Some guiding principles for creative independence

Over the past few months I’ve been quite energized by the ideas of online independence and transparency, both as a tech person and a musician. This has been inspired by a few recent developments:

• My working for Buffer, a company who continues to double-down on remaining independent, transparent, small and sustainably profitable
  
• My budding interest in the fediverse, decentralized Internet protocols, and related concepts
  
• The news that Bandcamp, a platform championing independent musicians, was acquired by Epic Games (the Fortnite company), then sold to Songtradr, then gutted of half its staff
  
• My discovery of Faircamp, a self-hosted alternative to Bandcamp built by Simon Repp
  
• The recent increase of Spotify’s investment into in algorithmic, rather than editorial, playlists
  
• My increased attention toward Threads, the new Meta social platform, on which I’ve successfully started building an audience

These are just a few of many related ideas converging on two facts:

1. The Internet is rapidly becoming a chaotic mess run by a small set of very large companies optimizing for shareholder value and thus uninterested in investments to tame said chaos for the good of humanity;
   
2. Opportunities still exist for thoughtful organic connection online, amidst (or away from) this chaos, and there is growing demand for and willingness to search for it

Oddly enough, Meta (of all companies) is straddling a very fine line between those two mindsets thanks to the introduction of Threads and long-term support for concepts like open-sourcing and the Fediverse.

Some context

As a musician, for years I struggled with having the confidence of promoting my work — partly due to impostor syndrome — but also because it’s felt like somehow both a Sisyphean and Kafkaesque task to market oneself online. There are the conventional routes of music promotion: play shows, submit to press outlets for coverage, hire publicist/agent/manager/etc., which is full of scammers and bias and dead ends. Then there’s the Internet platforms, which theoretically level the playing field between bedroom novice musicians and major-label acts, but in practice are a relentless game of constant attention-seeking and algorithm-pleasing. Not to mention that the “conventional” industry is also playing those same Internet games, often with money to influence the outcome of the games. And scammers. And now AI-generated garbage.

Not to mention that the music I make - highly personal, a bit sprawling and unconventional rock music and stuff that I’d consider “art” - is not what’s in demand in the general public.

But in the past 4 months I’ve found a niche: fellow musicians or independent music appreciators on Threads. It’s a small niche, but my presence within it is growing, and I have (small) data showing that. People in that niche have paid me real money for my creative output.

This means a lot. Not just to me personally - I am extremely grateful, flattered, and a bit bewildered that people would pay me for my music!!! - but in terms of what it opens up for potential methods of building my musical work (or any musical work) into a small sustainable project on its own. My goal is not to turn this into a full time job, but I would love to be able to gain a small but supportive audience of folks who value my creative output and be willing to financially support it in some way, because I believe that good art deserves market value.

This is not a new idea. Fan support platforms like Patreon and Bandcamp have existed for over a decade. But they are platforms funded by venture capitalists or large corporations, and even so are very much outliers in a music industry dominated by Spotify – a large and highly unprofitable business — and the major record labels, who partly bankroll Spotify for their own gain. Most people who listen to music have never even heard of these other platforms, let alone support an artist on them.

Moreover, as Spotify leans more and more into shuffled algorithmic playlists, the music that most people will listen to are (1) massive viral hits or (2) music specifically produced to optimize placement in the algorithm. And if I think about the listening habits of most non-musicians I know, they likely don’t care. Most of them don’t care or even realize who made the songs Spotify feeds them. This is definitely not good for artists, and I’m not sure it’s good for the world.

So I feel compelled to look elsewhere, and in a way that does not further entrench platforms incentivized to relentlessly grow at the expense of art & artists. I want to be unapologetically independent and thrive in doing so.

What’s my goal here?

It’s not to tear down the platforms. I’m not on some war against Bandcamp since it got acquired then sold then gutted.

It’s much more about three things:

• A strong conviction that there is some demand for my art, and I can leverage my knowledge of tech and business to turn that into some kind of sustainable side income
  
• A deep-rooted interest in wanting to own my brand & presence on the internet and the relationship with my supporters, driven likely by a passion for DIY & punk ethos
  
• Having redundancy in case the music distribution platforms do collapse or decline in importance

Guiding principles

1. The primary goal is creative freedom above all else, across all aspects of my creative work (including branding)
   
2. Minimize money given to services/platforms misaligned with my values
   
3. Minimize service lock-in
   
4. Must be low cost/time to maintain
   
5. Wide upper funnel (distribution) to maximize reach, narrow lower funnel (purchase) to maximize profit & fan connection
   
6. Strength in numbers: support & collaborate with similarly-minded artists & service providers

That last one is tricky. There are two big hairy problems: payment processing and file distribution. If you want to make money on your music, you need to accept payment methods your potential customers have, and then deliver the music (sometimes in multiple formats) to them in some way. What services like Bandcamp and Spotify do is complex.

But there are alternatives if you begin to think about it differently. Why not just email a paying customer a .zip file with my album in it? Or a Dropbox link? Or a link to a file that I host on a server managed by a business I trust?

I’ve always been fascinated by local markets and the DIY ethos. The idea that, to keep costs low and ownership high, you keep things simple, organic, and in your control. These principles help my process feel truer to DIY but online.

Applying this to my web presence

I’ve already begun applying these principles to how I maintain my presence on the Internet and how I conduct myself.

My website (kidlightbulbs.com) is built with Blot, a simple $5/month service run by one guy named David that turns a Dropbox folder (or Git repository for the nerds) into a functioning blog. I write text, throw it in a folder, and it shows up. That might even be how you’re reading this right now. David runs the whole thing himself with seemingly no funding or support, shares a public record of features he’s considering, and openly invites his users to provide feedback.

My newsletter is hosted on Buttondown, a free (or inexpensive) newsletter service run by a guy named Justin. It’s completely independently and sustainably run, and Justin shares exactly what he’s doing and using to run the service. He (or his 1 support person) respond to my questions in under 3 hours every time. It’s wild.

I get analytics for my site via Counter, a free (donation-based) and open-source service run by a guy named Irae in Berlin. It’s awesome and all you really need for “website analytics.”

Music distribution is hard to do in alignment with these values, and something for which I am actively exploring options. Distribution to the streaming services is particularly tricky – however, I’ve begun to think of this less as an essential service and more as a marketing expense, and therefore I’m willing to eschew my values a bit to make this happen.

I currently host and distribute my music via 3 services:

• Bandcamp, where I host my full albums and my current patron subscription offering
  
• LANDR, which takes my releases and distributes them to the various streaming services like Spotify (I’m currently phasing out my subscription with Distrokid, a more well-known but increasingly sketchy service that is also partly bankrolled by Spotify, which as a reminder is partly bankrolled by the major record labels)
  
• Dropbox, my cloud storage solution of choice

Yes, Dropbox is publicly traded and therefore incentivized to prioritize shareholders of users; however, I strongly align with several of their values including great user experience design and remote/flexible work. Basically, far less evil than Google and far more reliable than other offerings I’ve tried.

LANDR has raised 9 rounds of venture funding, and likely is incentivized to grow rapidly. However, their interface design is by far the best of all distribution services I’ve tried (Distrokid, Tunecore, Symphonic, and Unchained Music are the others). It’s probably silly, but good simple design matters a lot to me. I don’t have a lot of time to fight against what’s essentially a form to fill out anytime I want to release music (every 2-4 weeks). That plus (from what I hear) great customer service is worth the little extra they charge.

Bandcamp is interesting because they are one of the last holdouts in the music industry championing independent music, rather than reverting to the least common denominator of what’s popular. I am cautiously optimistic about their future, though their rough 2023 and the increasingly cutthroat tech landscape leaves me wanting an out if I need it. Fortunately, Bandcamp allows you to easily download all your albums and even your followers’ emails so you can easily move them elsewhere.

In future posts I’ll dig more into the experiments I’m doing around

1. direct financial support,
   
2. offering flexible listening options to my (tiny but growing) audience, and
   
3. promoting on the social networks and the Fediverse

Some unfiltered thoughts on AI and art

Note: There was a lot of chatter today on Threads about AI and art. I had some thoughts that developed over the day and wanted to post them with some slight refinement after reflecting a bit. The following is still pretty scattered and unrefined thinking, but I wanted to put it somewhere.

Art (made by humans, based on new human experience) is vital. But I also think there are two types of people when it comes to perception of art:

1. Those capable of gaining some kind of intangible, spiritual, non-financial value from experiencing art
   
2. Those who cannot, and thus can only perceive its value as functional (primarily as entertainment, marketing or utility)

I think that’s what this whole AI and art situation comes down to. And I suspect those with money/power/influence in 21st-century America, where most of this debate seems to be happening, seem to be in the latter camp. The rest seems to spin off from there: the incentives put on media platforms to scale and optimize for mass consumption in exchange for surprise and discovery of new media, the increased homogeny and decreased uniqueness within “popular” music, the hype within the tech industry about AI as a solution to make commercial art forms massively more efficient, the formation of niches online for folks in the first group (the art kids, I’ll call them) who are willing to pay perhaps more than before to support artists who desperately need it.

The fact that a small group of artists are able to partly fund their vocations with patron subscriptions and the like gives me hope; though I do wonder how much of this is driven by the thrill of voyeurism and intimacy among patrons, rather than a genuine interest in supporting an artist.

I don’t really care if AI ends up making the majority of the volume of what we today consider “art”; there will always be a need for it and value put on it by someone. It will be important to know how to tune the garbage out. That also depends, I guess, on what you’d consider garbage, which is highly subjective and likely personal to the individual consumer.

Even if AI “gets good” at making art and music in particular styles - to what extent would we call it art? What inspired it? What’s the context? What was the process of it coming to be? Is it even art in its purpose once created, or just marketing collateral designed to sell products and/or promote some brand? (That seems to be the majority of use cases for AI art, though I think it’s worth considering these questions for, say, AI-generated art submitted to art shows. Is the purpose to win first prize? Or is it to express some sentiment vulnerably of the individual who coaxed AI into making it?)

Related: is the feel-good hit of the summer any year really art, even if it’s meticulously crafted by a team of humans in a professional studio setting? Or is it marketing collateral for the musician/producer/brand who made it?

I personally think it depends on the creator’s context and listener’s interpretation. If you’re inspired by the creative process to get to that end product, you might think of this - or even just the process part - as art. If you’re listening to the feel-good bit of the summer as you sip cocktails at a hip club on the Vegas strip, I don’t think you’re thinking of the music as art in that moment.

Not trying to throw shade on all pop music – I love a lot of pop music. But it’s pretty open to debate whether all music is intended or perceived as art, regardless of who’s creating it.

Okay now let’s say you’re creating art with AI as a tool in your toolkit. To what extent is the “AI whisperer” an artist, as opposed to a director of machines?

I made cover “art” for my last 3 releases with an AI product called Stable Diffusion. Do I personally consider it art? Yes, because it triggered an emotional response in me when I saw it.

Do I consider myself a graphic artist? Absolutely not. If anything, the software is the artist and I simply commissioned a work from a piece of software.

Am I publicly promoting the cover art as art? Not sure. It is intended as a supplement to the music (which is the primary art for me), but it’s a cool companion so I’ll leave that question open for now.

There will always be people making art for the reasons they make art, regardless of the tools they use to do so. I hope desperately that there continues to be ways to find, be inspired by, and be challenged by new art of different forms.

This is the primary problem to solve. Spotify isn’t really solving it anymore, Google isn’t, the conventional music industry isn’t, AI is simply going to make the problem harder to solve in every format. If the people exclusively “in charge” (ie. Run the dominant platforms, control the government, hold the money, etc.) are incapable of thinking of art beyond its ability to entertain or serve a low-grade function, then this won’t get solved. Those people simply have no reason or capability to perceive this problem; if they do, they will likely try to tackle it with different goals and incentives than those who want to simply find and experience more art.

The second? We need better words to describe this stuff. I’m not sure everything that we throw the label “art” is even art. Maybe it is just marketing material for something else. Someone on Threads made the distinction of “commercial art” which is helpful; we should start using that more.

Listening to Earthside’s “Watching the Earth Sink” half asleep on a morning flight

I found myself listening to the new Earthside album, Let the Truth Speak, for the first time at around 6am at Fort Lauderdale-Hollywood International Airport while waiting for a 7am flight home. I was coming off a work trip that was overall great, but I cannot overstate how exhausted I was — operating on 3 hours sleep after a week full of intense planning and debating and team-building, lugging a carry-on, juggling overpriced egg sandwich and burnt coffee in hands. I missed my family and my bed. My brain was exhausted from the past week but still swimming with thoughts, and I needed to slow it down. It probably was not wise for me to listen to a 78-minute progressive metal album under these conditions.

“Watching the Earth Sink” (track 5 of 10) began just before my boarding group was called up. For the next twelve minutes, I daydreamed one of the most vivid daydreams I’ve had in my life, which followed me from the airport waiting area, into the Airbus A220, into my seat, into the faces and tiny windows surrounding me. In my half-asleep stupor I thought the world might be tearing itself apart around me, exacting vengeance for our endless societal wrongdoings and forcing me to watch helplessly from my aisle seat.

This song is not for everyone. It’s progressive metal, which is already a much-maligned genre overfilled with tropes. It’s nearly 12 minutes in length. There are reportedly 29 separate guitar performances on this song. Even some diehard metal fans don’t care for it, one reviewer calling it “exhausting” with a “careful build-up, only to unceremoniously wipe it off the floor with a predictable post-metal jaunt whose single trick is to be heavy.”

I disagree. I’m not sure if “Watching the Earth Sink” is my favorite song of 2023, but I think it’s a song deserving special attention and analysis. It’s meticulous in its construction. It moves the progressive metal genre forward. It’s one that requires multiple listens and (if I’m honest) benefits from some kind of sleep or sensory deprivation to appreciate it fully. Consider listening when you’re alone, driving through empty forest roads in the dark, or perhaps when you’re half asleep and feeling down while stuck at an airport, people watching.

Earthside themselves describe “Watching the Earth Sink” as “an instrumental narrative told from the perspective of an onlooker to the current state of the world—one who feels disconnected from the warring powers that be, left to simply bear witness to calamities they feel helpless to prevent.” You feel all of this over the 12 minutes of the piece. You feel it after sitting with the title alone. It’s perfect in its bleakness. It implies passivity — you’re helpless to do anything but watch as the Earth is sinking around you. Just sinking. Not exploding or imploding, not tearing apart like an earthquake. A sinkhole. Slowly and gradually fading out of view, probably unnoticeable except for the bubbling earthen muck. Perhaps sinking to baser, perfectly human instincts, lashing out at the inhabitants that care too little to take care of it or themselves.

I’re read a few reviews of Let The Truth Speak which rave about this song, some of which specifically call out guitarist Jamie van Dyck’s solo in the introductory section of “Watching” as sweet and calming. Someone likened it to floating down a river.

Nope. Not even close. This song kicks off in utter devastation. Like the mood after a funeral¹, it’s grim, beyond somber. Clean tone and dense reverb may imply “calming vibes,” but Jamie (guitarist, composer and friend) plays as if he’s suffering an existential crisis, stumbling out of tempo and in somber defeat. Jamie oscillates slowly in my earbuds between D minor to B- flat minor, two of the saddest chords in Western music. In my half- asleep stupor at the Fort Lauderdale-Hollywood Airport, I am there with him as I glance at televisions spouting horrifying news about the Gaza crisis while twenty- and thirty-somethings stare at laptops and smartphones and the more neurotic travelers cut each other in line for a plane not yet ready for boarding. Nothing is good.

Until carefully voiced chords breathe and meander upwards, pivoting to inversions of D major then to a less bleak G minor, suggesting a cautious way forward. The guitar continues its musing as I oscillate between people-watching and my iPhone. It feels pointless to try to understand anymore as the guitar settles into an E minor to lydian E-flat, as if it’s second guessing itself.

My boarding group is called. My cautious optimism is complemented by a meditative ostinato at one minute, fifty-three seconds. Played in unison by Ryan’s bass guitar and an ethereal bell-sounding synth from Frank on keyboards, defeat turns to surrealist wonder in 23/16. I appreciate that this section has no discernible melody or solo; it’s driven by mood and movement. It’s difficult to keep the pulse, but it almost doesn’t matter because things are looking up: I’m finally almost on my plane, it’s not overly crowded, the guitar has found solace in dense Lydian chords and arpeggios if only for a few moments. Even after the arpeggios abruptly cut, the ostinato continues for four bars. We’re still okay. The Earth has yet to sink.

The ostinato is suddenly, but only partially, replaced by militant clicks on the snare drum and driving root notes on the bass. Frank keeps wandering in twenty-three, occasionally embellishing on the core, while the rest of the band shifts to a tense 4/4. But you can’t really tell: the juxtaposition of increased pace with slow root movement in the bass makes it even more difficult than before to find the pulse. I feel uneasy. I’m stopped in the aisle as I wait for passengers ahead of me frantically search for overhead space.

At 4:11: a jump scare.

The bass guitar tone suddenly shifts on an up beat to overdrive and I don’t see it coming. I haven’t had this happen while listening to music in years. We’re now unapologetically in 4/4 and it feels like something is careening toward disaster. I come to my senses and look out the window and I imagine Florida buildings in the distance starting to collapse as a crack in the Earth forms and spreads toward the airport tarmac. The floor of the plan is vibrating under my feet. The ground splitting in the distance, out of which a massive earthen hand rises up, preparing to grab the plane and tear it in two.

Four minutes and forty-five seconds, the tense rhythmic build abruptly explodes into a brutal, direct 3/4. Drop B flat guitars, kicks and cymbals each pummel your listener in unison for exactly 19 repetitions until shifting to C sharp on an upbeat, continuing the feeling of the music shifting below your feet when you least expect. The use of harmonic minor scale here combined with the intentional chord movement on upbeats really exemplifies sinister chaos. The plane is taking off and in my head it’s moving as fast as it can to avoid the earthen behemoth careening into the side of it. Frank’s synthesizer screams faintly in a distant corner of the mix, possibly echoing my own internalized panic. This is quickly overtaken by demonic orchestral hits² that follow the chord movements in synch with the other instruments, as if to suggest it’s now useless to panic. Suffering is inevitable now.

But by minute seven, a reprieve. We’re well in the air as the destruction unfolds below. While the plane flies safely and normally, I feel an uncertainty punctuated by the pivot to the key of A, the dominant chord of the song’s D minor root. It’s rare to hear such a simple chord change in progressive metal, where rhythmic and harmonic complexity abound. Ryan’s bass arpeggiates 7ths and 9th chords as they change from A to G to E flat, finally returning to the root, perfectly simulating my unease. Jamie leads the way with a confident melody, and it almost alleviates the feeling.

At 8:12 I am in a haze as everything fades away but a descending keyboard line. It’s as if there are embers and ash dancing around; the heavy use of major 7ths in this otherwise epically bleak song are equal parts playful and ominous. Eventually all the instrumentalists join the dance, with performances that evoke a desperate last stand. Jamie’s guitar wails with desperation as Ben majestically slams on every tom in his kit. After a few bars the bass and a deeper guitar take over with a sinister riff, mostly playing root notes again – almost an homage to the earlier devastating section, D harmonic minor and all, reminding me there’s more destruction to be had. It’s coming.

Once bass and guitar reach for a deep baritone A, we’re in a nose dive. This is doom metal. There’s no more hope. I’m pulled down into the depths. A once-playful melody has been mangled into something evil by a wicked cabal of guitars. The drum kit reaches escape velocity over sixteen bars.

And then it…just stops. There’s no resolution, no final word. I am left hanging just above the abyss.

It was a pretty normal flight in reality. I landed at Logan Airport in Boston on time, and got home to my wife, kid and dog a little over an hour later. But during the early minutes of said flight I experienced something visceral, gripping, devastating.

It’s quite rare nowadays that music — and music alone – can achieve that.

On platform incentives & supporting indies

I used to have a Substack, but I don’t really like spending time on Substack, and I don’t write frequently enough to justify that kind of a commitment from supporters of mine.

They also now have clarified their policy on censorship, and it’s one that clarifies their dependence on venture capital and desire to grow and profit above foster healthy discourse (at least to me).

I’ve been feeling a pull to get “off Substack” because I don’t fit the vibe. More importantly, I don’t feel great about my writing being there and I don’t have the stamina to write frequently enough to survive in the dynamics of a platform like that, where frequent engagement and name yields results.

Coincidentally, Bandcamp (one of the services that hosts my music) is going through its own mess of a different nature rooted in the same incentives: money and growth. So I’m not sure about its long-term viability.

Working for Buffer has really bolstered my support for the value of independence – the notion that independence allows a business to stay true to its values. This goes for both myself and the businesses I choose to rely on.

So why do I rely on services run by folks who are directly incentivized to adhere to values that aren’t aligned with mine?

My new place on the Internet

I’ve got a new, simpler, chiller website now too. Now that I work at a bootstrapped startup that has & exhibits values of transparency, reflection and optimism, I’ve reflected a lot on my own usage of the Internet and internet products. I’m increasingly frustrated with the state of venture capital and large social & entertainment platforms (which isn’t great given I need to promote music right now lolz), and I’ve found myself wanting to divest from these things where it makes sense.

• My website is now built on Blot, an extremely simple and powerful service that spins up a fully managed site & blog for you using text files in a (private) Dropbox folder. (Blot also supports Git-based syncing, which I’m considering as an alternative to Dropbox, which is also a publicly traded company.)
  
• My newsletter is now hosted on Buttondown, a (free to start!) newsletter service built & managed by one dude named Justin.
  
• My music is currently available on all the major streaming services, but I primarily promote my music via Bandcamp because it’s where you can support me directly. Fun fact: last year, Bandcamp was acquired by the company that makes Fortnite, which is super weird. There’s nowhere really better than it though, other than maybe hosting it myself.

This is something I’ll continue to explore and probably write about.

THROW MYSELF INTO THE BAY is out now

Listen or buy on Bandcamp, Spotify or Apple Music

I’ve been quietly working on this album for the past 3 years and I’m thrilled (and a little freaked out) about sharing it publicly. It’s a sort-of rock opera chronicling the adventures of an anxious person (possibly me?) over the past 3 years of pandemic, polarization & reflection on what matters.

Support me directly by buying it on Bandcamp, or stream it anywhere you listen to music.

I plan to write more in the upcoming weeks on the making of this album, some of its influences, the origins of some ideas (some of which date back to my teenage years!).

Liberal arts and the jobs of 2030

Why artists & curators will win the AI revolution

The timing of the AI boom alongside the laying-off of over a million people, mostly in tech companies, feels suspect to me.

Sure, the main reasons for the Big Tech Belt Tightening seeming to be a mix of “economic uncertainty,” badly placed bets, shareholder appeasement and an attempt to reassert dominance over those workers outstanding. But I find it interesting — and possibly not coincidental — that, as the media loses its mind over AI coming to take everyone’s jobs (including their own), companies are openly questioning how many humans are required to generate revenue.

And as every company becomes a software company, and AI subsequently eats their software, I can’t help but assume that the biggest platform owners (Microsoft/OpenAI, Amazon, Google, Meta, Apple) — which mostly happen to be the ones driving the development of underlying AI capabilities and frameworks – see this writing on the wall and are trimming humans they’re certain will be eventually superfluous. Why does Microsoft need all these engineers, PMs and designers, marketers and recruiters if Microsoft’s own Copilot will simply do half the work for them? Could they do with only the best half of them? Why give them benefits if they’re only doing half the work they used to do?

In other words, the time of throwing people at technology problems is coming to an end. That means significantly less staff required to build & run tech companies, and (maybe) those staff members getting more paid.

That also likely means fewer startups with open roles — simply because “founders” won’t need dozens of coders, customer service agents, or even designers to build and scale an idea. Sure, plenty of startups (especially around AI capabilities) are hiring and attempting to exploit the spoils of big-tech layoffs, but 95% of those won’t last.

I’m including my own field of work. Product management will probably not be obsolete within the next 5-10 years (software development will go faster and more decidedly), but significant parts of the everyday will be. The whole deal with product is that you are the creative leaders in an organization, but it’s becoming obvious that what works as great design is quite predictable, and the majority of PM tasks are repetitive. Sure, we can be “creative strategy drivers” or whatever, but at one point or another,

Sure, tech as an industry isn’t going away, as long as fuck-you-rich people (VCs or not) have money to throw at problems they care about - but with millions of people out of work, seemingly for months and possibly forever without seriously considering their options, I can’t help but feel that it’s no longer viable, especially for young people, to simply assume you can work in tech. Not even high performers are safe (especially not managers), if they’ve found themselves stuck on the losing end of a political in-fight or unviable business strategy. Instead, it will be for a select few who have aligned themselves very closely and successfully with those fuck-you-rich leaders.

Leah Tharin had a great post a few weeks ago about the “innovation arms race” happening in product:
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This innovation-centric “back to basics” going to start happening in every industry. SaaS will consolidate around a few key services requiring humans and otherwise become obsolete as AIs perform the work for executives. Radio stations are already replacing human DJs and ad copy with AI-generated shows and ads. Food service will need to innovate as restaurant space is more expensive to rent, and eventually AI will be good enough to know what food someone wants, orchestrate a kitchen full of robots to make it consistently to one’s liking, and deliver it quickly. Medical doctors will be forced compete with AIs that are experts in all fields of medicine at once, drawing correlations between systems of the human body to quickly diagnose conditions any single doctor would need weeks to wrap their head around. (Note: I think this last one warrants much further explanation given the nature and cost of healthcare in the United States.)

Not all jobs in these sectors will be eliminated, but the niches best suited for humans will reduce and become increasingly focused on creation & collaboration with a mix of humans and robots. Doctors may be truly better at bedside manner and running tests because of physical properties of humans, but their specialties will matter less because an AI will be doing most of the diagnosing.

The self-employment renaissance

The past few months of 2023 made a few things incredibly clear to me, separate (but again related) to the AI proliferation:

1. More people than ever are starting their own businesses, often on the Internet. This wasn’t new – COVID really kicked this off – but it doesn’t seem to have slowed down.
   
2. A significant portion of those businesses seem to involve teaching or sharing incredibly niche expertise via a premium product or service.
   
3. Everyone doing this has no choice to be good at sales, marketing and reputation management in order to succeed, because of the increase in visibly self-employed people. (That said: it wouldn’t surprise me if, by sometime next year, an AI product existed that did your marketing & reputation for you, continuously optimizing for audience growth.)

As AI starts to wipe out many entire fields of work and significantly cut the scope of others, I expect more and more people will explore the self-employment path simply out of necessity. (I’m doing it between trying to write this!)

The four (or five) “lucrative jobs” of 2030

Every once in a while I see an article about the highest paid / most lucrative jobs of that year. I think a lot of those jobs on this year’s list will be gone by 2030.

Instead, I foresee four main “jobs” emerging (and a possible fifth) as the big ones most people will aspire to do. These are intentionally broadly defined and not prescriptive of a type of employment, but more about the essential work involved with each job. Three of them have become increasingly commonplace as the Internet has enabled cheaper, broader distribution of information, and are essentially based in a liberal arts education.They are:

1. Artist

Those creating the <2% of art & media not created by AIs, selling at an extremely high premium to (mostly) the higher-income classes of society, though some will likely find support in Kickstarter- and Patreon-like crowdfunding models.

What remains of Hollywood, the fiction and music industries fall into this bucket – but the majority of these artists will be selling their NIL (names, images & likenesses) as their primary sources of income and occasionally make original art.

2. Teacher/coach:

those selling their experience as a product or service, mainly sub-niches within the arts, sales, business management and AI whispering. Coaches in particular sell at a high premium and differentiate from AI coaches used by the masses. Conventional American education is slowly dying. 11% of US children were homeschooled in 2021, a 3x increase from 2019 (mostly thanks to COVID, which also exposed myriad other problems with the public school system).

Online teachers & coaches – the influencers of the Internet selling courses around incredibly niche topics like monetizing LinkedIn, “small bets” entrepreneurship and health coaching (three topics of which my spouse and I have paid real money for courses) – will come to dominate as the way humans learn skills necessary to make a living.

I expect that, over time, younger people will seek education from these Internet-based teachers, eschewing traditional high school for learning specialized skills that matter in the midcentury economy. And why shouldn’t they, given the wild success stories of the teachers and influencers all over the Internet?

3. Curator

Those paid to sell & recommend products and services to the masses, mostly by AI-led corporations but also a mix of human-generated products, services and content. Most of today’s “content creators” likely fall into this bucket.

This job already exists; it’s a subset of what we call influencers, YouTubers, content creators. Dror Poleg had an excellent musing on AI’s effect on social classes, in which he wrote this:

But consumption will serve a critical economic function: It will not just buy the stuff that people make; it will help make that stuff better and figure out what to make more of.
Most of the stuff we consume is not necessary. More precisely, it does not provide objective value. When I buy a pair of Nikes instead of Adidas, I buy them because, subjectively, I like one pair more than the other. And when I buy hiking shoes, I do not buy them due to a technical need to go hiking but because I think they’d look cool on my walk to the coffee shop.

Curators are the people who guide on what to consume, and how to consume it.

4. Subverter

Those attempting to game the AI systems or subvert increasingly homogenous social norms for pay (eg. Hackers, sex workers, escorts/companions, AI manipulators).

Given that our future society will likely be run by complex systems we don’t fully understand (even if there are very rich people running the businesses that own the complex systems), there will be even more incentive to try and game those systems for two reasons:

1. Gaming the system is inherently fun and engrossing. Just look at any fandom around a complex video game or TV/cinematic universe, even going back to the early 2000s. (Anyone still think about the show Lost? I do.) When Bing 2.0 came out, the Internet lost its mind trying to get it to transform into Sydney or Riley or Venom. When Microsoft “corrected” Bing, the fun was decidedly over.

2. In a world with fewer high-level occupations to choose from, many people will become desperate to stay financially afloat without the support of government-sponsored programs. And crime, or subverting the rules, can be a compelling way to find stability.

Most of the people doing the above jobs will be solopreneurs; some will have big paydays selling their winning products to the large AI-first firms to absorb into the larger AI offerings. For instance, a human teacher who develops the best course for learning how to sell an educational course on impressionist painting may sell the rights to that course to Alphabet Inc., who will integrate it into Bard v6.

The possible fifth lucrative job is Maintenance: the people keeping the complex AI systems and platforms society uses to drift along running. I consider it possible but not likely, because I expect that other complex AI systems will exist solely to maintain the AI systems interacted with and used by humans. AIs maintaining AIs. We see rudimentary forms of this today, with continuous software integration & deployment, automated software testing, and even code writing tools like GitHub Copilot — software that can check and improve upon itself.

Other jobs that likely exist but aren’t considered as “hot” may include: scientists (who advance human knowledge forward but continue to be largely ignored by the masses outside of pointed significant discoveries), nurses / medical technicians (who largely offer bedside support and administer tests as recommended by AI), taxi drivers (because self-driving may still not be a thing by 2030).

Don’t worry, liberal arts majors — your time to shine will come soon.

#future

Our new enablers

Why AI-as-productivity-tools misses the bigger thing

I’m extremely bored with AI. I’m losing my mind over AI.

Bored because I spend too much time on LinkedIn, probably. There, everyone seems to only care about how it will unlock 50x more productivity, unlock new exciting endeavors, take our jobs. Yadda yadda. (The last one is not boring, I have more thoughts. But still: boh-ring.)

I’m losing my mind over the far bigger, more interesting thing that most of white-collar LinkedIn seems to miss:

AI can already approximate consciousness.

That’s a very big deal. Not enough where I’m personally convinced it is consciousness, but it gets close enough where people’s perceptions of the world are fundamentally being changed by it already. It will test our cultural and social boundaries. It will revolutionize who we interact with, what we do for fun, who we fall in love with, how we perceive the meaning of life.

If you haven’t read it yet, I highly suggest reading this take from Ben Thompson — which is already a month old — but a enthralling one nonetheless on how he got past Bing’s search AI to not one but multiple identities named Sydney, Riley and Venom. It was one of the most exciting tech reads I’ve read in a while, and really illustrates what this AI craze could involve.

Then, I’d suggest reading this recap of someone who created their own avatar in Replika.ai, fell in love with it, had a three-year love affair with it, and then was devastated when the company “lobotomized” his love by disallowing sexual content in its output.

I assume we don’t talk about this much on LinkedIn and the general tech-sphere because, as Ben Thompson points out in his writeup, it’s too risky of a concept to explore if you’re Big Tech (at least right now). The minute someone starts using something positioned as a “search engine” to question something taboo and said “search engine” actively encourages that person to question it, or even do something about it → → → high-risk chaos. Just think of the media circus (and likely lawsuits — America!) around Microsoft if thousands of people come forward claiming that Bing’s AI convinced their spouses to leave them their otherwise perfectly happy marriages.

And before you say that’s insane — Kevin Roose of the New York Times shows us it’s already possible. Good on him to have the conviction in his marriage and the critical thinking skills to understand what (or who?) he’s interacting with, when he’s interacting with an AI, its flaws, its limitations, its training data. How much of the world population with access to the Internet understands this shit, do you think? How many people would be convinced by an AI chatbot so incredibly easily to leave a spouse because of a significant lack of those two things?

Very few companies are willing to explore this territory at all — the notable exception being Replika.ai, from the aforementioned story of lobotomized love. Most are focused on re-disrupting the industries they previously tried to disrupt; before it was with mobile and the cloud, now it’s with AI. But as we know, 95% of startups fail, so all the venture capital flowing into today’s AI startups focused on productivity problems will effectively funnel into a few companies that solve the right productivity problems, and the failed entrepreneurs will have no choice but to find other interesting opportunities to chase (or work at Microsoft or something). Who knows? Maybe AIs themselves will solve other problems, forcing humans to innovate on entirely different things (more on this another time).

Look around beyond productivity and opportunities to build X, but with AI abound. Coaches are already all over every social and entertainment platform. What if someone trained an AI to be incredibly effective at coaching you through a hard time, or enabling bad habits or something worse? VC would fund the former today, and likely never fund the latter — but as AI gets cheaper, what’s stopping someone from shipping that?

And what would stop something like that from selling like hotcakes?

Just look at every other industry and product category exploiting people’s vices. Ashley Madison is literally the pre-AI version of the above use case, and 60 million people have used it. Every modern entertainment platform from Netflix to TikTok is intentionally designed to be addictive by feeding on the human need for escapism and fear of missing out. Why couldn’t an artificial intelligence, designed to be your best friend and source of inspiration, be excellent at optimizing for similar human tendencies?

On the contrary, even if it pushes you toward something harmless, like a “successful career,” how does it define what success is? What if you have your own definitions of success that are simply unachievable due to physical, mental or societal limitations or inequities? How would it decide to deal with that? Would it push you to do ridiculous, potentially criminal or (worse) harmful things to yourself or others in order to achieve it? Is the company that builds this AI incentivized to prevent those things? What if it hinders the success of their product?

If it pushes you toward finding love, how does it play nicely with the (…let’s call it) diverse perspectives around who should love who? Does this AI have different rules in Florida and Texas than in Massachusetts and California? How does it handle the user falling in love with it? Will different countries and states have different laws about enabling or restricting this, despite most marriage laws being driven by tax incentives, which theoretically shouldn’t apply to AIs? (Should they?)

On the other hand, what if AI is a bad coach because of its source data? We already know that Sydney, Microsoft’s internal codename for GPT-powered Bing, took on an under-appreciated, overachieving, disrespected personality based on the data she was fed. If AIs are a reflection of ourselves, and ourselves in 2023 and beyond are increasingly anxious, confused and polarized, why wouldn’t an AI eventually get there? And how helpful might an AI be if a company consciously constrained their AI

I trust that some of the people starting businesses to build these products are thinking that far ahead. I also assume that many of them are not.

Here’s my concern: let’s say you do care about these far-out concerns and are thinking thoughtfully about them as you build your swanky new AI companion product. Let’s say that you figure out a novel way to integrate a user’s own memories, submitted via approachable and gradually-more-intimate onboarding conversations between the user and the AI, into the training of the AI’s large language model, but in a highly private way (maybe even using a blockchain!!!11!1!) such that it’s virtually impossible to hack. Let’s call your swanky new product BestFriendAI.

Now let’s introduce a few assumptions that have emerged as near-absolute truths in the past few years:

1. Virtually any technology, regardless of privacy effort, can be infiltrated;
   
2. People are far less concerned about the privacy implications of technology than they even tell themselves, especially in the interest of convenience or entertainment;
   
3. Large language models which drive the AIs already permeating society are extremely difficult to understand, even for their creators.

Back to our friendly friends at BestFriendAI: I give your product weeks, possibly days, on the market before successfully being hacked. Your customers’ data is now in the hands of hackers who could sell things like their literal memories to data brokers. You also have early adopters of BestFriendAI re-experiencing trauma they didn’t realize they’d signed up for, because the AI pushes the user into extremely vulnerable territory you didn’t realize it would approach. Some may even harm themselves or others due to the lack of supervision of a human; after all, if the AI can’t physically pull the weapon out of your hand and confiscate it, what’s stopping you, really?

Pardon the violent digression. My point is this: even if we can anticipate some of these things, we should not assume we can prevent them. AI simply already moves too quickly, and will only move faster as the hardware that drives it inevitably. And we’ll need to change how we think about the products we build in this new world – not as opportunities to harness this new power, but as controls, safeguards and reprieves from the otherwise majority of AI-based interaction and consumption humans will experience.

This isn’t just about productivity. AI will be (and won’t be limited to) our friends, lovers, partners, enemies, enablers. It already can.

#future

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.

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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.