Strip It Down

I had trouble falling asleep last night which doesn’t happen that often (I’m pretty professional at sleep). I lie awake, mind spinning. I wasn’t worrying that things were “falling through the cracks” or that I had commitments I couldn’t make good on. I tend to do a good job writing down what I need to get done but I think I was lying awake because I didn’t know what I needed to do.

It can be romantic to tear it all down. Trash your software, burn your notebooks. Clean slate, empty mind. Fresh approach. For fun or for pageviews.

When you lay awake, it’s time to do something about it. Kiss and make up. Don’t go to bed angry. Work it out or walk away. I’m doing this for me not doing this for flow.

Your workflows won’t show up at your funeral. When it’s your hobby, “workflow” means time away from sunshine, from the warmth of smiles, from the world around (which just happens to be magical). If those aren’t important to you, cool, but I’ve been missing out.

My job is creating productivity software for people in big businesses—manufacturing, healthcare, supply chain. Workflow matters but flow is there to support experience. My work is creating experiences and the experiences in my life aren’t going to come from a list. What’s your real job? Who’s your boss. Is your list your master? Who does actually care about the work you do? What you get done? The person you are when you get home from work? Someone cares more about the person you are when you get home from work than how you work.

But there is a place for flow. Flow can mean that when it’s time to fall asleep at night, I fall asleep. But if everything’s a task then everything’s a task, or something like that. I’d rather be at 30,000 feet in a plane on an adventure to a place I’ve never been before than 30,000 feet in my “system.”

I review my system more often than I call my mother. Who the fuck am I?

I won’t let a computer tell me what to do. I’m going to choose what I want to do with my life, thank you very much. Then I’m going to do it and not tweet about it and just sit outside with a beer and watch the sun set. Because I’ve missed too many of those sitting in front of this harsh, heartless machine.

Not what is the goal but what is the point? There is a point, it’s just not a goal. It’s something, some place, someone. “Have fun” has never shown up on my to-do list. “Laugh until my face hurts” hasn’t made it on my calendar. The Work is important but what are you working towards? What’s the point of your work?

What I need to do is different than what I need to get done. I need to make people more important than priorities. Experience more than analyze. Care more than capture.

What are you going to do today?

Making Tools, Technology, and Ideas Accessible

For much of the time that it’s been a part of our lives, technology hasn’t been very accessible. From how we build it all the way to how it’s used, technology hasn’t been easy for people to get close to. I was just barely at the tail end of the generation who was around for the internet before it was ubiquitous in the western world. Those much more “seasoned”—older—than I am would laugh at even how good I had it with my first 14.4K modem. There’s been a Wild West mentality in the becoming of the internet and the culture around it. Keyboard cowboys, cavalier in their convictions, broke trail and set standards for the world we’d newly navigate. This scene wasn’t for everyone and only those with the bravest of hearts and the sturdiest desk chairs have made marks. Through that we’ve come a long way. At least in the first world, internet connections are as important of a utility as electricity and nearly as available. Availability isn’t necessarily accessibility though. We’ve come to trust that when you flip the light switch or turn the tap, that service will be there for you. It’s reliable. Yet we still have to think about “uptime” of our online services and need technicians to come to our house to fix the little blinking internet box thing again. And remember, this is in the most advanced parts of the world. We’ve got it the best out of anybody and it still sucks.

Our relationship with technology can be rocky. We’re introduced to new hardware, services, interfaces, and interactions all of the time. We’re encouraged to learn these things through practice and not be worried about poking around the new updated version of a thing we love (or at least just use a lot). Our culture mostly accepts the new and cool because we always want to be new and cool. But it’s not easy. Many people aren’t these cavalier keyboard cowboys and don’t have the time, patience, or desire to tinker their way through learning technology.

Making these tools, technology, and ideas accessible is something that managers, designers, makers, and marketers need to improve on. In all parts of what we set out to do, we need to lower the barrier and ease people in to familiarity with the pieces of our work that they touch. Code that we write and share needs to be accessible so that more people will contribute and help grow what it can do. It needs to be documented and use familiar frameworks so people can get in to it easier. Ideas we spread need to be accessible so that people understand what we mean and build a community around these ideas.

In September, I spent the day at the Hardware Innovation Workshop here in New York. It was put together by Make Magazine who was also hosting the Maker Faire that weekend. The sessions were mostly focused on the gap between prototyping hardware using tools like Arduino and getting your hardware product in to mass production. There were discussions about the business side of doing that, how to design in a way that simplifies the way your product can be manufactured, and even how branding can have an effect on your hardwares attractiveness to customers.

One of the ideas that caught my attention was the unfamiliarity that many consumers had with these types of hardware in their homes and lives. Some were systems that could monitor the safety and happenings in your house when you were away or were little hardware bits that you could use to build circuits but were just so simple and magical that they could be used for kids to build toys or for artists, or engineers. These things were new. They were ideas that hadn’t become part of people’s regular thinking habits. But some of these products had succeeded in designing their hardware so it was approachable and their end user wasn’t scared to try it. Once they tried it, they recognized that it was useful. They could figure out how to use it, why they should, and didn’t feel uncomfortable using it.

So how do we designers, makers, writer, scientists, make tools, technology, and ideas accessible?

We have to recognize and try our best to understand the people who we are making each of these things for. We need to understand them and we need to care for them deeply. These design challenges aren’t easy to solve so to get through the frustrating iterations, we need to stay focused on the care we have and the care we believe we can deliver, whether it be to fellow developers making it easier to build great things or to our customers who need a little help in their lives and are looking towards us and our products for that support.

Caring a lot will guide each of us through the challenges in making tools, technology, and ideas accessible.


“Nice bike,” he says, breaking the courteous silence in the elevator as it plummets towards to wintery streets of midtown Manhattan after a long day at the office. “It doesn’t have anything you don’t need,” he elaborates as a nod to not just its aesthetics but craftsmanship. I mutter a thanks in the way that I’ve always done, struggling to be humble in the glow of a compliment. I lower my chin and gaze back down, assuming the customary elevator apathy, hoping it’s not apparent that I’m blushing as if he were a dame gushing over my especially-striking-in-my-own-narrative good looks.

I’ve come to appreciate the honesty of simplicity—where craftsmanship is an understanding and acceptance of what’s important and more importantly, what’s not. The honesty comes from not trying to be something more through embellishment or striving for minimal design by giving it a coat of white paint rather than distilling out the unnecessary parts.

As I’ve started to spend more time away from my desk, out of my head, and getting lost in the world around me, I notice these honest designs more often. I’m less interested in software and more interested in people and the things they make in real world materials. I’ve been burned by hacks that fail at the wrong time and complex tools which have let me down. I’ve begun to deeply appreciate when something endures because of the decisions made by some industrial designer in their tight grey-colored shirt and two-days worth of beard. This idea has always been part of the DNA of Hack/Make but I feel it will become more center stage here as time goes on.

Bleed Out on Blank Pages

For the first time since I published Toothbrushes, that task reappeared in my list this past week. “Pick up new toothbrush” it read, though saying more now than the last time I saw that reminder.

Now it tells me something like, “Pick up new toothbrush and reflect on the last few months of your life.”

I had thought that Day One might become part of my own life story telling but only a few times in months have I filled it with what’s on my mind. I’m just never compelled to open the app. I’m desiring less screen time and I find, though I’m not a paper fanatic, that scribbling in a pocket notebook is more visceral and right. Though apps try to pull us in by being “delightful,” being instinctive matters more to me and pulling a notebook out of my back pocket has become more true to me than pixels lighting a ghostly glow on my face. It feels natural to open a blank page and fill them.

Why isn’t it good enough reason to fall in love
with New York just because that’s where I am now?

Why do I always have to be
dreaming about being somewhere else?

In notebooks, I’ve found it a unique way to see the ink of my life spill together on the pages. Mundane lists, sketches you can’t decipher anymore, phone numbers you can never call again because of the pain on the other end of the line, meeting notes from an hour of your life you won’t ever get back. They flow together on paper in a way that matches our bleeding lives. Talking about buckets and scaffolding rarely tells the story that the bucket is our last hope to catch drips leaking from the broken pipe of our unmanaged time and that the scaffolding we set up is mostly intended to hide the crumbling facade rather than support the rebuilding of our lives.

On paper, we can see the mess that we are or the greatness that we’re becoming. These stories all draw together in ink stains and by letting ourselves spill out in pages—where our work and life aren’t trying desperately to be balanced and sandboxed—we can get a glimpse at the beautiful lives we ride.

And in a blink, we rise above the tarmac
and the city shrinks. The problems there
seem miniscule instantly compared to the
grandeur of the world around. You transform
in moments from the ants milling about into
the birds soaring above.

I’m not arguing the merits of paper versus software but trying to seed a reminder that each of those devices are meant to address our needs as humans and support our own purpose.

Wherever intentions lie, a pen or keyboard will work towards them.

When being introspective about our work and lives, be it one toothbrush at a time or ongoing, we make agreements with ourselves by choosing the words we write down. We promise to be more mindful, thoughtful, kind; to make more, eat better, relax. We scribble fragments of who we want to be so that we can convince ourselves we are. We document our days because sometimes it feels that if we don’t, no one will remember us, or we clack out ways we think we can start being more memorable.

It doesn’t matter where but that we do bleed out on blank pages.

A Reddit Quick Start Guide for Geeks Who Aren’t Into Memes and Listicals

Just by calling itself “the front page of the internet,” Reddit scares away people who have come to learn through years of their own honest investment that the internet can be a vapid place. The intelligent geeks that we (think we) are see reddit links thrown around for this meme and that listical and figure said front page is more US Weekly than The Economist. Turns out, reddit is an interesting place once you look beyond /r/gifs and /r/aww.

Getting Started

  1. Create an account: You want it to be your internet front page. Reddit doesn’t seem to do sleazy “social” things like Facebook so you shouldn’t be too worried about creating an account.

  2. Unsubscribe from pretty much every default subreddit: Subreddits are topic based areas of posts and conversation. Go to /subreddits and hit that red “unsubscribe” button for pretty much everything. The defaults tend to be the popular meme-type subreddits which is what we want to avoid. I left a couple like /r/worldnews and /r/EarthPorn which seemed interesting and possibly not too much of a time suck.

  3. Use the search box on /subreddits to subscribe to a few of your interest: This is where Reddit shines. Like Twitter and ADN, by subscribing only to the subreddits you want to see, Reddit becomes what you like and nothing else. One of my favorites is /r/nyc. It gives me a way to see and read about what’s going on in the city in a way I can’t on Twitter. Hashtags are a poor way to follow topics—just try to get something useful out of #NYC.

    A couple that may pique your interest:

    Or maybe even:

  4. Use it for a few weeks: Don’t start by subscribing to a whole bunch of subreddits to a point where you feel overwhelmed as you start using it. Just find one or two. For several weeks, I just went straight to /r/nyc before I figured out the whole frontpage thing. You’ll start to get a sense of which topics work well in the reddit format and then will start to get curious.

    When you’re signed in, the frontpage will be a selection of posts from your subscribed subreddits. You’ll see the list of your subreddits at the top.

    Clicking on the blue title of post will sometimes take you to another site to show you the linked article or sometimes take you directly to the thread if it’s not a link post. This behavior is similar to Daring Fireball type link list posts. You’ll either see the domain beside the title or self.subredditName.

    Clicking on Comments under the title takes you to the thread to show the conversation ranked “by best” by default. Upvotes and magic determines what’s best. You’ll start to see different subreddits communities have different personalities but most will bury “First!” comments and other junk.

    Up or downvote articles to your taste. I don’t think it does anything to help some algorithm “tailor your experience” but helps shape the conversation.

  5. Stay curious: Once you start to become familiar with a few subreddits, start exploring a few more. Some may be similar, like how /r/travel led me to /r/solotravel, or maybe remind you that you’ve always wanted to learn piano and you find yourself following /r/piano/.

    There’s a lot of interesting things on the internet disguised beyond what gets most people’s attention. Stay curious and know where to look.


This isn’t the disclaimer you were expecting. Somewhere along the way, “productivity” started encouraging us to turn away from things that didn’t directly create an output. People on the internet started discouraging us from “consuming” and we’ve started to feel empowered when finding a comfortable corner of the internet that wants to read and listen and use what we create. But when you throw away the superficial layer of time and attention and look at what something like Reddit or what the knowledge base of the internet as a whole is and can be, you may see a glimpse in to a place that takes you out of your productive place and makes you uncomfortable. You may see ideas and cultures you haven’t thought about before. You may become dangerously entangled in what the world has to offer. You might get lost in history or poetry. You risk becoming less productive but might just open yourself up to interesting new things about the world around you.

Twenty Thirteen

For me, 2012 was largely about working on understanding myself and where I fit in in the world around me. I had just recently moved to New York at that point and was still very fresh in the technology world. I began exploring tools that could help me get my work done, ways of thinking that would allow me to stay relatively stress free, and ideas that would become catalysts for a way of life. At the same time, I was feeling lonely and lost in a big city with no friends and needed help. I started hanging out in coffee shops and writing. To paraphrase one of my favorite struggling, not-really-a-writer writers, I began writing because I needed to start taking the advice I was giving others. Writing was much less of a part of my life this year compared to last. In 2013, I found myself more on a pursuit of creating and exploring from the platform I had set up. I wanted this year to be about using my scaffolding create interesting things. I had set up the system and then it was time to use it.

I’ve missed writing though and as I’m thinking back about this past year as we’re wont to do around this time, I figured I’d recap some interesting parts of my year and see if I can find some lessons in there.

Picking Up Where I Left Off

Publishing to this site was a really important part of my exploration in 2012. The searching I did through writing helped me learn but by publishing those words I was able to learn that the things I was dealing with were shared with other people, many of you which I now call friends. It gave me hope that I was on the right track. I started off 2013 by collecting the best things I had written up to that point and published Coffee Shop Contemplations on the 1st of January.

Even though I ended up doing more physically dangerous things, putting this book out was the scariest thing I did all year. I’m generally comfortable “putting myself out there” in front of people, whether in a meeting or speaking in public, but packaging up my work and telling people it’s worth something was intimidating. It was an important lesson to learn though. It’s up to you to shape your work in a way that people can digest. They won’t put in the work themselves to dig up the best and connect the dots so if you want your work presented well, that’s on you. You might be a great writer but if the site you’re publishing doesn’t make it easy to read, you’re doing a disservice to yourself and making your ideas less accessible. By putting together some essays into a package, I found it more formally tells the story of my exploration through writing and now exists in a way that I can share with other people. More importantly to me, it’s easy to pick up and review the ideas as a sort of valuable reference resource and guidelines of my own methodologies . As I revisit, I can question whether that idea or approach is still valid.

Formatting my past writing and ideas helped me establish a foundation to work from and way to share ideas with others.

I did write a few articles I was happy with this year though.

Methodical — I think the most picturesque thing I’ve written. Full of imagery but also connects to an important aspect of mindfulness and approaching our work in a persistent way.

Scaffolding — This helped me put in perspective the place that tools and frameworks have in the creative process. The idea of scaffolding doesn’t discount the value of modular tools in doing work but reminds us of the importance of the creation and not the method of creating.

A Glacial Pace — Approaching things at a glacial pace reminds me not to get caught up in the short cycles of fixation, discourse, creativity, criticism, and accolades because they aren’t lasting. By giving them the appropriate attention I can focus myself on creating something that might endure.

Toothbrushes — There’s a lot that I’ve let slip away which are real, human, and precious. I need to pay more attention to embracing them.

Digging Deep and Shipping

Through January and February, I did some of the work I’m most proud of even though it was by no means my best work or even a creative place I’d like to ever be in again. I’m sure we’ve all been in those crushing situations where a project is over promised in an impossible deadline—one that’s set up from the beginning to fail— and that breeds an environment of anger, doubt, and mistrust.

That was Project Oslo and my job was to make sure Oslo shipped.

To save you the drama (and there was plenty), it did ship on time and without any hitches. The hard work with Oslo wasn’t the work at all. The grueling part was holding myself up and my team when we all wanted to stop. It was the mindfulness to put my headphones on, clench my jaw a little, and keep my mouth shut. Everything was on the edge of disaster and me bitching wasn’t going to get it shipped. Productivity tools and scaffolding failed and became irrelevant. Frameworks didn’t help. Project Oslo shipped because my team found some grit in themselves and I feel I helped lead them to that place. That’s why I’m proud of that work.

Mindful Computing and Data Integrity

I continued thinking and investing time into ownership and control of my digital identity this year. Years ago I moved from a gmail.com account to a personal domain hosted on Google Apps. In 2012, I migrated to Fastmail, hosted all my own websites, and set up infrastructure for computers to do the computing for me. This past year, I reaped the benefits of that by having to think less about maintenance and not worry about potential catastrophe and data loss. For a couple years, I didn’t have a desktop or laptop at home. I just ran a headless Mac mini on my network to do tasks for me. This worked well because I was writing and doing other “lighter” work on my iPad but recently I’ve been working on coding projects and you can’t beat BBEdit and a mechanical keyboard for that.

This was a big change in my computing habits. I’ve liked the simplicity of an iPad being my main machine. It felt comfortable to grab my iPad and use simple apps to do the work I wanted and then put it down and go do something else. By using a desktop again, I’ve found it welcomes stagnation. Instead of doing your work and walking away, it feels like I’m much more likely to get stuck there and start tabbing through Twitter and Alpha and email, and all these things I don’t need to be doing. What I need is either get up and do something active or be intentional and creative on my computer.

For me, iPad encourages mindful use. I believe the physicality of holding iPad—using your hands to type and navigate and draw—alongside with the focused nature of the software provides a great interface for activating the creative mind. By often having to hold it like a book or by touching the software rather than through the proxy of a keyboard, iPad feels like it requires a more conscious decision of active participation. It’s a disease to frequently slouch in front of a computer and just click around for hours burning time without intent.

I want to better manage this again where it becomes habit to use a more mindful tool by default and just use my desktop when it’s appropriate. It might help to constrain the software configuration to make my desktop the pickup truck it is so it’s set up for work and not much else.

Part of what that computer is configured for is helping me manage data integrity and control. I’ve spent a lot of time implementing online systems that help keep my information safe but my local setup for backups and data integrity was lacking. I needed more storage, better automated backups, and most importantly, a system that was comprehensive so that I could trust it and remove the weight of doubt and failure in my system.

I’ve posted some notes about my backup system but, in brief, I wanted a robust and reliable NAS that could do Time Machine and long-term storage, a cloud backup service, and an offsite bootable image. I’m using the Synology RS812 NAS, Backblaze for cloud backups, and a 500GB external hard drive in a custom built, heavy duty enclosure. With this setup, I have redundant and automated backups and no longer have to worry about losing important documents, photos, or work.

If you don’t have a system you trust, please pick up a couple external hard drives and subscribe to a service like Backblaze so you can have a reliable setup. I’ve heard so many horror stories about lost information and back ups are a necessary part of a solid system. The minimum I think you should have is a drive doing Time Machine, a mirror of your computer using SuperDuper! or CarbonCopyCloner on a drive you take offsite, and having a cloud back up.

Putting My Talents to Good Use

After working on the tech side of a startup for a couple years, I had picked up a lot of skills. From front-end coding, to administrating databases and server systems, managing development teams and running technical operations, I learned a unique set of talents but stayed generalized enough to be able to speak many languages—translating business speak to developers and communicate technical challenges back into business impacts.

But I felt like there was more I could be doing with my technical talents. I realized that the hobby projects that I had been doing to ease small pains and improve my digital life could completely change other peoples’ lives. You can read more about the story of this realization in my post It Takes a Village to Raise a Framework. My friend Justin Lancy has been curious about technology since he was a kid and wanted to help in similar ways.

I challenge you to think about how your talents could be put to use for something greater. I’ve gained a lot from writing for myself, from improving the way I work or improving the design and speed of my website in my free time but I wasn’t satisfied with that being all I brought to the world. Does the world need the voice another 20-some-year old kid living in New York shouting into the abyss of the internet? Is that who I want to be or can my time and talents bring something more to people who don’t get a lot of attention?

Maybe your time could be better put to use help Village Science, your church or local homeless outreach, or with your family who’s desperately wanting your attention. Or maybe being a voice online is how you have an impact. It’s just worth being mindful that your time and talents can make a big impact on people outside of your online community and that impressing the internet may be an empty pursuit.

Starting Something New

I started a new job in August with Hook & Loop, the internal creative think tank for an enterprise software company called Infor. I was a bit burnt out from the emotional investment and stress of my previous position, being the tech and product team lead at a startup. That position meant that pretty much anything having to do with the non-business side of the small company fell on me and though this was a great opportunity for me to learn it also meant there were a lot of problems which were (or became) my job to solve.

Starting a new position at a larger company offered me a chance to better frame the expectations of who I wanted to be on that team and the type of work I wanted to do. That’s been a challenge in the first few months of working here. I’ve taken some risks by pushing back on projects that I didn’t want to be involved with because I felt I would get tangled up in their mess and get stuck in a place where I couldn’t do good work. Saying No to high profile projects your boss hands to you is hard. I felt a little like it came off that I couldn’t handle the project rather than didn’t want to which isn’t a nice impression to be making early on. In the short term, it may have hurt building rapport but I’m hoping that it cleared the way for the projects and products I am working on to be successful.

I tend to be good at fixing projects that are going wrong. Often I’ve been handed sinking ships and told I’m the new captain. When I would right that ship and fix things, the praise would be overshadowed by the memory of how bad the project began. That was a losing trajectory for me. I wanted to be architecting the pieces that would help solve a need not be coming in part way and glueing together the pieces that hadn’t shattered yet. By being a problem fixer, I attracted a lot of problems.

Set a precedent for who you want to be to others.

In setting the foundation for my role, I want to be very mindful about the type and way that I solve things in my work. Both my grandfathers were janitors but I don’t want to always be showing up to projects with a mop and bucket. Maybe I can help by guiding coworkers through fixing their own projects or maybe I don’t get involved at all. I don’t know the solution to this yet but I know it’s a challenge to keep aware of.

Last Year’s “Three Words”

I didn’t think much about my Three Words throughout the year. They were Curiosity, Voice, and Flow. I left off the post by stringing together these words into a focused sentence: “I want to define my voice by letting curiosity lead me through the flow of learning and living.” Retrospectively it seems that I was able to stay on track with this guiding principle but it’s also vague so pretty much just existing for the past year would have made me successful in this poetic yet hollow goal statement.

I think the romanticism and poetics of high-level thinking is something I’ve gotten over this past year (and may be why I’ve written less recently). My writing in the past was often vague and when I now re-read it I think, “OK, that sounds pretty but what does it actually mean?” I’d consciously choose words and poetic ideas to try to prove to you and mostly myself that I’m eloquent but that often left me feeling like a charlatan rather than a polymath. I appreciate the straightforward communication that people like John Roderick use. I find that not just a clear, concrete idea is important but that talking and writing in an appropriate level of language is critical for sharing the idea and opening the person up to listening and trusting you as a storyteller.

I want to be more true to myself and the ideas I share by using simple language and clear ideas free of fancy words and complex constructs.

Some Favorite New Things from 2013

In previous years, I’ve posted favorite new things I purchased, started using, or learned about in that year. In 2011 they were: Field Notes, Raw denim jeans, 5by5, Traditional wet shaving, Merlin Mann, and GORUCK GR1. In 2012: Aeropress, Waking up early, Roderick on the Line, OmniFocus, Launch Center Pro, and Noise.

For 2013, a few favorite new things are:

Wolverine 1000 Mile Boot in Rust — An entire post about these boots coming soon.

Panic’s Status Board — This app has become part of my daily life and routine. I believe software should do work for us without us having to be it’s master and so I’ve put in some up-front work developing widgets for Status Board that brings me the ongoing benefit of presenting me information that’s timely and relevant. At a glance is things like weather, calendar, and task information as well as server statuses and system health. I don’t want to have to pull out my phone in the morning and dig for an app or log in to my machine and go to some website to check information. Status Board is able to do that for me and means less time in front of a screen. A pilot can’t always be checking every gauge and screen but they have the system to alert them when things are wrong. That’s Status Board for me. I have an iPad connected to a vertical 27” display which is large enough so that I can see information as I walk by. The display is always on so I can depend on what I’m looking for being there and grow a habit around glancing at that screen rather than pulling out my phone. I can get what I need and get back to life and work without having to use a computer. But at the same time, I’m considering breaking this all down and not using it this year. I’m interested in finding a way to manage reviewing important information without an additional screen. Maybe this is one of those “if you love it, give it away” moments.

Synology RS812 NAS — This thing is a beast. It’s a 1U rack mountable 4 bay network attached storage device that’s the companion to my Mac mini (also mounted in a rack using a Rackmac mini). I have 4 x 3TB WD Red drives in it which serves iTunes media, stores archives of files, and runs various download and backup tasks. On it’s own the RS812 or any Synology would be a great option for a home server because it can handle many web and media services but my Mac mini helps with some tasks like video conversion which it does much faster than the NAS.

BusyCal — I never really liked Calendar on Mac but for a while didn’t have much reason to try anything else. I used a calendar in my personal system and a little at work but my previous job didn’t use meeting invites, unlike my new job. Right around the time of starting my new job, BusyCal began supporting Exchange which is what we use at work. I downloaded the 30 day trial version and immediately began enjoying the added features of it as well as the idea of having a more reliable calendar as part of my “trusted system.” BusyCal’s Smart Filters act kind of like Perspectives in OmniFocus, giving you multiple, custom views in to your information.

Aloksak Bags — Ziploc bags are handy but suck. They aren’t built tough and often rip or the zip part fails if you’re doing anything more with it than bringing your bologna sandwich to work. Aloksak bags are built strong and work well if you want to keep things like papers, identification, or electronics dry when traveling. I also use them for organization and storage in first aid and dopp kits.

So To Recap My Recap…

This year, I:

  • Published a book
  • Shipped a major site redesign and 1.0 of an iPhone app within 8 weeks
  • Went ice climbing for the first time
  • Did a GORUCK Light and Nasty Challenge
  • Began playing recreational volleyball after work and won two championships
  • Developed the beta hardware and software platform for a non-profit’s pilot project
  • Started a new job
  • Started a new company
  • Overhauled major parts of my computer and backup system
  • Published around 24,000 words (down from 65,000 in 2012)

I outline these things in part to remind myself that working hard brings great rewards and as an example of what “productivity” is. It’s not software or scaffolding—they help along the way—but when we talk about improving the way we work we need to talk about the work that we’ve done.

I remember in math class having to “show your work.” I guess the idea was that if you got the wrong answer, you could still get some marks for being close or being on the right track. This isn’t 9th grade math class anymore though and how you get your answers doesn’t matter so much, just that you delivered that project on time, pulled off planning the extravagant date with your significant other, or did what you had to do to pay off your debt. The process does matter but mostly just to you. Everyone else only cares about the interesting things you do.

You’ll make a dent by what you do not how you do it.

So what’s to come in 2014? I haven’t thought much about it yet but there are a few things I want to do, pay more attention to, or better understand in the next year:

  • Travel
  • Reddit; once you look beyond /r/aww there is a lot of interesting conversations going on
  • Bitcoin; the future is digital
  • Reducing my cost of living; because Rule #8, lighter is better
  • Have more personal connections with people; I’m human and not everything about the future is digital
  • Spend less time in front of a screen

I wish I could leave you with a detailed check list of things that would help make this next year a successful one for you, but it doesn’t work like that. This year might be a rough one for you or me. It might be a blessed one. Most likely it’ll be both. This is all I can say:

Care about people and work hard.


It seems like I’ve been marking the passage of time with toothbrushes.

I don’t know why I started doing it or if it’s even Dentist Approved™ but maybe two years ago I set a recurring thing in OmniFocus to tell me to buy a new toothbrush every three months. Like clockwork, I’d go buy a new one when I was told to and then not think about it until I was reminded again. It was systematic. I didn’t have to think about it and I liked it that way.

Recently the time between toothbrushes has seemed to disappear.

The conversations and moments in between pass by quickly and the memories of them have mostly fallen through the cracks. Even though I can recall the fun we had, I can’t remember whether I visited my friends in Toronto this past May or was it already over a year ago? I have to scroll back in my calendar to confirm that it’s been six toothbrushes since that long weekend. My calendar doesn’t have the guts to tell me but I know I’m missing out on some essence of life.

I’m missing out on the way the past can influence the future.

That’s something I’ve started to realize as I try to reflect and recall. My past is engrained in my nature but it doesn’t seem emblazoned in my mind. As I’ve become more aware and mindful of how I can approach my life by design, I feel like I’m much more “forward thinking” and spend less time tracking, reviewing, and thinking about what has passed. I don’t often ask the questions of why or when or what in the past tense, to myself or to others. And even when I do, it’s hard to find answers.

Systems help me solve other problems but I’m not sure a system is what I need to encourage reflection. Part of the problem is just how much of my life has become systematic. When we automate things, we do it to free up cognitive cycles so we can focus that attention in more appropriate places. But I think that we can start to expect ‘automatic’ and then we struggle with the things that aren’t. We’re training ourselves to believe everything should come easily and that software and workflows can solve our problems when many problems are about awareness. They’re about presence and like mindful meditation, presence is a path—a practice—and that’s intrinsic not systematic.

So how do I make it intrinsic to organize my thoughts of things that passed? How can I do it in a way where they are archived and indexed for when my memory fails? It’s not that I want to begin spending a lot of my time reminiscing but I want a practice that means when I do, I can do so well.

I think part of the answer is Day One. It’s not the whole answer though and that’s the challenging part. I already use Day One occasionally and can see benefits in saving things to it but like my friend Andrew Marvin said in a conversation on Alpha, there’s no immediate consequences to not have a practice of writing down what has passed. It can instantly affect us when we forget an idea that we think is genius. A name for the app we’re working on, a sentence we think will pull the whole piece together, that thing we have to grab from the drug store, or a link to the answer which will fix the bug we’ve been working on. We’ve been learning to capture these things before they sublimate into creative despair because having that idea leave us can be painful. But memories fade much slower. It feels like there’s a lot less riding—within our jobs, relationships, and projects—on keeping clarity of the past as remembering what needs to happen in the future.

How can we be as mindful about capturing our past as we are for our future?

I think the answer manifests itself in the idea of it being a practice rather than a system. With a system, B can work and A doesn’t. It’s trial and error. With a practice, it’s a much longer path and one that’s about being aware of the things which bring pure joy, the conversations that have hurt, and the scenes that are beauty in its essence. Those are the moments that we can’t let slip by.

Those are what we need to practice holding on to so when it’s time for a new toothbrush we have moments to embrace which remind us our path is filled with blessings.


Making things on the internet means that we’re creating a lot more within public view. “Making” now isn’t just crafting in your basement like it used to be. There’s a massive platform and audience online and so it can be intimidating to create and share when we aren’t always so confident in the things we’re creating. In a list of writing tips, Matt Gemmell calls it as it is:

If you’re going to be a football player, you’d better get comfortable with running around on grass. If you’re going to be a writer, get comfortable with hating your work but carrying on anyway. You’re a shit-shoveller, and that stuff is your own. Now make it into sandcastles.

Believe your shit is worth shoveling. Just like back in high school essays, write from the viewpoint that your argument is right and at the same time, try your hardest to actually be right. Just as much as you’re convincing your readers about your argument, you’ll probably have to be convincing yourself of the same thing. If you’re not making educated assumptions and believing them then you’re not pushing your ideas forward. Work in confidence based on your previous experiences because there’s a lot of weight in the things you’ve done before.

It’s those experiences that define the flavor of what you write and what you make. They are your terroir. The things you’ve worked on before, the mistakes you’ve made, the things you think you don’t know, these all give a certain characteristic to what you’re working on. Some of those things are scary but they are part of the job description, so get comfortable with them. As long as you know what you’ve done it’s fine to not know what you’re doing.


How about this? I do know what I’m doing, because I’m writing for you guys, and I feel like I have a firm grasp of what’s going on and what you all think, and what you’d be interested in reading. And years before that, I was designing books, so even though I didn’t know how to ship a book when I sat down to write one a couple years ago, I knew how to make one, and figured out the rest. I have the ability to think in systems and can be incisive and empathetic by understanding how things fit together. I have a knack for saying things lots of other people are thinking. I can have the special courage of stupidity and privilege, because I don’t have to risk much to speak up.

Frank Chimero in his essay The Inferno of Independence mentions that his past experiences have had a major impact of the book he wrote. It also shows that just as much as you should be comfortable with the idea that the thing you’re making is crap and to keep working through that, you need to get comfortable with the idea that what you’re making is great and that you’re the right person to be making it.

When you carry that bit of confidence it lets a richer flavor come through in to what you make.

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