Chapter 1 The Reality of Freelancing

When I embarked on my freelancing journey, I wish someone had shared these insights with me. The internet is filled with enticing tales of success that often encourage individuals to leave their stable jobs in favor of the freelance lifestyle. They promise a blissful existence with four-hour workdays and the freedom to embark on multiple exotic vacations throughout the year. (Of course, there's always a pricey course available to teach you how to achieve this.)

Yet, these narratives often gloss over the real struggles of making freelancing work. Even when they do touch on the challenges, it’s usually through tired clichés.

"I faced impostor syndrome and it held me back."

"I couldn't sleep, always stressing over my workload."

While these sentiments are genuine challenges, they are far from the only obstacles one encounters. After 15 years in this field, I can confidently say that issues like impostor syndrome and anxiety can be managed or even resolved over time. However, certain problems are inherent to freelancing and should be carefully considered before leaping into this career path.

Transitioning from a regular job to freelancing may seem straightforward, but reversing that decision can be quite the challenge. The longer you freelance, the tougher it becomes to return to a conventional job.

Despite these hurdles, I have chosen to continue freelancing. At the end of this discussion, I'll explain why I've embraced the idea of becoming virtually unemployable.

Chapter 2 The Modern Workplace's Limitations for Freelancers

I started my freelance career 15 years ago, at a time when remote work was not entirely novel. Although society has become more accepting of it since then, it still feels somewhat unconventional. Much of today’s infrastructure seems tailored to accommodate traditional 9-to-5 employees, leaving freelancers like myself at a disadvantage.

In fact, the tax system in my country treats me like an anomaly. I've faced more audits than anyone I know, each one an exhausting process requiring a meticulous review of every invoice and receipt from the last seven years.

I must ensure my filings are immaculate. I don't hold the tax authorities responsible; the contrast between my income and expenses as a freelancer versus a regular employee is stark, often flagging me for audits.

Moreover, I can't count on the same health insurance or pension plans that most employees enjoy. I have to navigate health insurance options and plan for my retirement on my own.

It's also frustrating to define my "profession" on official paperwork. I often struggle to answer questions related to my employment status on forms for banking, taxes, or immigration.

Freelancing means I don't always get to focus on the same projects. It's a "feast or famine" kind of work, where I might find myself writing a cartoon script for one client while simultaneously drafting a report on corporate mergers for another.

This juggling act poses a challenge when trying to articulate what I do.

Chapter 3 The Quest for Specialized Skills

As a freelancer, you quickly learn to adapt to a wide array of projects, which broadens your skill set. However, this variety also makes it difficult to develop specialized expertise.

In a traditional corporate role, you benefit from the stability of a structured environment, allowing for deeper learning. Mistakes are often buffered by the organization, giving employees the opportunity to master their craft.

Freelancers, on the other hand, must cultivate a diverse skill set to thrive, which might be fine for those with an entrepreneurial mindset. However, if you're balancing both corporate and freelance work, you may find yourself stuck in freelancing for too long, complicating a return to the corporate world.

Even if you manage to switch back, you may have to settle for a generalist role, which might not align with your career aspirations.

Chapter 4 The Hard Lessons Learned

In my 15 years of freelancing, I’ve developed a tough exterior. It became necessary to cope with the many humiliations I've faced in this line of work.

I often encountered clients with more resources who took advantage of my situation. There were times when I dedicated hours to a project, only for the client to vanish without payment.

Once this happens, my recourse is limited. A demand letter has little power behind it when I lack the means to enforce it.

I've experienced having my work stolen and faced skepticism from prospects questioning why they should collaborate with someone they perceive as a nobody. This kind of humiliation can also come from former colleagues who no longer return my calls.

Even my long-term bank or credit card company downgraded my status, citing my changed circumstances. It's all just business, but it can feel personal.

Having been in this arena for so long, these experiences have become less impactful for me. However, they can be discouraging for others who encounter similar challenges.

Chapter 5 The Realities of Financial Stability

I’m not here to dissuade you from pursuing freelancing or leaving your 9-to-5 job. The key takeaway is simple: don’t pursue freelancing solely for financial gain, as you may end up disappointed.

When I left my corporate job in 2007 to pursue freelancing, I was not alone. A former colleague joined me, but she eventually returned to the corporate world after struggling to find success. She flourished as a recruiter, accumulating enough commissions to build a real estate portfolio and achieve financial independence.

While I have managed to make a living through freelancing, my former colleague thrived in her career. Many people initially think they can earn more as freelancers compared to their corporate jobs, and it’s often feasible in the early stages.

However, as time passes, your freelance income might plateau, and you might still be earning only a fraction of what your former colleagues have achieved through promotions and raises.

This is a reality that you must accept. The potential earnings as a freelancer can vary widely, from just enough to get by to significantly higher than a previous salary.

The only certainty in freelancing is the freedom to choose your hours, projects, and clients.

For me, that freedom outweighs any financial considerations.

Freelancing also provides unique experiences that you may never encounter in a corporate job. The stories you'll gather are priceless.

Reflecting on my years as a freelancer, I’ve had experiences ranging from the mundane to the extraordinary. From writing about water purifiers to drafting scripts for educational cartoons that never aired, each opportunity has contributed to a thrilling journey.

I even convinced a human trafficker to change his ways, helped a lawyer uncover hidden assets, and created a business plan for what would have been my country’s largest nursing home.

Although not all these ventures were financially rewarding, they have collectively created an unforgettable adventure I wouldn't trade for anything.

For more insights on financial management, be sure to explore this curated list of articles.

This article is for informational purposes only and shouldn't be taken as financial or legal advice. Always consult a financial professional before making significant decisions.