The Truth About Freelancing: My First 90 Days Without a Boss (And What I’d Do Differently)

I always thought freedom would feel... different. Maybe lighter. Or more exciting. But if I’m being honest, my first three months as a freelancer felt more like freefalling than flying.

This article isn’t a “how I made $10K in 30 days” story. It’s the truth. The messy, often stressful, sometimes wonderful truth about what really happens when you quit your job to work for yourself online.

🧳 Why I Left My Job

I didn’t hate my job. But I hated what it was doing to me. The endless meetings, the feeling of doing work that didn’t matter, the tension on Sunday nights — it wore me down. I’d stare at the clock and think, “Is this it? Is this my life?”

I started freelancing on the side. Small gigs — $50 logos, $80 blog posts. Nothing special. But the feeling of earning money from something I created? Addictive.

So in April 2025, I gave my notice. Two weeks later, I was a full-time freelancer. Alone. Terrified. And slightly thrilled.

📆 Month 1: Panic & Overthinking

The first week felt like vacation. I slept in. I worked in pajamas. I told everyone I was “living the dream.”

By week two, the panic started. I had two clients and no new leads. I spent hours refreshing Upwork, rewriting my Fiverr profile, and questioning everything.

I made $723 that first month. Not bad. But not sustainable either.

📉 Month 2: Crashing Confidence

This was the hardest part.

I underpriced my work just to get projects. I said yes to awful clients. One guy paid me $40 to rewrite product descriptions — and then ghosted me halfway.

I started waking up with anxiety. I’d open my laptop and immediately feel sick. Was I cut out for this?

That’s when I stumbled on a video from a freelancer who said, “Freelancing isn’t freedom. It’s self-managed discipline.” That line stuck with me. I realized I wasn’t running a business — I was reacting to chaos.

🔁 Month 3: Turning Point

I decided to treat freelancing like a real job. I made a schedule. I started my day with outreach — not Instagram scrolling. I wrote better proposals. I followed up twice instead of once.

I raised my rates (even if it scared me). I also created a “No Clients List” of people who wasted my time or gave bad vibes.

That month, I landed a long-term client at $500/week — writing newsletters. That changed everything.