Author Archives → David Hoang

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.

Mastery for generalists

Originally posted on Proof of Concept

When I was the Product team at One Medical, our clinical and Ops teams were critical partners in how we shipped work. It was common to visit the offices to observe (going to gemba). During my four years at the health tech company, I learned about the various roles on clinical teams: primary care providers, registered nurses, care navigators, specialists, phlebotomists, and many more. In my research work, I spent the majority of the time with primary care providers (generalists).

“Why did you decide to be a generalist instead of a specialist?”, I’d ask each provider. What compelled them to general care vs. being a specialist. Primary care physicians experience more burnout and specialists make more money. The truth is you make more money as a specialists, so what would compel someone to general care. The answer was consistent: to have a broader range to care for their patients’ health.

The path for specialists is more clear than generalists. If one chooses the generalist path, what does mastery look like? The notion of mastery as a generalist sounds oxymoronic. Let’s challenge that and identify how to grow in your craft in a generalist role. In order to master being a generalist, let’s reflect on how to know if you are a generalist, the impact they make, and leveling up as generalist practitioners.

You might be a generalist…

If you grew up in the 90s and experiencing lower back pain, you may remember comedian Jeff Foxworthy’s “You might be a redneck” routine: “If you’ve been on the television more than five times describing what the tornado sounds like, you might be a redneck.” We can remix that and play it back with being a generalist:

  • If you can’t decide if you want to be a product manager, designer, or engineer, you might be a generalist
  • If you find yourself always wanting to learn new things outside of what you do, you might be a generalist
  • If you highly enjoy collaborating with every department, you might be a generalist
  • If you get excited about trying out emerging technology and tools, you might be a generalist
  • If you get bored by doing one thing, you might be a generalist
  • If you’re comfortable hiring people better than you at everything, you might be a generalist

Generalists are people who love variety, connecting the dots, and curious. In contrast, specialists usually focus and go deeper on a certain practice. I use the clinical metaphor above a lot when describing generalists and specialists. A brain surgeon could conduct a physical if needed the same way a primary care provider could do certain operations in the case of an emergency. However, based on the level of skill and precision, a specialist is more effective. Every designer can contribute to a design system and having a specialist in design systems will merit in more effective outcomes.

Why be a generalist?

“Jack of all trades, master of none” can sound negative—almost implying one isn’t good at anything. Do you ever feel like you don’t fit into a specialty? Being a generalist allows flexibility and have broader range in what you can do. This is a great skill for early stage startups when wearing multiple hats is common. As the company grows, it’ll specialize at scale, and it makes sense. You don’t want your generalist co-founder to continue being responsible for people experience or finance and bring in the specialists. What happens to people who when they relinquish the said hats? You’re able to freelance and move around more. There might be a new initiative that needs to get spun up. If you’re interested in management, many people managers are generalists.

Generalists spark alchemy

In the article “Generalists CEOs Not Specialists Spur Innovation,” there is a great excerpt on how generalist spark innovation:

“Under generalist CEOs, companies tend to engage in more ‘exploitative’ innovation, which involves improving or refining something that already exists, and also more ‘exploratory’ innovation — that is, engaging in a risky search for radical and transformative innovation. However, the difference between specialist CEOs and generalists is especially pronounced in exploratory innovation.”

You don’t see many specialist CEOs unless the business does something specific to it. A generalist can start an important initiative and collaborate with specialists to drastically improve it.

Building mastery as a generalist

“Mastery as a generalist” is an oxymoron, but let’s embrace the duality. How does one become a better generalist? Great teams need a blend of generalists and specialists.

Be an expert at learning

If there’s one specialty a generalist has, it’s learning to learn. Build familiarity in a discipline enough to understand the mechanics, develop experience, and when it scales, find a specialist. If you’ve ever had a manager who understands what you do because they’ve done it before, they can build more advocacy for the effort of your work. A designer understanding how the software development cycle works can anticipate questions that come up.

Understand every role

I’ve worked in so many aspects of design: UI Designer, Information Architect, Marketing Designer, Motion Designer, Researcher, or Product Designer, I’ve worked in dozens of roles. Understanding everyone’s roles and responsibilities helps you influence at a higher scale since you have a sense of what everyone is doing. It allows you to give better input and direction.

Build connective skills

Understand how every org works and connecting the dots across them. One of the services I was most passionate at while at One Medical was pediatrics and family practice. Whenever I had a coffee break or free time, I’d make time to connect with people who were passionate about that program and ways to support it. Learn how to synthesize, story tell, and connect to the big picture.

Mastering the generalist path means everyone will be better than you at something, but you’re better than everyone at every little thing.

Being a generalist does not mean the work is shallow. It’s right sizing the amount of up skill needed to get the job done. If the path of a generalist resonates with you, continue diversifying your skill portfolio and extend your range.

Blonde rival in Top Gun – I don’t like you because you’re unsafe.

Blonde rival in Top Gun: Maverick – I don’t like you because you’re too safe.

I really enjoyed The Batman. I try not to rank other films, so not sure where I feel it falls with other Batman films. I love longer films that are slower with beautiful wide shots, and man, did this one deliver.