The Curse of Could’ve
Like many other creatives, I’ve rarely ever had a shortage of ideas living in my head, completely rent-free. The shortage I’ve been blessed with to make up for these gifts, however, is that of willpower, focus, or abilities to channel those ideas into anything remotely productive. A lifetime supply of business ideas that could’ve made millions, jokes that could’ve launched my career as a stand-up comedian, lyrics that could’ve inspired a whole generation, content that could’ve gone viral. This is me. The guy that could’ve.
My ideas have always had bad timing. They come to me in moments that aren’t conducive to expanding on them or exploring them more deeply. Like when I’m on a subway and I have to get off at the next stop. Or when I’m running out of the shower to jump on a Zoom call that I’m already late to. For the most part, these ideas only exist in the interstitial space of doing other things. They’re never on time, and they leave almost as soon as they arrive. A few make it to the back pages of my Moleskine, scribbled no doubt. If lucky, some will get a shiny new entry on my Notes app.
Years later, I’ll be scrolling through my phone and discover a gem like this.
In the brief moment when this was committed to the page (or the pixel), it made perfect sense. A seed of a brilliant idea. The start of a joke. An idea for a webcomic. Or perhaps it was something philosophical. Who knows. I wrote that down in 2017. In 2022, it’s meaningless scrawl.
Similar morsels of audio can be found on my phone from over the years. Basslines that were never recorded. Hums that sounded genius in the moments they were conceived. These could’ve been songs by now. “Could’ve” has been the dominant story of my life so far.
Since 2015, and perhaps even earlier, I’ve had “Publish Medium Post” and “Start YouTube Channel” on my list of things to do. As platforms where I’ve spent the bulk of my internet cache-money, I’ve always been curious about what I might want to create or contribute to these spaces. Entertainment?Education? Esoteric ramblings? Year after year, the to-do list would lapse, and I’d find myself with a whole new 365 days to figure it all out.
At the start of this year, I discovered a note on my phone from September 2014 titled, “things I’ve learned in my 25 years here.” Like most of my notes, it was simply a seed of an idea, and barely two sentences had been written on the subject, but the memory of me typing out those words was sharp and brought into focus. It was the day I turned 25. I was living in Singapore. I was the youngest member on a team at a company I had always dreamed of working at. I was making decent money. I had a good set of friends. Life was pretty neat, and making it to a quarter century without any debilitating setbacks felt like enough of an accomplishment to warrant me writing about what I had learned or picked up that had helped me along the way.
For some reason, that idea had been sitting in drafts for 8 years.
I’ve never been one to pay heed to regret. I’ve always believed in owning my choices and accepting the consequences of my actions and words. Of recognizing my misgivings, learning from mistakes, and finding ways to move on. Of reflecting on foiled plans and making better ones for the future. But something about this particular note filled me with both sadness and regret. I had missed an opportunity to document a moment that felt personally significant. I had an idea about something I wanted to share with the world, but somewhere along the line, didn’t think it was important enough, or that anyone would care, or that I was even the right person to share it. Imposter syndrome. Procrastination. The lethal duo that has claimed every single one of my ideas.
I could only feel like I had somehow let down a younger version of myself. 25-year-old George seemed more optimistic, perhaps even naive, but now as a 30-something-year-old, I was responsible for not seeing his plans through. Things get strange when you think about yourself in the third person, or when you reckon with the unfulfilled goals of a younger you. I had an out-of-body experience that day that terrified me.
I’m scared to live a life of could’ves. This isn’t about posting on a blog or recording a song. Hardly that. It’s the fear that I’ll continue leaving ideas unexplored. That I’ll give up on them before I even give them a chance. That I’ll become used to telling myself that I’m not the right person to do something. I’ve had to recognize that it’s not bad timing—I’ve just had bad habits. Or more truthfully, I’ve had no habits when it comes to incubating, encouraging, or even implementing my ideas. I’ve barely ever given them the time of day.
I’ve been complicit in the curse of could’ve.
Over the past year, I’ve been trying to develop intentionality around my habits. I’ve tried to be more diligent with documenting ideas as they arrive, using tools like Notion to capture and categorize them. Structure has been my friend. My current goal is to create more discipline and rigor around my daily practices to find the time, space, and mental clarity to focus on these unexplored ideas.
After years of going unchecked, I finally crossed those two items off my to-do list. In Jan, I published my first piece on Medium. Last week, I uploaded my first video to YouTube. These aren’t big accomplishments by any means, and hardly worth celebrating. But they’re a start to something, and I’m excited to see where it goes. I don’t know if this is the stuff I even care about sharing. I don’t if there’s an audience for any of this. I don’t know how to motivate myself to keep momentum. I don’t know if I’ll burn out.
All I know is that there’s a leap of faith one has to take when putting stuff out into the world. And sometimes the best way forward is to just hit “Publish.”
