Managing time as a manager

At Automattic, I manage a team of extremely talented developers. One of them is training to become a Team Lead himself and sent me the following list of questions about time management:

When you became a team lead, what was the biggest adjustment for you in how you managed your time?

Infantry wins battles, logistics wins wars

General John J. Pershing,

When you are an individual contributor, you optimize for turnaround: grabbing the most tasks and churning them as quickly as possible.

With the switch to a manager role, your output is the sum output of your team, but the force multiplier is proactively removing blockers so that everybody else can keep momentum.

As I wrote in Sort by Surprising, the biggest slowdowns come from discovering an underspecified area. Then everybody sits on their hands, waiting for decisions/clarity.

So as a Team Lead, you have to figure things out 2 chess moves into the future and keep the pipeline running before your team even realizes what they need.

Imagine your team is a factory assembly line. You need everybody operating at peak efficiency while ensuring the components are delivered on time, and the finished product shipped, all while solving minor drama.

To answer the original question: a cliche response would be that “communication” takes more time, but this is not enough. You need to communicate decisions and direction to make sure all work aligns when it should. Apart from communication, you need a plan and authority to make decisions.

The activities I now perform more as a team lead are:

  1. Drafting documents with roadmaps/plans, etc.
  2. DMing like crazy while “managing up” to ensure alignment on these roadmaps
  3. Dropping into comments/threads/issues to resolve confusion and push final decisions so we can stop discussing and move on

It is really hard to report what did I actually do by the end of the day. This takes us to…

What does your day-to-day look like? And do you have any regular routines and/or habits throughout your day?

The critical thing to remember about me is that I have ADHD and a small child. I both appreciate consistent habits, get bored by them and find them hard to implement due to family constraints. I also find daily habits more conducive to personal goals, while weekly ones are better for professional obligations.

I will rephrase that question into a few pointers on what I have found helpful in managing my day-to-day:

  • I try to batch meetings. That leaves you exhausted but ensures you have blocks of time on other days. A pro tip is not to have meetings back-to-back but leave 15 minutes between them. Most 60-minute meetings can be 45 instead.
  • Ensure you have one day/week exclusively devoted to updating documents, project threads, and reporting. Make a list of documents you have to update regularly.
  • Keep all the documents you use regularly bookmarked and launchable from the keyboard by something like Alfred.
  • If you work in Europe, you can do your IC work in the morning because after East Coast comes online, you will get buried by pings. That means that if you start your day reading internal blog posts, you will do nothing during that day. Start the hard work as soon as possible.
  • Try to respond to everything before wrapping your workday, so East / West Coast is not blocked by a question they have for you.
  • The only way to be productive after a long Zoom block is to immediately log out, and go to a gym.
  • Beer at lunchtime will always leave you useless

My morning routine (mostly personal)

  1. Be woken up by the dog wagging its tail incessantly, jump out of the bed
  2. Drink Athletic greens (It feels illegal to talk about AG without an affiliate link)
  3. Get the cover out of the bed because the dog will jump on it immediately upon returning from the walk. During winter dog will be dirty regardless of how long I try to clean her
  4. Walk the dog. If the weather is crap, listen to an audiobook/podcast (see Principles for reading). When it’s lovely – enjoy the walk.
  5. Feed the dog
  6. If it’s still before 8 am, go to the pool (I have a small pool in my building), and swim 1km. Doubles as the morning shower.
  7. Eat breakfast
  8. Negotiate with my baby if she will go to preschool today
  9. Somehow get her to the preschool
  10. Go back home / to a cowork / to a coffee shop
  11. Make coffee, and log in to work.
  12. I check, in order:
    • Slack pings for drama, and if something blew up overnight
    • GitHub and Phabricator comments for blockers, info on what got shipped, etc.
    • P2 (our internal blog system) for comments,
    • Slack scrollback, but on some days, I skip that.

How do you balance meetings and independent working time?

I, of course, try to have as few meetings as possible. That being said, the 1:1s consistently allow for re-syncing our mutual understanding of the priorities, where things are, etc.

The team I manage is quite small at the moment, so fortunately, this is not a very big issue.

Do you take notes during your meetings? If so, how (i.e. pen and paper, notetaking app, etc.)?

  1. I have a running shared Google Doc for every meeting that I attend. I always open it up and ask to fill in advance (sometimes we both fail tho)
  2. That doc gets automatically synced to my Logseq (notetaking app of choice) so that I can cross-reference with other note content. I described it a bit here.

How do you keep track of everything you need to do? Do you use a task manager / To Do app at all?

I am a big fan of GTD. Having a single list with all your commitments frees up the brain cycles from remembering all the “stuff” you have to do.

For work stuff, I try to report bigger tasks in Github, as the code issues already live there. I recommend using the private-for-the-team repository explicitly for that purpose.

But most of my tasks live in Logseq, which also has a built-in to-do system.

How do you know what information to pay attention to and what not to? How do you prioritize the information that comes at you?

Your task is to tweak the Gannt chart continually. Here is what I do, in order:

  1. Tend to any urgent fires
  2. Ensure everybody has immediate stuff to do to maintain momentum
  3. Figure out what may be surprising and impact our priorities, Prioritize figuring this out (Sort by Surprising).
  4. Maintain a backlog of tasks/projects for the team

I devote little time to “keeping in the loop” unless I get a ping. New information that gets published internally tends to change before the actual implementation, and by this time, I will get a ping about it.

But I dig into older posts when trying to design a roadmap/align direction. I find older posts more reliable than new ones.

What’s the biggest piece of advice you’d give a brand new lead when it comes to managing and organizing their time?

In the beginning, decide with your direct manager what worthwhile things you will not spend time on.

HR will proactively generate lists of stuff for you to do, but your first goal is to ensure the team has work to do and they are proceeding in a sensible direction.

I would advise postponing any “Managerial” tasks until you have 3 months of a roadmap designed. By then, you bought yourself enough time to focus on this “Team Lead” stuff.

You should also read Paul Graham’s Maker’s Schedule, Manager’s schedule.

Personal Logistics

Adulting is hard, and I wonder why.

On the one hand, it is easy to make fun of grown humans lamenting about not knowing how to clean the house, meet new people or cook. On the other, there is a number of life skills that I feel like we would all benefit from, and yet I’m not confident we all perform them at a level we aspire to:

  • Cooking healthy meals without effort and a big deal
  • Maintaining healthy fitness habits
  • Meeting new friends and maintaining relationships in adulthood
  • Dealing with stress, politics, and competing expectations at work
  • Finding joy and fulfillment at work and dealing with marketing ourselves in the job market
  • Dealing with expectations and caring for our parents and grandparents
  • Managing home projects and the basics of repairing and maintaining stuff
  • Managing our budgets, investing, and thriving as a tiny part of Capitalism
  • Dating and Parenting are whole other stories

Discussing those topics in adulthood is like talking about sex in junior high school: We are all sure everybody else has this figured out while being too ashamed to admit we could use a few pointers ourselves. Yes, of course, my fridge has plenty (of healthy meals), and it’s sooo good. Why do you ask?

Some of us deal with this by making fun of our own incompetence – cue all the “adulting” memes about eating only takeout and barely keeping up with rent.

Others not only seem like but really do have everything figured out. They are effortlessly organized and manage to do stuff on time without drama or valiant battles. Where is the difference?

It’s always Plato’s fault.

I know it’s a cheap shot, but I couldn’t deny myself blaming Plato again: He pioneered the idea of mind-body duality and the toxic notion that purely intellectual pursuits are somehow nobler.

We teach children the number of sheep in 1957 Yugoslavia and the exact dates of every minor battle instead of valuable skills that they will really need. But the real lesson kids will remember is that personal logistics skills are not worth learning. After all, the sheep exam is coming.

For those not fortunate enough to learn these skills at home, their ignorance of them becomes a point of pride: they are made for better things in life.

The highly stratified societies of the past could get away with the “upper class” learning only about topics they could comment on in their mansions, balls, and gentlemen’s clubs. With the (arguably) more equal societies of today, we are teaching another generation not to bother themselves with the down-to-earth. It’s like we are all royalty.

Modernity likes the helpless you.

Compared to the past generations, we live like royalty thanks to the smoothly running society where you can outsource any task to a professional. By paying for every little thing in life, you grease the gears of commerce and keep people employed and needed, all while getting the level of indulgence unheard of before (like Doner Kebab on demand).

This is not necessarily bad, but:

  1. You need a certain level of competence to delegate. Learning the basics of everything is always a good idea.
  2. By doing things yourself (aka “vertically integrated”), you can ensure a higher quality than by delegating. This may sound counterintuitive, but this is how luxury brands operate (Apple is one prominent example)
  3. You cannot outsource making friends. You may only pretend.
  4. Everything you feel is beneath you will eventually blindside you.

Personal logistics is a learnable and transferrable skillset

I was a scout for 14 years, spending every summer building a camp to live with my friends for the following month. These are one of the best memories of my childhood, and apart from specific skills, they taught me mostly that I can figure things out, the building is fun, and everything is learnable.

Over the last 10 years, a space of Personal Productivity has emerged to transfer business learnings to help individuals manage their personal affairs, learnings, and knowledge. I hope we can extend this movement to include a variety of tacit knowledge that was previously passed around by grandmas, mixed with timeless advice updated for the modern world. Business logistics principles can help you manage your fridge and the experience of running a smooth household transfers to being a dependable professional.

We need more curators.

It took me writing this whole piece to understand that my wife may be onto something with her Grandmotherly Wisdom newsletter. The Hacker News commenters think it’s great, too.

There is an enormous opportunity to repackage timeless ideas, curate youtube videos and create a basic human curriculum for the next generation.

On the one hand, humanity did not change that much over the last 50 years, on the other – the world changed quite a lot. We all need the same things as our grandparents, but our environment is quite different.

Send me your best instructional Youtube videos about mundane stuff. I am recently exploring how to teach my baby daughter to swim.

Random curated advice

  • Tom Vanderbilt shares the joys and transformative power of lifelong learning on the Art of Manliness podcast.
  • Freddie Wong explains that filtering for 3.5 stars when searching for Chinese restaurants finds those good enough to stay in business despite providing mediocre customer service.
  • Visakan shares his tips on how to DM your heroes so they respond if they ever end up following your on Twitter:
    • 1. specific proof-of-work: “I’ve been a fan of your work and writing since the livejournal days”
    • 2. share sth specific about yourself, their influence on you: “your work shaped the way I now do X”
    • 3. ask easy-to-answer specific Q

2022 – A year of coming to terms with mediocrity

I have pretty simple ambitions.

I like to look at mountains, spend time outside, swim in the lakes, go on bike rides, and enjoy good food, all preferably with friends and family. Professionally, I love building cool things that other people enjoy and giving them tools to achieve more than they thought possible. I like to tinker and connect things that were not connected before.

I hate doing things that make no sense, so I try to be deliberate about my approach. I read books, listen to expert podcasts, and get inspired by other people’s stories.

And that is the tricky part. Popular books, podcasts, and materials are about achieving the absolute best of human performance, getting to the very top, and winning. But I don’t want to win – I want the most awesome average life possible. It’s pretty tricky to learn from the best without comparing ourselves to them and without normalizing a success cult lifestyle.

I think I have figured out how to walk that line in 2022. While I previously had no grandiose ambition, I felt guilty for not striving to do more – to build a startup or a company, at least. But no, the life of a Remote employee in a big company is pretty great, even if it’s not the absolute top. My wife has phrased it all more eloquently (and you should subscribe to her substack):

The End Goal of the Hero’s Journey Is to Become a Normie

So how was my 2022?

War & peace

The Russian invasion of Ukraine was kind of a big deal in Poland. Of course, any war is devastating, and this one is needlessly brutal, but on top of that – this wasn’t supposed to happen in the 21st century. We were at the end of history, but one of our old-but-now-supposedly-reformed-and-civilized-oppressors attacked our neighbor, 500 km from where I live.

I started the year with a goal of publishing 50 posts in 2022, but after that invasion, I felt no point in sharing productivity tips or advice. I also dramatically cut down on my reading as my priorities shifted.

Regardless of how much we helped, it felt so very little compared to the needs of victims and the sacrifice of others. My dear friend (a father of 2) was constantly on the road, driving an ambulance from the warzone, transporting sick Ukrainian children to Polish hospitals. I cannot express how much respect I have for him.

Even if the war continues, life does as well.


Parenting is a very humbling and grounding experience. You may think you have everything figured out and dialed in, but your baby is there to remind you of the everyday struggles of the majority of humanity. For example -we haven’t been able to figure out a foolproof method of putting our daughter to sleep, and every night is a negotiation.

One big success is her daycare. She made a few friends who she misses when we are traveling. My wife and I like to complain about the downsides of the public education system, and at the same time, our daughter loves the institution, and we have more time for ourselves when she is there.

As I said, a humbling experience.

And yet, when your child is in a good mood, there is nothing more rewarding than parenting. I am constantly surprised that my daughter is such a wonderful human being. I am sure many parents believe the same about their children.

My job

2022 was tough at work. Just as my team successfully launched a very complicated, demanding, and supposedly strategically important project for Tumblr (I wrote more here), we were moved to another place within the organization where that wasn’t important.

I spent almost the entire year trying to align multiple business units around different approaches to synergy. Still, ultimately none of them were accepted, and I felt like I had accomplished nothing and paid a lot to do so. I fell through the cracks in the corporate machine, and it was the first time I genuinely felt the downsides of working inside a big organization. As I am reading Tony Fadell’s book “Build”, his experience with Nest after being acquired by Google feels eerily similar despite the massive difference in scale. Fortunately, I found a way out.

One of the perks I get at work is professional coaching. Out of all things, my new coach has challenged me to rely on permissions less. No one who knows me has ever said this, so I decided to take it at face value and run with it.

As of 2023, I am giving up on leading the strategic synergy and am focusing on improving the lives of creators on and returning to my role of Earn Product Manager. And I launched our AI product offering by accident. Stay tuned for updates on that front.

Memorable experiences

Our RV continues to be a gift that keeps on giving, and RVing around Alps does not get boring. Some of the fantastic places we’ve seen this year include my bucketlist items:

  • Hiking to the top of Brunelleschi’s Dome in Florence.
  • Hiking between Cinque Terre villages
  • Seeing the inside of the Neuschwanstein castle
  • Swimming to the island of Lake Bled
  • Seeing the castle in Marseille where the Count of Monte Cristo was imprisoned

One thing that brought me a lot of joy is biking with my daughter. So I am looking into buying a trailer for her.

Goals for 2023

My theme for 2022 was “Leisure,” and I don’t think I am satisfied with how it turned out. The demands of everyday life, the stresses of work, parenting, and marriage have encroached on my Leisurely ambitions. This is what happens if you don’t have a plan.

In 2023, I want to put more ambition behind my leisure, as contradictory as it sounds. I want to have concrete goals with concrete leisurely payoffs:

  • I want more swimming in the lakes and more bike rides in 2023. Preferably with friends.
  • I want to get a driver’s license for trucks so that I can look into really fancy RVs.
  • I want to learn how to eFoil because it looks like my kind of fun
  • I want to take a stab at getting a pilot license so I can figure out if this is my kind of fun
  • I need to train my dog to become calmer so we can all relax
  • I need to take my fitness more seriously so I can feel healthier doing all the leisurely stuff I want to do. My provisional goal is to lose 10 kg.
  • We need to teach our baby how to sleep and play alone because that is a major stressor in our family life.
  • I want to take a stab at learning Italian because we know we’ll end up RVing in Italy anyway.

How was your 2022? Any new goals?

Work of Art in the age of mechanical reproduction

In all the arts there is a physical component which can no longer be considered or treated as it used to be, which cannot remain unaffected by our modern knowledge and power

Walter Benjamin, 1935

In a few recent blog posts (What do you wish existed, Artificial Vanity for the masses), I described a series of technological advancements unlocking on-demand Artificial Intelligence image generation. As I continue to play with this technology, one question remains potent:

“Is this real Art? Is this real fantasy?”

Bohemian Rhapsody (and some creativity)

There are two good times to quote Freddie Mercury: Now and Forever. This instance is no different, but the paraphrase (changing the dichotomy of real and fantasy to separate questions) has a deeper meaning, as these are separate questions:

  1. Is AI art “Art”?
  2. Is this even a creative endeavor?

I understand how illustrators and artists can feel uneasy about this topic: These models ( the biggest ones being Stable Diffusion, Midjourney, and DALL-E ) were trained on the publicly accessible works of others. The computer seems to be producing some random blend of all available data guided by the text prompt without any attribution whatsoever.

One interesting angle to note is that with technological advancement, Humanity seems a little less remarkable: Copernicus dared to insinuate that the Earth is not the center of the Universe, and Darwin suggested that we are, in fact, part of the animal kingdom. AI “Art” is chipping away at our confidence in Art and Creativity being uniquely human.

Despite my techno-optimism, I recognize this is a very complex topic. In my research, I found a 1935 essay by Walter Benjamin titled:

Work of Art in the age of mechanical reproduction

In the essay, Walter Benjamin focuses on photography and film as new art forms. He argues that they are uniquely different since they only exist to be consumed by the public. No “art object” is attached to them, contrary to preexisting art like paintings, sculptures, etc.

Works of art are received and valued on different planes. Two polar types stand out:
1 – with one, the accent is on the cult value
2 – with the other, on the exhibition value of the work.
Artistic production begins with ceremonial objects destined to serve in a cult. One may assume that what mattered was their existence, not their being on view

He argues that after removing the “ritualistic magic” trapped in the art object, only its exhibition can be of value. That exhibition is subjective, and art’s reception can only be connected to the current political discourse:

photographic negative, for example, one can make any number of prints; to ask for the ‘authentic’ print makes no sense. But the instant the criterion of authenticity ceases to be applicable to artistic production, the total function of art is reversed. Instead of being based on ritual, it begins to be based on another practice—politics

I am going somewhere with this, I promise.

AI and Film

While reading this 1935 essay, it occurred to me that the questions regarding the “authenticity” of AI-generated Art are an extension of controversies surrounding photography and film:

But the difficulties which photography caused traditional aesthetics were mere child’s play as compared to those raised by the film.

One point of view Benjamin explores is that there is “substance” to film. The entire artwork is in operating the point of reference and frame used during the filming:

The camera that presents the performance of the film actor to the public need not respect the performance as an integral whole. Guided by the cameraman, the camera continually changes its position with respect to the performance. The sequence of positional views which the editor composes from the material supplied him constitutes the completed film. (…) There is no such place for the movie scene that is being shot. Its illusionary nature is that of the second degree, the result of cutting.

This analogy carries very well to AI-generated images: The artistic process in AI-Generated Art consists primarily of:

  • Picking and changing the reference frame – that is, crafting the prompt
  • Selecting, discarding, and curating the output

Producing AI-generated images is like owning a camera and a magic portal to the entirety of recorded existence.

Is the photographer less of an artist because he can only arrange preexisting elements?

Democratizing publishing

The mission of our company is to “Democratize Publishing”. I am happy to read that this was already accomplished in 1935:

For centuries a small number of writers were confronted by many thousands of readers. This changed toward the end of the last century. With the increasing extension of the press, which kept placing new political, religious, scientific, professional, and local organs before the readers, an increasing number of readers became writers—at first, occasional ones. It began with the daily press opening to its readers space for “letters to the editor.” And today there is hardly a gainfully employed European who could not, in principle, find an opportunity to publish somewhere or other comments on his work, grievances, documentary reports, or that sort of thing. Thus, the distinction between author and public is about to lose its basic character.

Coauthor – AI Writing Assistant and Artist

Last week, I (re)wrote a WordPress plugin to put the power of AI inside your WordPress editor. The plugin introduces two new blocks:

  • Coauthor Paragraph will take your content above the block, automatically generate GPT-3 completion to the text, and insert it into the blog post.
  • Coauthor Image will generate 4 images according to your prompt with DALL-E 2, upload the one you select and replace itself with an Image block.

You can find the Coauthor plugin in the WordPress plugin repository.

It is ok to be ordinary

It is easy to forget how good modern life is. Water, shelter, fire, food – all our basic needs are taken care of. We have running (hot!) water, access to medical care, and exotic meals on demand. All for a price most of us can afford without much concern. I am not an American, nor did I celebrate thanksgiving, but I am pretty grateful for the gifts of modernity, including industrial crop farming driving food prices down.

You don’t have to be a CEO, a billionaire, or particularly rich to afford luxurious things: I pay for catered meals, housekeeping, and Virtual Assistant and the total cost of all of those is about $300/week (yeah, Poland’s pretty cheap).

And yet, our default success metric is being extraordinary – CEO, director, celebrity, a famous person. Despite now being 8 billion of us, we all compare ourselves to a select elite.

In a great article, “Being OK With Not Being Extraordinary”, Tiffany shares how normalizing comparison to “winners” is not a sustainable way to live:

My constant exposure to these amazing stories of success has normalized the extraordinary. I started comparing myself to these “normal” extraordinary people, and wondered why I was not them.

We need to redefine extraordinary

Nassim Taleb points out that globalization turned the modern world into an “Extremistan”. Previously, it was possible to be an ok musician and make a good living just because you were the only option in town. Now people can listen to Taylor Swift or Mozart on demand. There are only a few winners, and you compete with everybody else on the planet.

On the one hand – we can enjoy the fantastic achievements of modernity, like running water. On the other, dating, writing, and much more of human experience have turned into winner-takes-all hunger games.

It seems like the only winning move is not to play. You don’t have to be extraordinary to make your life count. It is totally ok to have middle-class values.

Life is not a competition, and you don’t “lose” if you are not famous nor rich, or powerful. You lose if you’re trying to play somebody else’s game.

I feel like this is misaligned with what I wrote in The Triumph Economy, and yet I stand behind both of those posts.

Tiffany shared her advice on how to deal with the extraordinary trap:

Because the ledge is not the only thing that exists. There is a vast amount of space under it, other ledges, crooks, and crannies, that most people forget about. That space is just as valuable.

I expanded on that view in Competence is fractal. Plus transgenic trees

On the topic of Trees:

How would you plan for the next 200 years?

After their defeat and loss at Copenhagen in 1807, the Danes responded by planting 90,000 oak trees toward the Navy’s rebirth. The Danish Nature Agency, the successor to the royal forester, informed the Defense Ministry in 2007 that their trees were ready.

These centuries-long projects are fascinating. What will change in 200 years? What will stay the same?

I create software for a living and am sometimes unable to run a project created last year because its dependencies no longer compile. Planning for the next 200 years requires black magic. The Clock of the Long Now presents an interesting exercise of a group of engineers building a clock intended to run for the next 10 000 years.

A thing I’ve read

Crazy new ideas

In this article, Paul Graham explores the fragility of good ideas. The status quo is very resilient, and a better idea not always wins:

People build whole careers on some ideas. When someone claims they’re false or obsolete, they feel threatened.

A good litmus test is to depend on the personal credibility of a person proposing a new idea:

If the person proposing the idea is reasonable, then they know how implausible it sounds. And yet they’re proposing it anyway. That suggests they know something you don’t. And if they have deep domain expertise, that’s probably the source of it

We like to think that it comes down to the battle of ideas: things are the way they are because these are the best ideas we have implemented.

But ultimately, it all comes down to the credibility of the person proposing the idea and the person rejecting it.

Finally, we will not run out of good ideas:

You can observe big new ideas being born all around you right now. Just look for a reasonable domain expert proposing something that sounds wrong.

How to be lucky

Emma shares some tips on how to maximize your “luck”. It all boils down to the following:

  1. Leaving space for opportunities to appear
  2. Being prepared to take advantage

When you stop procrastinating and these mundane things are finally taken care of, they will no longer take up headspace. You’ll enhance your ability to be observant, present, inspired and curious, all of which will have a profound impact on building your serendipity muscle.

serendipity hook strategy’ (whenever you meet someone new, cast a few hooks – concrete examples of your current interests, hobbies and vocation, thus maximising the chance you and the other person will latch on to common ground and shared passions, triggering serendipity).

Wiseman found that people who self-identified as lucky used more open body language (such as fully facing the other person in conversation), made more eye contact and smiled twice as often as ‘unlucky’ people, all of which made others trust them and feel more ‘attracted’ to them.

Ask people What are you most interested in at the moment?’ instead of ‘What do you do?’

What is your favorite cheese?

David suggests another great icebreaker:

Ages ago my brother suggested at a family gathering that “What’s your favourite cheese?” was the best opening question to ask someone new. None of us were 100% convinced until we realised we’d spent about half an hour after he said this talking about cheese

Boring Innovation

Real innovation is boring, unsexy and incremental. Only the results are sometimes transformative.

Tech coverage in 2010s was terrible. Mediocre startups claimed to be “game changers” and “disruptive” to the status quo, while in reality their entire business model rested on low interest rates and cheap VC funding.

Venture Capitalists were counting on disruptive change in order to become market leaders in new niches / business models where they could capture exponential growth.

Is there such thing as disruptive innovation?

Disruption” happens when enough of those small innovations unlock use cases previously impossible. Each innovation seems inconsequential, but at some point, a “phase transition” (Safi Bahcall on phase transitions in innovation) happens, and we live in an entirely different world.

  • Smartphones were only possible after 3g became widely accessible
  • Silicon Valley was possible in California because that state prohibits Non-Compete clauses, bolstering competition in knowledge industries

Because the world is a very complex system, you cannot “target” disruption. You can only unlock new potential with boring innovation, and if you are lucky – ride the wave of the subsequent phase transition.

Boring Innovation

So what is boring innovation?

It’s an incremental improvement to a boring piece that is considered “the yuckiest”. It’s something people shy away from, and there is a reason that problem is still unsolved.

  • It most likely requires expertise in 2 areas that rarely go together. The challenges of the future are in the seams of things.
  • Solving it may require some manual steps.
  • It may require reading up on regulations.
  • It may require understanding the business.
  • It may require being an expert on some bizarre corner case.
  • It probably will not be a flashy Conference Talk because your peers will not consider it sexy.

Boring innovation is usually about making things work together

Because transformative change (I’m using this term because I hate “disruption”) only happens in systems, it is triggered by optimizing how things work well together. I expanded on this in Composability is the only game in town.

Here are some examples of boring innovation targeting a laborious and messy processes:

  • Visa created a credit card network to replace cheques, and later PayPal pioneered online payments. Stripe is doing the boring innovation work in simplifying the entirety of commercial infrastructure.
  • AWS presented an alternative to costly on-premises hosting
  • Shipping container is a backbone of the entire modern commerce.

Boring innovation focuses on an acute problem that customers are already aware of. It is easy to monetize, and does not need grandiose claims, press releases, and sponsored articles.

The best boring innovation is a one that everybody eventually depends on, but few consider innovative.

So-Called “Disruption”Boring Innovation
Discarding previous system, replacing with naive implementationRespect towards complex systems, gradual improvements
Grandiose vague claimsFocused on a single problem
Convoluted business modelsCustomers ready to pay
Overpromise and UnderdeliverReliable

Isn’t it time for some boring innovation?

If you have a favorite example of a boring innovation – send it! I would love to curate a collection.

Great career advice

The job market in Tech isn’t what it used to be. Even the biggest tech giants are laying off thousands of employees in preparation for the upcoming market downturn. Those who have coasted in their jobs may have a hard time keeping them, and I think (as always) this is a good time to:

  1. Be good at your job
  2. Make sure people know that.

A few links with good career advice

I gathered a few links to help you with that:

Writing in Public, Inside your company

Brie Wolfson helped shape the writing culture inside Stripe. In this piece, she shares advice on how to keep your colleagues in the loop, superiors well-informed and yourself recognized for your great work. The writing culture at Stripe sounds similar to the company I work for (Automattic), where we put great emphasis on writing things down and distributing them to colleagues as well. Brie writes:

Without meeting notes and documentation, companies become reliant on unreliable verbal accounts, 1:1 updates, and needing to be in the room to get things done

She outlines 2 broader categories of documents you should be producing:

  • Paper trails (Decision Logs, Meeting notes, FAQs), designed to be searched later,
  • Curations,

While paper trails are about accurately reflecting the state of some area, curations are more creative – they let you connect a few seemingly disparate pieces of information into a strategic recommendation. if you make them a joy to read, you will garner a bit of a reputation, or even some impact, which I can attest to.

One memo I wrote in 2018 garnered the attention of the CEO and resulted in me leading the introduction of Creator Economy offering to and later Tumblr.

In her piece, Brie also advises keeping some other documents up-to-date and handy for when that performance review comes around:

Brag document: I call mine “what Brie is proud of” and it includes things I did and things others have said about me or my work that makes me smile.

Personal OKR/Shipped List: An OSR (ongoing/objective stack rank) is simply a list of all projects in the order you will do them. I also include any signs of ongoing impact that can be attributed to these ships.

What I learned today: A personal FAQ of sorts. Transcribing something usually helps me internalize it better.

Re-writing my job description: what I actually do. I re-write this every 6 months or so and talk to my manager about this

You should definitely read “Writing in Public, inside your company”

Willingness to look stupid

Dan Luu advocates keeping your ego in check and risking looking stupid if you want to do great work:

when I learned things that were hard for me and tried to think of this feeling as “the feeling of learning something” instead of “feeling dumb”, which half worked (I now associate that feeling with the former as well as the latter

don’t necessarily have to be particularly smart or talented or hardworking to come up with valuable solutions. Often, the dumb solution is something any idiot could’ve come up with and the reason the problem hasn’t been solved is because no one was willing to think the dumb thought until an idiot like me looked at the problem.

Work on What Matters

A great blog for Staff Engineers gives great guidance on how to do the work that matters:

If you’re in a well-run organization, at some point, you’re going to run out of things that are both high-impact and easy. This leaves you with a choice between shifting right to hard and high-impact or shifting down to easy and low-impact. The latter choice–easy and low-impact–is what Walk refers to as snacking.

Instead, the most effective places to work are those that matter to your company but still have enough room to actually do work. What are priorities that will become critical in the future, where you can do great work ahead of time? Where are areas that are doing ok but could be doing great with your support?

Grueling interview process is the whole point

Tech interview processes are famously broken. Hadrous shares on Hacker News why it may be the whole point:

FAANG (& similar) have more applicants who can do the job than they have positions, so instead of checking for that and calling it a day, they filter for some combination of IQ and how bad you want it—willing to do a ton of otherwise-low-value prep work & practice, and to go through the painful interview process itself, likely several times at different companies, even for successful candidates.

The reputation of their interviews also means they likely don’t get a ton of candidates who can’t do the job. So they could likely just start randomly selecting from their candidate pool and do damn near as well as they do with all the interview effort—except as soon as that become known, they wouldn’t be able to do that anymore. Plus they’d lose the hazing factor, which likely helps build company in-group identity. Having a lot of your employees feel like they only have their job because the finally got “lucky” in an interview may also help with retention, especially when everyone else who pays as much interviews in similar ways.

In a sense, being a huge, unpleasant waste of time is the whole point of their interview processes.

A thing I wrote:

Last week I published a thread summarizing my last 2 years of work: Unlocking the economic potential of Tumblr users and enabling them to sell on Tumblr. The hard part was making sure our solution plays nice with the Apple App Store rules. If you are curious about building marketplaces on top of the App Store, give it a read:

Party Animals!

Bob Venables has created fantastic illustrations of party animals for a Casino in Thessaloniki. Check out his page for other beautiful work.

Artificial Vanity for the masses

Do you know what most people really like? Themselves. More particularly, seeing how awesome they are. The absolutely best use case for AI may be just that: “Hey Siri, show me how awesome I am“.

Viewer discretion advised: You will see a lot of faces of myself. You are welcome.

During the past month, we have seen a use case of AI design take off: Avatars. Two one-man companies sprung up seemingly over the weekend, offering to turn your face into an array of stylized scenes for $25: and

I gave AvatarAI a spin, and the results are hilarious. To be fair, I own very few photos of myself, and I’ve seen people have even better results.

The magic of Open Source

In What do you wish existed, I wrote about DALLE and Midjourney – the two AI Models to generate images from text. That was in August, 3 months ago, or 30 years in AI time.

Since then, a third entrant has considerably shaken up the space: Stability AI released a free and Open Source model called Stable Diffusion (you can play with Stable Diffusion here). Emad Mostaque, a former hedge fund manager has spent $600 000 and hired a team of brilliant scientists to train this model and release it entirely for free. It is not as polished as Midjourney and DALLE, but it’s a perfect Open Source story: The community quickly embraced it and started improving, productizing, and introducing new use cases.

In particular, Google Research has extended Stable Diffusion to release (again, Open Source) DreamBooth. DreamBooth is a way to “tweak” Stable Diffusion with about 20 photos to produce variations of these photos in different styles. It works for People, Dogs, and Product Photography. and are running DreamBooth, on top of Stable Diffusion in the cloud with Astria. Pieter, founder of AvatarAI summarized this at the bottom of his landing page:

Built by a mere scriptkiddie on the shoulders of machine learning giants.

There is also a trick to make Midjourney create an avatar for you without prior training:

The future of AI companies

It’s easy to take this piece in a predictable dystopian direction, crying out that “AI will pamper our egos while artists starve and also get morbidly obese like in WALL-E“. I trust that New York Times will stand up to this editorial challenge, so I’ll leave it to them.

For years now, the future of AI was both “settled” and a little dystopian: The giants of the Internet (Googles, Facebooks, TikToks, etc.) will gather proprietary data (which we hand off to them in exchange for “free” products) to train their models, which in turn give them further advantage to squash any competition from the little guys.

It was so fun to see those assumptions turn out false! Stable Diffusion was trained on images freely available on the Internet. Instead of relying on proprietary data to learn how to generate them, the researchers added random noise and train the model to “pull images out” of noise.

Not only did the dataset not turn out to be an moat, but the very expensive-to-train model itself was also released for free! Now every script kiddie can have a head start on Google in bringing an AI use case to the market.

I think this is the future we are heading towards: There will be a few “general purpose” models like Stable Diffusion (or whatever the Open Source version of GPT-3 will be), and the money will be made in slightly tweaking those to a specific niche, using some domain insights and finding novel and creative ways to augment computer-human interactions.

Go go script kiddies!

A thing I’ve read

The great creator-arbitrage opportunity

Like Script Kiddies, Online Creators have a bright future ahead of them. Paul Millerd shares why he is excited about the years ahead for Online Creators:

I believe that we are in the early days of what will be remembered as one of the greatest times to be alive for hyper-curious people who are willing to be creative, connect with others, and share their ideas online.

His piece is a love letter to connecting with other people over ideas. Writing online is a multiplayer sport and sharing your own ideas is an invitation to play:

Sharing Your Unique Interests Online Is Good. Full Stop

Throughout history, people have risked death for the ability to share their ideas. Now almost everyone has unfettered access to the internet and most people are sitting there and thinking “eh, I’m good.” People will look back at us and wonder what the hell was wrong with us

Read the full piece here

How to get insanely rich in the creator economy

The only true way to be a creator is to be a “professional dyletant”. If you take the “creator economy” too seriously, you will just create a job to hate for yourself. Nat Eliason published a fantastic piece about getting insanely rich in the creator economy, exemplifying why I frankly hate this term:

Comb through all the videos of people whose success fills you with jealous rage. Take notes on what they’re doing and how they’re doing it.

We want a strategy that we know will work, which is why your goal is to feed the algorithm. To figure out not what people like but what TikTok and YouTube and Twitter like so they put you in front of the scrolling masses who can subscribe to you. You thought you were breaking out of having a boss? Hah, no, your boss is now the codebase of hungover 20-somethings in San Bruno. Good luck getting a promotion.

It will feel awkward at first, but eventually, that little nagging voice in the back of your head saying, “this doesn’t feel authentic!” will get drowned out by an endless stream of dopamine

People like paying for the sense of progress, and they value the information more just because it’s behind a paywall.

Read the whole piece here

Discussing Elon is tedious now

Elon is up to more stuff. And it’s so tedious to talk about.


Yup, after considerable drama, Elon is now the owner of Twitter. A few shares that I had were liquidated and delisted from NASDAQ, so I am $20 richer from my investing schemes, as Elon is $31B poorer.

If you have been living under a rock, Elon has made moves to join Twitter’s board of directors, offered to buy the company, escalated to enact a hostile takeover, did not like what he saw inside, and tried to get out of the deal, the Twitter board did not let him off the hook, and he finally bought the company. For quality coverage, I recommend Matt Levine’s opinion column on Bloomberg.

For more than a year now, I refrain from discussing Elon, as it becomes impossible to avoid a conversational minefield. Any opinion on the man and his ventures quickly becomes a proxy for some of the most heated debates our society faces right now:

  • Is capitalism an ethical way to organize individuals? Is one person allowed to amass such a fortune and enjoy the spoils of such public success?
  • Conversely, is doing a good thing while getting rich at all possible? Aren’t people claiming to do both really lying?
  • No committee, government body, or voting scheme “allowed” Elon to garner so much influence. Should that be possible? Should we have some checks in place?
  • Technological progress is pushing the world into Extremistan in the Taleb sense: People who succeed can enjoy disproportionate returns, but it becomes harder to be “moderately” successful. Is this the future we want?
  • Has tech been covered without due diligence? We were promised all these breakthroughs that would make society a better place, and most of them went nowhere. Who should we trust?
  • As I wrote in Climate Care Industry, “ringing bells”, condemnations, and hostile language of the climate debate are not helping to further its goals. Huge swaths of the population turned numb and distrustful towards the cause, including the promises of electric cars and solar panels.
  • All of Elon’s companies are famously very demanding places to work in, and yet SpaceX and Tesla are both top choices of the engineering students. Should we allow people to do rewarding work in exchange for personal costs? At 22, are they too inexperienced to make that tradeoff?
  • I am sure this Twitter acquisition will add some fun topics to the universe of Elon: Social Engineering, Free Speech, Media & Technology overlap.
  • He sets unreasonable expectations on what one person should be able to do during the day. I am proud when I manage to put together this newsletter.

At this point, discussing Elon becomes counterproductive: It becomes a tangled mess of opinions about a broad area of topics that really have little to do with the man himself. The only way out is to take it with a smile, and I am so here for it. And so are others.

Last week, two actors posed as “laid off employees” in front of the Twitter HQ, sharing hilarious interviews. One of them – Rahul Ligma, carried a cardboard box and an autobiography of Michell Obama. As reported by the Verge:

“Ligma” is, of course, also an internet hoax designed to elicit the response “lick my balls” from people who are in on the joke. That didn’t stop multiple outlets, inluding CNBC and Bloomberg, from running headlines Friday saying that laid-off Twitter employees were leaving the building carrying boxes.

Elon (father of 10!) is also not taking the matter very seriously, seizing the opportunity to make a cringy dad joke. After the acquisition, he carried a sink to the Twitter HQ to “Let that sink in“:

Why does Twitter matter at all?

Twitter has a disproportionate influence on the press and public debate compared to other rising networks – particularly TikTok. Facebook is often blamed for polarization of society, but you rarely see journalists referring to something they read on Facebook.

Twitter continues to be the easiest way for very popular and busy people to interact with everybody else without becoming overwhelmed. It requires less attention to react to 280 characters, so it can be used by people whose attention is scarce. There is no risk of getting drawn into a stream-of-consciousness narrative or having to watch a 45-minute meandering video to join the conversation (as a sidenote, I am working on a tool to transcribe videos, so you don’t have to watch them). You can do so in 10 seconds. For a trigger-happy Elon whose attention is already fragmented, it is a perfect home.

Everyone who matters already is likely to already be on Twitter, so that’s where journalists are searching for scoops and stories. That’s where they interact with their readers, keeping the platform popular.

As I wrote in Trying out Twitter, it is a perfect platform to try out ideas and polish your writing. Despite popular sentiment, if you do not engage in politics and do not follow people who do, your Twitter feed can be a very cozy experience. Here is my recommendation.

A thing I did

I wrote a WordPress plugin for the Logseq note-taking tool. It makes it easy to write my posts there and publish them to my blog while retaining formatting and internal link structure. Have a look here if you use Logseq.

A thing I’ve seen

Have a look at the website of, “The algorithmically powered in-home physical caching platform

Our journey.

In the summer of 2016, my girlfriend and I received a gift that started a revolution in the world of in-home physical caching. To her, it was an antique blown-glass display piece. To me, it was and always will be shitbowl.