October 13, 2020
The City, Inc. board of directors
This post owes its inspiration, as so many posts do, to a tweet from patio11. I have tremendous respect for Patrick, and enjoy every conversation I have with him, but in one particular case I think he’s wrong, and he’s wrong in a subtle way that took me a long time to understand, because it goes against our idea of what an elected official in the US does, especially at the local level.
I’m going to put this in corporate tech-ish business terms, because that’s my bias and most of my readership: Your elected officials aren’t individual contributors. They aren’t even management. They are the Board of Directors.
This might seem obvious, but I really want to play it out. In most municipalities, especially those with a weak Mayor / strong City Manager government, your City Council or Board of Supervisors aren’t even members of the executive team for your city. They have, effectively, the same powers as large corporate boards do: They can vote on policy initiatives, they can authorize spending money, and they can hire or fire the CEO, who in your city is probably the City Manager.
Where I live, in Alameda, we have strong CEO / weak Chair of the Board governance, by which I mean a strong City Manager / weak Mayor system. The reporting chain for the City Staff, who are the people actually spending the money and enacting the programs and doing the work that affects us as citizens directly, goes up to the City Manager. That City Manager wields enormous power in how this money is spent and who the City is hiring to do the spending. The City Manager is hired, reviewed, and fired by the City Council. The City Council cannot themselves hire or fire any City Staff, and they themselves cannot spend one dollar of the City’s money directly.
Why does all this matter? Because it means that the qualities we look for in our elected officials should be management qualities and values qualities, more than effectiveness or expertise as an Individual Contributor. The job of a City Council member is a management job. When a candidate says they deserve our vote because they’re going to “get things done” at City Hall (or the Statehouse, or the Capital) we should remember how they will actually get things done: by suggesting policies, and building coalitions with their fellow elected officials to pass policies, and by hiring or firing the Chief Executive.
As an aside, the one way that government differs from most corporate structures is there are often multiple Chief Executives who can be hired or fired. For example, the City Manager, the Chief of Police, and the Fire Chief are all hired, fired, and reviewed by the City Council. In this case, those three departments operate like three different companies with the same board and funding source, so the analogy still holds, I think.
For me, this means that it often isn’t in my best interests to vote for the person who completely aligns with my values, even if such a person who isn’t me could exist. It also means it’s not in my best interests to vote for the most incredibly effective, deeply expert technocrat. My winning strategy, and I suggest the winning strategy for most of us, is to vote for people who:
- Mostly align with our values
- Have a demonstrated capacity to learn new information and make good decisons based on that
- Have a good head around managing people and collaborating with peers
Candidates who have a Master’s in Public Policy or Public Adminstration are great. But in the same way I’d hire an engineer from a bootcamp with seven years of experience over a freshly-graduated Master’s, I’ll take the activist who’s been coalition building and running an NGO for a decade over the first-time-running technocrat every day.
When you vote for a representative, at the State, Local, or Federal level, you’re voting for the Board of Directors of the organization that controls where you live, in a way you can very rarely vote at work. Vote for the Board you wish you had.
July 14, 2020
Where are we going? Tech and the Bay Area in 2025
In 2017, I attended one of the first Arena Summits in Raleigh, NC. Arena is an organization that formed after the 2016 election to try to solve a problem: The Democrats in 2016 had no “bench”. Bench is a sports term, here, and if you spend any time in politics you’ll know that the American political community adores sports metaphors. When we say that in 2016 the Democrats had no bench, what we mean is that Democrats were finding it hard to field candidates for national office in rural areas because young Democrats weren’t running for state and local office in rural areas. “Young” here has that particular American politics definition that means “under 40”, but the point stands. It was hard, in 2016, to field qualified Democratic congressional candidates in some regions, because there weren’t many qualified Democratic State Assembly Candidates. There weren’t many qualified State Assembly candidates because there weren’t many Democratic County supervisor or city council candidates, and so on all the way down.
This is one of the side effects of the massive coastal-and-urban concentration of well-paying jobs for college-educated folks. One of the ideas that Arena presented to counter this was “Go Home”. Throughout the summit, there was an exhortation to figure out some way to leave the major urban centers and return from whence you came, especially if you could be convinced to run for local office there.
I think there’s a lot of merit to this idea, but it had some cognitive dissonance for me, because I am from one of the major liberal urban strongholds: I grew up and still live in the Bay Area. I could, and did, get involved in local politics. But the idea of making a huge difference by moving to where I was born and advocating for the liberal values of “all men are created equal” wasn’t going to have the same impact in a region that started jumping on the Sanctuary City movement as early as Jan 21, 2017.
There was additional cognitive load from the fact that, for most of my adult life, the Bay Area has been the destination if you work in tech. We are the Northern partner to the Hollywood Dream; where multiple generations have traveled to Southern California to make it big on the Silver Screen, we are now at the end of the second or third generation of immigrants to Northern California who want to make it big in Silicon Valley. Being from here, but working in tech, gives me something of an out-of-body experience: I can see what it was like here before the Silicon Valley explosion, and I can see what’s changed as a result. Some people I’ve met seem to think that the Bay Area and Silicon Valley are synonymous. To me, Silicon Valley is just another part of the Bay Area.
This is an interesting time to exist in the world, and a doubly interesting time to be from the Bay Area, and a triply interesting time to be from the Bay Area and working in tech. For decades, Silicon Valley has drawn some of the best and brightest here, having us work on tools for lightning fast global communication while requiring us to all work out of the same office in San Francisco. Video conferencing has existed for at least a decade, realtime chat has existed for at least two, and email is around its 40th birthday. Even with all that, before March of this year, fully distributed Silicon Valley companies were seen as quirky rebels. The very idea of hiring a remote employee at many startups required VP-level approval. The world changed quickly: thanks to COVID-19, all Silicon Valley companies are now fully distributed.
We can’t know until it happens what effect a forcibly distributed Silicon Valley will have on the Bay Area. We’re starting to see early results, but we won’t really know what’s changing until it’s changed. The rest of this article is my attempt to make a prediction on what I think is going to happen, based on the trends I’m seeing.
So let’s talk about those trends. I find it hard to believe that any Silicon Valley company will be returning full-force to an office in 2020, and some may never do so. Even if we put aside the mega-corps that have publicly stated they won’t require employees back at the office ever, I’ve heard rumors of a half-dozen companies who are planning to not renew their SF office lease in late 2020 or early 2021. Those companies aren’t claiming to be fully distributed forever, they’re instead claiming to be remote “for the foreseeable future”. In internet years, that’s forever, and so I expect to see more and more Silicon Valley companies with an SF P.O. Box, and little else.
At the same time, tech workers are waking up to the fact that they don’t have to be in the Bay Area and work in tech. Beyond the articles breathlessly suggesting mass migrations, I can think of 5 engineers without checking Twitter who are moving out of the Bay Area but keeping their current job. It’s a sign of where we are that that idea seems normalized to me, only three months in. For most of these folks, had they asked to relocate in February their boss would’ve interpreted that as a resignation. This flexibility is having an impact on hiring for Silicon Valley as well. I’m a hiring manager, and I talk to a lot of other hiring managers. I can say for myself I have no real intention to hire from the Bay Area candidate pool in 2020, mostly because of cost.
The Bay Area is, currently, an expensive place to live, with a shitty regional public transit system, and a dominant economic industry that couples with disjointed civic governments to promote rapid gentrification and displacement. I don’t blame a single soul for taking advantage of the small silver lining COVID-19 is providing, and taking their tech salary to somewhere they like better.
As a result of all of this, I’m already seeing some immediate changes that give us a glimpse of where the Bay Area is headed. Home price is a rough indicator of the desirability of a region, and since so many people have, over the past two decades, flocked to the Bay Area, home prices have steadily gone up. Even in 2008, home prices in the circle of Bay Cities didn’t fall so much as flatline. Right now, I’m seeing the beginnings of a fall. Homes that I’ve been watching in Alameda, where I’m from, have lost as much as $100k in predicted resale value in the past 30 days, and for the first time I can remember I’m seeing sellers lower listing prices to attract more bids. Two years ago, that was unthinkable.
So let’s play these trends out, and show you where I think the Bay Area is going. Where will we be, 5 years from now, in 2025? These are a series of bets, and if anyone wants to stake some monopoly money (read: cryptocurrency) or beers on me being wrong, reach out.
In 2025, we still have Silicon Valley in the Bay Area, but it looks pretty different. Most tech companies still have a Bay Area address, because there’s still cultural cachet attached, but for many companies that amounts to little more than a P.O. Box. Most executives of those tech companies still have pied-a-terre’s in the area around San Francisco, as do a large number of sales folks, because the types of work that benefitted from in-person meetings in early 2020 still benefit from in-person meetings. Tech Venture Capital is still largely clustered in the Bay Area, but the companies they’re funding have the most distributed workforce they’ve ever seen, and VCs are full-throatedly encouraging distributed hiring for the cost savings.
As for the tech workers themselves, the majority of those left in the Bay Area are the ones who still want to be here, because being in the Bay Area is no longer be any sort of requirement for working in tech and making a good salary. Speaking of, those salary prices have dropped dramatically in the Bay Area, but have risen in the rest of the country. Tech VC money is spread through more of the country than ever, because tech workers can now live wherever they want.
In 2025, the 2010s career path of “move to SF” → “get an internship / take a bootcamp” → “land a job in SF” has been replaced with “take an online bootcamp” → “get a remote job in tech” → “live where you want”. This started in the middle half of 2020, and has been slowly gaining ground ever since.
2025 is also a special year for the Bay Area: it’s starting to feel like a thriving region again after 4 years of COVID-and-recession driven pain. The slow exodus of tech workers spreading money around, combined with COVID closures, meant that the vibrant restaurant scene that was building in the Bay Area ground to a halt in 2020, and neighborhoods that were up-and-coming became food deserts almost overnight. House prices dropped significantly as a result, and the value of commercial real estate plummeted. Especially in 2021 and 2022, the Bay cities were unable to handle the rapid drop in the tax base, and struggled to restructure their budgets to match the region’s new needs. There were a few attempts in late 2021 and early 2022 to privatize ever more services, and Uber briefly experimented with getting into the paramedic business, before realizing that there wasn’t enough left of the ridiculously affluent population to support their business needs, and that most of their drivers had also moved to where it was cheaper.
The inner cities of Oakland and San Francisco started feeling emptier than they had in the past decade, but this was no real surprise to Bay Area lifers — it felt like 1995 all over again. BART, no longer crushed under capacity, was able to use its bond funds to make major upgrades throughout the region.
By late 2022, cities were starting to figure out how to handle this new world, and they found great and greater partnership in their citizenry. The people who were in the Bay Area were now there because they wanted to be, and those communities built on the activism of the late 2010s to rally around a greater sense of regional community.
Where we are now, in 2025, we’re seeing a reverse migration of some of the folks who were driven out by the booming 2010s, and are now drawn back by the cheaper housing. The commercial real estate quickly abandoned in 2020 and 2021 by tech companies is being leased for a song to new restaurant concepts, new community spaces, new art galleries, and new, smaller, tech companies with a local focus. While the Bay Area, and most of the world, struggled with how to adapt to a recession and a pandemic, tech entrepreneurship continued on its late 2010s path of profitable, small, boutique companies that were focused not on total market capture but on building the perfect product for their community. In 2025, many of these companies are flourishing in the Bay Area, but just as many are springing up across the country, from Buffalo to Boise.
As we reach the midpoint of 2025, we by no means have anything close to a utopia, in the Bay Area or anywhere, but the de-concentration of this country’s best and brightest is already being felt. Communities in the center of the country that were close to death are being revitalized, and learning from the successful late 2010s campaigns of cities like Tulsa on how to attract remote tech workers.
The Bay Area is my home, so I’m still here, and I’m one of the people working with boutique software companies and partnering with civic governments. Our community feels tighter than ever, because we know the people around us will be here for years. Instead of being pushed out by gentrification or pressured to cash out of their startup and move somewhere cheaper, we’re putting down roots. The people who want to live in the Bay Area live in the Bay Area, and the people who wanted to go home went home, and the people who wanted a new home found one.
This was a doozy, and thanks for sticking with this post. I’m sure I’m wrong about some of this, and I’d love to hear where you disagree with me. Ping me on twitter @phildini or email [email protected].
July 10, 2020
Trail blazing, path paving
Growing up, I was incredibly lucky to have regular access to two staggeringly beautiful places. One was the Santa Cruz mountains, and specifically the camp in Felton where my family often volunteered and vacationed. The other was the property my great-grandparents owned in the Calabasas highlands. From one angle, these places are shockingly different. The forests of Santa Cruz are lush and verdant all year round; the valleys of Calabasas tend towards the scrubby and dry. From another angle, these places are incredibly similar: they are elevated preserves of what the regions offer, entire ecosystems wrapped around hills. Humanity can only access these places by making trails through the peaks and valleys.
My time in Santa Cruz and Calabasas taught me two things to know about trails. The first is that trails happen in two parts: the trail blazing, and the path paving.
Trail blazing is looking at the shape of the land and seeing the way of least resistance across it or up it. You pull on pants that won’t catch on the bushes, grab a machete and maybe a shovel, and work with the land to find a way from where you are to where you want to go, with the minimum of fuss. Fuss is still required, of course. You’ll need to cut branches out of the way, or move boulders that would be too hard to navigate around, and sometimes dig into the side of the hill to be sure of your footing when you come back. But you work with the land to accomplish your goal. When you’re done what you’re left with is a trail that is functional, that the adventurous can follow, but needs work for most to walk it.
Path paving comes after trail blazing. Paving is when a group comes along and makes the trail, which is still totally usable for ambitious, and transforms it into a path more people can use. This is when the brush and ground are edged back, when steps up the mountain are installed, when handrails and solid bridges are built. Path paving takes the work of the trail blazer, functional but still daunting, and turns it into a friendly road for all.
This is to my mind the ideal model for building applications on the internet, and exactly backward of how many companies build today. Trail blazing for apps starts with just the backend and the browser. We build something functional, something useful, but something that is still rough, and only really accessible to those who are willing to get hit in the face with a tree branch every once in a while. We don’t build just an API and throw it over the wall, we build the basic, but complete, experience. Frameworks like Django and Ruby on Rails shine here, and in many ways this is what they were made for.
With a functional, usable, but still largely unfriendly application, we begin path paving. We replace the basic styles we started with, like Bootstrap or Tailwind, with work that is customized for the app’s needs. We add reactive components and features to provide a better experience for the customer, and add the digital equivalent of stairs and handrails to make our app accessible to all. We carefully go over each potential snag and place a user could fall, and point out the way around it, or move it slightly off the path.
It’s important to see there that nowhere are we clear cutting or steamrolling. The web has a natural shape, a flow, a way it wants to be used, and our job is to go with the flow of the web.
This is how we build at Galaxy Brain. Philip, or Philip and Liam together, blaze trail, and get a functional backend and front end that brave early adopters could use in its entirety. Then Liam, or Liam and Philip together, pave path, and with the experiences of their early hikers to guide them, make the app accessible to all. We are judicious in where we use technologies like React, which is the web equivalent of industrial farming, but rely deeply on tools like Sass and Stimulus and Django, which were built to work with the grain of the web.
This approach helps with the second thing to know about trails and, correspondingly, web apps: They both need maintenance, and often the more complicated they are, the more complicated the maintenance. When you over-farm a field, you have to regularly re-invigorate the soil with expensive, external nutrients. When you cut a road into the side of the mountain, you need to invest in expensive retaining walls that need regular repair. When you overwrite the shape of the web, the tools the browser provides, with your own replacements, you have made a retaining wall of code. Your hope is that the next browser version will not cause a landslide of API changes.
This approach to apps influences not just technology choices, but product choices. There are things that the browser does not naturally want to do; we’ve all seen apps where the behavior of the “back” and “forward” buttons is unpredicatable. We’ve chosen not to do anything that’s the equivalent of blowing holes in mountains on the web, and as a result we can build a maintain a suite of apps with only two veyr-part-time developers.
We blaze trail, and then we pave path, and we do both with tools that fit the shape of the web. Doing this lets us deliver apps we’re proud of faster, with less time focusing on the technology, and more time focusing on our business and our lives. If this is possible for us, it’s possible for you.
If you want to learn more, or work with us, drop us a line at [email protected].
April 19, 2020
Management Reading List
Many of us have more free time than we expected right now. As a result, I’ve gotten a number of requests for my management reading list, since I’m known to read a lot of books on management — I will effectively buy any management book someone recommends to see if there’s any value to glean from it.
What follows is a list of all the management books I’ve read, broken into some rough sections.
I also owe a huge debt of gratitude to Jacob Kaplan-Moss, not just for his continued guidance and support, but for his reading list for new engineering managers, which was the starting point for this list.
If you have not read these, go buy them right now and read them. They are part of my essential toolkit as a manager.
This is the book I recommend to every new manager, or everyone who wants to become a manager. Andy Grove nailed most of modern management in a concise volume two decades ago. I like this book so much I wrote a post on touring the breakfast factory.
A fantastic nuts-and-bolts reference on what it’s actually like to be a modern manager of knowledge workers. I don’t agree with every opinion, but the amazing thing about this book is that you could follow it word-for-word and be better than 70% of managers.
This book changed my thinking on what it means to be a manager, and helped reset my thoughts on who my peers are as a manager. Spoiler: Your peers are now the other managers at your level, and how you handle that can make or break your company.
The Goal by Eliyahu M. Goldratt and Jeff Cox
I normally hate “business fiction”, because I would prefer real stories. The Goal is that rarest of business fiction tales that crosses into being a good parable. The message: What actually controls your business’ output is constraints, and you need some concrete theories on getting a handle on them.
These are books I thoroughly enjoyed, and which have changed my thinking on how to be a better manager. Although they’re not as critical as the Essentials, they’re worth reading.
This is a classic for a reason. The GTD system is useful for dealing with the deluge that comes at you as a manager, and the more you can exhibit the system in your own life the more productive you’ll be. The nicest part for me is that even half-adopting it makes you more productive.
The Checklist Manifesto pairs nicely with GTD. Both books are trying to convince you that your brain is meant for having ideas, not holding them. By the end of this, you’re hopefully convinced that all the rituals you go through with your team on a regular basis ought to be repeatable checklists, and that you’ll be faster as a result.
This is the infamous “Netflix Culture Deck” in book form, and it changed my thinking on how to hire, fire, and evaluate team members for high-performing teams. I went into the book with one idea about the Netflix philosophy and came out appreciating it more.
The Basecamp founders have been writing about their work practices for years, and this is the latest iteration of their work practices. Each chapter is full of ideas that made me reconsider my beliefs on the optimal environment and motivation for people to do their best work.
This set of books is worth reading, especially after you’ve gone through the first two sets. The first three of these are solid works that will help engineering managers especially, and the last is an approach to leadership that I found fascinating.
I had the great fortune of working with Will at Stripe. In An Elegant Puzzle, he brings his thoughtfulness and growth mindset to the problem of managing engineers, and provides a playbook on how to build good engineering teams.
If you’re just starting on the path of moving from engineer to manager, or trying to decide if that path is right for you, read this book. It lays out the entire managment career path from IC to CTO, and does a great job explaining how the role changes along the way.
Rands, yes that rands, from rands in repose, wrote a book on management! This is that book. The first half of the book is full of excellent stories about practicing the craft of being an Engineering Manager. The second half of the book is full of less-excellent stories on the same topic.
There are some truly fantastic ideas in this book, all centered around one core idea: As you go through your day as a leader, are you above the line or below the line? The first two-thirds of this book dive deep into this management philosophy in way that really resonated with me. That last third went in a “power of positive thinking” direction that didn’t land with me as well.
These books are fine and entertaining books to read if you have the time, but they didn’t make a big impact on me or my management style.
Getting to Yes is a classic for negotiators and those who regularly have to ngeotiate, like managers. I found the ideas useful to help me reframe negotiations around a shared goal. I would have rather read this book as a long blog post or whitepaper.
This book was a very fun read, but I can’t say I really learned anything. Ostensibly, it’s a guide to staying creative in the face of corporate domination. I found it to be more of a manager’s memoir, and in that light it’s fabulous.
Allison Green runs a very popular blog by the same name. This book is effectively a copy of the best posts from that blog, with some extra footnotes and thoughts. If you read her blog and are hungry for more, this book is for you.
February 18, 2020
Maker <-> Puzzler
Every engineer I’ve met falls somewhere on this spectrum:
One side is Maker, the people who like engineering because they like building things. They often get joy and satisfaction from seeing a thing they built out in the world and used by people. Makers tend to flock to product-focused companies.
One side is Puzzler. A Puzzler gets their joy and satisfaction from overcoming difficult problems. They might feel an electric sense when all the pieces come together, and when the universe feels theirs to command. Puzzlers tend to flock to companies with deep pockets of thorny technical problems.
This specturm comes from the answers to this question: “What do you like about engineering?” I’ve asked this question to dozens, maybe hundreds, of engineers, and the answers I’ve received gravitate towards either “I like to make things” or “I like solving puzzles.” That “gravitate” here is an important word, as is the fact that I’m calling this a spectrum, not a binary.
Every engineer I’ve met is closer to one pole than another, but I’ve never met anyone who is entirely one or the other. Beyond that, how much an engineer leans towards Maker or Puzzler can change over the course of their careers, because of the company they’ve joined, or even from project to project.
I know about myself that I lean heavily towards Maker. I get deep satisfaction from building systems that others use. I still get the electric thrill from solving a thorny technical problem, but my deep well of satisfaction comes from having built something and continuing to improve it.
Where you fall on this spectrum says nothing about your quality as an engineer. Excellent engineers come at every spot on the line. What it tells you is where you’re likely to draw the most satisfaction, and how you’re likely to go find new projects. If you know you lean Maker, a project that involves a lot of research and technical spelunking might exhaust you. If you lean Puzzler, a project that provides value to the user by cloning an existing pattern might leave you feeling unsatisfied.
For technical leaders, this is another criteria by which to evaluate your next hire. I strive for balance in my teams, a healthy blend of people who focus on building and getting things done alongside those who delight in technical puzzle deep-dives. I think about this spectrum and my current team make-up when I’m crafting a job posting and developing the interview panel for a role.
Where do you fall on the spectrum? Where do you think your teammates fall? What aspects of the Maker <-> Puzzler spectrum might need balancing on your team?
February 5, 2020
Minimalism’s Natural Habitat
I’ve been thinking about minimalism wrong for a few years now, and it took my first trip to Japan for me to realize it. If you had asked me before my trip, before November of 2019, I would have said that simplicity was the point of minimalism. This sounds like a tautology, because my logic was flawed — I thought simplicity for the sake of simplicity was part of minimalism’s ultimate goal.
There are elements to modern Japanese design that are breath-taking in their simplicity. I’m thinking here of the single perfectly pruned flower in a vase, or the whorls of sand around a stone in a garden, or the striking architecture of a temple gate leading off a city street. I use “breath-taking” because it conjures a feeling of surprise, and that’s part of what I mean. I was surprised by some of the simple beauty that I saw, but the nature of surprise means that what I’m seeing was different than what I expected.
What I came to expect as I wandered Tokyo was not minimalism, but a sensory assault. Tokyo is a city that wants you, the visitor, to buy things, and buy lots of them. Encouraging you to buy requires advertisements. The only ads in Tokyo that are truly minimal are for perfume, and most of those appear to be placed by Western companies. Minimalism is highly present in Tokyo, but in my experience the minimal spaces were the spaces designed as an escape from the life outside. Our hotel room was sparely furnished, and those furnishings were simple. After a day in Tokyo that minimal space, which would have felt like a cloister cell in California, was a welcome relief for our senses. I was surprised by the minimalism in Japan constantly — because it was so different from what my mind became trained to expect.
Minimalism surprises, and minimalism highlights. The element of surprise gets all our senses focused on what the artist is trying to highlight. The simple design of Japanese restaurants focuses attention on the food the chef is preparing. The simple architecture of a home highlights the color and beauty of formal Japanese dress. The crowd and noise and signage of the streets highlights the peace of the temple.
Before Tokyo, I thought about Minimalism wrong because I wasn’t using the simplicity to surprise and highlight. I was advocating for simplicity for the sake of simplicity, with no clear subject to focus on. Minimalism’s natural habitat is in crowd, so that through it’s calmness it can point out what matters most.