• 2023

  • Tough decisions

  • It’s hard to reconcile tough decisions.

    I often have to find a quiet place when I’m facing a tough or difficult challenge. It can be pretty difficult to find a quiet place here in NYC. Even my own apartment can be filled with noises from the street, sidewalk, traffic, neighbors and loud TVs.

    Luckily, I live nearby a park. I recommend going on a long walk or jog to clear your head. Though, not all are blessed with a quiet oasis in this loud urban jungle. Nowadays noise-cancelling headphones are abound. Couldn’t recommend them more. Even if you live in a quiet spot, I guarantee you’ll get some mileage out of a good pair of headphones in a coffee house or while traveling.

    Get to a quiet place. Breathe. Turn off notifications, and take your time. Don’t fret if you need to come back and repeat another day (or at a later hour). Dissect the issues and problems bit-by-bit. Challenging problems normally present themselves like an overgrown tree. Trim and tease out the simple problems first, then tackle the complex. I like to use a simple text editor like Visual Studio Code or iA Writer to compose little tables or lists.

  • 2018

  • The Surprising Power of The Long Game

  • From The Farnam Street Blog:

    The long game is the opposite of the short game, it means paying a small price today to make tomorrow’s tomorrow easier. If we can do this long enough to see the results, it feeds on itself. From the outside, the long game looks pretty boring:

    • Saving money and investing it for tomorrow
    • Leaving the party early to go get some sleep
    • Investing time in your relationship today so you have a foundation when something happens
    • Doing your homework before you go out to play
    • Going to the gym rather than watching Netflix

    The author closes with excellent food for thought:

    In everything you do, you’re either playing a short term or long term game. You can’t opt out and you can’t play a long-term game in everything, you need to pick what matters to you. But in everything you do time amplifies the difference between long and short-term games. The question you need to think about is when and where to play a long-term game. A good place to start is with things that compound: knowledge, relationships, and finances.

  • David Letterman’s Paper Monuments

  • For the uninitiated, from 1982 to 2015 David Letterman played host to the Late Night with David Letterman. That’s 32 years. A long commitment to say the least. Most productions like these take the summers off, but apart from a short summer reprieve — running a continuous late-night series like Letterman took some real work. Taking stock of your labors can take many forms:

    For artists, it’s their sketchbooks.

    Writers, it’s their notebooks.

    Readers, it’s their libraries.

    For others, their Retweets? Their Github contributions?

    For Letterman, it was his paper cups.

    These paper monuments keep us going I suppose. Ephemeral things — a growing glory like that ivy plant in your apartment. Something to ponder.

  • Be the Maize God

  • I’ve been thinking a lot about the Aztecs lately. Primarily about their maize god, Centeotl. Earlier pan-Mesoamerican civilizations had different names for this highly regarded deity but he (and/or she, as it’s a hermaphroditic deity) has a great origin story. Quetzalcoatl, a shape-shifting serpent god basically stole a kernel of maize from the netherworld and gave it to the humans. Later, Centeotl ultimately became the arbiter of the corn, overseeing growth and maturity of every ear of corn that grows. The Aztecs would put on huge festivals, perform blood-letting rituals, and perform sacrifices in the name of a good harvest thanks to Centeotl. Sounds like a good time.

    I think it’s fascinating that early Mesoamericans forged tales that honored their primary source of life. Rightly so too. Corn was everything for them. But what is the maize god for you or your organization? What or whom do you worship to stay alive?

    Image from @iorni, on Unsplash

    If you’re in the business of producing work for others, do you worship your top client? Perhaps you worship an industry or product you have always served. That makes sense, right?

    But consider the other side. You don’t want to be in the position of worshiping. It’s a rough trade. It’s can often be one-sided. Spending your hours slaving away, and sacrificing your time for your powerful god — only to be betrayed when there’s a change of heart. That’s a tough path few can follow.

    What you really want to be in the position of is, being worshipped.

    Be the resource (a linchpin if you will) to everyone you work for. If you disappear, everything suffers. Just like the maize god.

    If you’re producing work for clients and they are dictating your work, or don’t have faith in your solutions — they’re not believers. It’s possible they never were in the first place. You were the one summoned to solve a problem and make things work. Don’t waste a second more of your valuable time being art director’ed or micro-managed by the client. Just leave them behind.

    Non-believers are looking for miracles. You may be inclined to present such a miracle. But if you do, you’re now in the business of having to regularly provide miracles to re-up their faith in you — and ultimately you’ll part ways anyways because miracles do not grow on trees. Don’t waste your time, just go.

    Furthermore, if you work or freelance for an organization, and you feel overworked, spread-thin, under-appreciated or underpaid — leave. Time to spice up the resumé, and start the job search again.

    Chances are, someone is willing to worship you for your time and your talents.

  • Checklists and Post-mortems

  • As far as I can tell, I’ve never really been a morning person. I don’t know if that will ever change, but maybe one day I’ll figure it out. Mornings for me, are all about getting aligned for the day. I take my shower, I eat my breakfast, have my coffee, feed the pets, queue my podcasts, read the headlines and I’m out the door.

    However, more often than not, while at the office I feel most productive after 2 pm, and before 6 pm — that’s problematic because I’m of course expected to be productive during the entire day. But other days, I’m most productive from 10 am to 3 pm. So what’s going on here?

    Let’s pause for a moment. Productivity isn’t linear, and neither is creativity. When I think about tracking productivity, I think about probability densities. The knowableness of the Hydrogen electron exists in a quantum state, and the viewer can know the movements of an electron or the speed of such a body — but not both. The sheer act of measuring one property seems to affect the certainty of the other. Seriously cool stuff.

    Probability densities for the electron of a hydrogen atom in different quantum states. Wikipedia.

    Back to our Newtonian realm, we can track time worked on a project and drill down just how much each team member contributed. But now what? I suppose that data will serve its purpose in future estimates. But, what if it was a bad timeline proposal to begin with? What if the deliverables took more time to produce than the actual comps? Were there too many hands on deck? Should there have been two teams instead of one? What if this project was just uniquely complex?

    After a project is checked-off, the uncertainty remains. It now seems that productivity is a quantum problem.

    Jason Contreras’ icon illustrations, inspired by the Schrodinger’s thought experiment.

    Furthermore, tracking time at work can be a miserable affair. This is mostly due to the fact that it isn’t passively done. A user has to actively log entries or worst, someone logs them for you. No one enjoys this. It can take mental effort and increases your cognitive load. Yuck.

    I believe the best tools for time-tracking lie unbuilt and undiscovered. Ideally, I’d like to see a machine-learning passive bot that observes, tracks and tags my work, keystrokes, and time-to-complete. Wouldn’t that be nice? Obviously training this bot to understand individual habits would be unique to an organization, and therefore training the bot, in the beginning, will take time. A film studio editor and say a museum director, work in two completely different ways and probably use vastly different tools to get work done. Perhaps the bot idea would track all the wrong things? Perhaps, a bot is a bad solution here…

    A machine learning bot has a high barrier to entry for any sort of software tool, even today. It would likely take a several years to build, model, train, and test.

    But there’s a simpler solution. If you use project management software like Basecamp or Asana that’s a good start. But, when you complete a task, that’s it. It’s just… over. But there’s a missed opportunity here.

    Enter The Post-mortem

    Project post-mortems are incredibly useful. No doubt about that. However, I have yet to see productivity software that employs one following a completed project. I mean, wouldn’t it be nice to know:

    • How was this project for you?
    • Could the process be improved?
    • How much time did you spend working on this?
    • How were time estimates compared to actual time worked?
    • How complex was this project?
    • Did we miss or meet expectations?
    • Did you feel like your contribution was worth your time?
    • Do you feel your talents are being used to their full potential?

    Credit goes where credit is due — Basecamp has a feature called Automatic Check-ins, which is just about the closest you’ll get to an end-of-project post-mortem.

    Obviously, these conversations happen anyways albeit in Slack or at the water cooler or in a Basecamp check-in — but why not survey and collate them at the ceremonial completion of a project? Especially while it is fresh on everyone’s minds. Even if you don’t use project management software, you should be asking these questions as often as possible to get a pulse on your team.


    Getting back to the linear problem at hand — why is my productivity all over the place? I won’t claim to know exactly why (apart from my penchant for distraction), but I do know my routines help me stay organized, and reduce my cognitive load during the workday.

    Ben Orenstein wrote a fantastic little piece on his morning routine and even wrote a shell script to jumpstart his day. I thought it was cool. But I really enjoyed his perspective on routines:

    I don’t always start my day with a checklist, but the days where I do seem to go better.

    If I want my productivity to begin earlier and last longer, I’ll need to integrate a task with my morning routine. For example, after decluttering my email inbox, I’ll move forward with hot items, then the lesser items, and so forth. Working my way backward in priority.

    I also think I’m going to take a page from Ben’s playbook and start a morning checklist for when I arrive at the office. Maybe even go a step further and make an additional after-lunch, and evening checklist too.

    The Full Orbit

    Measuring productivity doesn’t have to be cumbersome or annoying. I really think the current state of time-tracking software is horrible, unproductive and provides a select few with actionable insights. But the actual time it takes to track, tag and log — is a complete waste of time (oh the irony).

    I say, stick to two principles: checklists and post-mortems. Stick to a routine, and understand why (or how) something worked (or didn’t work). Time tracking is, well, a waste of time.

  • The Memory Remains

  • Frank Chimero, is a Brooklyn-based designer and author. He has a captivating blog and an incredible resumé. I'll spare you his backstory, but it's worth checking out. Thanks to Austin Kleon I discovered he recently interviewed with Milanote  (a fantastic blog) regarding his design process on various projects. At Chimero's own admission, this process probably won't work for everyone and every project but it's really something:

    I’m a big proponent of ‘once through, cleanly’. You think about your idea, sketch, then put some glue in your chair and bang it out in one sitting. All of my best work happens this way: posters, collages, essays, outlines for talks, and so on. The work seems to be more cohesive and the energy more concentrated and palpable. If you sit down and what you make is bunk, you walk away, come back later and start over. You don’t keep any of what you’ve done before, you only retain the memory of what went wrong. It’s a silly method, but it works for me.

    I work in a pretty similar way. The most exciting work happens in quick sprints and explorations. Most of the time, it ends with good work and that's the end of that. But, if I'm forced to revisit the work at a later time and find myself frustrated or burned-out — I start over, tabula rasa. Literally re-building a project from the ground up can be really cathartic for me. I've never given it any thought before until now, but the memory of the failures or problems remains, even after the work is gone. This is how you become a better writer, designer, developer or better person in general — retaining some record of failure, frustration or inspiration.

    That's what pushes us forward.

    @jerin1405 on Unsplash

    As a side note, when I was in college, there was a sort of saying that went around and I'm certainly paraphrasing my mentors here:

    Technology has sped up the rate at which designers produce work, but it has not sped up the rate at which designers produce great work.

    It's true. Technology has sped up our processes. But it doesn't speed up great work. The time it takes to reach good work can still vary tremendously. Mainly because creative problem solving depends on different conclusions from different processes.

    While some may have messy or complex processes, others have simple and iterative processes. Technology has allowed us to go lightspeed with briefs, projects, and deadlines. But creativity, inspiration, design processes and learning new things — these all have an unknowable trajectory. And that's okay. It's important that others understand that too. Jeez, no wonder it's so difficult to plan for anything.

    It's okay to sit there, staring at the screen and say, "I dunno about this. I don't know what to do." Just table it, trash it or come back later. Start anew if you have to. But no matter what, the memory remains, even after the work is gone.

  • Slack Adds Actions, for Better or for Worse

  • You’ve’ll Float Too

    There’s a problem with Slack. It adds noise to the workplace. It has added more keystrokes to my daily tasks. It’s just another thing I have to check-in with before proceeding with an actual task at hand.

    It simultaneously befuddles processes, and untangles messes. Both are true.

    However, Slack has never been a project management tool. It’s no doubt proved useful to teams, big and small (with a $5.1 billion valuation). I’m a firm believer that if your organization employs Slack and Email and no project management software… you’re in for a world of hurt.

    But if you’re in the camp that employs the holy trinity (Slack, Email, and any PMS tool), Slack Actions might be your knight in shining armor.

    You see, the problem is (as it currently exists) when an email thread goes off the rails, and your sidebar with your co-worker or project manager on Slack — everyone on the email chain is cut off from your singular conversation.

    But what if there was a way to loop a Slack conversation back into the communication trinity? An example from The Verge:

    In the work-tracking service Asana, for example, you’ll be able to turn a Slack message into a task, complete with the person responsible, due date, and corresponding project. You can also add Slack messages to existing Asana tasks to provide additional context.

    Which hopefully emails a notification to the responsible parties. Elementary documentation of record keeps everyone in the loop.

    Image from Slack.com

    The expanded definition of a Slack Action, from Slack’s documentation:

    Actions allow your users to quickly send messages from Slack directly to your app, enabling them to create tasks, comment on messages, follow-up from tickets, and more.

    Actions are one way of integrating your app with Slack, similar to the integration points provided by slash commands or interactive messages.

    When an action is selected in Slack, your app will be notified with some relevant info; your app could then follow up by:

    I believe this helps Slack’s continuity problem. This should prove useful, turning little strings of text into actionable tasks. Any feature improvement that reduces keystrokes for creating a task, or improves productivity is a win.

    But, I also believe this is a loss. A loss for those who do not use project management tools. Any feature improvement that excludes workplaces will feel left out and see no positive benefit. I’d like to see a default Slack Action, called Email the Team. Basically, instead of creating an Asana Task, or a Jira Issue, why not open the Mail.app composer and a snippet of the quoted text from our Slack conversation? That would easily be the fastest and sure-fire way to loop my singular conversation back to the main team. Hell, I’d even settle for an Action to Slack DM quoted text to a channel or teammate.

    Again, it all comes back to reducing keystrokes. In productivity, that’s the ultimate endgame.


  • The user interface of Lobe AI


  • Lobe, is a visual composer of sorts — for building, training, and exporting custom deep learning models. The interface is very Quartz Composer-esque. Check it out:

    If you’re in a hurry, watch from 6:12 for a walkthrough on how to create a project from scratch.

    Lobe is a start-up from Mike Matas, Markus Beissinger and Adam Menges. Matas, an ex-Apple and ex-Facebook Silicon Valley designer veteran — previously released published this demo called The Brain (see below), which was entirely built in Quartz Composer. A fucking awesome demo.

    No wonder Lobe looks like a Quartz composition. Keep in mind, this was published about one year ago:

    This is really really exciting stuff. Building and training deep learning models are simple in concept, but complex in reality. Lobe, may just be the first visual tool to bridge that divide.

    To quote John Gruber:

    Lobe is to CoreML what Illustrator was to PostScript — a profoundly powerful tool that exposes the underlying technology to non-experts through an intuitive visual interface.

    Gruber’s analogy is probably the best, and he’s right. When Desktop Publishing Software exploded in popularity the late 80’s and late 90’s, everything changed. Productivity skyrocketed, and progress in tooling, production and creative software just took of and to be honest, it never really cooled down. We’re still in living in that same epoch, but having different conversations about the same problems.

    Lobe truly exposes a whole new world of problem-solving to non-experts and that will lead to some really exciting tools. Hats off to everyone at Lobe. Remarkable work.

  • 2017

  • The Time is Now

    The Time is Now

  • Recently, I came across a great Tweet from Paul Graham (@paulg) that is worth mentioning:

    I started working on web startups 3 months after Netscape shipped, and it felt almost too late.

    — Paul Graham (@paulg) October 13, 2017

    For perspective, Netscape launched in January of 2004. Since then, the web has had explosive growth. It’s a viable component of society now. Even online dating has had measurable effects on the nature of our society.

    The best time to launch your web startup was yesterday. Don’t waste your time pondering, “if only we got this out the door sooner.” It’s wasted energy. Time is the enemy.

    I would also recommend Paul’s essay, Ideas for Startups. Amazing insights for those who may have a nugget of an idea. Great notes for startups.

  • 2016

  • Freelancers Make Up 35% of the Workforce

  • Have you read this? Wow that is amazing. I’m shocked to see such a large percentage, but I can’t say that I’m surprised. Because, simply put jobs can be boring.

    Are we seeing the dead-cat bounce of America job satisfaction? As the last tenured career prospectors of yore begin to retire or die, are more and more jobs moving into the freelance domain?

    Why do people even freelance in the first place? Well first, you can satisfy your creativity. You can make your own schedule, and work only as hard as you need to. Most can even “be their own boss.” There is something so thrilling about not having to be tied down to the 9–5 grind.

    Secondly, the study suggests that technology enables more and more creatives to freelance.

    And Finally, it’s not like Corporate America is giving many young Americans a choice. We have more and more graduates leaving college each year, and that saturation of opportunity will cost us. Not everyone can squeeze into the cookie-cutter jobs so many graduates will likely MacGyver the shit out of their resumé and attempt to freelance something until something stable comes around.

    All of that sounds pretty morose and bleak — and it could be. But really, it’s not all bad. I freelance when I’m available. It’s fun, and it helps pay the bills. I can’t say no to helping small businesses I believe in. Honestly, if more and more graduates are moving to freelance it could be a sign of responsible career adaptability. And if technology permits a more free-lifestyle, it could make the American labor force a bit more happy! 🙂

    Besides who can say no to inflating their portfolio. I sure can’t!

  • Don’t Pigeonhole Yourself

  • Recently I was asked, “Stephen are you a web designer, or a web developer?”

    Wait a minute. I have to choose? I can’t do a little bit of both? What are you implying?

    There was a lot of questions. The problem in corporate workspaces is mainly flexibility. And by flexibility I mean transmutability. Older, deep-rooted conservative organizations prefer pigeonholing their employees into neatly organized genres like this:

    He’s a dev…

    She’s an accountant…

    She’s the copywriter….

    Instead of organizing people into cookie-cutter shapes, organizations should be putting people into larger teams of well-rounded doers:

    He’s on the web team….

    She’s on the marketing team….

    She’s on the web and email team…

    I’ve always wanted to be part of that kind of culture in an organization. I want to be able to transmute from one task into the other. I would prefer to be where I’m needed as opposed to being pushed through a cookie-cutter.

    Food for thought I guess.


    The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.

    –F. Scott Fitzgerald


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  • The Best, Worst Mistake I Ever Made

  • Several years ago, I made the mistake of snoozing my alarm clock one too many times. I was running late for my 8:00am Typography II class. I didn’t know it yet, but it was the last time I’d ever be late to a class. I was in a rut. I was rude and callused in my critiques. I pretended to fit into the classes, and I thought I was a fraud. I would join the chorus of students who groaned at the idea of doing more than 100 thumbnails of sketches. I was quietly becoming one of the pessimists and didn’t even know it.

    I ultimately landed a ‘D’ in the Type course and was told that if was to remain in the program, I was to re-take Typography II next year. With no promise of even making the senior cut of the highly competitive Communication Design program at the University of North Texas (and bills mounting), I decided to say to hell with it and left the program. A world of sorrow and pessimism left me, I shed my sophist skin and bootstrapped my life back together.

    I began pursuing my other interests in life. I began reading more about science and film, and began entrepreneurial pursuits and even began freelancing design and illustration work in my free-time. While doing all this, I also reviewed a lot of sites and here are some of the Top Ten reviews site. All in all it was a great change. I decided to finish college in a less-rigid program in the visual arts, and began to focus on computer sciences. Ultimately, I got extremely interested in web development and built a few websites.

    Looking back, I’m a happier person and better for choosing my own adventure. I tend to recall that year of my life as the best, worst thing that ever happened to me. I owe so much to my friends, mentors and co-workers who believed in my ideas, work and words. Even in the face of such an embarrassing failure, all was well. I don’t have to tell you twice about how much failures suck. But they happen. The next time you mess up, consider finding the silver-lining before you tear yourself apart.

    I was inspired to share my story after I read Linda Eliasen’s post on why she quit her job at Dropbox. Our time is limited. Don’t waste it living someone else’s life.