The real pros and cons of being a Freelancer: freedom meets responsibility

Choosing to become a freelancer is often described as “taking the leap,” and it truly is.

A leap into more freedom, more creativity, and more ownership, but also a leap into uncertainty, self-leadership, and sometimes, solitude (there is no coffee break with a colleague).

Freelancing isn’t just a career choice; it’s a mindset shift. And like any big shift, it comes with both light and shadow.

Below is an honest look at the ups and the downs, the empowering sides and the challenging ones, so you can recognise your own patterns, strengths, and blind spots along the way.

This article took me a long time to write because there was so much to reflect on and share. I hope you’ll take from it whatever resonates most with you.

The Pros: freedom, variety, and personal ownership.

You design your work fully.

One of the biggest perks of freelancing is the autonomy it offers.

You choose the projects you want to take on, the people you want to collaborate with, and the way you want to deliver your work.

There’s a sense of ownership that’s difficult to match in a traditional job.

You work on your own timing.

Whether your productivity peaks at 6 AM or 10 PM or during the weekends, and perhaps in the middle of nowhere where the internet is not stable (it happened to me), freelancing lets you flow with your natural rhythms.

You’re not locked into office hours and the classical 9-5. You can organise your days around your energy levels, personal commitments, or even your international travel schedule.

I recently discovered (it took me years) that I do not have to wait until 5 PM to do my gym training, but I can go whenever I’m free (I know, so stupid from me that I didn’t start earlier).

I was definitely stuck in my previous schedule, and it took me a while to get comfortable with a new routine.

You can work from anywhere (my forever favorite).

Laptop + WiFi = your entire office.
A café, a co-working space, your living room, another country, your career moves with you.

A small note, it depends a lot on the job you do. I need a quiet space to have my 1:1 client sessions, but for the rest of the tasks, I’m good to be anywhere.

This freedom often becomes not just a lifestyle but a new way of seeing the world.

You get variety and constant learning.

Different clients, different industries, different ways of thinking.

It’s stimulating. Every project challenges you, stretches you, and adds new tools to your toolkit.

Freelancers tend to grow quickly simply because their environment is always shifting.

The Cons: blind spots, loneliness in decision-making, and no built-in feedback loop.

There’s no one to tell you when you’re going in the wrong direction.

This is the part no one really talks about.

When you’re employed, you have team leaders, colleagues, and performance reviews.

You get guidance, feedback, and perspective, whether you ask for it or not, whether you like it or not. And believe I couldn’t wait to leave my 9-5 job to avoid all of these but.. as a freelancer?

You are the one making the calls.
All of them.

Sometimes that’s empowering. Sometimes it’s confusing. Sometimes it leads to staying too long on a strategy that isn’t working.

There’s no one to tap you on the shoulder saying:

• “Maybe that’s not the best idea.”

• “This pricing doesn’t align with the market.”

• “Your messaging isn’t clear.”

• “Perhaps it’s time to pivot.”

• “You’re focusing on the wrong task, move on”.

This lack of real-time correction can create blind spots, and those blind spots can be expensive.

You carry all the responsibility.

Admin, taxes, planning, client management, business development.

Even if you love what you do, your time gets split between your craft and the responsibilities of running a business.

This can be overwhelming, especially during busy seasons.

External structure is not naturally there.

No deadlines unless you set them.
No reminders.
No colleague pushing you to finish something.
No built-in accountability unless you have an accountable partner (e.g, your Coach).

You need to build your own systems and refine them constantly.

Income can feel, and it’s most of the time unpredictable.

Some months feel abundant. Others feel lean.
Financial planning becomes a non-negotiable skill when you don’t have a fixed salary.

The emotional load is real.

When a project goes well, you celebrate alone.

When something feels off, you also deal with it alone.

Freelancing can test your resilience, your boundaries, and your ability to stay grounded when things fluctuate.

On a closing note…

Freelancing offers a level of freedom that can be deeply fulfilling, creative freedom, geographical freedom, and the freedom to shape your work exactly the way you want it.

But that same freedom comes with the need for strong self-awareness, discipline, and a willingness to question your own ideas, strategies, and assumptions.

The beauty of freelancing is that it pushes you to grow.
To trust yourself.
To refine your vision.
To stay curious.
To be brave enough to pivot when something isn’t working because there’s no one else making those decisions for you.

If you’re already freelancing, take this as an invitation to pause and reflect:
Where do you feel strong and energized? And where do you feel you’re navigating without a map?

If you're considering taking the leap, know this: it’s not always easy, but it can be incredibly rewarding when you’re intentional about how you build your path.

Personally, I’m doing whatever it takes to make it work because I know this is the lifestyle and mindset I want to have.

Sincerely,

Your Coach Cinzia