Paolo, are you saying there’s a difference between Gen Y and Gen Z in freelancing, and companies should approach or hire them differently?

Yes, you’re absolutely right. There is a difference between how Gen Y and Gen Z approach freelancing, and companies definitely need to adapt their hiring strategies based on who they’re working with. These two generations come from different experiences and have developed distinct relationships with work, which means a one-size-fits-all approach won’t work.

Let’s start with Gen Y, or Millennials. They entered the workforce at a time when the traditional career path was still the dominant expectation. Many grew up thinking they’d follow the standard trajectory—get a degree, find a stable job, climb the corporate ladder, and eventually settle into a long-term career. But reality didn’t exactly match those expectations. They faced economic recessions, job instability, and the erosion of that “job security” promise they were raised with. As a result, a lot of Millennials turned to freelancing not as a first choice, but as a necessity. It became an alternative when the traditional job market couldn’t deliver what it had promised.

Because of this, Millennials often approach freelancing with a blend of **pragmatism** and experience. They’ve seen the flaws in the old system and freelancing has given them a way to take control, but there’s still this underlying connection to the idea of job stability. When companies work with Millennials as freelancers, they’re often dealing with professionals who have built up years of experience in traditional roles before jumping into freelancing. So, companies can expect a bit more confidence and perhaps a strategic approach from Gen Y freelancers. They often know what they’re worth, and they’re looking for meaningful projects where they can contribute their expertise. They may also be more likely to balance freelancing with other responsibilities or side projects, which means they’re going to be more strategic about how they allocate their time.

Now, Gen Z? They’re an entirely different story. They’ve grown up in a world where freelancing isn’t just a backup plan—it’s part of the mainstream. For them, freelancing represents freedom and autonomy right from the start. They don’t have the same attachment to the traditional career path that Millennials had, because they’ve seen from day one that it doesn’t always lead to success or security. Gen Z is more likely to embrace freelancing as a first choice, not out of necessity, but because it fits their vision of work: flexible, dynamic, and driven by purpose.

What companies need to realize is that Gen Z freelancers are more likely to be in exploration mode. They’re still defining their skills, testing out different projects, and figuring out what excites them. They may not have the deep well of experience that Millennials bring, but they make up for it with adaptability, creativity, and a willingness to take risks. Companies should approach Gen Z freelancers with that in mind. They might need more guidance or mentorship at first, but their energy and fresh perspectives can bring a lot of value to the table. They’re not looking for the same level of stability as Gen Y—they want flexibility and the chance to work on projects that align with their passions and values.

So, yes, companies absolutely need to adjust their approach depending on whether they’re hiring a Gen Y or a Gen Z freelancer. With Millennials, it’s about tapping into their deep experience and offering them projects that challenge them and align with their expertise. With Gen Z, it’s about providing opportunities for growth, experimentation, and creative freedom. Companies need to recognize that while both generations value autonomy, they come to freelancing from different angles and with different expectations. Treating them the same would be missing the point—and missing out on their unique strengths.