Mailing It In

I’m not very good at pretending to like things. I don’t like manually doing repetitive work that feels like it could be automated, or eliminated by a better process. I don’t like adhering to bad procedures simply because “that’s how things are done”. I don’t like avoiding a problem because acknowledging the existence of a problem makes someone important uncomfortable.

I don’t like any of these things. But… of course, I will do them if doing them makes sense in the grand scheme of things, no matter how dysfunctional and inefficient that grand scheme may appear to be. I grudgingly do all sorts of things for work, not because I think they are great ideas, but because I think they are the best decisions to make for my organization at the time. 

At first, this sounds incredibly high-maintenance, and to normal people, probably pretty annoying. I completely understand that, and trust me, I work very hard to make my philosophy as tolerable and non-instrusive as possible. And in my defense, there’s a good reason I fight against doing work just for the sake of work — I don’t believe in half-assing things

This is something I’ve found makes me a bit of an outlier. Half-assing is a huge part of American culture, business, politics, and just about everything else. Token efforts, olive branches, and “good faith” (even if it’s really the opposite) are key steps in the horrifying sausage-making that is getting something done in most organizations, not because they have to be, but just because a lot of our office and business habits grew out of historically low-information environments where asking questions was (and still is) often associated with rocking the boat or being difficult. Questions are percieved as inherently combative, even if they’re tactfully constructed and designed to reduce confusion, while mailing in a dumb task is somehow weirdly acceptable, or even seen as an example of good judgment. 

I’ve always had a bit of a problem with this, but people — smart people, mentors — have been trying to explain the importance of half-assing unimportant things to me for years. Once, when I was home from college, I was helping my Dad build some steps in our yard. Being unskilled (especially compared to Dad) my job was to drill holes in the steps, and then put in the screws. I wasn’t very good at it, and eventually, I stripped the head of one of the screws as it sat halfway in the hole. 

At first, I was frustrated, and a little embarassed. After all, to me, Dad always took his time, and always did things the right way. He built things with stone foundations, always pre-drilled holes, measured everything, and used lots of graph paper. If we were going to build stairs, we were going to build stairs the right way, dammit. They’d probably last two hundred years. 

Reluctantly, I showed him the screwhead I had shredded, and asked him what to do next.

“Oh yeah, this happens all the time,” he said. “Let me show you what I do.” He took the drill from me, flipped it over, and slammed the base onto the screw.


“Sometimes it can be a little stubborn.”


“There you go.”

He laughed, and handed the drill back to me. I was flabbergasted, and I think he could tell. 

“I mean, I have more screws,” he said. “But… they’re all the way up in the garage.” This time, I laughed, even if it was partially in disbelief. Even my father, the engineer, who once designed and built me a beautiful, amazingly playable outdoor basketball court out of bricks that still stands today, knew when to hold them, and when to fold them. The stairs just weren’t that important. If they were, he probably would have made them out of stone. 

In truth though, Dad wasn’t really half-assing the stairs project per se — he was just preventing the perfect from being the enemy of the good, which is actually really important. Good projects, systems, and even products are increasingly built iteratively (with good reason), and the last thing you want to do is build big, expensive, labor intensive stone steps when you’re not even sure how long you’ll want steps at all, and you need to finish that retaining wall on the other side of the property before winter. 

(As my Dad said at the time, half-jokingly, “in a couple of years, your mother will probably have me tear these out and put in a ramp, anyways.”)

No, the kind of thing I can’t stand is work that is designed to fail, which is what a lot of people spend way, way too much time doing. Dealing with potential investors at EEx (especially big, institutional investors and funds) became incredibly frustrating for me, because after a while I felt like the goalposts were CONSTANTLY moving, and eventually, that they were simply designed to move forever. They might tell you that your pitch deck was too long, but after somehow getting it down to six slides, they’d demand that you include more financial information. Then, when you did, they’d tell you that weren’t thinking big enough, and to include more long-term vision. So you’d do that, and they’d laugh and say “you have to explain how you’re going to do this”, so you’d do that and all of a sudden you’d be at twenty-five slides again, and the whole cycle would repeat, except you’d be out three weeks and a bunch of money, and you’d have flown to San Francisco twice. At some point, you just have to admit to yourself that all the great work you’re doing is pointless and isn’t helping your business, but in a lot of jobs, that’s not encouraged. You’d just keep making that deck again, and again, and again until someone told you to do something else, and then you’d do that. 

Back at Bamboo, like any ambitious, growing company, we had a few bad ideas that we really wanted to work, but never made a lot of sense. I remember working really, really hard on landing pages, email campaigns, and messaging for ideas with huge, obvious strategic holes in them that we either wished away, or refused to engage with altogether, because the project was exciting to someone with influence in the company. Then, after the project failed (of course it did), we’d sweep it under the rug and never speak of it again, until the next bad idea started to gain momentum. Those failures were exhausting and demoralizing for me primarily because I didn’t half-ass them (some of my best work isn’t available online because it was for these doomed projects, and has been taken down), even though — looking back — I probably should have done exactly that, and saved my ammunition for better thought out initiatives with real potential, which we also had a few of.

Part of me has always wanted to get better at making this kind of distinction, but another, louder part of me thinks my stubborn insistence on quality whenever possible is exactly what makes me valuable in the first place. Like most things, the answer is probably somewhere in the middle, and I’m just going to have to keep working on finding that happy medium. But the next time you find yourself wondering why we’re still debating the merits of something, remember — when I eventually do it, I’ll do it well