Life update 2023 edition

Starting with the news: I’ve parted ways (amicably) with my last company and I’m back on the job market.

It’s weird saying that in the current market. Millions of people’s jobs were ripped right from them due to ambiguous “market concerns” and/or dark incentives at play.

Anyway, I am grateful for the experience and looking forward to whatever’s next.

LinkedIn mostly knows me as a product guy. I’ve had the great fortune of working in many different, usually quite complex, spaces in my 11+ years doing it: talent booking in the music industry, two-sided marketplaces, collaboration in the enterprise, furniture delivery, messy platform scaling. I believe that diversity of experience, combined with tenure in both early-stage and FAANG-scale organizations, gives me a unique perspective as a PM. I’ve also worked with and led some amazing product thinkers and operators around the world, and that’s been awesome.

But I also make music, write, tinker, and mentor/coach fellow product people a bit. In fact, I believe the best product people have backgrounds in highly creative places. I want to start doing more of these things and talking more about them to bring visibility to this idea.

People tend to be impressed and surprised by the fact that I’m a classically-trained pianist. I won awards for it as a kid. I think my mom still has a few of them up on the piano of my childhood home. (I should take some photos for social proof 😬)

During the angstiest of my teen years, I swore off piano and taught myself bass, then guitar, and now I dabble in those and a few other instruments. I went to school for music and composed some odd pieces, like one for solo 5-string bass and live looped electronics. I’ve performed with and produced for several bands and musicians. I played bass in an instrumental prog-rock band in high school, the other members of which went on to form Earthside (link in comments — check them out, especially if you’re into epic rock/metal stuff, they’re great).

I married an artist and photographer, who went to school for design and quickly became disenchanted with it. She is now an amazing photographer of women and young families, and creates art prints of things in nature that were recently described as “like old Renaissance paintings, but photos” (link to her work in comments).

In my late 20s, deep in my product career, I rediscovered writing prose and songs, both for fun and as a means to get ideas out in to the world. I also revitalized my love for the piano; now most of the songs I write start on a piano, and you can hear that across the 4 albums I’ve released (link to listen in comments - note some songs contain profanity and are noted as such). But I quickly ran out of time to do this stuff, especially after my daughter was born.

When you’re a PM, you are incentivized to be “all in” on your product or problem space — it becomes extremely difficult to find the time and/or mental fortitude to keep other interests moving forward. Now that I’m in between full-time gigs, my wife and I plan to spend much more of our days helping each other in our creative pursuits, working on some of them together, and bringing our 2-year-old daughter in the mix as she likes.

So, what’s next?

Oh god, I have both no idea and too many ideas.

First, I’m taking a beat, to be — really be — with my family.

Ideally, I’d find a senior/staff/principal IC product role at a company with a strong product culture, or perhaps a product leadership role at an early-stage joint, doing interesting things in the arts, content, productivity, automation, wellness or climate tech spaces. I’m also very open to consulting or fractional engagements.

But I’ve also got a bunch of other ideas in my brain and some time to explore them.

You’ll probably see me writing more about the intersection of things I care about: product craft, operations, music/art, remote work, parenting, and the like. Tone deaf color blind is an acknowledgment of my imperfections as a human and the impostor syndrome that inevitably comes with “success” in light of those imperfections, so most of my writing will be through that lens. I am committing myself one long-form piece of writing each week (this one counts for this week).

I also plan to use this opportunity to finish multiple half-finished music projects and perhaps reestablish myself a bit as a music person. I’ve written 4 (!) albums of music! And I have a fifth one pretty close to being done! I should put it out into the world. I’ve got another release almost ready to go, that is a doozy of a left-turn that parents should particularly enjoy.

Where we’re going, there are a million roads

Rethinking the product roadmap as a tool of PMs

It’s kind of silly to me how the concept of a product roadmap has, in a lot of cases, devolved into essentially a calendar. Too often do product managers say “this is what we’re doing, when” — sure, there are some assumptions and unknowns to acknowledge, but the plan is the plan and the timeline is the timeline, even if it realistically could change. A series of commitments on a timeline.

In fact, this idea has totally taken over as the primary meaning of the word “roadmap.” When I Google the word, this is what I get:

And when I see what teams put forth as “roadmaps,” they often look something like this:

We PMs know this isn’t representative of reality.

I don’t care what anyone says or what any roadmap might suggest: product building is inherently ambiguous. We rarely truly know with 100% certainty what our users want, or what will work in the real world. Building something to address a problem or capture an opportunity usually involves a windy difficult series of roads with divergent paths, odd roadblocks, and interesting opportunities along the way. There are a million options, or roads, for how we get to our shiny objective.

In fact, you may want to reach your objective, or you may also find a different one that’s more compelling to achieve. Or you might end up at a dead end due to unforeseen circumstances and need to move on to the next thing. You may find out halfway toward building your north star that it’s not nearly as impactful or exciting of a north star as you thought.

But we still use the roadmap as the artifact representing the work we plan to do. We’ve rewired our brains to think of roadmaps as a set of promises to our stakeholders and our users — the directions instead of the map itself.

And I get why — it’s about providing that clarity of direction. I’ve been in dozens of situations where I’ve felt a pull to promise a clear set of deliverables, a tractor beam of targets, or even a list of things I won’t commit to, mostly to address the need for direction or (to be honest) peace of mind. There is value in this. I do not deny it.

But I also worry that it obfuscates (or worse, trivializes) the actual work that product managers and their teams do: talking to customers, interpreting what they say, brainstorming interesting solutions to the problems that emerge, worrying about what could go wrong, navigating sometimes intense bureaucracies of partner teams, getting blocked by and unblocking weird blockers, testing the product, shipping the product, analyzing the product, and then maybe (but not always) actually meeting the objective(s) they sought out.

Adding just a space to change my Google image search query to “road map” yields slightly different results, some of which show a web of possible routes to take:

I’ve always had a fascination with maps, especially highway and subway maps. They suggest possibilities — different routes to take to different destinations. Let’s look at the New York City Subway map:

Say I want to get from a hypothetical home in Hoboken, NJ to La Guardia Airport to meet a friend flying in to visit. There’s a bunch of ways I can get there. (Stating a disclaimer now: I am not an NYC resident and have a limited understanding of how the subway works in practice, so all of the following might be horribly thought out. The point is not to find the best way to LGA, but to illustrate a point about optionality and ambiguity in product development.)

In all cases, I need to at least take the PATH train simply to get into Manhattan, where I’m connected to the rest of the subway system. From there, I have a number of options to reach my destination — all of them involve a bus in some form, but my most efficient path likely involves minimizing bus time. So, I can take a number of paths:

• I can take any of the 1, 2, 3, A, B, C or D trains up toward the Bronx and pick up a bus to LGA there. I’d likely opt for an express train (2, 3, A or B) unless there’s somewhere I can stop on the way via local train to, say, pick up food so I’m also not starving when I meet my friend.
  
• Alternatively, I could wait for the E train and take it northeast into Jackson Heights, Queens, where I can pick up a bus there. That’s a fairly long trek on the subway, but the bus ride is extremely short.
  
• I could also walk a bit north from Penn Station to Times Square and pick up the 7 train — particularly the <7> Express, which likely will get me to that Queens shuttle bus faster. That said, there is now a walk involved. And possibly another subway fare I need to pay.

I’d probably opt for the <7> express option, but let’s say that line is closed for service — or worse, a train breaks down while I’m on it. Unforeseen consequences that make me question the direction I took. A local train may have more frequent stops, giving me the option to get off more frequently and seek an alternate route if I need to.

Now let’s say my friend’s flight gets messed up and needs to land at JFK instead (disclaimer: I’m not an air traffic controller and have no idea if that would realistically happen, I haven’t flown in 3+ years 😅), I now have a different destination I need to get to. But, I still need to take the PATH train into Manhattan regardless. From there, I can either deal with the hour-plus-long slog of the A train, or perhaps find a more optimal route involving transfers which may or may not get me there faster.

I have a final option: I could always ride in an Uber/Lyft/taxi. But this is likely (1) far more expensive, (2) may not actually be faster thanks to NYC bridge and tunnel traffic, or (3) may come with other positive and negative unintended effects (my driver may be awesome or terrible).

There are a TON of parallels in the world of product development. A ton of things can go wrong, a ton of options present themselves for the way forward, and a ton of opportunities exist between the origin and destination.

Let’s stop thinking of roadmaps like calendars and more like what they really are: maps. Maps that get us different possible destinations.

When I’m thinking about a roadmap, especially when there’s a lot of ambiguity around where to go, I sometimes will create something akin to a flowchart — but instead of parts of a flow, the items are assumptions to be tested, features to address needs, capabilities to unlock value –which may or may not lead to various possible outcomes. Almost like a “choose your own adventure”. Almost like a map without the directions fully defined yet.

I may start with a possible destination / outcome / North Star, a starting point, and a first decision I need to make.

Then continue to map out possibilities, assumptions and open questions from there. I tend to let my mind naturally flow through these first, and then attempt to sequence them based on risk and sensible sequence. That may result in something like this:

I obviously need to provide some guidance on when I hope to tackle the questions or ideas laid out there, so I color-code different types of items (actual features to build, assumptions to test, decision points) so it’s clear when we’re building, testing or researching:

And so I end up essentially a different representation of the same commitments I may put on a classic “roadmap slide” — but with all the possible paths, justifications and logical sequencing that drives the things we may or may not achieve. Add in a rough timeline and you’ve got all the key ingredients:

This concept obviously contains a bunch of assumptions in its own right, and clearly oversimplifies the reality of building products. Regardless, I really like this for a few reasons:

1. As a PM, this is how I actually think about the roadmap. I’ve personally made visuals like this in previous roles to map out possible roadmaps, for my eyes only, simply to make sense of a problem space.
   
2. It healthily and clearly establishes the notion that we may not achieve the singular outcome we hope to achieve, but we may achieve other outcomes along the way or instead.
   
3. It especially feels useful when building 0-to-1 products, where my team may be iterating toward a presumed ideal state but we simply don’t know what it looks like yet.

I also realize it falls short in one very important way: it is way too cumbersome for any non-product/technical person to be willing to navigate. There is immense value in the “executive summary,” the punchlines of a complex map like this. I created this in Whimsical, which was the best-looking flowchart tool I could find. Ideally there would be a way to easily collapse all the possible routes, highlighting the big features, themes and questions, for stakeholder digestion — but from what I can tell, such a tool does not exist for this (admittedly niche) purpose.

What if there was a way to minimize (without hiding) the other nodes in this map, such that the primary milestones or deliverables were prominently displayed against the timeframe, but the ambiguities and possible directions were still clear? I would love a simple way to toggle between the complicated map above and a simpler view for stakeholders that showed direction while acknowledging those possible outcomes and weird realities of building software, and even showed my team’s confidence around hitting certain outcomes. Perhaps something like this:

How might this play out in the wild?

So I’ve tried this type of roadmap artifact in a few previous roles — mostly for myself to personally keep track of all the options, but to also share with stakeholders as a way to envision the ways (not way) forward. While it’s certainly not a perfect document, it helped to convey the idea that while we (the product/design/technology function) did not know exactly what this product would look like, we did know the problem it should solve, what success may look like, and a few variations of how much work it may take to get there.

But the document didn’t solve for that on its own. Communication is also critical – as you test your assumptions and potentially change direction, you need to (1) update the living document and (2) communicate that change. I fell into a good cycle of this every 2 weeks; that may work better or worse in some contexts, depending on how quickly you need to learn or how complex/risky your problem space is.

Finally, none of this works without a clearly articulated vision, strategy and — most importantly, I’d argue — guiding principles. Principles to guide what success is and isn’t, what features or even design conventions are in scope and aligned with your vision, and the values of the customer you build for.

My overarching conclusion here is that, above all else, we as product managers and leaders should be critically reviewing not just our work, not just how we work, but the artifacts we use to document our work.

The roadmap is such a core part of the work of product managers, an essential tool for communicating the direction of your and your team’s work. But it also, at best, obfuscates the hard work of PMs. At worst, risks creating false confidence based on expectations that may simply be wrong — not to anyone’s fault, but due to a simple lack of acknowledging the assumptions and options of how to move your product forward.

So let’s humor new ways of communicating how we move forward.

Location agnosticism

My life totally changed over the course of 2020 as did most people’s, but really it started that metamorphosis when I took a job that didn’t require commuting to an office. In July 2019 I was living in a smallish townhouse in a suburb of Boston, easily commutable to Wayfair’s central HQ in the bustling Back Bay neighborhood but ever-so-slightly quieter and cheaper than downtown. My first day working for Abstract was weird in a sense: I was still paying overpriced rent for a climate-controlled box, but instead of leaving, I was taking three or four hours of Zoom calls from said box. It was both urban and disappointingly disconnected. I relished the opportunity for sustained “focus time” at my desk in the tiny second bedroom Alicia and I shared as an “office,” but I still had to take a train or bus to a decent coffee shop or co-working space if I wanted to get away.

Regardless, I loved the underlying principles of remote work (or, to be precise, distributed work): a team need not be co-located or working synchronously in order to solve great problems, and an individual can perform better in a space they control and are comfortable with. So when my wife and I decided that being near nature was more important that being near a city, we leaned further into it: we cashed out most of the equity I was extremely fortunate to have accumulated from my tenure at Wayfair and bought a house, not in a connected suburb of Boston but a rural town over an hour away from the city limits. Not in the middle of nowhere, but twenty minutes’ drive from an interstate highway in a town offering the “right to farm.” Fortunately, we got pretty lucky with the house: not perfect but with great bones, well in the bounds of what we could afford, and in a nice, safe neighborhood over farmland next to a forest. Not everyone is so lucky or privileged.

The lockdowns started four months in. As I noted two weeks ago, I struggled a bit with depression and nihilism while watching the pandemic spread and our government prove incapable of the basic management of it. Nevertheless, my family was extremely fortunate to realize that, in spite of being unable to engage in “normal society,” we were able to bring important aspects of it into our home to replicate the aspects of it we missed most, like the coffee shops I used to frequent and the meals I used to crave at my favorite spots. We started FaceTiming almost weekly with our parents and siblings, and now feel closer to them than ever. I took on new hobbies (mainly centered around improving the house) and creative outlets (like writing this) to fill time previously spent at shows, bars with coworkers, and warehouse practice spaces with musician friends.

This is what we chose to do. Not everyone thrives in a rural environment. Most important about the past year of discovery was not that we should all move to peace & quiet, but that the situation in 2021 enables us to be and have exactly what we want, pretty much anywhere — even if that somewhere is home. I didn’t attempt to replicate my old music hangs, but if I wanted to, I had the option to pretend I was at a show, courtesy of Instagram Live and Patreon and others, or in a warehouse practice space thanks to those same platforms and tools like Zoom, Twitch and JamKazam, if I so pleased. I could even sign up for high-definition live performance video of my city’s symphony orchestra to re-live the joy of the lower balcony of Boston’s Symphony Hall. With a sub-$500 TV and surround sound system (or even a couple of HomePods), it comes damn close to the real thing.

To be clear: 4K video and livestreaming are absolutely not a replacement for in-person entertainment… but it has closed the gap a bit. And that gap will only get smaller over time such that you won’t need to live in a major city to experience the happenings exclusive to the major city, nor will you need to move to the middle of nowhere to experience the joy of silence in nature.

What is location agnosticism?

The idea of location agnosticism is this: Anything I want to have or do is available at my fingertips, no matter where I am, and in the format with which I am most comfortable.

It’s not really anything new. It’s not simply about defining a methodology for remote work. It’s a values system that can govern many—or all—aspects of your life, as you see fit. It’s something you can decide is important or not to how you live your life, something that helps guide decisions around where you go and what you invest in.

It’s not an excuse for homebody-ism. Sure, I love being at and around my house, but I also get stir crazy. We all crave social interaction. I talk to my neighbors at a social distance and occasionally enjoy the light banter of my mask-covered grocery cashier. I would love to drive back into Boston’s Allston neighborhood to catch a punk show at one of my favorite former dives. In lieu of that, I have alternatives at home that are becoming increasingly compelling.

It’s not something only for homeowners or rural dwellers to leverage. City dwellers obviously have their travel options too — sure, airports during a pandemic are risky, but flying sure is cheap — and options abound for bringing more of the world into a tiny apartment. Modular storage systems, convertible surfaces and even rental furniture, are a thing now blogged about by thousands across the Internet. Delicious coffee from around the world is something you can subscribe to. You can even recreate brick oven pizza in a 8’x6’ kitchen if you wanted.

It’s not digital nomadism, either. I don’t want my possessions to be location agnostic just so I can sell my house and freely travel the world — I might’ve mentioned that I love being at home. A lot. But city-dwellers who love living in cities, or nomads who love to travel the world whenever they please, should have access to the most important things to them in their location of choice.

And in 2021 we’re quite close to that being a reality, not thanks to AR or VR, but because of some key advances in a few areas and, more importantly, the mindset shift that the pandemic forced upon many of us.

Adjusting

Say what you will about the pandemic. This sucks. I know people are in survival mode. We’ve all had to adjust. People have left the major cities in droves. Some have decided they regret it, and they’re being gaslighted by the Wall Street Journal. Instead of focusing on ways to make it easier for the people who want to return to cities to do so, we’re forced to choose a side: urban or rural. With location agnosticism, why should it matter?

On a more dire note, I’ve also talked to dozens of folks struggling and suffering. I’ve watched hundreds of creators shift from live to virtual performances, from sponsor-driven revenue to subscriptions paid for by their biggest fans. Jobless folks have turned to Patreon, Twitch, Substack and OnlyFans to try new forms of income — and while millions are still struggling, it’s working out for some. I truly wish success for all these folks, not only because they deserve some amount of financial stability, but also to beg the question: how many of us really want to go back to the old way of working?

If you were considered disposable by your previous employer, why would you want to go work for them again if you didn’t need to? That’s a difficult mental shift, especially in America where so many of our decisions—including where to go and what to invest in—are driven by the power of massive corporations. As more individuals are able to work from anywhere, increasingly for themselves, we remove our dependence on these corporations and can introduce different values into our lives.

Enablers

I cannot emphasize how grateful I am for the list of innovations I am about to walk through which have expanded the possibilities for location agnosticism:

Modern Apple hardware. Between the most recent round of iPhones, iPads and the new Apple Silicon Mac lineup, there’s no reason for concern of an unreliable computing machine anymore (of course, assuming you can afford it). Each of these devices are so rock-solid for doing any kind of work on a computer — either at home or on the go. (Not that I go much of anywhere, but it’s great to know that I can work from the parking lot of my grocery store while masked.)

Reliable virtual desktopping and intuitive automation. The fact that my Apple hardware is just so reliable means I can access any of it anywhere. If I’m out and about but need to grab a file from my Mac mini at home, I have multiple ways of doing that, either by logging in remotely with Screens, SSHing in with a-shell, or with one of several Shortcuts I had already created for some specific cases.

Reliable noise-canceling headphones, specifically (in my opinion) the AirPods Pro. If I need to step away from my family in a pinch, I can enter a world all to myself. If I need to pay attention to the world, I just hold my earbud for a quarter second and can then hear everything around me.

Reliable video collaboration. Say how tired you are of Zoom. I don’t care — it’s near-perfect at helping people talk to each other, especially if you have reliable internet. Speaking of which,

Finally affordable gigabit internet. A year after we moved into our current house, our introductory discounted Internet offer from Comcast expired. You know what was only $8/month more expensive than the shitty default package? Gigabit download speeds. Arguably the most invaluable service I pay for other than electricity itself.

Smarter, unified smart home technology. I’m able to secure my home using a secure protocol honed by Apple, including a virtual alarm system I configured and manage myself that functions like an actual alarm system, without having to pay a creepy third party ridiculous fees to watch my house and call 911 for me. Why does this matter? If I ever want or need to leave the house, the last thing I’m worrying about is whether I’ll know if we’re getting intruders or that my dog is safe.

Increased financial options and improved access to financial information & best practices. All this would be impossible without an increased awareness of my financial options. I am grateful for all the advice I’ve received from parents and in-laws, but I’m even more grateful to have tools like Nerdwallet and Credit Karma and the countless budgeting apps to help me understand what I can do with my credit score and how I can manage debt.

Access to affordable food & health product via Amazon and other online vendors. An example from the past few months: We just bought a portable treadmill for $300 so Alicia could go on walks without having to risk slipping her pregnant body on ice. I remember when it was a big deal for my parents to buy a NordicTrack when I was a kid. Another example: all the gluten-free foods that are available not just in grocery stores, but on Amazon and Thrive Market, shipped to me on an automatic recurring basis.

Where we could keep going

Technology is enabling location-agnostic living, but there’s so much further we can go. If the pandemic doesn’t end quickly, or we find ourselves in another one soon after, there will continue to be massive investments in helping people live more of their lives at home or wherever they choose to be. Those investments fall into three major buckets: logistics, job creation and collaboration.

Logistics

Amazon and Apple have proven that it’s possible to ship massive quantities of products worldwide in pretty quick timeframes. I already mentioned I started getting some cheap, portable exercise equipment for the house; in a matter of 3 days I had a small home gym.

Shipping perishable food at scale is a really hard problem. Yet hundreds of restaurants both shifted toward takeout and delivery to sustain their business and even began selling their recipes & ingredients to customers. And why not? Why scour the internet for a recipe you’ll struggle to get right, or deal with the repetitive mediocrity of services like HelloFresh, when you can choose to get amazing food from your local restaurant of choice or have them enable a fun at-home cooking experience for you and your family? But this only goes so far: you’re location-locked. There is a decent Mexican family-style restaurant in my town, but what if I want a particular dish from this Venezuelan dive I loved in Bushwick? There’s a realistic future in which I could order the ingredients and recipe from that restaurant’s website, powered by Shopify, and have them shipped to my house four hours away. As a customer I don’t care whether they necessarily came from the physical restaurant location, as long as I know exactly how to recreate the amazing shredded beef arepas I so dearly miss to this day. Were they deep-fried? I don’t remember, but if so, I can get a deep fryer from Amazon in a day or two for 60 bucks — and that time to deliver will keep decreasing, even as the next pandemic triggers the next frantic search for toilet paper.

What’s harder than moving food? Moving our entire lives. A lot of people stay put not because they love where they live, but because the process of moving — let alone leasing or buying a house or apartment — is a ridiculous amount of work. The Internet has made it really easy to find new places to visit or live, but the process of actually moving to those locations is somehow still tedious, expensive and confusing in 2021 between open houses, inspections, the slow process due to the legal and financial burden you’re incurring. If people continue to move out of cities thanks to remote work, what if a startup were to disrupt the legal aspects of renting or buying a house? Drones and great iPhone cameras already make it easy for property managers or realtors to provide virtual tours of a house — what if you could perform a home inspection virtually, hire a property lawyer and close on your new house entirely from your old house? (Sure, most of this is already technically possible, but I hope that over time, folks in legal professions will grow comfortable with new, secure document and video collaboration tools to make this possible.)

As I think about other places I could live in the future, I start to think of Airbnb not just as a way to vacation, but as a way to scout new places to live. I remember staying at a tiny Airbnb in Williamsburg, Brooklyn when Alicia and I considered living there for a while. We wanted to have a hipster New York weekend, but we also wanted to feel out what it would be like to live there. Imagine using the remote Airbnb cabin you book next not just as a getaway, but as a taste of what remote cabin living would look like.

What if, in a few years, you could move out to a cabin in the woods and have access to pretty much all the things you had before, thanks to a process you did entirely virtually with all the transparency you’d have from an in-person real estate agent? What if you hated cabin living and wanted to move back, but you could sell your cabin and get back into a city apartment in a matter of, say, two weeks?

What if you wanted to change up your furniture look for the new house, so you got all your furniture re-sold via Letgo, Poshmark and Facebook Marketplace and rented some new stuff to try via Fernish? What if you could plan out the entire look and feel of your home without even being there thanks to high-res 3D renderings of the home, provided to you by the previous owner or their realtor in a format even they understood?

Job creation

As much as it’s likely been painful for millions of people to survive 2020 due to job loss (I am immensely privileged and lucky to not know this feeling), it’s comforting to know simply how many options exist to both educate and employ oneself, thanks to the Internet. Learning how to code is free or incredibly cheap now. Anyone can start making money by setting up an OnlyFans or Twitch account about any topic they find interesting. You could even build an entire business with a bunch of cheap online services without any coding experience; there’s an entire community of thousands dedicated to developing and shipping these ideas. I visit Indie Hackers every few weeks to skim the new ideas people are building and am constantly impressed, not necessarily with the ideas but with the diversity of folks exploring new ways to sustain a living.

Let’s say these trends continue. We already know and embrace robots taking over many jobs previously covered by humans; I’m not about to begin complaining about retail self-checkout, self-driving cars or drones delivering my packages. Why not embrace these inevitable changes as improvements to our daily lives, and encourage more creation of new ideas? The beauty of these kinds of jobs is that, in most cases, they can be done from anywhere you have access to the Internet.

Collaboration

I don’t want to talk about web SaaS Products or the business side of collaboration. Remote work will inevitably continue to improve because so many companies are simply bad about it now. The collaboration investments that will matter will help resolve the issue of isolation: the feeling of being socially present, in a shared space with others.

Let’s assume VR keeps advancing. I still debate whether it’ll ever be as good as sci-fi movies purport, but in the meantime, our video collaboration software and hardware is also getting better and better. I avoid Facebook as much as possible, but its Portal can already follow you around your house while you talk to the family. Imagine what Apple’s rumored AR glasses could do with FaceTime or Zoom integrated. Imagine a Fitness mirror but for your family gatherings or job interviews. Imagine an entire wall of your apartment that you could share with your friends in an entirely different house, seeing a virtually live feed of each other’s half of a virtual party. AR, or even a large tablet screen, could enable a near-live game of Monopoly or Catan, as if everyone is literally sitting next to each other (depending on the layout of course). We have a mostly-bare wall in our living room currently, and I get excited thinking about the virtual window it could open to, whether it be my sister’s new house, a shared coworking space with my coworkers, or the Isabella Stewart Gardner Museum. If the video quality and proportions are right, it’ll be like I’m there, and my kitchen is three steps behind me.

The hilarious truth is that we’re really not far away. Fitness mirrors and live virtual classes exist. The only thing holding these things back from being truly compelling are internet speeds, picture quality and cost — each of which will improve quicker than we’ll realize.

And for some of us, it’s already good enough. This guy tried to replicate Disney World for his kids. Was it perfect? No, but a toddler wouldn’t notice.

I often wonder how happy (or depressed) I’d be if I was alone in this house. (Of course, if I was not married, I’d probably have no reason to buy a house in rural Massachusetts and my life would look quite different). Having a spouse and dog I love, plus a child on the way, are truly the elements that made our version of location agnostic living an enjoyable way to live.

I wonder how the ideas of companionship and roommates will shift as the developed world shifts. Not to say that I believe nobody should live alone — I wanted this for myself for a long time — but I wonder about the mental well-being of those living alone while respecting the seriousness of the pandemic. In TV and movies, there’s often the trope of the hacker personality living alone, endlessly staring at a computer screen or the lenses of a VR headset, as a means of coping with loneliness or social anxiety. One of my favorite all-time shows, Mr. Robot, centers around one of these characters. I do genuinely hope that investments in virtual space-sharing will destroy this notion that we are all alone, hunched behind a screen with our pajama bottoms and hoodies on, and that’s the only way to collaborate.

On privilege, location & minimalism

As I wrote this, I kept thinking about how much of the concept of location agnosticism is one of luxury: so many of the decisions I noted were made possible by money I accumulated working a white-collar tech job in a highly segregated city as a straight white man with a liberal arts degree. Even with all that considered, our life is far from perfect, and I still struggle with financial insecurity. I literally have no possible means to imagine the desperation some people are facing right now.

In writing this, I realized that location agnosticism need not be a symbol of privilege, but rather a priority one can make for their life. So many of the innovations of 2020 can bring aspects of location agnosticism to more people than ever, and ultimately it’s up to the individual as to how important it is to have access to your most important things, experiences, and loved ones and in what ways. One does not need next-day delivery from Amazon or quick access to an airport or a huge house to achieve a location-agnostic lifestyle. It’s far more about knowing what aspects of your life are important to you, and ensuring you have the systems and tools available to get at it wherever or whenever you happen to be.

In my case, I’ve decided that a bunch of the services I used to rely on are not worth keeping. I’ve stopped impulse-buying things I don’t need. I’ve instead learned so much about cooking and baking over the last few months, and not only can I prepare a steak in multiple ways better than the best nearby steakhouse, and my family is saving a ton of money in the process because I’m using meat that is delivered to my house every few weeks — and I’m enjoying myself learning these new things. This was one of several intentional decisions made over the past year to cut out crutches and stay focused on the values my family and I care about.

—
The pandemic obviously accelerated much of the shift to remote work, and the isolation that comes with it. I also do not expect the pandemic to go away quickly, nor do I expect it to be the only one in my lifetime. That said, I feel more prepared than ever, and I hope that some of the developments that have resulted allow us to live more flexibly and comfortably, in whichever way that is for a given individual. Sure, it doesn’t come without a fair degree of privilege, but as innovation continues and prices go down for some of these modern conveniences, more of will be able to live in the way we desire.

Creativity & LinkedIn

Quotes on display, and other outlets I don’t understand

Before I get into anything: I was going to post a newsletter today primarily talking about creative outlets, and then [a treasonous coup attempt happened less than 7 hours away from my house]. I won’t use my small platform to talk about this — there’s plenty that’s been said already by people better informed than me — but I do want to acknowledge that it feels incredibly uncomfortable to publish content from my limited, privileged point of view about trying to do better as a human when so many people in America have not only given up on doing so, but seem to now believe that ignorance and brutality are somehow the right values to pursue. Let’s hope that the people ignoring this disheartening reality have finally taken notice and it shows in their actions.

takes a breath

I’ve been working with a leadership coach through my employer. During one of my last sessions, we got into a dialogue about what activities I use to exercise the creative muscle I won’t stop going on about. I mentioned music, as I typically do in these types of conversations, but also the fact that I’ve struggled to see it as a purely fun endeavor. I expressed my need to write something, and over the course of the conversation we landed on the fact that I could start writing freely in the mornings to get thoughts down, and gradually they may evolve into more concrete ideas for newsletters, fiction, whatever they may be. These ideas could come from anywhere and solely exist as manifestations of small ideas I have. I’ve had a horrible habit of not writing things down throughout my life — I blame my excellent memory for details for this — and through this coaching session, I discovered that this may have contributed to my inability to feel creatively accomplished as of late. To quickly report: writing almost every day since that session has helped me center my mood immensely, and I have started writing this newsletter again as a result.

At one point during the conversation, as an example of a possible use of this writing down of things, the coach interjects his own creative outlet: Using [Canva] to create little visuals of quotes he likes, and then posting them on LinkedIn.

I’ll be candid: I reacted viscerally. Almost every word in the sentence made me cringe: Canva, quotes, visuals, LinkedIn. I’ve never been a visual person. I married a designer/photographer because she complements my strengths and weaknesses, and one of those weakness is visual thought. When we think of an improvement to our home, I am usually completely unable to visualize what it will look like; I have to trust her vision (and I am usually impressed with the result). I’ve never used Canva and don’t see a reason to start — it appears to be a tool almost exclusively for designing social media posts, and the simple fact that a business can exist on that value proposition makes me want to die inside.

I’ve never been one to, as they say, capture quotes that inspire me. I’ve never personally felt inspired by something someone else said. In fact, quotes often feel to me like a cop-out for both original thought and careful nuance applied to a given situation. Nuance is arguably the most important element to bring to human society & culture in 2021; quotes and platitudes oversimplify, and as a result, lead to overly simplistic thinking and solutions to deeply complicated problems.

Let’s talk about LinkedIn. I despise it. It’s the worst kind of social network: one centered around the cutthroat, fake-supportive, workaholic white-collar culture mostly bred in America (and bleeding overseas), in which professionals are directly incentivized to shamelessly spew platitudes, share mostly hollow wins that don’t improve our society, and half-heartedly congratulate their peers over all of it. Where Facebook and Twitter are cesspools of vitriol and Instagram is a scrollable billboard, LinkedIn is a virtual circle-jerk for the professional community. I don’t know whether the content shared on LinkedIn is done genuinely, but years of experience in the consumer & enterprise technology industry and other social media platforms have wired my brain to think that is not. I’m unhappy I have to use LinkedIn to get this read by people. I hope you sign up for my newsletter so you don’t need to use LinkedIn to find it.

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Yet, for some reason, I visit it compulsively three or four times a day. My time on LinkedIn is truly a compulsion: I don’t want to go there because the content and underlying premise of LinkedIn makes me want to die but, subconsciously, something makes me do it. I think it roots to a former deep insecurity about my career prospects — I wouldn’t post, but I would seek approval and encouragement from others, or scour the job boards to consider my options. I also am reasonably certain that active contribution to the LinkedIn cesspool does in fact improve my chances of consideration for work posted on LinkedIn — that must be part of the algorithm, because it serves everyone (especially Microsoft, who — friendly reminder — owns LinkedIn).

My coach had me thinking: Do LinkedIn users post things as a creative outlet, or to shamelessly promote themselves, or both, or something else entirely?

On another dimension: Is a creative outlet intrinsically tied to promoting one’s work, business or the desire to generate income, or can one separate those two ideas from each other?

Do either of those questions even need to be answered? Obviously they don’t. Anything that one considers a creative outlet can be considered a creative outlet, even if it’s weirdly tied to a thing that helps one find or promote their work. It took me several days to understand how posting anything at all on LinkedIn — of all social networks — could be considered just a fun creative thing to do.

Additionally, I don’t need to be capturing field recordings for my next piece of ambient music, or brainstorming a work of epic fiction to be “exercising my creative muscles.” I could just write. I could even write something to post on social media — which by the way, as I already mentioned, {I will have done with this newsletter}. It’s not about the distribution method, it’s about the ideas being explored and shared, which can be as simple as thinking about and sharing a quote you like, or as complex as a collection of carefully structured ideas set to music. I don’t need to build creativity up to something more than it is the act of creating.

Fits & starts

Hey, it’s 2020 now! Cue things about resolutions and intentions and bettering selves. This year I intend to drive for more clarity and intentionality with what I put out to the world and how I spend my time doing it.

At work, most of us try to optimize how we spend our working time using a tool called Clockwise. It enables you to set preferences for how & when you like to work, automatically scans everyone’s calendars for meetings, and automatically reschedules those meetings to give each participant as much “focus time” based on their own preferences. On the surface, it’s wonderful for creating meeting block periods without having to think about arranging my day, and some of my colleagues thrive in long periods of deep focus.

But I barely use the focus time as Clockwise probably intends. Being at home, even in a relatively bare spare room / office space, I’m constantly distracted by my personal life: my wife, our things, my new puppy, my Nintendo Switch, my Apple Music library, Wikipedia, trees, cars driving by, a lightning strike of an idea, snacks.

For a while this frustrated me. I had thought working from home was the ultimate path to deep focus and productivity: no commute, no distractions by coworkers, no proverbial watercooler to seek out gossip (though I do enjoy my kitchen), no weird internal IT rules that prevent me from running my work computer the way I want. But I still find myself distracted, often by my own bullshit, which results in a very fits-and-starts style of work through much of the workday. Twenty minutes of deeply focused writing or backlog admin might be suddenly interrupted by my own desire to update my near-perfect playlist to cook to. Alicia might suddenly be having an awful symptom flare-up and I now suddenly need to make lunch and find her medication. Having a puppy isn’t quite like having children, but it’s certainly tested my ability to context switch on a dime to avoid pee stains all over the house.

I’ve very recently learned to accept this reality of working. It’s okay to get distracted by life. It’s okay to feel a little bored trying to improve how teams design products after hammering away at a product requirements document for a bit. It’s okay to stop and cuddle with my wife or a dog because that provides me so much more joy and fulfillment than how much time I can put into staring at a laptop screen.

I can still be quite intentional even if I’m bouncing between the many things in my life in fits & starts. An optimally-placed three hour block of time to write a song or a strategy document won’t solve for me being clear in what I’m looking to do and why; I can be comfortable working ten minutes here, ten minutes there, as long as I know why I’m doing it.

Out of nowhere

Obligatory retrospective write-up for 2020

Sometime around May this year, I fell into a few different forms of writer’s block: I stopped being able to write music, I mostly stopped sharing things on social media, and I stopped writing this newsletter. If you are one of the impressive nineteen people who get this post in your email inbox, firstly, thank you; also, you probably didn’t notice (which is obviously fine).

I felt uncomfortable sharing thoughts, music, opinions, really anything at all when so many people around me were suffering. 2020 was, in many ways, the year of loads of people crying out — to be heard, to be helped, to argue, to defend their beliefs and values. Not only did I not want to add to the noise, but I found myself actively resistant to the idea of participating in my largely progressive, highly privilege-driven echo chamber.

I also stopped writing and talking about music after rushing out [my last album Full Life] in May. I primarily wanted to just get it off my plate. I’m not proud of how it sounds — it’s a lazy production in several regards, and I didn’t care to promote it. So many of my friends needed to figure out new ways to sustain a living and it fell terrible trying to promote my own music as a person with a stable income. I did have things to say; I didn’t feel like asking people to listen.

Thankfully, 2020 is over and we can look forward to a still-painful-but-slightly-more-optimistic 2021 thanks to a number of developments.

I’ve also gotten over myself a bit. I realized only recently that it’s not about adding noise to the echo chamber — instead, it’s about finding something I’m genuinely excited to talk about, and talking about that thing. I think I was depressed for much of the early phase of the pandemic. That kept me in a state devoid of joy and falling into (mostly unhealthy) patterns: complaining, doom-scrolling, doing the basic things that need getting done instead of truly taking care of myself and the few around me.

I’m not sure what specifically caused a turnaround for me — in reality, it was probably a number of things starting or resolving themselves (more on that later). Now I’m pleasantly surprised to be, for the first time in a while, excited and unconcerned about the future. I am aware of the privilege that has led to my own lack of worry about the future — the world around me is still pretty miserable for quite a lot of people — but I’m happy to have my mind in a good place, and from there I hope to maybe lift others a little bit.

I also hope to bring some joy into the world: my wife and I conceived of a baby daughter, and she’s due in March. If I cannot take on the world’s challenges myself, I can at least raise a good human to perpetuate some good in the world after I’m too far gone.

Before moving on, yes: we are having a child during a pandemic. We are also going to be having it in our home, not in a hospital. This was not a decision triggered by the pandemic, but something the pandemic reiterated the value of doing. Home birth is a completely safe and, in my opinion, superior option to hospital-based birth in 2020, and if you don’t agree with me, you should do some light research on the topic and [why plenty of doctors prefer it themselves].

A scattershot retelling of what happened

Time both flew by and stopped, as everyone has already felt and reported. So, in a number of ways, a lot changed, but a lot stayed the same. As the year came to an end, I found myself struggling to succinctly answer: what did I actually do this year?

After thinking about it for a few minutes, I found myself amused, because quite a few really big important things did happen, starting with the aforementioned future daughter. People have written on the fact that the pandemic didn’t create, but instead accelerated, a lot of meaningful changes across the world — the shift to remote work and learning, the funding of vaccine development, the political landscape, just to mention a few — and in many ways, the same occurred. For me, remote work was not new, but I really settled into it thanks to a concerted effort across [my company] to embrace the realities of pandemic/remote life. Almost gone are superfluous, ritualistic meetings; what we now have (mostly) are short intentional calls, bouts of meaningful focus or personal time, and opportunities to simply socialize. Just before the December holidays, my team did a virtual Christmas cookie bake-off.

I learned so much about maintaining and improving a home. I installed some flooring and an entirely new staircase & railing in my house. I also planted a garden, built a garden fence, installed some smart light switches, replaced all the doorknobs in the house with modern-looking ones, learned how to use a zero-turn riding lawnmower, organized the garage a few times, and started installing a drop ceiling in my unfinished basement.

I learned to simply love being home. Home cooking, drinking, relaxing, socializing, all of it. Between food allergies, health & life changes, and the pandemic, Alicia and I gradually grew averse to the limited going-out options we had — and replaced them with suitable alternatives in and around our home, including:

• Bathing Rosie and trimming her nails in our guest bathtub, a la a dog groomer (the nail trimmers and grooming supplies cost the equivalent of, like, 2 groomer appointments);
  
• My wife learning to cut her own and my hair (the professional barber kit we bought cost the equivalent of, like, 3 haircuts);
  
• Me learning to make soups, roast vegetables and grill steaks arguably better than any nearby restaurant (if only we had a pizza oven, I’d probably have no reason to eat out ever again);
  
• Converting one corner of our kitchen into a cute little breakfast nook resembling the coffee shop I stopped being able to visit;
  
• Leaning heavily into the Chemex pour-over coffee lifestyle, and having some of the best coffee I’ve ever had as a result;
  
• Converting our never-used dining room into a fun lounge for sitting, talking, drinking cocktails and listening to records; and
  
• Turning our bedroom into a day spa, complete with relaxing chaise lounge overlooking our yard, ambient music and self-taught massage techniques.

I spent roughly 2 hours of every day walking and/or playing with my adorable little monster pup Rosie. I also started exercising more, but these 2 hours always fill my Apple Watch activity rings on their own.

I almost entirely weened myself off social networks as forms of entertainment and distractions. I now spend this time listening to music, watching great TV, playing with my dog, cuddling with my pregnant wife and (more recently) writing.

I finally experienced the masterpiece that is The Sopranos, which I put off watching for years inexplicably. I don’t love mob movies, and I assumed this was just another one spread over six seasons, but Jesus Christ was I wrong. The commentary on mental health, American crime, toxic masculinity — in many ways it was ahead of its time and very prescient in 2020. (It’s also wonderful seeing the nuances of Italian American culture I’ve experienced through my wife’s family on screen. My grandmother-in-law is basically Livia Soprano minus the sociopathy).

A job I was admittedly on-the-fence about transformed into one of my favorite jobs of my product management career. I can’t say much about why at this moment, but I’ll have more to share later in 2021.

I [started a goddamn podcast]. Sure, we only did 5 episodes, but it’s something I can hang my hat on — and we’ll probably bring it back in some form next year (albeit with less direct involvement from me — thanks, future kid).

I found myself communicating with my family more than I have since I moved out of my house at 18. FaceTime chatter with my parents has become a near-weekly occurrence; I am now closer with my sister and her husband than ever before.

I also ate a ridiculous amount of trail mix, which has secretly become my favorite food of 2020. 365 brand Cherry Chocolate Carnival, here’s lookin’ at you.

Lastly, I came into the year thinking about how I can achieve clarity on my values, and, while I didn’t necessarily accomplish the specific things I wanted to complete, I believe my values and priorities are clearer than ever thanks to the events of this year.

• My family comes first. I don’t think I truly embodied that value until the second half of this year, and with a daughter coming, I won’t compromise this.
  
• True balance between professional and personal, and presence within each. Working remotely has made this truly possible where a commute never could; bringing more of my interests into my home has enabled balance in ways I could never have imagined.
  
• As a corollary to the last point: location flexibility. This extends beyond just “remote work” and is a value I want to publicly talk about more, as a means of enabling balance and stay closer to one’s values. Sure, many of us are working entirely at home right now — but there is no reason why we can’t make that a wonderful place to be both professionals and loving family members. It also doesn’t mean we shouldn’t be able to continue working in the same way from a campsite in the woods of New Hampshire or a coffee shop in Berlin. Expect me to write more on this subject this year.
  
• Minimalism, appropriately applied. I’ve learned so much this year about what my family does and does not need. This first manifested as, admittedly, an explosion of credit card debt, and I first felt deep anxiety about it. As we worked to get this under control, we made difficult calls about our priorities and what we thought was worth spending money on, and have landed on an approach of what we’re calling “minimal of quality” — we don’t need a lot, but what we need must be very good: organic food & clothing, reliable and purpose-built technology, and the like.
  
• Time for and openness to new forms of creativity. Music has always been my go-to-creative outlet, but it need not be the only one. Simply getting thoughts written down — no matter how unformed or crazy — has proven an effective outlet. So is noodling on a potential future product idea.

My favorite music of 2020

A year-end/year-start write-up would not be complete without a shortlist of the music I liked most from the past year.

Haim Women In Music, Part III — What a wonderful collection of songs. This might be my favorite of the year. “Up From A Dream” almost single-handedly got me fascinated with bass guitar tone again, yet also served as a come-to-Jesus that I am not a good mixer/masterer of audio. That song just sounds perfect.

Perfume Genius Set My Heart On Fire Immediately — I admittedly was very late to the party of Perfume Genius, and I’m still not sure whether I like his older stuff, but Jesus this album is warm & inviting. I picked up this album for the first time in mid-December and I’ve had “Describe” stuck in my head pretty much nonstop since then. The density and overwhelming sense of pleasure in that song just gets me every time.

Bad Moves Untenable — I appreciated that there was some good punk rock that came out in 2020, though most of it reflected the anger and depression that most felt in 2020. I found Untenable to a lot of fun in a year otherwise sparse of fun. Best track is the opener “Local Radio” — if you don’t find yourself banging your head and dancing around to it, just give up.

Run The Jewels RTJ4 — I only listened to this a few times but when I did, God, it was a gut punch.

Fiona Apple Fetch The Bolt Cutters — This album is so fun and clever. I’m honestly most disappointed that I can’t blast it in the house because my dog flips out every time she hears Fiona’s dogs audibly barking throughout.

Nine Inch Nails, Ghosts V: Together — I listened to this a lot in 2020. As more and more of my life moved into my home, and a lot of intense realities of the world and our lives came into and out of focus, Together was the calm ambience that helped center me often.

Olafur Arnalds Some Kind of Peace — Second-place for the album that helped center and calm me.

Prince Sign O’ The Times Super Deluxe Edition — Okay, not a new album, but the newly released tracks (plus the original, weirder version of “Strange Relationship”) make this completely interesting as a new collection of its own.

2021

I’m very excited about 2021, but I’m keeping expectations about the world around me pretty low. We’ll still be in a pandemic, it won’t go away, and I’m comfortable with that. On the other hand, I’ll have a daughter to raise, and a set of values I’m more firm on than ever.

I made a podcast about product

So I’ve been busy making a podcast.

I’ve also been a little depressed, infuriated, overwhelmed, grateful, loopy. A real who’s who of feelings. Typical for these days, I imagine, but it had gotten in the way of writing.

A significant coping mechanism I’ve embraced during the pandemic is to accept the reality of things, and then avoid thinking about them by doing literally anything else productive with which I can fill time. I started (finally) recording music again. I bought and tinkered with a Raspberry Pi to run more smart home nonsense, a media server, retro games emulator and security camera all in one. My wife and I started a garden. I built a fence around said garden.

I’ve always had a serious itch for the podcasting game, though, due to my love of hearing people I respect ramble on, unfiltered about really interesting stuff, and the sheer exercise of recording audio. Fortunately my friend and former colleague Ben seemed to as well, and we both had some things to talk about.

So we started one called Product Therapy, which is pretty much what it sounds like: two product guys talking out some things that excite us, frustrate us, and others we can’t really make sense of about the kind of work we’re doing. We noticed that while there are a ton of business, tech & even product-themed podcasts out there, there’s virtually none which get into the really messy stuff about it — the reality of doing the job every day. Everyone seems intent on interviewing leaders of the tech giants, sharing killer insights, and the like.

We’ll ramble a lot, and we hope you find it entertaining and perhaps helpful (even if you’re not a product manager). It’s available everywhere you find podcasts:

• Apple Podcasts
  
• Overcast
  
• Spotify
  
• Stitcher
  
• Pocket Casts

You can also subscribe directly to our Substack page, which is a cool way to directly show your support, plus a way to get members-only episodes if we ever decide to do that.

Clarity is out the disinfected window

I don’t know about you, but I am very overwhelmed at the moment and pretty much all the time. Leave it to a global pandemic to cause people to fundamentally reconsider how people work and communicate and live their lives.

I’m not personally leading a vastly different life compared to how it was two weeks ago: working remote in a farm town with no close friends less than a 45-minute drive away doesn’t really lend itself to lifestyle changes in the face of a highly contagious virus. I’m not even terribly stir-crazy, since our puppy Rosie is getting me outside four to five times a day to urinate, defecate and/or run around the yard.

But I’m feeling a different stir-craziness, one that is much more psychological. My mind is racing constantly despite multiple attempts to calm it down. I am exhausted at the end of every day, passing out in my bed but somehow waking up feeling poorly rested. It took something like seven attempts to even get this short and not-particularly-groundbreaking post together.

I referred back to my “clarity” note which drove my goals for 2020, and pretty much everything is out the window at this point: it’s a struggle to be intentional, I’m not reading, I’m not actively creating, breathing only helps for a few minutes before this weird reality sets back in. The only thing that is progressing is my ability to let anxiety about homeownership go, simply because it’s the last thing on my mind right now.

I am having visceral urges to create something but I can’t form a single complete thought around what I could do. It almost feels like the entire world is up for disruption, so there’s a need (or opportunity?) to create things in these trying times, but I can’t achieve the level of mental fortitude required to actually do it. It’s a struggle to come up with an original thought when everyone is seemingly feeling the same: either “I am terrified and confused” or “I refuse to acknowledge this reality.”

I don’t really have anything to share for insights, advice, or reflection that hasn’t been already shared. If this experience has taught me anything, it’s that the Internet is wonderful for not feeling alone, but it kind of sucks if you’re feeling the urge to do something original.

But mostly I thought the title of this post was cheeky, and wanted to post it for that.

Earworms

I don’t want to talk about work or technology or bettering oneself. I want to talk about the thing that was stuck in my head for the majority of the past week, which was the following phrase: “We can’t find the books; they must be in La Jolla.”

This is from a sample used in the song “If Not Now, Whenever” by The Books, a wonderful experimental folk duo that was moderately popular in hipster circles in the early-mid 2000s. The song itself is fine: pretty repetitive, hypnotic melody, a little boring but also fun for a deep cut. There’s a seemingly random string of voices throughout the song — they don’t tell a story from what I can tell, but the end of one phrase seems to lead into the next. This sample comes up randomly in the middle in the song, after a few old women asking about “the books.” It’s unclear whether this is a meta-reference to the band or a commentary on how people consume media.

I don’t know what else it could be, but the phrase just sounds good to me. It sits in the rhythm really nicely, and it’s spoken sardonically and cool. It’s not some deeply catchy, intricately-produced melody manufactured to optimize profits; it’s a passing sample likely meant as a joke.

I have a horrible habit of getting small parts of songs stuck in my head for long periods of time, and then having those songs incessantly distract me.

I just discovered Poppy, whose whole vibe and backstory is insane, and essentially put out a melodic death metal record. There are parts of her new album I Disagree which are certainly catchy, but metal rarely captures my attention these days. I’ve had various parts of the lead track “Concrete” stuck in my head for weeks (something about that “sugar on my teeth” line), and recently became obsessed with the refrain from “Fill The Crown.”

Back-to-back with Poppy has been “You Make My Dreams” by Hall & Oates. Talk about a topic jump: from being ironically buried alive in concrete, I move to a simple love confession. I’ve had this track on-and-off stuck in my head since 2016, when it was on seemingly infinite repeat during my best man’s own bachelor party. There’s no need to explain what makes this song an ear worm: it’s probably stuck in your head too from time to time. One scientist calls it a “cognitive itch,” which seems appropriate for this particular track.

Cognitive itching seems overall appropriate for the whole sensation inspiring this post. Instead of scratching a technical itch or a career itch, I find myself regularly and incessantly scratching sonic itches in my brain. Sometimes this comes to the detriment of one of those other itches; I think my inability to parse Swift documentation and make sense of inexplicable bugs partly relates to my brain being distracted by those melodies and samples that won’t leave.

Some of these songs are incredibly catchy and have fair right to be called earworms, but others get stuck in my head for seemingly no reason whatsoever. I said the word “cocoon” this morning, and now I have “Cocoon” by Björk stuck in my head. It’s not even that catchy of a song; her vocal melodies are usually more meandering than crisp. (This was not written for effect — this specifically happened at 8am this morning, Monday, March 2nd.) I’ve been following the pianist/MC Jason Charles Beck (aka Chilly Gonzales) for a while, and I’ve had his track “I Am Europe” stuck in my head recently. It’s got a somewhat catchy piano riff, but vocally there’s nothing to hang onto whatsoever: there’s a weird string of spoken-word metaphors in the middle of the song that ring quite hollow (“I’m a dog shit ashtray”; “I’m a toilet with no seat, flushing tradition down”), but the piano line, undercut with pitched moans, just works for me. I haven’t listened to this song or album in years, and there’s no reason for me to either –– it’s not that great. But it’s in my head.

Sometimes the nature of these earworms are subtle and specific. Another song I frequently get stuck in my head is “You With Air” by Young Magic, which is fun and catchy as hell. It shares a vocal line almost identically with Purity Ring’s “Grandloves”, but I rarely if ever think about that song. I have no idea why, despite having the Young Magic version of the line in my head frequently. The context of the backing rhythm and overall vibe seem to matter.

It feels narcissistic to get one of my own songs stuck in my head, but I have a little guitar and bass line loop stuck in my head. I guess one could call that part of the songwriting process, but this particular loop has been in and out of my head since 2009. I guess you could call it catchy once the vocal melody is attached, but the guitar loop is kind of nothing on its own. I can’t explain it, which I guess is the whole thesis of this post. (I guess it’s also weird to link to said song in my own newsletter. Shameless.)

I wonder what some earworms tell me about my inner demons. I have a strong distaste for horror movies –– inexplicable gore and chaos make me very uncomfortable –– but sometimes I’ll scratch an aural itch that would be terrifying to most people. Mr. Bungle, a bizarre, fun and sometimes confusing band from the 90s recently announced a small set of reunion shows in California which prompted me to revisit some of their music. I recently got stuck in my head a song of theirs called “Carry Stress In The Jaw”, a song about grinding one’s teeth during sleep, specifically the jittery saxophone line that begins the song and a bit of the following verse. Any rational person would likely find this song terrifying, between the jarring tonal & genre shifts, the chainsaw-sounding guitars, and Mike Patton’s meandering recitation of an Edgar Allan Poe excerpt which builds to a high-pitched wail. But I find it a fascinating and ultimately entertaining listen, and I apparently get fixated on parts of it from time to time. What does this say about me? The aforementioned Poppy tracks are unconventional and dark but ultimately (as her moniker states –– hey!) poppy and interesting social commentary; “Carry Stress In The Jaw” is chaotic, strange, and sometimes gross without a clear point. Is this a reflection that my mind is in a proverbial gutter? Is this a manifestation of the actual teeth-grinding I do while I sleep? Am I a glutton for aural punishment?

More likely I just am fascinated by sound, but I can’t help but worry about my sanity with a track like this.

I made a playlist of these songs that I keep pretty up-to-date, for those interested; there’s a lot rattling around in my brain. Check it out here.

This was fun to write. I didn’t really learn anything for have any nuggets of value to share, but it was nice to shove stressful or effortful things aside and just ramble about songs I like. We should be doing more stuff like this.

Found my stuff

I’m incredibly lucky to have a little bit of time to pursue hobbies or interests outside of my work and family life. One of the interests I’d been exploring was app development: I am deeply in love with the iOS/iPadOS ecosystem and have always wanted to tinker within it and contribute to it. Plus, I’d played a little with development before by running a few Wordpress sites in the past, doing low-complexity coding and bug fixes in previous gigs, and spending most of my workweek talking with other developers for a job. And I had an idea for an app that would actually be useful to me.

So I tried picking up Swift and SwiftUI to develop said app. After about 10 days I’ve given up. I either don’t have the brain, or the patience, for software development. I get the model-view-controller framework completely — I need to at least understand this concept to do my day job, but while I can sort of read code, it’s a whole order of magnitude of complexity for me to write it and not run into a dozen build failures or inexplicable crashed. The place where I got stuck, specifically, was around supporting Siri Intents: the idea involved needing to talk to Siri, or build Shortcuts, around locating a specific piece of data, and I got incredibly frustrated trying to figure this out. Tech pundits are right when they say Apple’s documentation is not useful, and I don’t have the skillset to adapt examples from other people to my own use cases.

The idea stuck, though. It came out of an episode of the wonderful Reconcilable Differences podcast. In this one, John Siracusa talks about his use of Apple Notes to keep a running list of where random things are in his house. Turns out I could have used one of those: My wife and I move random items around the house regularly and then forget where we put them. Some of these are easy to track down, such as AirPods or our phones, because we can yell out to Siri and then a loud bell will be emitted from said device. I wanted to be able to yell out to Siri, “Where’s my goddamn box cutters?” when I have a dozen cardboard boxes to break down and can’t find them. The only options I could think of were to buy a Tile or wait for Apple’s competing product, but I also don’t want to spend hundreds (possibly thousands) of dollars putting a Bluetooth tracker on all my tools, random cables, passport, etc. Not to mention all the problems with Bluetooth security and electromagnetic radiation in the house.

So instead of frustrating myself endlessly trying to build a swanky app to solve this problem and then monetizing it for no good reason, I built a group of shortcuts to help me with keeping track of shit around the house.

Found It, the shortcut suite

Collectively they’re called Found It, and they enable you to securely tell Siri where your stuff is around the house. When you can’t find one of those things, just ask Siri and she’ll tell you. If you put that thing somewhere else, just tell Siri and she’ll remember next time you can’t find it.

If you like, you can tap on the links below to download Found It and all its components:

• Found It (the master Shortcut, which does everything)
  
• Keep Track of Something (just asks Siri to track something new)
  
• Help Me Find Something (just asks Siri to look up where something is)
  
• I Moved Something (just tells Siri the new location of something)

From there, you can start tracking your own stuff. These shortcuts also support custom inputs, so you can make your own mini-Shortcuts that ask Siri for a specific item (so you don’t have to re-specify every single time). For example, I made a shortcut to ask Siri “Where’s the hammer?” since I keep leaving my hammer in random places around the house, and she’ll just tell me that. You can get that example here; you’ll just need to tell Siri where your hammer is first.

The master shortcut is available on RoutineHub, which is a community and directory of crazy-powerful Shortcuts.

If this is interesting to you, let’s talk

I’ve realized over the past week that Shortcuts creation is basically a lightweight form of programming, and it’s proven very helpful in the solving of everyday problems around the house. I’m going to be writing more about my explorations here (like some people are already doing — see Federico Viticci or Matthew Cassinelli for just two great examples). If you have a problem you need solving and I might be able to help you solve it with a Shortcut, or if you just find this interesting, let me know or subscribe to this newsletter. Thanks for listening!