It’s no secret that younger generations, Millennials and Gen Z, are leading the freelance revolution. Nearly half of Gen Z say they’re freelancing. But that doesn’t mean that older folks, Boomers and Gen X, aren’t taking part as well. In fact, North America in particular has a much wider range of age groups living a freelance life compared to other regions across the globe. Many older people have taken up freelancing for the same reasons as millennials and Gen Z: flexibility, work-life balance, being your own boss, etc. But each generation has its own priorities and approach.


Flexibility is at the center of our freelancing revolution in this country and is the primary reason younger workers are pursuing a freelance lifestyle. In fact, many Gen Z are skipping traditional work altogether and becoming freelancers right out of school. As the popularity of freelancing has grown, so has its perceived viability. The past decade has seen a massive increase in freelancing, which has created clear pathways for younger talent to follow.

Millennials and Gen Z aren’t fools. They understand that this lifestyle is difficult, but having grown up in a digital world, work and play have already blurred together. They’re comfortable with any hour of any day being a work hour or a play hour. Gens Y & Z have entirely redefined what we mean by work-life balance. Rather than having a boss that’s chill about when you take your vacation, they would prefer not to have to run their decisions by anyone. Work on the beach today, go on a hike tomorrow.


Older generations of workers definitely care about flexibility, but it’s not as big of a priority. Many report higher satisfaction when working at a company that allows greater work-life balance, but Boomers and Xers aren’t going out on their own just for the freedom. A lot of them have too many commitments for that to be the reality. Mortgages, car payments, and the exorbitant cost of kids drive a greater dependency on steady income that’s unlikely in freelancing.

Pursuing a freelance lifestyle is also a significant cultural shift. Workers who are a bit more ‘long in the tooth’ came of age in a time when the traditional employment relationship was the only option for them. That’s what they’re used to, and change is hard. Even when they do make the switch to freelancing, many boomers and Xers tend to recreate the full-time career they had in a freelance capacity. That being said, their decades of work give Xers and Boomers a big advantage, with richer portfolios of work and more established networks. They can leverage these assets to recreate the “job” they had before, as a freelancer. While these workers may have more financial commitments, they also have greater financial stability than younger people. They have the savings to start a freelance career without worrying about when their cash flow will become more consistent.

Perhaps the biggest reason these generations (Boomers especially) are stepping toward freelancing is that people are living longer. Stopping work at 65 and living off social security isn’t realistic if people are living an extra ten years. Whether it’s to stay active or shore up their savings, older folks are pushing off retirement to keep working, and that work is freelance. They’re finding it to be a good option too; allowing them to work on their own schedule, as a nice transition into eventual retirement.


As many experts have said, the pandemic has mostly accelerated changes that were already progressing. Freelancing is a good example. Work has steadily decentralized over the past century, with each generation pushing it a bit further from the 9-5, Monday-Friday reality of the 1950’s, 60’s, 70’s, 80’s, etc. Innovation was happening, and world-shaping events like the pandemic serve as tipping points. Much of the reason we’re seeing this trend accelerate is that freelancing really works! Freelancing is a practical and rewarding way to make a living, and every age group is primed for it.

Freelancing is the new reality for knowledge workers, across all generations. Anyone can freelance, and freelance well. So if you’re on the fence because of your current age or stage in life, know that no matter your generation, it’s time to get in the game.