What It Takes to Ship

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.

Shipping Imperfections

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.

GORUCK Challenge Light Class 001

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.

  1. If you’re not familiar with GORUCK Challenges, the whole thing is done wearing a backpack (referred to as a ruck) with bricks in it. For the Light, we had to carry four. 

  2. Not sure what a burpee is? Do yourself a favor and never find out.