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The Weight of Old Habits: Why Many Struggle to Start Freelancing

Step out of the comfort zone and embrace freelancing. Explore the mindset shift, challenges, and freedom Millennials need to break free and reinvent their careers.
December 14, 2024 by
The Weight of Old Habits: Why Many Struggle to Start Freelancing
Laura De Troia
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On the heels of yesterday’s reflection, I found myself thinking about all those who dream of leaving the comfort zone of traditional employment to embrace the thrill of freelancing. These are the people who genuinely believe in their ideas, their ability to carve out a new path, and their readiness to build something of their own.

Theoretically, it seems straightforward. You have the idea, the intention, and the skills to turn it into reality. But then, something happens—or doesn’t—and you’re stuck in limbo, unable to move forward and bring your vision to life.

AUTHOR : Laura De Troia

X-Wise Lead | Business Growth Mentor

Laura De Troia heads X-Wise, the business academy of Xtroverso, with a passion for empowering professionals. Combining strategic insight and practical expertise, she helps freelancers and entrepreneurs master the skills needed to thrive and grow in today’s dynamic world.


The Freelancing Limbo: Why Can’t We Move Forward?

This question hits particularly close to home for us Millennials. Why? Because we’re the product of decades spent in the traditional workforce. We’ve grown up professionally in environments—big or small—shaped by rigid structures, defined hierarchies, and management systems. Call them what you want, but these systems have become our cages.

For Boomers and Gen Xers, the story is slightly different. Many of them are nearing the end of their careers, making them less inclined to embrace change or venture into the unknown. For them, the road ahead feels shorter, and the comfort of the familiar often outweighs the thrill of starting anew.

But Millennials? We’re stuck right in the middle. We’re at the midpoint of our professional lives, standing at a crossroads. Do we continue spinning on the same merry-go-round, bound by the safety of a steady paycheck, or do we take the leap, carrying our accumulated knowledge and skills into the uncharted territory of freelancing?

Carrying the Weight of Old Habits

Here’s the catch: many of us try to dip our toes into freelancing but never fully take the plunge. Why? Because we’re dragging a heavy, often unconscious, weight that keeps us tethered to the familiar. This weight isn’t just practical concerns like finances or stability; it’s the mindset we’ve internalized from years of working within systems designed by someone else.

We’re trained to follow rules, navigate hierarchies, and operate within the confines of predefined roles. Breaking free from that structure isn’t just a logistical challenge; it’s a psychological one.

If we don’t shed this employee mindset, we’re destined to stay stuck in limbo, endlessly circling our ambitions without ever landing on solid ground.

The Path to Reinvention

The good news? It’s possible to break free. But let’s not sugarcoat it: it’s a tough journey. Stepping away from the safety net of traditional employment means facing fears, climbing steep hills, and navigating the unknown.

But the view from the top is worth it.

As Millennials, we’re uniquely positioned to bridge the gap between the old and the new. We can take the humanity, the skills, and the lessons we’ve gained from our time in the corporate world and use them to create something entirely our own.

The Invitation to Reinvent

This is a call to action for Millennials. Let go of the cages that have confined you. Abandon the mental and physical structures that have dictated your work life. Keep the best of what you’ve learned, but use it to write a new professional story—one where you make the rules, because you’re the one inventing the game.

Freelancing isn’t just a career choice; it’s a mindset. It’s about reclaiming your autonomy, embracing the chaos, and trusting that you have what it takes to create something fulfilling, meaningful, and entirely yours.

The question isn’t whether it’s possible—the question is whether you’re ready to take the first step.


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