Entrepreneurship

Side Hustle Became Career

5 min read
By Sam Taylor
Entrepreneur working on laptop celebrating business success

Eight months ago, I was working a full-time job and freelancing on weekends. Today, I'm full-time self-employed making more than I ever did with a salary.

Here's the honest timeline of how it happened—including the revenue numbers, the failures, and what actually made the difference.

Month 1: The $47 Start

Revenue: $47
Hours worked: ~30
Hourly rate: $1.57 (ouch)

I started with Upwork. Took any project I could get. Wrote blog posts for $15 each. Designed logos for $25.

I was terrible at pricing. Worse at saying no. But I was learning.

What worked: Just starting. Getting my first client review.
What didn't: Underpricing. Taking projects outside my expertise.

Month 2: The Reality Check

Revenue: $180
Hours worked: ~35
Hourly rate: $5.14

Better, but still not sustainable. I was exhausted. Working 9-5, then 7-11 PM every night. Weekends gone.

My partner asked: "Is this worth it?"

Honest answer: I didn't know yet.

What worked: Started specializing (web design only, no more random tasks).
What didn't: Still saying yes to low-budget projects.

Month 3: The First Real Client

Revenue: $850
Hours worked: ~25
Hourly rate: $34

This was the turning point. One client paid $600 for a website redesign. Suddenly, the math made sense.

I realized: one good client beats ten cheap ones.

What worked: Raised my rates. Focused on quality over quantity.
What didn't: Still doing all work myself (no systems, no templates).

Month 4: The System

Revenue: $1,200
Hours worked: ~22
Hourly rate: $54.55

I built templates. Created a process. Stopped reinventing the wheel for every project.

Same quality work, half the time.

What worked: Systemizing my workflow. Using templates.
What didn't: Marketing. Still relying on Upwork instead of direct clients.

Month 5: The Pivot

Revenue: $2,100
Hours worked: ~28
Hourly rate: $75

Started reaching out directly to businesses. Cold emails. LinkedIn messages. Scary but effective.

First direct client paid $1,500 for a project that would've been $300 on Upwork.

What worked: Direct outreach. Higher-value clients.
What didn't: Time management. Burning out from full-time job + side hustle.

Month 6: The Decision Point

Revenue: $3,400
Hours worked: ~30
Hourly rate: $113.33

This was more than half my salary. I started doing the math.

If I went full-time, could I replace my income? Probably.
Should I? That was scarier.

What worked: Building a client pipeline. Repeat customers.
What didn't: Fear. Overthinking. Waiting for "perfect" conditions.

Month 7: The Leap

Revenue: $4,800
Hours worked: ~35
Hourly rate: $137.14

I gave notice. Two weeks later, I was full-time self-employed.

Terrifying. Exhilarating. No going back.

What worked: Having 3 months of expenses saved. Having active clients.
What didn't: My sleep schedule (too excited/nervous to sleep well).

Month 8: The Proof

Revenue: $8,200
Hours worked: ~45
Hourly rate: $182.22

First full month self-employed. Made more than I ever did with a salary.

Not because I worked more hours. Because I could finally focus.

What worked: Full-time focus. No more splitting energy.
What didn't: Work-life balance (still figuring this out).

What Actually Made the Difference

Looking back, five things mattered most:

1. Starting Small But Starting

I didn't wait for the perfect business plan. I started with what I knew and learned as I went.

2. Tracking Everything

I knew exactly what I made, what I spent, and what my time was worth. Numbers don't lie.

3. Raising Rates Regularly

Every month, I charged new clients 10-20% more. Existing clients stayed at their rate, but new ones paid what I was worth.

4. Building Systems

Templates. Processes. Automation. I stopped doing everything from scratch.

5. Focusing on Fewer, Better Clients

One $2,000 client beats twenty $100 clients. Less stress, more profit.

The Honest Truth

It's not all sunshine. Some months are still tough. Client work is unpredictable. There's no paid vacation or sick leave.

But I'm in control. I choose my clients. I set my rates. I work when and where I want.

For me, that's worth the uncertainty.

If You're Thinking About It

You don't need to quit your job tomorrow. Start small:

Month 1-2: Test the waters. Take small projects. Learn what you like.
Month 3-4: Specialize. Raise your rates. Build systems.
Month 5-6: Go direct. Find better clients. Build a pipeline.
Month 7-8: Make the decision. Do the math. Take the leap (or don't).

There's no shame in keeping the side hustle as a side hustle. Not everyone wants to go full-time, and that's fine.

But if you do? It's possible. I'm proof.

The Numbers Don't Lie

Total side hustle revenue (8 months): $20,777
Current monthly average: $8,200
Old salary: $5,800/month
Increase: 41%

And I'm just getting started.

Your timeline might be different. Your numbers will definitely be different. But the principle is the same:

Start. Track. Improve. Repeat.

The side hustle that becomes a career isn't the one with the perfect plan. It's the one you actually start.

Tags

side-hustlefreelancebusinessentrepreneurship