Month Two Week Three: Trust Your Instruments

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What is Startup in a Month?

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The downward slope of Month Two, is it really here again? Are we really here in the last week of the month?

Before we dive into the meat of this week’s wrapup post, I have an announcement: the development of Month Two’s startup, Pic Story, will be extending two weeks into Month Three. You may recall that I stopped production on Month One’s startup, Plotters, due to the fact that I had hit the end of the month and was nowhere close to finishing. Back then, oh so long ago, I felt the need to commit to my format in order to give myself the positive pressure to keep things small and simple. I’m once again in a position where I’ve bitten off more than I can chew in a single month, but I don’t think it would be right to not finish a second time.

Adhere too strictly to the rules, and they can transform from something that informs your success to something which impedes your success. More on that idea below 👇

I am a little bit disappointed to once more miss my target, but it also offers some exciting opportunities for experimentation! I’ve got a long list of things which I’d like to build, but some of them are really tiny: not enough to fill up a whole month. I figure I can spend the final two weeks of Month Three to build out one of these extra tiny startup products to see what happens with it. Stay tuned.

Hard Lesson of the Week

And now for (what used to be called) the failure of the week feature! This weird world is great at showcasing a success, but behind every success lies ten hard-won lessons, and we don’t get to see very many of those. In each weekly recap, I’m going to put these hard lessons up front to show you that it takes a lot of trial and error to get anything right in the end.

I’ve been trying to find a better word than “failure” for the things I’m experiencing. If you take a sampling of dictionary entries for the word “failure” (so cliché, I know), you see things like:

  • “The fact of failing to effect one’s purpose”
  • “A thing or person that proves unsuccessful”
  • “A falling short”
  • “A failing to perform a duty or expected action”

But none of those definitions is what I’ve been writing about in this recurring segment, is it? I’ve been writing about confounded expectations, unexpected outcomes, hidden truths, secondary implications of the things that I’m setting out to do. Really what I’ve been documenting is the gap between expectation and reality. I’m not really “failing” in the sense that I’m not achieving my purpose, it’s more like a process of feeling out the territory. Learning the moves. Hitting that Goomba as many times as it takes until you learn to jump to avoid it.

So anyway, what is the Goomba of the Week then? This time around, it’s adhering too rigidly to my schedule, and sacrificing the things that help me build a balanced, sustainable tempo of work when I feel like I’m falling behind.

Workers in a factory

Chopping up Infinity

On the one hand, this year is all about experimentation: rapidly iterating on a bunch of different ideas until I key in on one that works. Trying out different ideas, ways of working, variations on themes; anything that brings me closer to my goal of establishing a self-sustaining income counts! On the face of it, that amount of freedom seems amazing, but at least for me, it’s also kinda scary. If you’ve ever done anything creative, you know one of the most difficult parts of the act of creation is simply starting. Taking that big empty page in front of you and filling it in with something, anything, is so hard when you don’t have any boundaries to work within.

We’ve all got inherently limited minds, and they are thirsty for structure. Some of this is attributable to growing up in the wake of the Second Industrial Revolution: the shift starts at 9 AM sharp, you work until your scheduled break, you must produce units of work on a fixed schedule and quota.

But a lot of structure comes from the natural world too: day and night, spring and summer, monsoon and dry season. Hibernating in the winter, migrating in the spring, stockpiling acorns in the fall. These things all follow cycles and patterns, and the big biological clocks housing these modern minds of ours are still synchronized with those cycles, even if we don’t have eyes to see it most of the time.

At any rate, it all speaks to an inherent need to chop the world up into comprehensible pieces with some kind of regularity in form or tempo so we can understand the world around us and make decisions and predictions about it. Whether any of this is “right” or “good” to do, or whether any of these divisions are valid at all, is another question entirely, but we seem to desire it on some level.

Hell, this need for structure and order is what draws me to Clojure and LISP in the first place: the language places very simple but very strict limitations on what can be done. Thou shall not mutate a variable, thou shalt perform sequential transformations on data with a threading macro, thou shalt not worry about types too much. And yet, this rigidity has the confounding effect of giving you more freedom than you would have had otherwise. By restricting your possibilities to a handful of broad but nevertheless restrictive paths, you avoid the completely stupid, completely avoidable, almost inevitable pitfalls that imperative-style coding puts in front of you.

Workers in a factory

Push and Shove

And so, knowing all of this, and appreciating the benefits that structure can bring, we come to the subject of my schedule. I’ve been attempting to craft a weekly schedule which achieves balance. My dream day would go something like this:

  • Wake up at a reasonable hour after a restful night’s sleep,
  • Do yoga, followed by a walk,
  • Reap the literally brain-transforming benefits of aforementioned exercise, enjoy a healthy breakfast,
  • Do the Work, unimpeded by anything that’s not directly related to producing a great product,
  • Write a reflection piece at the end of the work day,
  • Get on with the rest of my evening, sleeping soundly with the knowledge that I did the very best I could.

Sounds great right? The right amount of structure coupled with plenty of freedom to flex, stretch and explore what’s possible.

But god damn man, when push comes to shove, it all comes back to the bottom line in the end. Every time I hit a ditch in the road, and I’m presented with the choice of getting out of the car and muscling the thing out of the ditch (read: fixing a bug, slogging through an unexpectedly complicated feature) or just sitting down on the side of the road and trusting that help will come soon (read: giving it a rest when things get too hard, taking care of my mind and body), I take the slog.

Every single time.

Time is money, production must stay constant, clear and obvious forward motion at all costs. What, you want to go for a run? That’s insane! Think of all the work you could be getting done instead! Go for a run when you’ve started to earn some money!

Workers in a factory

Flying on Instruments

I really enjoy watercolor painting videos. Really, anything that shows the process of creation draws me in like a moth to a porch light, but watercolor in particular blows my mind. Harumichi Shibasaki is the kindly Japanese grandpa we all need, and James Gurney is great too. When I was up late on Wednesday night, unable to sleep, mind wracked with thoughts of all of the stuff I wanted to do and how little of it I got done, I watched this. This line in particular is exactly what I needed in that moment:

Most of my paintings go through an “ugly stage,” where it seems impossible to see my way clear to the finish. You may imagine from my calm voice that I know exactly where I’m going, but in truth I feel like a pilot lifting the aircraft through a layer of blind clouds. At this stage I have to fly on instruments with faith that the clear air is waiting for me on the other side.

I started to reevaluate this week in terms of it being my “ugly stage”: the moment where I’ve gotten fairly deep into the startup, and where the complexity really starts to show its head. After graduating from implementing the basics, you start to get deeper into the complexity of what you’re attempting to undertake, and your past decisions start to force your hand in sometimes uncomfortable ways. The idea that you can’t do it or won’t finish starts to creep in, or that it won’t be good enough. If only you put in another half hour here or there, it’d all come together.

And what are my “instruments” in this example? Sleeping well. Eating well. Taking breaks. Taking time to reflect on what’s happening. Acknowledging when something isn’t working and making thoughtful course corrections. Above all: exercise. It’s like knocking out beams in the first floor of your skyscraper when you let exercise lapse. Sure, you could get away with it a few times, but how many exactly? How soon until the whole thing collapses?

When things get weird, disregarding your instruments and shoving the throttle forward is a really easy choice to make. It is so easy to mistrust and disregard the things keeping the plane steady and to try to pull through the cloudy parts. It’s easy to imagine that there’s nothing except for you controling the plane. But all of that eminently ignorable stuff behind the instrument panel is really the stuff that’s doing the flying. The very things which are so easy to write off as a “waste of time” or a “distraction” from the Work are the very things that enable the Work to continue apace.

I need my instruments. However loathe I am to give up my sense of autonomy to them, my feelings of invincibility, the sense that I know what to do during the weird, ugly parts of this flight, I need them.

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