to do your writing. If you’re serious about writing, don’t “find time”—make it.

The 200 Series

Though I don’t have a distinct them for each hundred series, I use it as a reflection point to think about what I want to experiment with in the future. From a production standpoint, I’m considering using Procreate to brush up (heh) my digital art skills.

In terms of written content, I’m interested in the following areas:

• Tech lore: Capturing the stories from the 2000s and 2010s of the iconic moments. How cool would it be to interview Loren Brichter about pull-to-refresh?

• The craft of management: Being a manager is a completely different role than individual contributor, yet not as much is written about the craft. I will write about this with caution as I don’t want this to become a newsletter for managers

• Creative tool critiques: I love Brian Lovin’s App Dissections will take it as inspiration to talk about creative tools

Please let me know what you’d like to read about. Though I love writing about what’s interesting to me I want this newsletter to be useful.

Whether this is your first issue or you’ve been a reader from the beginning, thank you for your support and creating such a joyous place on the internet for me.

P.S. If you’re going to Figma Config, please say hello.