Gustavo Figueroa
08/13/2025
It all started in 2020 with a nagging feeling. I was knee-deep in an online bootcamp, tasked with my first major project: find a problem, and design a solution. The world was my oyster, but my mind kept circling back to one thing, planning. Or rather, the utter chaos of planning.
I knew there was a problem because, despite living in a world of cutting-edge technology, I still felt my trusty pen and paper was the best method. Something was broken. Have you ever tried to wrangle your daily life with Google Calendar? It's great for that repeating Tuesday meeting, but what about the spontaneous, ever-shifting reality of our days? Creating a new entry for every little thing felt like a chore. "Repeat?" my calendar would ask. Honestly, who knows? Some parts of our lives are predictable, but so many aren't.
Pen and paper, my old friend, wasn't without its flaws. Lugging a notebook everywhere is a hassle, and have you ever tried to erase a canceled plan five times? It's a messy, frustrating experience. Sharing your hand-crafted paper plan with others? Forget about it, it's near impossible.
My quest for a better way led me down a rabbit hole of productivity apps. I downloaded them all, and a familiar pattern emerged. Each one greeted me with the same blank slate: "What do you want to create?" So, I'd spend what felt like an eternity dumping my to-do list into the void. For some, this digital dedication is a way of life. They've mastered the art of constant updates and have become one with their chosen app. For me, it felt like I had just signed up for a second job. Instead of making my life easier, it was just more work.
I found a temporary haven in my phone's notepad. It was simple, quick, and always with me. I got hooked on the convenience during my iPhone days and even found a worthy replacement when I switched to Android. But let's be honest, a notepad is a beautiful mess at best. Organization? Not its strong suit.
This journey through the digital and analog tools of planning brought me to a critical realization: it wasn't just about my own frustrations. I needed to know how everyone else was coping. I mean planning is a part of all of our lives whether we like it or not.
So, I started talking to people. I interviewed friends, colleagues, and strangers about their planning pains, and what I discovered was fascinating. It turns out, the world is divided into two camps: the dedicated planners and the non-planners.
The serious planners thrived on structure. They found joy in the organization and were often the designated "planner" of their friend group. While they sometimes felt the pressure of that role, they loved the sense of control it gave them. On the other side of the spectrum were those who saw planning as a creativity killer, a rigid set of rules that sucked the spontaneity out of life. Interestingly, even this group admitted that having a loose plan to reference was helpful; they just didn't want to be chained to it.
All of this invaluable insight led to a single "aha!" moment. What if there was a way to cater to both?
And so, Dayout was born.
It was designed to be the bridge between the planners and the non-planners. An app that empowered the organizers to create and share their brilliant plans, and allowed the more free-spirited among us to easily view, adopt, and adapt those plans to our own calendars. The key was flexibility. Edits were simple, making the plan less of a rigid decree and more of a starting point.
That's the origin story of Dayout. It's a tale of personal frustration turned into a collective solution. And as they say, the rest is history.
