Side Hustles That Stand the Test of Time: Lessons from Projects That Evolved

Late 2023, I created an Instagram account with the intention of posting daily to grow an audience surrounding my thoughts on primarily on productivity and parenting. I crafted a content calendar, social media strategy, and brand colors to kick off my new account with a sense of professional and aesthetic unity. My struggles began when I started trying to fill that calendar. I spent hours tapping from Instagram story to the next and swiping through reel after reel, frantically taking note of the latest trends and popular themes within the sector I wanted to enter.Yearning to replicate that success, I attempted my own versions of those posts, but the resulting content felt uninspired and mediocre. I became disillusioned as those lackluster posts garnered even worse than subpar engagement once published.

Photo by Garrhet Sampson on Unsplash

Over a few months, my efforts steadily dwindled until I finally stopped entertaining the idea that I would make something of this account and stopped altogether. I just couldn’t muster any excitement to do the necessary work, reluctantly deciding to instead accept my failure and move on.

This was not my first failed side project - regrettably, there were many. I started a different Instagram account in 2020 to showcase my artwork. I uploaded a few sketches before my enthusiasm fizzled out and I stopped a few months later. In 2017, I started a blog to document a study abroad trip to Brazil. I posted once and then never again. In 2015, I attempted to mimic an influencer who actively tried to reduce her trash production, collecting all her waste in a single mason jar. My efforts for that ended after a couple months. Each time, I faced the disappointment and frustration of yet another side project failure.

This most recent failure, however, ended differently. Instead brushing it aside and moving on to something else, I seriously thought about why I failed. After a few weeks of deep thought, I finally discovered the root of the problem and its remedy. My main flaw in creating content was an intense desire for somewhat immediate success, which had led me to an almost obsessive focus on churning out trendy, popular posts. The realization struck me hard, as I recognized how this single-minded pursuit of external validation had been the downfall of so many of my past side projects.

Projects driven by a desire for immediate external validation - like chasing views, clicks, and likes - end up trapping the creator in an incessant cycle of constantly seeking approval from their audience. The momentary pleasure of that external validation is short-lived, leading to an insatiable need to keep generating more of it. This places the creator's psyche and their work at the mercy of their audience, as they prioritize seeking approval over developing true self-respect and honing their craft. Ultimately, projects pursued solely for external validation are easily abandoned when they don't gain traction quickly or the validation dries up.

For example, I was charmed by my colleagues’ praise for being more conscious about my trash production, but it was not enough to motivate me to do uncomfortable things like bringing my own containers or avoiding plastic-wrapped items. With the blog, I was so preoccupied with what others would think that I could never actually publish anything. And with the art account, I was so consumed by creating content that would be loved by others that I ended up paralyzed, unable to even put pencil to paper.

I came to know that same paralysis again when trying to brainstorm ideas for my most recent Instagram account. The overemphasis on trends sapped me of creativity, leaving me with ideas that felt unoriginal and boring. Focusing too much on the success of these posts stifled my ability to generate original and exciting ideas, as I was solely preoccupied with stimulating popularity. I was living, once again, the reality that side projects driven by external validation often lack sustainability and value.

By 2024, however, I was equipped with new knowledge stemming from 6 years of start-up experience, which left me with a greater understanding of the trajectory of successful businesses. Over night successes are exceedingly rare if not nonexistent. In actuality, young businesses that turn into something over time go through various stages of iterations, often transforming into something very different from its original form.

For example, the YouTuber MrBeast started his channel in 2012 at age 13, initially producing low-quality video game streams on his brother's old laptop. After saving for six months, he was able to upgrade his equipment. MrBeast finally went viral in 2017 with his "counting to 100,000" video. From there, his ideas continued to grow in scale, rapidly gaining subscribers and expanding his business to include brands like MrBeast Burger and Feastables, as well as philanthropic efforts. By 2024, MrBeast had become the creator of the most-subscribed channel on YouTube.

Another example is VanDamme Academy, a K-8 private school in Southern California founded by Lisa VanDamme. Before starting the school, the then-20-something VanDamme was initially recruited to homeschool just two children. Over the course of 25 years, this small homeschooling effort evolved into a successful private school with 14 faculty members.

How were MrBeast and VanDamme able to sustain such multi-year efforts? In short, they were not doing it for me or you or the general public. They were acting on a deep and personal internal motivation.

VanDamme, for instance, recalls taking the homeschooling job as a form of protest against her own education. On the VanDamme Academy website, she states, "This job would be an opportunity for me to offer my students an educational experience utterly unlike my own." That underlying motivation to provide a radically different educational approach than what she had experienced herself stayed with her, and it was this very idea that ultimately led to the development of VanDamme Academy.

MrBeast recalls his desire to make ever better videos, games, and services, stating in an interview with Lex Fridman “I want to obsess over making a great product.”

While their motivations differ drastically, VanDamme and MrBeast had one important similarity: they wanted to create something that they wanted to see more of in the world. They came to their work with a deep, personal desire to fulfill a personal goal, to fill some gap they saw in the world, and they did.

Instead of relying on trends and worrying about what others want, the lesson here is to strive to create something that you want to see more of in the world. To quote MrBeast in regards to his audience, “I don’t try to pertain to them, I just make whatever I think is interesting and good content.”

Adopting this outlook transformed the way that I think about my projects. Now, I prioritize the topics that I personally find to be the most fascinating and important. I share my work with the sincere hope that other people will find it as valuable and meaningful as I do. This shift in mindset has reignited my passion and drive, propelling me forward in a way that feels deeply fulfilling and sustainable.

In all honesty, I don’t have a personal goal or mission succinctly defined like that of VanDamme or MrBeast. But I have a direction, which is more than I have ever had in the past. I know that I want to see better, more thoughtful writing on subjects surrounding art and design, but I am still figuring out the specifics.

That being said, I don’t think it’s necessary to have a mission all figured out to start. There is still room to perfect your craft without a well-defined personal call-to-action. The underlying motivation is important for a long-lasting endeavor, but the specifics will emerge over time, experience, and introspection.

For now, just get started on something you care about. Look around and find what you want to see more of and create it.