HACK / MAKE

The Simplest Tool Built for the Job

A few months ago I moved in to a new apartment. It’s taken me a little while to settle in and I finally got around to hanging up some shelves and a bike rack. In the past, I’ve used whatever hack possible to sink a drywall anchor because I didn’t want to spend the money on a drill and didn’t really want the extra things to store in a tiny New York flat. I finally wanted to get a drill so I could properly sink the drywall anchors on not have my bike crashing down from its hanger. When I was at the hardware store I looked around and found a manual, crank-by-hand drill. It was small, inexpensive, and tailored exactly for what I needed. No extra features, no batteries. It wasn’t the best drill on the market. It was the simplest tool built for the job and it was the perfect tool for the job.

We can’t forget to look for what’s the perfect fit for us, not just what’s the best based on features or what other people think.

Changing Perspective using Trello

I think I was in 9th or 10th grade when my older brother brought home a copy of Getting Things Done. I don’t really remember the way he described it or what convinced me to get in to it but he gave me a copy and I dug in. At that age you’re easy to influence and like many I’m sure whose brother came home with beer or drugs, I got in to GTD at a time that it greatly impacted my perspective.

I picked up GTD at a time where I needed a map for life but now I think it’s been leading me off course.

I started using Things in the early beta days and used that through highschool and college. A few years ago when I learned about people who were using OmniFocus and really trusted it, so I made the move. You’re always changing so your processes should evolve too and eventually I felt over OmniFocus. It just didn’t fit the model of how I wanted to work and live. I don’t believe that switching software can lead to transformative change but I do think it can help nudge your habits enough to starting seeing things differently—from a new perspective.


Trello is about giving you vision in to what you’ve written down, not about actually doing it. It’s almost a stale trope at this point, but I’ll reiterate it anyway: we don’t need to do more things we need to be more conscious about the things we do. Just like the world around us not really caring about what we do, neither does Trello. It doesn’t sit there taunting us, telling how much we haven’t gotten done. A blank card is just a blank card. It’s not an obligation, a promise to yourself, an expectation, or another opportunity for you to let yourself or someone else down. A card is just a card. Use it for a project you want to do, a reminder for a thing you should say to someone special, a divider or break point in a list, a thing that makes you happy and that you should do more often. The card isn’t begging you to check it off as done then evaporate. There isn’t even a check box on the card. Let your Bucket List sit right beside your Today list. Who’s to tell you that your work today is more important than the rest of your life? Leave it there, let that list sit in front of you all day, everyday. Don’t let that thing disappear. Let it fester as a reminder of what’s important to you and let fade away your little tingly feeling of marking off another thing as done.

From the Trello launch blog post in 2011:

Trello is probably the simplest thing in the world: it’s a web page where you make a bunch of lists. Each list contains cards. Each card is a thing that someone might want to work on.

It is simple (and you should keep your life that way). Here are some things I like about Trello:

  • It’s a website
    • Forget about sync, updates, OS compatibility
    • The web links a lot better than apps, internally within Trello and externally
    • Trello’s success isn’t at the hands of Apple approving their updates (I’m becoming that guy)
    • Web back ends have APIs
      • I’ve wasted so much time hacking at things like of-export to get information
      • HTTPS is king
      • I could actually build reliable tools using Trello data
  • The back of a card is a workspace
    • It does markdown
    • Half of this post was written on the back of a Trello card
    • OF’s notes field and file attachments suck
  • Comments
    • Leave comments/log for myself
    • More than it’s done but how I did it
    • See progress as an idea evolves
  • Trello, Inc
    • Now its own company, not a part of Fog Creek
    • Joel knows how to build exceptional companies

Maybe some day I’ll go in to more detail about how I use Trello but I think that’s less relavant since the process of setting it up fresh without a lot of bloggers telling you how to use it is a great opportunity for introspection on the way you work and good practice in figuring out what you need. I’ve been using it full time for 3 months now actually kind of enjoy using it. It’s given me what I need and nothing more. I don’t obsess about what’s in Trello or how it’s organized like I did with OmniFocus. I don’t need to do maintenance to keep it useable. I go in, get my work done, and get out.


I’m starting to reduce what value I perceive these tools to be in my life and that’s causing the perspective shift. GTD was a user manual for a tool that I followed until I began to master the craft. With a little more experience, I recognized that the tools just helped guide me through the craft until I was comfortable doing my work without those instructions. I used to depended on them for success but now I can lift my head out of the manual and go learn something else.

Made to Last

Gear that’s made to last simplifies my life. Build quality tends to be the first consideration for whether gear will last but it shouldn’t be the only one. Other factors beyond durability could mean that a piece won’t always work for you.

I’ve come to appreciate the BuyItForLife subreddit1 as a good source of discussion around the values of quality gear.

Buy It For Life, or BIFL, is this idea that you can buy something of quality once and it’ll last for a lifetime. Once you’ve purchased that item, you don’t need to ever think about it again; you just use and enjoy that gear. Even if you invest a large amount of money in buying that one thing, its value shows over time because it’ll last so long. My mom, who is Polish (and hence frugal), used to teach me that when I could, spending money on something of quality often meant it lasted longer than the extra you paid. So a $150 Jansport backpack wouldn’t just last 3 times longer than a $50 backpack, but if I cared for that gear, it would probably last my lifetime. That backpack is over 10 years old already and my Dad uses it now.

But how much you pay and the quality of that gear doesn’t mean it’ll last forever. After the last life cycle of jeans, I decided to spend about twice as much to get a higher quality, 18oz Japanese denim in hopes they would last. The good news is that they’ve lasted longer and still have a lot of life left in them. They’ve gone through repairs once and are held together in a few places with the best hand stitching I could do with just the memory of what my mom showed me years ago. But they finally need to be replaced and not because of quality: I started weight training a few months ago and have been putting on some much needed weight. Adding fifteen pounds has made my skinny jeans a little too skinny and though they’re still in decent enough condition to continue wearing, the fit isn’t there anymore. I spent a lot of money on these jeans and, much sooner than I was expecting, I’m no longer able to wear them. I feel almost like I’ve duped myself into thinking that even if it’s as simple as a pair of jeans, money can always buy something immortal.

So some factors to consider when choosing Made to Last gear:

  • The ease of use/experience of using a product: Sure it may be built like a tank but it being built like a tank could be its downfall. Maybe it’s heavy, clunky, or using it is just a pain. It’s easy to buy something thinking it’ll last forever but you only end up using it for a few months before you get annoyed and it just sits there on a shelf.
  • Style: This matters mostly for clothes and outerwear. I know that jacket you bought in the 80s was really well made. But it was also purple with green stripes and now you can’t really wear it out in public. Buying gear that has a traditional and lasting style, like 1000 Mile boots will allow you to wear them through the decades.
  • Sizing: Just like my too-skinny skinny jeans, clothes are tough to be considered BIFL. The hope is that as we age we keep our lean, tight, 25-year-old bodies but somewhere along the road, gravity and ice cream will both have their way with us.
  • Regimen of care: All gear needs to be cared for but is the amount and frequency of maintenance sustainable? My dad has a fishing boat motor that was passed on to him from a friend. It’s from the 60s and still starts on the first pull. It needs care but draining it and the end of the season and storing it indoors, then cleaning and oiling it at the beginning of the season is enough to keep it working well. If you need to constantly be maintaining the gear for it to work well, chances are that at some point, you’ll lapse with that regimen and that will cause issues.
  • Repairability: Lasting quality doesn’t mean your thing will be in mint condition in 20 years. You’ll need to care for your gear and over time, repairs will help keep it in working condition. Shoes made with a Goodyear welt are easily resoled which adds life to the shoes.
  • Warranty/Guarantee: Whether it’s for repair or replacement, items with guarantees can last indefinitely. My sister had bought some Tupperware at a second hand store and when the lid cracked, she was able to send it back to the company and have it replaced. She’s now guaranteed to have a working, functional container forever—whether it’s that exact piece or not.
  • Reliability of the company: Lifetime guarantees only count if the company is still in business, so take this in to consideration. I wouldn’t bank on being able to fulfill your lifetime guarantee on that bag you bought on Kickstarter.

It’s been taking me years to get the hang of this for even a few good items I’ve purchased (and that’s, like, forever, for an increasingly short-attentioned 25 year old). Part of taking ownership of your belongings is investing your attention in them before you even buy them and taking these factors in to consideration will help you commit to, love, and use that gear for a long time to come.


  1. If you shy away from Reddit, I encourage you to read my guide on getting started

Paradox and Perspective

I had thought I’d found some place of enlightenment. A quite little place in my head where I recognized that my practice of managing the things that need to get done in my life wasn’t important and I could just move on. I could just walk away from the 5 step process and be free.

Distancing myself from that has felt like I’ve distanced myself from one of the only things I’m good at. It’s heartbreaking as I realize while typing this that GTD is one of the lone things in my life I’ve been working to master. Not being a socialite, not some extreme sport, not the cello—I’ve been focusing on getting arbitrary things checked off a list so I’d have more room to do other arbitrary things. I do feel like this method has led me to some valuable accomplishments but there has to be more to it than this.

So I started to spend less time reading, writing, and generally practicing towards mastering the way I work to spend more time mastering the way I live. Through this, I have began to unveil more of life but often feel left as the master of nothing.

Maybe it’s a paradox of passion. I still have feelings for the way I used to manage my work. I’ve stripped it all down but I don’t think I’ve quite let it go. There’s been a thread through everything I’ve done for almost a decade and moving on from that can leave a sting. I feel less sharp, less on top of things, and sometimes less driven to get work done because I want to let life happen.

The trusted system I’ve long worked on is pretty much abandoned. Having a trusted system means you gain the mental capacity to take on more but do we always have the human capacity to take on more? Our goal when we organize our lives and work is so that any time we sit down with our list of things we want to do, it’s clear what needs to happen and we can jump right in. But the most rewarding stuff in life doesn’t manifest itself on a list, so our focus on organizing life is futile.

I’ve been struggling with this balance: organized enough that the tasks get captured—out of my head—and done, but freeing myself from the grips of obsessive organization to give me the mental and human capacity to live.


The above was a draft that I was struggling to shape over a week or two, sitting in my drafts folder mocking me that not only had I slipped from my comfortable perch as a productivity guru but also as a productivity blogger—unable to connect the ideas and simplify it so you could digest it, flipping through your RSS feeds while sipping your particularly brewed morning joe. It just wasn’t meshing. I couldn’t grasp where I wanted the article to go. I couldn’t find where I wanted to find myself in the article, what hacking on the keyboard could teach myself. So I left it. I went to the woods for a weekend away and while reading on Sunday morning, held down in the little wood shelter in the Adirondacks by the down-pouring morning rain, something shifted. The above remains unedited from where I left it and the below is the part that matters.


Stephen Covey in the introductory paragraphs of The 7 Habits of Highly Effective People:

It becomes obvious that if we want to make relatively minor changes in our lives we can perhaps appropriately focus on our attitudes and behaviors. But if we want to make significant, quantum change, we need to work on our basic paradigms.

Forgive his use of paradigm. Originally published in ‘89, it was much before the modern-day marketers and executives got a hold of the word and made it meaningless. The way I read it, Covey uses paradigm like perspective.

My perspective was self-serving and the basic way I saw things needed to change. Productivity was only ever about myself and though I’ve been seeking something more significant, clinging on to old “attitudes and behaviors” held me to minor changes in how I can impact others.

It wasn’t that those habits were containing me. The angst in Strip It Down was directed at the way I was working so I tried to strip away those behaviors to make way for change. The behaviors or attitudes themselves weren’t to blame but the focus on them was distracting me from putting in the work to see things from a new perspective.

I want to change the way I look at my life, the people around me, and the way I work and these are a few ideas that I want to build my new perspective on:

  • Just stay above water enough with the tasks I have to do to give people in my life the time and respect they deserve—it’s probably much more than I’m giving them right now. Try to shift my perspective of mastery and craftsmanship of bits and lists, to people and relationships.
  • Use the scaffolding I’ve built to better grow and support these human relationships.
  • The more I bow to others, the more I’ll be able to bow to myself, and somewhere mixed in, I’ll be granted the time and ability to make great things.
  • Pay less attention to tracking and accomplishing what happens day-to-day and figure out how to see patterns year-to-year—that’s the timeframe where big things will happen.

When I go back and read old posts, like 20,000 Feet from two years ago, I recognize that including the needs of the people around me has always been baked in to the way I structure my tasks. And then I write sentances like that and know where everything is wrong.

Me, one sentence ago:

I recognize that including the needs of the people around me has always been baked in to the way I structure my tasks.

What this needs to be is:

People are important to me and I need to structure my life so I put them first.

That’s a different paradigm and I need more vision to do that than paper or lists can handle.

Updated Daily Carry to Add Watch and Sleeve Wallet + Money Clip

1000 Miles

I figure the guy who first muttered “Life is about the journey” was having an ale at the only pub near the little inn he was staying at that night, consoling, convincing himself after a hard days travel, still far away from where he wanted to be.

The way I see it, there’s four important parts in a journey: where you are, where you’re going, the bag you’ve got, and the boots you wear. Only one of these really matter—where you’re at right now—but the other three count for something too. Where you’re going gives you something to work towards. An idea that pushes society, culture, people forward. Your contribution. Your bag and what’s in it helps you get there. The jacket that’s your shelter from the elements, the book that keeps you safe from loneliness, and the notebook that protects you from your self. They’re in your bag and everywhere you go are a reminder of the physical weight of anything but ideas and conversation.

But your boots, they feel the weight of every step. They feel the renewal of a walk in the spring’s fresh grass, the joyful lightness as you dance, scuffing up your neighbor’s kitchen floor. Your boots are what grounds you to this earth and the world’s your beat.

Where am I? In front of a keyboard, this friend that has so humbly taken a beating yet has pulled words out of me I didn’t know I had. Where am I going? I only wish I knew. My bag is a GR1 and I wear 1000 Mile boots.

1000 miles is a long journey and long journeys need good companions. These boots, so comfortable and durable, the ad in the 1920’s Successful Farming magazine says, they’ll last you “1000 miles of wear.” There’s an elegance in the construction of these boots that make you want to take them on travels with you—an adaptable style that feels rugged yet can be cleaned up to look great with a sport coat. On a long journey, you’re going to be a lot of different places and your boots need to fit in like you do.

A good horse hair brush, some boot LP, and a little love and these boots will keep their form and stand up to a lot. But life’s hard and life’s hard on your boots so eventually down the road they’ll need a bit of work. Nothing goes unbroken on life’s travels. You’ll probably break down more often than your boots will. You’ll need a friend, a drink, a talking to to pick you up and get you back on the road but with wear comes tear and 1000 miles does a lot to the soles of your boots. But good engineering means they’re built to be rebuilt and a good cobbler, like your friend and a beer, can craft a new sole and you’re back on the road for a few more miles.

A few more miles lead to a few more and soon you’re in a place that’s hard to recognize. Everything starts showing that mileage. We can see how it wears on us but 1000 miles is hard to grasp. The trip out west and back will put about 4000 miles on you and your heart, something that was a lot harder to do in 1920. These boots haven’t made that trip with me yet but the rest of me still carries those miles in a lot of ways.

These boots have seen a Boston fall with a chill so deep the leaves that lingered stood no chance against the winter that crept so closely. They felt that winter which came soon after the last leaves left us, harsh and unforgiving. Digging out of snowbanks in Montreal and the longest of long winters New York City has felt. These boots saw that same winter slowly retreating, loosening it’s grasp on Minnesota and then the cherry blossoms in Washington this spring, exploding to celebrate a great defeat, a rebirth of the season.

There’s a lot of stories in 1000 miles if you just listen to the road and don’t mind getting your boots a little dirty.

Empathy and the CODE Keyboard

The Two Sentence Review

The layout of the CODE Keyboard is similar to the Filco Majestouch-2 tenkeyless that I’ve been using for a couple years but the feel of the CODE’s MX Cherry Clears aren’t quite as nice as the MX Cherry Blues. The CODE is much quieter though.

In Conclusion / A Seemingly Trivial and Unadorned Example of Where I Was Not Empathetic

As people who seek out nicely crafted items, desire well designed software, and are particular about the way we do things, we are familiar with tradeoffs that exist in choosing these items like the extra time it takes in the morning versus the taste and experience of a good cup of coffee or the cost of buying a finely crafted watch versus paying rent. But we might not always be taking the right things in to consideration and missing important tradeoffs.

I’m beginning to see impacts of how my decisions to prefer one product over others, this habit over that, or a certain attitude about something is affecting other people around me in a way which I never noticed before. I don’t think I’m oblivious to what the people around me feel but I think I’m slowly getting more in touch with not just that but how my choices don’t just impact me. Call it maturing, I guess, but I doubt I’m the only one reading this that could improve at that.

I think a lot of office workers avoid a clicky keyboard because of the sound. Not wanting to annoy coworkers is a legitimate reason but if you’re like me and didn’t empathize with your coworkers in your decision making, you may think, “oh the keyboard is not that noisy, it’s fine. It’s a busy office so the sound will just blend in.” And it kind of did just like the ongoing jokes about my 1990’s keyboard and the intense sound it makes.

The running joke was fun. People would come by my desk and comment on the keyboard and how they used to have one like that when they were running DOS, or how it reminded them of the office ambience in Mad Men, or an airline customer service rep typing in to their outdated terminal while apologizing for the inconvenience because your flight is yet again delayed. “It’s got a great feel, and I’m typing all day long so why not use something that feels good,” I’d say. “I really like it… But she’s not as big of a fan”, pointing over to my desk mate five feet to my left while letting out a little chuckled. She’d laugh too and kind of roll her eyes being a good sport and playing her part in the joke so that it would survive for another week.

And then I actually asked her about it. I wanted to know if it did really bother her. She said some days she’d actually have to work somewhere away from me because the noise of my furious typing would be too loud she couldn’t concentrate.

I was hit with a layered feeling of dread. The outer layer was a realization that for six months I was pecking away at that sweet, clicky, Cherry Blue keyboard, proud of and satisfied by the sound it made, projecting (to no one but myself, really) a desire for only the highest quality experiences but in my desire for “productivity” I was distracting those around me. Deeper than that, it hit me that in striving for better things—tools, process, gear—I wasn’t taking other people in to account in the process of choosing those things. Deep at the core of the dread that was knotted in my gut was a feeling that I had made this assumption that people weren’t bothered that much by my clackity sound but when I actually asked, I learned that my assumption was wrong. Are some, many, most of my assumptions wrong? What else am I wrong about it that I just need to ask about to find out?

Empathy needs to be at the root of the decisions we make. When we make decisions about what new things we take in to our lives we need to deeply consider if and how those better tools also make us better at loving and helping the people around us.

So maybe the CODE keyboard doesn’t have the best feel but it’s a better experience for me and the people around me. And that matters more.

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