A post-mortem on my first project

Hey Everyone,

I've been intending to make an introductory post with a win in hand but it turns out that all I have to show right now is a post-mortem. Estimated time of death: Monday, July 20th, 2020. Though it didn't live long, just shy of ten weeks, it was my first.

The project aimed to deliver daily doses of good; tasks with such a small ask that it would be easy for people to say "wow, I can be a hero too!" Using inspiring quotes and gamified social mechanics, the idea was to gradually orient users toward a path of virtuous action.

Funny thing, even though the project is decidedly and irrevocably dead, as of a few days ago, I still want to qualify that it's probably a better idea than it sounds. Admittedly, that's colored by the fact I'm still mourning, so let's just dive into some of the lessons learned!

Lesson #1: Make as many high-level decisions as possible upfront

I was under the impression that I had the high-level stuff figured out, at least in broad enough strokes to begin implementing, but over and over again, I kept going back and revising. Agility is a good thing, to be sure, but not always.

At such an early stage, momentum was far more important than agility. Without the higher-level decisions completely fleshed-out, lower-level decisions were not made with the proper context and the bleeding of momentum led to a death spiral.

Repeatedly, I compromised between the larger vision and the demands of getting an MVP to market, and repeatedly, I compromised by distilling down feature sets into tangible milestones and then designing for those milestones.

The product lost its soul and the guiding vision lost its coherence.

My take-away is to remain mindful that milestones must remain subservient to an overarching vision. Or perhaps, don't compromise the vision — unless you're getting paid; at least that way, you'll be able to make an economically justified trade-off.

Lesson #2: Build something for yourself

Through the course of constant adjustment, I relied heavily on cost/benefit analysis and guided myself down the path of least resistance. Ultimately, the product was distilled down to such an extent that I, personally, wouldn't ever use it.

The philosophy of marginal value-add, of efficiently delivering value, whittled away the value proposition into nothing.

Despite recognizing this quite early on, I continued pushing forward, trusting this was only the first milestone of many to come; trusting the product would grow into something that I would want to use. Eventually. As it turns out, no one cares about your vision and future milestones. If you don't believe in your product as-is, no one else will either, and you'll never have the opportunity to reach those later milestones.

My take-away is to not make decisions out of expedience. This early in the product's lifecycle, the most important driving force is the blood and sweat of the founder, and if I'm not delighting myself, what's even the point?

Lesson #3: Try not to dictate too much

In my quest to design the perfect user experience, to build something that truly delighted users, and validating through user-research, I got lost. In the grander scheme, none of these were true-value add activities.

Without a doubt, learning is important, but there was simply too much faith in my ability to learn and approximate perfection. I kept trying to make the idea work. I kept chasing the elusive dream of "ready."

I was focused on the marginal output, not the outcome: nothing. Ready was the output, success was the outcome. I was running in place.

In hindsight, I can see that I was working with an insignificant amount of data; getting lost in the weeds instead of just shipping the damn product. Maybe if I did, I could've crashed and burned sooner.

My take-away is that a product's success or failure is not entirely up to me. All I can do is show up, the product has to stand for itself. No amount of engineering, whether it be in marketing, design of technology, is going to dress-up a bad product.

Lesson #4: Listen to your gut

A few weeks ago, in fact, around the half-way point between the project's birth and death, there was a moment of realization where I suddenly realized I wanted to work on something else. Something a little closer to my original inspiration.

In response, I moved some things around on the roadmap. Rebuilt some of the infrastructure designed in anticipation of future feature sets into something more able to facilitate current lines of implementation. I also wrote in my journal a writing prompt: explore why I took this "massive detour" in the first place.

The language is telling, don't you think?

Still, I wanted to believe the product had some merit and decided it would be worth pushing out anyways. At the very least, there was still more learning to do. Probably.

As it turns out, there was more learning to do! The lesson that I had not yet acknowledged is that I was already in the weeds. When you're in the weeds, you think your way through things with such a limited perspective that your productivity becomes counter-productivity. My motivation drained away; worse and worse decisions were being made.

My take-away is to listen to your gut. Given a moment of serendipitous clarity, I chose to keep chugging along, sinking time that I'm not going to get back. I should've killed the project then and there.

Lesson #5: Articulate your thoughts, fully and often

There's a certain ceremonial pain associated with writing what feels like a for-show, non-value-add report, but I can honestly say it's worth it ... most of the time.

In a report designed for consumption, you're forced to be concise and tease out the most pertinent details of what's happening. I mean, it's one thing to talk about work with friends and family, another thing entirely when explaining a detail to your boss, right?

Truly, it's bitter medicine to realize reporting methodical articulation, at frequent and regular intervals, is good for you! Even when there's no one breathing down your back.

My take-away is that it isn't possible to show for something that hasn't been fully articulated. At one point, I suspected my thoughts weren't fully articulated because there wasn't yet anything to show, but now, I believe it to be the exact opposite. Yes, there is some overhead involved, but one well worth paying.

And on that note, I look forward to sharing with you all my next steps! Expect to see much more of me.