It's the middle of the year, and I quit.

14 Jun 2021

10 minute read

Well everybody, it’s the middle of the year and I quit. I’m hanging up my hat on Startup in a Month and moving on. Let me explain:

I’ve been having a tough time finding my rhythm this year. By all accounts, I should have nothing holding me back, right? I’m living on savings, I don’t have a job to sap my time and energy, it’s just me and my apps and a big open road. Perfect recipe for success, right? All the things that usually hold people back are no object at this unique time in my life.

And yet, I’ve had a lot of problems along the way that have stunted my progress, and the emotional experience of missing my targets has led to further setbacks. Like compounding frustration interest.

First, my ideas haven’t ever been small enough to fit within the framework of a single month. The scope of Plotters combined with simultaneously learning a brand new programming language meant that I hardly got halfway through before the month was up.

Then came Pic Story, which I thought was going to be smaller in scope than Plotters, but one month of work quickly ballooned into two, and resulted in a final product which was paradoxically too complicated and too sparse on features at the same time.

Then came Mail File, my least ambitious, smallest project this whole year. I think I actually could have built Mail File within the confines of a single, perfect, uninterrupted month. But do you know what happened with Mail File?

A shitload of life happened with Mail File.

A shitload of life

Right at the beginning of the month, I got the first shot of my COVID vaccine. Don’t get me wrong, this is a wonderful thing that I am super grateful for, but the shot completely knocked me on my ass for a week. I could hardly get out of bed, never mind get any work done.

That sudden halt in production was a bitter pill to swallow. I’ve missed practically every deadline I’ve set this year, and even after months of attempts, I was still falling short. I felt trapped in bed, helplessly watching my opportunities and goals wither and die on the vine. I’d done a few laps around the track by this point. I was feeling loose, confident, and keenly aware of how fortunate I am to even have the opportunity to work like this. Then a bunch of completely unpredictable nonsense hits me in the face out of nowhere, setting me back a whole precious week.

After recovering, along comes dose number two a couple weeks later. I had high hopes that I could skate by the side effects after having gotten thoroughly rocked by shot one … those hopes did not pan out. It wasn’t quite as bad as the first time around, but still very hard on my system. I was admittedly a lot more successful the second time around at managing expectations and being cool with being sick, but it was still a setback.

After all that, as I started to pick up my momentum again, my Grandpa passed away. This was obviously hard in personal ways that I will keep private, but even the little details surrounding the death were hard. We were all thrust into the pandemic life at mind-bending speed, but being yanked out of the pandemic life was hard in new and exciting ways.

A year ago I would cross the street if I saw someone walking towards me, fully believing that a wayward cough or a vigorous exhalation spelled certain death. Getting beyond those kinds of early, persistent impressions of the virus and doing once commonplace things like standing in a crowded airport security line, sitting shoulder to shoulder with dozens of strangers for hours on a flight, or even putting my mask down while eating at a restaurant: that was seriously hard.

Setbacks on top of setbacks. Missed deadlines, structural breakdowns, the loss of a family member. It’s hard.

The dark side of consistency

It’s easy to blow things out of proportion isn’t it? To extrapolate the consequences of a setback out into the far Lovecraftian reaches of madness. “At this rate, you won’t be releasing Mail File at all Andy!” intones the internal Critic. “If you were a Big Serious Business Man then of course none of this would have fazed you. Maximum commitment to the mission is paramount. External interference is to be ignored and brushed aside. Why, before you know it you’ll have failed math and given up your chance at a good job and a happy life full of hard work!”

Dumb, dumb George Michael!

But of course, I’m only human. There’s no way I could have anticipated any of this, and I’m just doing my best to get by. I wanted the startup in a month format to encourage consistency and rhythm in my work, but it’s become something which is hurting me more than it’s helping me.

The startup in a month format spoke to me because it gave me a clear structure to lean on. I thought it could help me avoid falling into an overambitious years-long development process for an idea that might not get any traction in the end.

It was supposed to be quick and to the point: a small idea executed over a short time frame with quick feedback. But I’m coming to realize that one month is too tight. A lot of other entrepreneurs have had success with it, but it’s too much pressure for this guy.

To be clear, consistency and rhythm are the lifeblood of progress. If you do a lot of small things with a consistent tempo over a medium to long duration, you can accomplish a ton of work. And accomplishing things feels great! Sticking to a plan and making obvious progress towards a goal is a virtuous cycle. It breeds more motivation to keep going, which makes it easier to be consistent.

And yet, there’s a dark side to consistency. Consistency can turn into a bludgeon to hit yourself over the head with when you don’t give yourself any room to breathe. Not meeting goals and pushing release dates back is hard. Watching my imaginary completion rate tick ever lower in my head is hard. It’s fallen from a supremely overambitious 12 startup products at the beginning of the year to maybe seven if I have a perfect second half of the year with zero setbacks.

When you add building in public to the equation, the importance of consistency takes on new dimensions. Social media algorithms love consistency, and people themselves like consistency too. We all operate on cycles and rhythms. If a given fan of the project knows that they can check out my blog or livestream and that there’s going to be something new waiting for them, that will deepen and reinforce their level of engagement with me.

Knowing this, the prospect of dropping the consistency ball once it’s up in the air can start to feel like a make-or-break proposition. If I can just keep the ball up there, I’m going to be making forward progress AND I’m going to keep people engaged with the project. If I drop it, then I start missing deadlines and followers. Losing both of those things at once can feel like a dire misstep.

I quit! Or maybe I just bend.

All that being said, I’m dropping the startup in a month format going forward. It feels scary to do so, but it’s also the right call. It feels like giving up in a way. I’ve been dragging some heavy “winners never quit, quitters never win!” baggage around with me for a long time. Starved, shriveled fingers are pointing at me from the black corners of my mind. Cursing me for giving up too soon and berating me for my foolishness. But I’ve seen enough to make a sound judgment call about this one.

I’ve developed a habit of seeking out symbols in the world ever since COVID hit. Could be a rabbit crossing my path in the middle of a run, could be a rainstorm, could be two people having an argument on the sidewalk. My mind has been grabbing onto these kinds of things, seeking the meaning and connections within. This video on Japanese knife making got caught in my net earlier in the week. Part of the video discusses how the combination of both hard and soft metals makes Japanese knives stronger:

Japanese swords are thin. Yet they never break, because there is soft iron inside. Hard steel covers the outside. This double structure prevents the sword from breaking. Japanese kitchen knives make use of this technique. Hard steel is in the middle with both sides wrapped in soft iron.

Pretty easy to connect a knife that’s too rigid to a schedule that’s too rigid eh? Life pushed too hard on my brittle knife, and it snapped. You can set all the hard deadlines and rigid structure that you want, and maybe you’ll reap the rewards of that structure for a while. But when life pushes too hard – and it will – you need some softness to bend with the pressure. Otherwise you’ll be left holding a broken knife. Much better to bend when you need to than to find yourself stuck with a grumbling stomach and a pile of uncut veggies.

The edge of uncertainty

So where does that leave me then? I’ve been thinking about a couple ways to add softness to my knife. Ways to make this thing I’m doing easier and more pliant when the winds of life come blowing. One way would be to get a partner to build with. When the whole world is riding on your shoulders, it’s hard to balance that big heavy rock on your back while simultaneously doing The Work.

I can go it alone. I have gone it alone a few times, but it’s been slow and painful each time. Having someone with me who could help me with the development work and avoid the pitfalls of becoming too stiff in my expectations and timelines would go a long way towards making things easier.

Formally moving to a two-month development cycle is another thing I’m going to try. If my ideas and development cycles are more or less naturally falling on a two-month interval anyway, then why not switch to that tempo instead? That way I get the benefit of structure without yanking my own chain too hard. Soft steel wrapped in hard iron.

We’ll see where this all leads.

I’ll leave you with a passage from Children of Dune by Frank Herbert. The theme at the heart of the Dune novels is prescience: the ability to see the future. Paul Atreides, the hero of the first book, acquired that knowledge at great expense to himself. He had absolute knowledge of the future, and it became a burden on him. He was forever trapped into one single, terrible path which he was doomed to walk, knowing where every single step would take him, yet unable to break free. His son Leto, seeing his father’s mistakes, has a different view on what it means to seek out knowledge of the future:

“Are you God, Namri, that you invoke absolutes?” Leto asked.

Both men merely stared at him without answering.

“Every judgment teeters on the brink of error,” Leto explained. “To claim absolute knowledge is to become monstrous. Knowledge is an unending adventure at the edge of uncertainty.”

I might feel a little foolish at the prospect of having “wasted” an opportunity such as this. Five months out of twelve spent toiling within a framework that didn’t work at all for me. All that time that could have been spent doing something easier with a higher chance of success.

And yet, the very price of gaining that knowledge of self is to adventure at the edge of uncertainty. To run your thumb against the edge of the knife, twist it and bend it to see how it responds, even to break the knife or cut your finger every once in a while. For the low price of a new knife, a bandage, and a little bit of time, I’ll be a better chef for it.

Alright, enough with the strained metaphors! Back to work ⛏👷‍♂️

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