HACK / MAKE

As people who are driven to find better ways to work, we seek out systems, workflows, and methodologies that we can use as guidelines for how we work. These give us nice little rules like “if it takes less than two minutes, just do it now” and teach us multi-step methods to gaining control of the open loops in our lives. These help tremendously but at a certain point can get in the way. The rules work in most cases but as we get more and more used to working within those guides it can become difficult to manage work that falls outside of that ruleset. Essentially, it works until it doesn’t, and that’s the time we need it most. We need a process that’s relative, adaptable, and appropriate for the work we do. We need to be approaching our “productivity” in a smarter way.

It’s easy to over engineer our workflows and create processes that work for us most days. When we get busy, when we get lazy, or when our attention shifts to something else, the complexity in the way we plan, organize, and structure our work and lives can lead to this system collapsing on itself leaving us in a worse place than we started. The opposite can happen too where the density of our process-oriented work can weigh on us and make it more difficult than it needs to be to make a grocery list. The problem comes in approaching these tools with the wrong mindset and not understanding how and when the pieces help. Methodologies can fail when you pick and chose the parts you want to use while other systems only become stronger when you leave behind the pieces that you don’t need.

Thinking of all the pieces that help us capture, organize, review, and do work as scaffolding will help give you an understanding of the value of each and provide a more relative outlook on your approach to “productivity” as a whole.

Scaffolding, like in construction, is a superstructure that gives a stable frame to get work done. It’s modular and the pieces are lightweight but when set up properly, create an incredibly stable system that’s adaptable, scaleable, and appropriate for the work that needs to happen. You can use scaffolding for construction that’s two stories tall and construction that’s twelve stories tall. It’s all about fitting the right pieces together so that the frame is appropriately sturdy for that work. For light work, you may not need much scaffold but as the scale of what you’re doing changes, so does the strength of the frame you do the work upon. Scaffolding isn’t the foundation. When the work on a building is done, you remove the superstructure around it and the work stands on it’s own. People who see the completed work may not ever see the scaffolding because the work is about the work, and not the way you do it.

Taking a scaffold-like approach is about creating the right levels of structure around the work you do to let it properly flow. You neither want to constrain your creativity by following weighty methods nor do you want to become overwhelmed by the work you have to do by alleviating yourself from process.

As I’ve been charting a direction for the next few years of my life (formally knowns as, but incorrectly named a “life plan”), I realize that granularity for timelines and details of things I want to happen in my life isn’t appropriate for the altitude I’m looking at. An OmniFocus project with next actions isn’t the right scaffold I need for ideas that are five years out. This isn’t a “plan” so it needs to be drawn up in a way that’s appropriate and adaptable for what it is. In this case, working in OmniOutliner gives me the flexibility I need to have a branch for what’s at 50,000 feet while being able to put more detail for what’s at 10,000 feet. I don’t need to ever think about, manage, or review what’s further out until I want to.

The same approach can be considered for all the work that we do. It starts with understanding the scale of the project we are undertaking. This helps us realize the stability and dependability of the frame we need to be working on top of. If there’s something I need to remember at the store when I go out this afternoon, writing it in my Field Notes is adequate. If it’s a three month development project with several milestones, dependancies, deliverables, and collaborative work along the way, I need something sturdier. Knowing these different tools, parts of workflows, and elements of frameworks allows you to fill the gaps that might exist in one of the others and support that with something you know works for you. Having one main software system that we trust can often feel like the best way to work, but imagine seeing a construction crew setting up scaffolding on a town house like they do at a skyscraper because “that’s the way they’re used to working.” We need to think about the tools that we have available and be assessing which ones are relevant for the work that we need to do. We need to be smart about choosing what fits together to build the right scaffold for the job at hand. Without that, we’re building scaffolding that’s too tall.

By seeing all of the elements of workflows, tools, and methodologies as pieces that could coexist or be substituted, we can learn to build strong and appropriate scaffolding to support the work we do.

I’ve often been asked and been curious myself about a simple and fluid way to get a list of tasks into OmniFocus on iOS. There have been some hacks using Pythonista and I’ve come very close to setting up a system with my Mac mini server to grab a text list, parse it out, and add it to OmniFocus using Applescript. But with a major assist from James Gowans comes a pretty straightforward way using Drafts 3.0’s new “List in Reminders” action.

This new action will list out the lines of your drafts as line items in Reminders and thanks to OmniFocus’s support for importing tasks from Reminders you can go from Drafts to OmniFocus in one tap.

The basic support in Drafts for “List in Reminders” dumps your draft straight into Reminders without even leaving the app. That’s smooth if you want your items to stay in Reminders but we want to trigger OmniFocus to scoop up the tasks so they don’t get left in between.

The trick to this is to “Allow URLs to trigger actions” in the Drafts settings. This means that Drafts can call it’s own actions in addition to the x-success callback function. Once everything is sent to Reminders, OmniFocus will open and grab all the new items.

Once you’ve set Drafts to allow URLs to trigger actions and have turned on Reminders Capture in OmniFocus, add this URL action to Drafts:

drafts://x-callback-url/create?text=[[draft]]&action=List%20in%20Reminders&x-success=omnifocus://

Selecting this action on your draft will send each line to Reminders, then switch to the OmniFocus app which imports each task into the inbox. I can’t find a way to deep-link into the Inbox view so you will be switched to wherever you last were in the app but you can be sure that your tasks were imported. If you know how to link into the OmniFocus inbox, please let me know. Unfortunately, contexts and projects still aren’t supported through the URL scheme but just look at what your amazing pocket computer can do.

I’ve been reading On the Road by Jack Kerouac and came across a couple sentences that caught my attention. As Dean, Sal, and Marylou drive west from New Orleans, Sal’s mind wanders through memories of his cavalier adventures. Sal (an autobiographical portrayal of Kerouac himself) goes on narrating that if it weren’t for his failing memory, he’d be able to recount those tales in more detail:

Ah, but we know time. Everything takes care of itself. I could close my eyes and this old car would take care of itself.

It’s both freeing and excruciating that everything will eventually take care of itself. I think the scary parts come in knowing that the inevitable isn’t a constant. If Sal closed his eyes, the inevitable could find that old car in a ditch. With his eyes open, the same could happen but most likely they would get to San Francisco safely.

We tend to battle with the inevitable. Without realizing that we aren’t in full control of it nor are completely removed from having an impact on how things end up, we drive our lives. If you close your eyes, your life will take care of itself. If you map out your life’s details, a different inevitable may—but by no guarantee—happen.

Every morning we have the option to shift the odds of what’s inevitable to something greater. No action or direction will be sure to happen. No level of control will stop bad things from eclipsing you or create every opportunity you hope for. But I believe we can lead what’s around us to take better care of itself. The great things we create, the people in our lives we care for, and the push we make to endure when we aren’t at our best helps build a place so that when “everything takes care of itself”, we can feel a little more comfortable that the care we invested will take care of us.

Patrick Rhone has recently been getting deeper into talking about work. Not work/life balance or doing better work, but he proposes that we look at everything we do as ‘work’ like they do at his daughter’s preschool:

In a Montessori environment, any purposeful activity is described as work. For instance, cutting up bananas to have as a snack is referred to as “banana work” or learning math skills by counting beads is referred to as “bead work”.

If you think seriously about living your life deliberately by aligning what you do and who you are¹, this idea of anything we do is work makes a lot of sense. Why is it that we work hard to impress people at work but then decide we can be an asshole to the person in front of us at the line in the grocery store? Is it because we think our work has more weight in what we believe will make us a success? What if we work towards treating the people outside of work as if they were the ones who would be doing our performance evaluations and giving us raises? Where we are should not change how passionately we do our life work.²

Finding work you love won’t necessarily make life easier if you end up passionately consumed:

Not everyone is cut out for it. It takes not only a passion for the work but plenty of sacrifice. It means there will be no paid vacations or retirement fund matching or group healthcare plan. It means years of saving and planning and struggling and scrapping. But you will know, in those tough years, if it is for you. Because those struggles will not deter you — they will fuel you. Because, that is all part of the work too.

Anything that has purpose is work but just calling everything by that name doesn’t change the fact that some things will be truly hard work. The hard work will trash your system. It’ll make sure everything that was running smooth won’t. It’ll keep you awake at night, sometimes in excitement, often in fear. But it’s the work you’ve set out to do and fighting is part of it. The decision to live a deliberate and driven life filled with good work will consume you. It’s not just working hard 9-5 anymore because your grocery work, your commute work, your talk work, your love work, and your life work, they require you to be present and working hard.

Are you ready to be passionately consumed?

Last Saturday at 0700, I met up with 68 men and women at the Irish Hunger Memorial in downtown Manhattan to get our asses kicked as part of the inaugural class of the GORUCK Light Challenge. I’ve been wanting to do a GORUCK Challenge for a while and when I found out they were doing a Light version and the first would be here in New York City, I was quick to sign up with my buddy. This was the very first Light Challenge so we didn’t really know what to expect. Most of us were aware of what the GORUCK Tough Challenges are all about but didn’t know where Light would sit on the suck scale.

As we loitered that morning, half dizzy as the second guessing swirled through our heads and half groggy because of the coffee we decided to forgo, our cadre startled us out of a daze as you would expect from a US Special Forces leader. At our cadre’s command, we attempted to organize ourselves into formation for role call, brick inspection¹, and splitting off into our two groups to start the challenge.

What we were about to get into was a military-inspired physical and mental endurance team challenge. I was confident that morning, as we saw the sun starting to peak above the skyline, that I would have the mental endurance to get through the day. I was nervous about my physical endurance but became even less sure when I could see we had 34 people but no team. We were a mess. We had trouble following basic orders and quickly realized that without pulling together, it would be a long day ahead of us.

GORUCK lives by the phrase Under Promise, Over Deliver and we learned early that Light did not mean easy.

Maybe it was the intense hour of pushups, bear crawls, and fireman carries, or it could have been the freezing cold pond we found ourselves waist-deep in, but that daze we began with started to lift. We started to see strengths and weaknesses in our teammates and figured out ways to work through them. We learned that it wasn’t a race but that time was still an important thing and we’d have consequences for missing time objectives.

The saying goes, “Embrace the suck.” Embracing it is the only option because the suck isn’t something you can fix. More training doesn’t fix the suck. The suck is baked in; it’s part of the Challenge. What you don’t have to embrace is the things that you suck at. We were too quiet. We weren’t telling our teammates when we were tired from carrying the team weights or our “coupon”—a special present from our Cadre that we picked up along the way, in this case, a big sandbag. We thought we were toughing it out by keeping our mouth shut but what it meant was that we were wrecking ourselves.

We marched through Manhattan to our different objectives as the morning sun gave way to a chilling wind. I guess we should have expected it because change can suck, but our objectives could quickly shift and our cadre would issue a FRAGO—where something happened in our imaginary battle and we would need to adapt. This usually meant “casualties.” We would have to carry our teammates. At the worst, we had five casualties. Carrying five people around the streets of Manhattan, through the busy St. Patrick’s Day parade crowds really sucked and that’s when we learned how to be team.

It was moments like this where we were getting near the edge of our physical capacity when we would have lapses in communication with our team. Walking through midtown Manhattan on a normal day is a challenge; doing it with a team of 34 people in already crowded streets with people on your shoulders makes things like all getting across the street together before the light goes red a real issue. It only happened once (because we learned from it fast) but only blocks away from one of our objectives of making it to the Empire State Building, our team got split up by a red light. Cutting through traffic carrying a litter with a casualty in it isn’t a great idea no matter how much of a New Yorker you think you are. We paid for our lapse of communication that caused the separation by doing lunge walks—CARRYING PEOPLE—for the last two blocks to our objective. The slowdown from the lunge walks caused us to be overtime by 1 minute and 30 seconds, which we paid for with 90 reps of some of our favorite PT exercises, like high-lifts of our brick-filled rucks and burpees².

We went from clouded to sharp minds when together we realized that the suck of the PT was something we’d have to embrace but the suck of our team communication could be fixed.

We each had to be open about when we were tired and needed help. By having team leaders constantly checking with how we were doing, swapping in fresh legs when needed, and rotating people through positions, we were able to work together to survive through the rest of the Challenge. The snow that started to fall in the last couple hours was a nice touch to see us through the end. In 11 miles and—in Under Promise, Over Deliver fashion—7 hours for what was advertised as only 4, we came to be Light Class 001.

With a Light patch on my ruck, it’s time to take things to the next level and train for Tough.

Aaron Mahnke, a designer, creator, and general shipper of things, says this about the difference between the two sides of the craft:

Making ideas is emotional at its core, and thwarted by practicality.

Shipping ideas is practical at its core, and thwarted by emotions.

Being good at the practical element of making doesn’t necessarily mean you’ll be good at the emotional experience of shipping. Shipping is hard work and a very different type of work than making. It only gets easier if you’re stagnant and don’t push harder and go further with what you create.

Fear will find its way in front of you delivering what you made into the world. It’s easy to let this fear manifest itself in things that sound practical. “It’s buggy.” “It’s not pixel perfect.” “It’s just not good enough.”

But if you believe what you’re making is art (and you should), than you will recognize your art is fundamentally flawed because it is a representation of the artist. And just between you and me, neither of us are perfect. What we need is more practice at both sides of our craft—the making and the shipping. The only way that we get practice shipping is by shipping something that isn’t perfect.

Introspection into the ways we work often leads to dependance on tools and methodologies as a way of structuring plans, approaching problems, and choosing what we do. Even when we start moving away from practicing methods to practicing mindfulness, we can find that our work gets done easier but we still lack the grit it takes to put our work into the world.

Seth Godin recently reset the focus from the methodologies we use to the act of shipping itself:

Perhaps you can quote the GTD literature chapter and verse, understand lean and MVP and the modern meeting standard. Maybe you now delete your emails with a swipe. It’s possible you’ve read not just this blog but fifty others, every day, and understand go to market strategies and even have a virtual assistant to dramatically increase your productivity.

That’s great. But the question remains, “what have you shipped?”

Without shipping, the things you do are just self indulgent; the good work you do, wasteful. The industry of productivity tends to focus on the ways to get work done but shipping requires something from much deeper than our work itself.

In an intense development cycle where process failed my team, my own tools became too complex to maintain under the time pressure, and I had to choose to let things fall through the cracks, any methodologies I’ve learned quickly crumpled. The systems I had set up were idealistic. OmniFocus became a train wreck and Trello, our software project management tool, gathered dust. When I had to make decisions between spending my time maintaining pristine feature boards and bug queues or putting my head down and coding (I’m not even really a developer), the systems were sacrificed to get us steps closer to finishing. Even with these core process and systems failures we shipped on time and without a single blindsiding issue. My team hasn’t done a project at this scale together or with the time constraints we had to deal with. There were outside issues we had to fight through to stay focused. There was frustration, conflict, and fear. With all of this around us, what made us pull through wasn’t “productivity.”

We shipped because we’ve shipped before.

The tools that help us every day can hurt us when we’re in the thick of hard work. We can rely on systems that don’t fit with work which has evolved. The scaffolding we build functions under the standard day-to-day but when that changes, we personally need to be prepared to do what it takes to ship. The only way to prepare ourselves for that is not practicing productivity, but shipping over and over again.