What Generational Gaps Between Side Hustlers Signal About the Future
By: Sid Khaitan
Tags: Freelancing, Side Hustle, Startup, Entrepreneurship, Generation Z

What Generational Gaps Between Side Hustlers Signal About the Future

A perfect storm of pessimism, idealism, and realism

Photo by Markus Spiske from Pexels

Why did you decide to start a side hustle as a millennial?

The professor looked in my direction, catching me completely off-guard. Born in ’94, I was the only Millennial on the panel. But I didn’t identify at first. Especially after spending a lifetime patronizing my little brother for his typical Gen Z ticks. A sign of the times.

What happened next reveals a glimpse into the future.

Generation X lived through the ’08 financial crisis

After some prodding, my fellow panelist Sam opened up about her journey. To her, starting an SEO agency after college was also about capitalizing on a gap in the market. Not many others were doing it, and she knew how. So she sold a service to open up another source of income.

Plain and simple, but also elegant.

As someone who survived the recession and watched her family live on a strict budget, she prioritized job security over freedom. Sam had no false qualms about the nighttime job replacing the daytime one. She asked clients for a 24-hour advance notice before calls, tiptoed the line around job expectations, and deployed a “don’t ask, don’t tell” policy.

The full-time gig took precedence between the hours of 9 to 5, and she took a structured and disciplined approach. It was a way of hedging against the continuous pessimism she felt about companies and the overall economic outlook.

70% of executives surveyed believe that Gen X make the best overall workers. But isn’t there a good chance that most of those executives are Gen X?

Millennials are independent and purpose-driven

I started my first business at 19 (*if you don’t count the lemonade stand or babysitter club). It was a fitness apparel and supplement line, built at the intersection of opportunistic spark and misdirected passion.

At the time, I began to see others launching brands in the space. It looked cool, and I wanted to make more money. The barriers to entry weren’t astronomically high. So I came up with a product, drafted a plan, sourced a supplier, hired a graphic designer, and started selling.

It was going pretty well until I realized that it wasn’t for me. I wasn’t excited about selling protein powder and t-shirts. I didn’t feel good about making money from it. I couldn’t convince myself that I was solving a big problem.

So I took a step back and decided to work full-time in healthcare. Sooner than later, the itch came back. Within a year I launched a side hustle of drafting technical B2B content for cybersecurity start-ups and hired two incredible writers to help.

It felt good. Aside from the fact that the companies and teams were making an incredible impact, I was doing work that I enjoyed. On my own terms. Even more importantly, I had some level of financial freedom and purpose. After surfing friend’s couches throughout college, it felt nice to not worry about job security.

Don’t get me wrong, I still reviewed company policies, notified managers, and contributed at work. But I didn’t feel much pressure, I knew that I had plenty of bargaining power of my own. So I bounced across industries and functions, invested in my spare time, wrote for clients and had fun with it.

The concept of social responsibility and ethics would bubble up from time to time. Was I leaving a positive footprint on the world? Then I’d go back to being lazy, making money, doing cool work, and creating more time.

To summarize, I initially started a business to seize a market opportunity. Over time, motivation became more intrinsic. The focus evolved into scratching an itch and fulfilling a lifestyle.

Generation Z meant to be digitally-enabled nomads

Pretty sure John was texting when his name was suddenly called during the panel. Asked about his start, he told a story going back to the middle school days.

John had been managing social media accounts for hard cash since the age of 15. He always had ambitions of bootstrapping a start-up, tapping into the power of technology early as a way of generating scale.

By the time he was 20, John had found a way to get bored at his job, hired and fired multiple employees, but then stumbled his way into being broke. Life had turned him into a realist, and he became skeptical of the American dream after watching his immigrant family struggle.

He grew up in a world in which social media and technology always existed, exposing him to continuous globalization, disruption, and “digital transformation”.

So he decided to figure it out on his own. Restarting the agency, he quickly sold his first product. It was an online course, and it was a hit. Thousands of positive reviews and ridiculous amounts of money to come with.

So I ask: Is the future so bad in the hands of millennials and Gen X? Maybe we won’t be the hardest workers, but we might just be the most capable when it comes to leveraging technology, building efficiency, and finding purpose.

And although we all bring different mindsets to the table, we can play to each other’s strengths and styles to build better companies. Ones that drive impact by fusing the pessimism, idealism, and realism spread across the generations.