Playing both sides: Lessons from my secret life as a freelancer

What freelancing while working full-time taught me about work

One gray Monday morning, at thirty years old, I stared at my laptop, overwhelmed by an uncomfortable truth: my career felt like a treadmill—endlessly running but going nowhere. It was far from the meaningful path I had envisioned as a starry-eyed university student.

Four years into my job as a marketing manager for a software company, my responsibilities felt detached from my interests. And I began to see that chasing a "dream job" wasn’t the answer. What I truly needed was a different way of working—one that allowed me to pursue my hobbies and interests.

I realized that switching jobs, no matter how exciting or prestigious, wouldn’t fix the underlying problem. I craved flexibility, control of my time, and the chance to tackle diverse challenges across industries.

That’s when I decided to try freelancing. But as someone who avoids uncertainty, I knew I couldn’t dive in headfirst. I needed the security of my full-time job on the side to start.

I imagined myself as a modern Samantha Jones, crafting compelling content for trendsetting companies.

Of course, reality didn’t match my daydreams. Starting methodically, I researched and pitched 24 promising companies. The response? Humbling. Only one encouraged me to check back months later.

Surprisingly, my first freelance gig didn’t come from cold outreach but through a connection. Six months in, I’m working with one client—not yet matching my full-time income, but already redefining how I view work, balance, and the possibilities ahead.

This is what I have learned.

Lesson #1: Start Before You’re Ready

Service proposal? I had never seen one before. Clarity in delivery times and formats? Nonexistent. Pricing? I had a paralyzing aversion to it.

I learned what freelancing entailed while freelancing. I threw myself into it without knowing how to manage a freelancing career, so everything felt like a challenge for the first couple of months.

All while trying to prove my worth.

Even when I felt like an expert in the subject area, I had no clue how to be a freelancer. And the thought of accidentally breaking some unwritten freelancing code popped into my head so many times.

I knew there were online courses and boot camps on how to start a freelancing career, but I realized early on that no amount of videos and research would prepare me to do the things the work required.

I built confidence by taking action: sending my monthly proposals, presenting my reports, listening to feedback, and making adjustments. Start, do, and repeat—month after month.

Lesson #2: Different Leaders, Different Growth

After four years at my full-time job, I can now anticipate the manager's reactions. I’m used to working without supervision and, after such a long time, with little feedback.

Freelancing meant adjusting to an entirely new management style while maintaining my working style at my full-time job.

This was very difficult at the beginning. I was used to doing things one way when suddenly I encountered a management style based on weekly feedback and short-term changes. A structure I hadn’t worked in.

As I switch between internet tabs to transition from working for one company to another, I also need to make a mental shift.

Adaptation was key to performing as my client wanted me to and, therefore, doing my freelance work successfully.

Lesson #3: Time is Elastic

During the first few months of freelancing, I learned that time is like a rubber band–it can stretch to accommodate your commitments, but only within limits before it snaps.

Despite an already almost full schedule, I have managed to take on freelancing without sacrificing free time by reassessing priorities (like dedicating Fridays exclusively to freelance projects), cutting back on unnecessary tasks (streamlining my workflow by using templates for proposals and batching content creation), and staying disciplined with my time management.

Careful planning and balance are key to avoiding burnout.

Lesson #4: Be the Expert They Need

Preparing my first proposal felt like assembling IKEA furniture without the instructions - in the dark.

To be agreeable, I asked the company in a previous meeting what they were looking for in their marketing efforts, and their response was, “We don’t know.”

After seconds of paralyzing doubt, I realized they expected me to tell them what they needed.

I’m the expert.

Before insecurity could swallow me up in one gulp, I told them about the marketing efforts of companies in their industry, and then we made some tweaks to accommodate how they captured leads.

It was that easy. I learned that I was not only there to deliver my work on time but to advise them as the expert I am.

Now, we do monthly reviews where I point out actions we can take to improve performance.

Lesson #5: Short Cycles, Clear Progress

Before freelancing, I wasn’t big on monthly performance reviews. I believed meaningful results took time, so I neglected monthly checks.

Now, I know that my grip on longer cycles was wrong.

Having to deliver monthly reports with the KPIs showing the results of my work (SEO keywords and audit, website performance, social media impressions, views, followers, etc.) has been the only way to push me into a results-driven professional.

I became data-driven through necessity, and now my results tell the story.

I try something, and after a month, I measure it. We discuss what I could improve, and I make changes. Because of this, I now approach my work in shorter cycles with more precise steps. I know how to measure it and what actions to take afterward.

These frequent small experiments also provide me with more data points and learning opportunities. I gather insights quickly and apply them to future iterations.

Lesson #6: Feedback is Your Friend

Before freelancing, I never received regular feedback. Now, as I adapt to my client's needs, feedback is ongoing.

Initially, it was difficult, and every critique made me think I wasn’t the right person for them, but after a few months, I realized that feedback was crucial for me to adapt to their needs and become that person.

Now, I see it as a way to strengthen my working relationships and learn. I just needed a shift in perspective.

Lesson #7: Deliver and Guide

Initially, I focused on staying in my lane, delivering my work on time, and ensuring its performance. However, after working in my client’s office a few times, I realized that I could also go beyond my deliverables and become someone who gives them advice on different topics in my area of expertise.

Now, we have discussed different approaches to bids, how companies in other industries approach specific issues, and how their sales team could take better advantage of their CRM.

This has also helped me realize that I master more areas than I was aware of and that the type of working relationship I want with my clients is one of advisorship.

Taking the plunge into freelancing was scary. I didn’t know if I would like it, and I was afraid I would feel trapped by it.

This journey has been challenging, as insecurities arrive when I least expect them, but it has also been an engine of professional growth. I now have a clearer vision of what I’m good at and what I need to improve.

I don’t know what is next for my freelance journey, but I’m proud of jumping right into it without all the preparation I thought I needed. It turns out the only way to truly know what’s right for you is by taking the leap and learning along the way.

–Catalina