Jon's Ink 🖋️

After reading Carse's Finite and Infinite Games, I've begun to recognize that the garden could be the most important metaphor for product development (at least the kind I like to do, anyway).

The key idea is that, as the gardener, you don't "make" anything happen. A garden isn't a machine that you create and control directly to get the outcome that you want. The machine approach is the default way that most people and companies think about product. Instead, a gardener creates the right environment for things to grow, and allows them to happen. This mindset of indirect action is an important mental shift.

But beyond the core concept, I realized this morning as I was watering my own (real) garden that I don't have a strong sense of where the gardener should apply intent in this model.

In gardening, I like the idea of serendipity. If I see something growing on its own when I didn't plant it myself, I like to let it go and see what happens. If it's growing on its own without any extra effort from me, there's a sense that it is the most robust thing that's perfectly suited for the time and place that it's growing. This approach can work well: last year, the most successful producer we had was a tomato plant that sprouted up this way.

This year, however, I have a dilemma. I have a zucchini plant that sprouted up spontaneously and is growing very well. Unfortunately, it's so big that it's crowding the sun from nearby cucumber plants that I had intentionally planted earlier. On one hand, the pure gardener's mindset of "seeing what happens" would indulge the zucchini - if it's showing the be the most successful, shouldn't I go with it? On the other hand, if I let it shade out the cucumber plants, I'll lose out on plants I really wanted to have happen. How does the gardener balance serendipity and intent?

This reveals that the gardener asserts intent (or doesn't) at several steps in the process. First is the seeding - you can intentionally choose what seeds you plant and where. The second is environmental control - what conditions do you foster for things to grow? A third is management - if different things sprout up, do you allow them to continue?

What's the best way to do all of these things? Perhaps there is no easy answer; it depends on the situation and the gardener and the garden. If you don't allow anything you didn't plant to grow, you forgo many opportunities that might be perfectly suited to your garden. If you allow anything to grow, you're at the mercy of pure serendipity and it may not provide you things you really wanted. At the end of the day, mindfulness and intent is still the most important thing.

One thing I've been thinking about a lot these days is the impact of the individual in the company relative to the impact of the company itself. As an individual contributor, how much of your performance and impact is determined by you, and how much is determined by the context in which you operate?

It's a question that has serious career implications. The answer potentially implies a big change in the kinds of narratives we tell ourselves about our careers and the careers of others.

As I saw the news about Squarespace being acquired by the PE firm Permira the other day and was reflecting on my own career, I was shocked to realize how much of the work I did as a product manager was really determined by the funding structure.

I've worked underneath several funding structures in my career: subsidiaries that had been acquired by large companies, a VC-backed firm, an Angel-funded firm seeking VC funding, a SPAC company, and a PE-owned company.

When I think about it, the funding structure guided almost everything, because it determined the company's motivations and incentives. At the subsidiaries, pure revenue and company performance weren't the guiding principle; it was whatever the parent company's priorities were. At the VC-backed companies, all of the work and cadence were dictated by what we could show at the next board meeting. The SPAC company was all about spending money and the ability to raise more money. And on and on.

A lot discussions of product management treat the discipline as if it exists in a bubble—there's a "good" way to operate and decide what you work on regardless of where you're at. But, in practice, to me, it seems that the organizational incentives from things like funding structure dictate the majority of what you actually work on. Maneuver within the lines best you can, but it's never an open field of opportunity.

The funding structure determines the end goal of what the company views as valuable. And that perspective on value dramatically narrows the range of "valid" initiatives you can actually pursue.

When interviewing, this comes in to play. Interviewers often judge you on what you worked on or perhaps how you decided to pursue an opportunity. But how much of that was really up to you? And are most interviewers sensitive to the layers of incentives that exist in an organization that bear down on all that? I don't think most do, even if they're product managers themselves.

If you're evaluating a place to work, don't discount the funding structure - it may be more impactful on you than the company's product, industry, leadership team, or any other factors we usually consider.

Vincent: "Seven fat years and seven lean years."

Sam: "That's what it says in the Bible."

When times get tough in my career or the industry overall, I find myself returning over and over to John Frankenheimer's classic film Ronin starring Robert De Niro, Jean Reno, Natascha McElhone, and other great character actors.

The movie is about a group of ex-operatives who have been brought together as mercenaries after the end of the Cold War. I won't go into spoilers about the story, but what really draws me back is how it feels.

Throughout the entire movie, there is this pervading feeling of paranoia, unease, anxiety, and desperation. In the old order, there were clear sides, right and wrong, and resources to match. But now, these agents, so skilled and capable, have been cast out on their own. There may have been a feeling of loyalty before; but now, it’s clear that was a mirage.

You can see where I'm going with this. Even we’ve had downturns in tech in the past 10-20 years, this feels different. Tens of thousands of people have been laid off over the past two years. Hiring still hasn’t come back, despite (or because of?) excitement over AI.

We’re in a new era of tech rōnin. Where do we go from here? What happens to all of us? Do we all become mercenaries, hiring ourselves out to whoever can give a payback? Does power become even more consolidated with the select crew and more unequal than before? Or is there some kind of rebalancing in the cards?

Wow, it's been almost seven months since my first post. No excuses, but I hope to make the third one come a lot sooner.

It's been a weird time in the tech world the past 12 months or so. After the tech layoffs started in late 2022, things got really dark and scary. The environment doesn't feel a whole lot different now, other than perhaps we've become slightly desensitized to it all with the passage of time.

The job market still feels really tough; there's still an extreme imbalance of the number of applicants to the number of job postings. If you're lucky enough to have a job, you've got to be incredibly careful not to get cast overboard. It feels like a death sentence.

Yes, there are a few hopeful signs out there. The AI boom is still in its early phases, but that feels like a wave that is only being enjoyed by the privileged few who are in a small set of companies. Signs are pointing to a soft landing for the economy. There have been some good earnings numbers recently, and we can only hope those result in more hiring down the line.

Welcome to my new blog! This is the first post. A blog in 2023 feels like an anachronism, but there are many internal and external factors that make it the right time.

Why a blog, why now?

I recently re-read the excellent book How to Take Smart Notes by Sönke Ahrens, which came out in a 2nd edition last year. When I first read the book a few years ago, my mind was blown by the concept of the Zettelkasten for taking notes; it felt like a huge piece of the puzzle I had been missing for years. Back then, I set up my own Zettelkasten in an initial burst of enthusiasm. Since, however, I haven't added to it consistently. This makes me feel a little guilty when reading books, like I'm wasting my time if I wasn't adding notes into the slip box. I still feel like that's the case, and I want to get back to the deeper level of thinking that comes with taking notes in the right way.

This blog is a part of my renewed effort to re-engage with my Zettelkasten. One thing I've I understand now is the necessity of having a final output step, such as writing, that uses your notes as input. Without using the notes, you don't have the feedback loop that makes the whole system complete. This blog is, in part, a place to do a little writing to help me complete the loop with my Zettelkasten.

And there are other reasons for starting a blog right now that come from recent events in the broader tech world.

One is the recent happenings at Twitter. Everyone knows about the recent rapid degradation of Twitter under its new management. Twitter was always my social media platform of choice, and so this is incredibly tragic to me. Over the years, I came to respect many of the ways the teams at Twitter managed the product with noble intent. It's been sad to see how quickly all that's been undone. While I do hope that many of the alternatives, like Mastodon, will be successful, the whole experience reminded me of the importance of owning one's own platform. With what we've seen happen, is it really wise to donate content to any proprietary platform right now?

A second development in the tech industry was the release of ChatGPT a couple months ago. While it has generated a lot of optimism about the impact that AI will have on the way people write, my reaction was the opposite. If we do go into a world where everyone relies on a tool like ChatGPT as a scaffold (or a crutch) for their writing, the people who actually know how to write well in an original, human voice will be at a fantastic advantage. I'm not there yet, but I hope that having a blog will help me develop my writing skills to prepare for the new world of an AI standardization of communication.

The path to a new blog

I've also taken a new approach to launch this blog.

In the past few years, I've had several false starts. Whenever I felt the urge to blog, I'd spend all this time trying to create one from scratch using the shiny technology du jour. This meant wasting a bunch of time learning things like NextJS, Gatsby, templating libraries, and hosted CMS systems before I got down to writing a single post. Invariably, I'd get bogged down in learning the technology and never launch.

Recently I read Steven Pressfield's The War of Art, and that taught me what I had been doing wrong. In the book, he talks about the many aspects of "Resistance," all of the mental barriers and obstacles that come in the way of doing any kind of creative or knowledge work. It made me realize that this desire to roll my own blog every time as a form of resistance that was getting in the way.

This time, I've chosen the absolute minimum approach to start by using a template with the absolute minimum of customization. In this case, I've used Matt Jennings' excellent SvelteKit blog template. Perhaps I'll customize it a lot further down the line, but not until I've got a lot more writing under my belt!