This is my story of how I came to create On Top. As background, I was an attorney practicing at a small litigation boutique, owned a few preschools with my wife, and am also the parent of two young children. I never had any experience with software or app development.
Ever since I was in high school, I had aspirations of being the kind of person who organizes their life in writing. As a teenager I was mildly obsessed with Moleskine notebooks. I bought various sizes from Barnes & Noble and purchased fancy-looking gel pens. I made attempt after attempt at using them to keep a journal or to use as a daily planner. If you dug those Moleskin notebooks out today, you’d find my dense, tiny scrawl across the first couple pages followed by an entirely blank notebook.
Still, my dream of being a “list person” never died. In law school it occurred to me that the problem with Moleskin notebooks was the non-spiral-bound spine, which forces the writer to use their non-writing hand to hold down the opposite pages. I thought getting a spiral-bound notebook would make all the difference. But again the result was the same–a few days of trying to make the habit stick before the notebook got abandoned to some high shelf.
Around 2015 I learned about bullet journaling and felt I’d found the missing formula. Perhaps the level of detail I had been putting into my attempts was the problem. A bullet-point system ought to fix that. I found a really fancy spiral-bound notebook on Amazon. It had thick, creamy pages. This attempt actually worked for a while, but slowly the habit started to fade until it too died away.
Two issues I’ve had all my life are clammy hands and gripping pens too tightly. So the experience of handwriting is genuinely unpleasant. The pages get damp from my hands and my fingers cramp up. So around 2018 I gave up on the idea of ever being a paper-and-pen person, but I still wanted to count myself among the hyper-organized. Workflow apps seemed to be the key. Over the past few years I’ve tried almost everything–Todoist, Notion, ___. Don’t get me wrong–every one of those apps is amazing and I wish I were the kind of person who could organize their life and automate workflows with all of the sophisticated features. But I didn’t have the discipline to make the habit stick, and I never found that the structure suited my way of thinking.
With so many things to keep track of in my life though–between the work at the law firm, the preschools, home, and kids–I needed something to keep track of it all. Eventually I settled on Microsoft’s to-do list app. I set up different lists for the different spheres in my life–work, business, home, shopping. But over time, I realized that I wasn’t even taking the few seconds it would take to find the right list. Instead, I was just putting everything into the default “Tasks” list that appeared when I opened the app.
When I say everything, I meant it. There would be a reminder to respond to some email opposing counsel sent me, then just the word “Coffee beans” to remind me to buy coffee beans, and under that would be a reminder to schedule a repairperson to look at some broken blinds at one of the preschools. When I went to the store, I would scroll up and down through the whole list and check off all the groceries as I grabbed them.
Eventually I realized that what I wanted was an app that could