Freelancing: The Good, the Bad, and What No One Tells You

We've all seen the posts. "Make your own hours! Be your own boss! Work from anywhere!" The freelancing life gets painted as this perfect escape from corporate constraints, and honestly, some of that appeal is real. But it's not for everyone.

I made the jump from structured corporate consulting to freelance work back in 2017. Since then, I've mentored others through the same decision. What I've learned is that while freelancing can be incredibly rewarding, there's another side that most people don't talk about. That is what this post is really about.

I started at a consulting back in 2010, working 50+ hour weeks at a mangerial accounting firm. The structure was clear, the expectations were set, and the paycheck was predictable (mostly). In 2017, I transitioned to freelance consulting with two partners. Eight years later, I've not only navigated my own freelance journey but built a team of 30+ freelancers. Working with so many different people has shown me patterns in who succeeds and who struggles.

This is what I've shared with those I've coached, and how to know if becoming a freelancer is the right move for you.

The Benefits of Freelancing (Why People Fall in Love with It)

Freedom and Flexibility really do exist. You set your own hours, choose your projects, and decide how you want to work. If you are most productive at 6AM or prefer working three-hour blocks, you can design your schedule around that. Want to work from a coffee shop, your home office, or while traveling? There's something powerful about having that level of control over your time.

Ownership is another major benefit. You get to build something that feels genuinely yours. Every client relationship, every project success, every business decision reflects your choices and efforts. That sense of ownership can be incredibly rewarding.

Variety keeps things interesting. Working with different clients and projects means you're constantly learning and adapting. Each client brings their own challenges, goals, and working style. That diversity can keep your work feeling fresh and engaging.

Potential Income Growth is real, but it comes with a big caveat I'll talk about later. Unlike a salary, your earnings potential isn't artificially capped. If you can find the right clients and deliver exceptional value, you can grow your income significantly.

These benefits are why so many people are drawn to freelancing, and they're legitimate reasons to consider it.

The Challenges of Freelancing (What Social Media Doesn't Show You)

Now for the parts that don't make it into the motivational posts.

Income Uncertainty is probably the hardest part to get used to for new freelancers making the transition from full-time employment. Some months you're booming, others can be uncomfortably lean. Even when you think you have a steady client, projects end, budgets get cut, or priorities shift. That predictable paycheck? Gone.

Wearing Every Hat means you're not just doing the work you love. You are also the marketer, the salesperson, the accountant, the project manager, and the customer service representative, just to name a few. If you became a freelancer to focus on your craft, you might be surprised by how much time you spend on everything else. This is one of the biggest differences between freelancing vs full-time employment.

No Built-In Benefits hits harder than most people expect. You're suddenly responsible for your own health insurance, retirement planning, and time off. There's no HR department, no company-matched 401k, and definitely no paid vacation days. Every day you don't work is a day you don't earn.

Constant Context Switching is mentally exhausting in ways you don't realize until you're there. In a traditional job, you essentially have one client - your employer. As a freelancer, you might juggle multiple clients, each with their own team members, communication styles, project management systems, and preferences. Remembering the different personalities and expectations across all your projects can be surprisingly draining.

The Hard Truths About Self-Employment

Here's what may not make it to your social media feed.

Not Everyone Is Cut Out for Freelancing. AND THAT IS OKAY! (She shouts from the hilltop.) I've seen talented, capable people struggle with freelancing not because they lack the skills, but because the lifestyle doesn't match their working style or personality. Freelancing involves a particular way of working that some people love and others find challenging, and that's completely okay.

Always Selling is exhausting and, in my experience, the number one reason people end up going back to corporate after freelancing. Even when you have plenty of work, you need to keep marketing yourself to maintain your pipeline. The hustle never really stops. You're constantly networking, pitching, following up, and trying to stay visible in your field.

Clients Can Be Demanding in ways you may not think. Scope creep is real. Late payments happen more often than you'd like. Unclear expectations can turn a dream project into a nightmare. You'll encounter clients who change their minds constantly without understanding the impact on your timeline, or who expect immediate responses to non-urgent requests.

Work-Life Boundaries Blur more than you might expect. We genuinely want to do good work for our clients, but that desire can lead to checking emails at 10pm or working on weekends. When your home is your office and your phone is your business line, it takes intentional effort to create boundaries that don't naturally exist. Learning to switch off is possible, but it doesn't come easy and takes time to master.

Who Should Become a Freelancer?

From my experience, certain types of people tend to do well as freelancers.

Self-motivated and adaptable people who can create their own structure and pivot when things change. If you need external accountability to stay productive, freelancing might be challenging.

Those comfortable with uncertainty and risk who can handle the ups and downs of irregular income and changing project demands. If financial predictability is important to your peace of mind, the freelance lifestyle might create more stress than freedom.

People who enjoy learning and like variety tend to thrive in the diversity that comes with running their own business. If you get energized by tackling different types of challenges, freelancing can be incredibly engaging.

Those who thrive on autonomy and problem-solving often love the independence that comes with being their own boss. This type of person may find the decision-making freedom refreshing rather than overwhelming.

Who Might Struggle with Self-Employment?

Not surprisingly, there are also patterns in who find freelancing harder to navigate.

People who need structured guidance and predictability might find the open-ended nature of freelancing overwhelming rather than liberating. Some people are most productive with established frameworks and processes.

Those who value a steady paycheck and built-in benefits might find the trade-offs harder than expected. The financial uncertainty and responsibility for your own benefits can be genuinely stressful.

People who dislike marketing or negotiating will struggle with the essential parts of freelancing. If the idea of constantly promoting yourself or negotiating rates makes you uncomfortable, freelancing might not be the right fit.

Those who get overwhelmed by juggling multiple roles might find the variety of responsibilities more exhausting than exciting. Not everyone enjoys switching between being a salesperson and a service provider multiple times in one day.

Should You Become a Freelancer?

Is freelancing right for you? It can be incredibly rewarding, but it's not a one-size-fits-all solution to work dissatisfaction. I've seen people thrive in ways they never could in traditional employment, and I've seen equally talented people struggle with aspects of self-employment that don't match their working style.

I personally love freelancing and wouldn't change it for the world. But I've learned that my enthusiasm doesn't mean it's right for everyone. What I want is for people considering this path to go in with their eyes wide open, understanding both the incredible opportunities and the real challenges.

What matters most is being honest about your own preference, work style, and risk tolerance. The freedom that energizes one person might feel overwhelming to another. The uncertainty that excites some people might create anxiety for others.

I personally enjoy the variety and autonomy that comes with freelancing, but I completely understand that it's not for everyone. What works for me might not work for you, and that's perfectly okay.

If you are considering making the transition to freelancing, take the time to really think about what motivates you, what drains you, and what kind of work environment helps you do your best work. Be honest about your relationship with risk and uncertainty. Consider whether you genuinely enjoy the business side of running your own operation, or if you'd prefer to focus purely on your craft.

The key thing to remember is that there's no wrong choice when it comes to freelancing vs traditional employment, and some do best in hybrid arrangements. What matters is finding what works for you.

I'd love to hear from you. What's your biggest question or fear about becoming a freelancer? Or if you're already self-employed, what aspect excites you most about it? Let me know in the comments.