Side Hustle Dreams, Side Business Realities: My Unfiltered Journey
From freelance gigs to late-night doubts, this is what building a side hustle really feels like when no one’s watching.
We live in an era where the term "side hustle" carries the same glam as a tech startup did a decade ago. Social media is buzzing with stories of people quitting their 9-to-5s after finding success in side hustle jobs or transforming passion projects into thriving side businesses. And while there are kernels of truth in those stories, here’s mine - unfiltered, unpolished, and (hopefully) a little more real.
The First Spark: Why I Needed a Side Hustle
It was never about the money at first.
Well… not just the money.
I had a job that looked great on paper. Decent pay, predictable hours, and health insurance. But it left me feeling like I was borrowing my life instead of living it. Something inside me kept whispering, *"There has to be more than this."
That whisper turned into a roar the day I stumbled upon this article: Learning a New Skill Changed My Life: The Unfiltered Truth. I saw myself in those lines. That frustration. That hunger.
I didn’t know where to begin, so I started where most people do: Google.
1: The Wild World of Side Hustle Jobs
What do you search when you feel stuck?
"How to make money on the side."
"Remote gigs for creatives."
"Side hustle jobs that don’t suck."
Each search gave me a listicle. I scrolled through pages of affiliate marketing, Etsy, freelance writing, dropshipping, tutoring, dog walking, and selling feet pics. (Yeah. That last one surprised me too.)
I tried three things in the first six months: freelance writing, teaching music lessons online, and flipping thrift store finds.
What I didn’t anticipate was the emotional rollercoaster. The excitement of a first client, the devastation of ghosting, the grind of doing hours of work for $25.
I also didn’t expect the joy that crept in. It wasn’t glamorous. But it was mine.
Reality Bites: Building a Side Business Is Not an Instagram Reel
The first truth you realize when building a side hustle?
Time is your most precious currency.
I was juggling a 40-hour workweek, a relationship, family expectations, and this new hustle. My evenings blurred into late nights. Weekends turned into work-ends.
People around me started asking, “Why are you always so tired?”
Because turning a side hustle into a side business isn't a straight path. It’s more like crawling through mud while convincing yourself it's still worth it.
At this point, I came across another perspective: Beyond the Glamour: The Hard Truth About Building a Profitable Side Hustle. It hit like a gut punch. Not because it was cynical. But because it was honest.
And honesty was what I needed.
The Myth of Overnight Success
You know those viral tweets about someone making $10K in a week from a Canva template?
They never mention the years of skill-building, marketing, failed launches, or the support system behind the scenes. The myth of overnight success is seductive, but it’s also soul-crushing if you fall for it.
Here’s what I learned:
- Most side hustle jobs won’t make you rich overnight.
- Some may never make you rich at all.
- But all of them can teach you something about yourself.
Burnout and the Breaking Point
There came a moment, eight months in, when I almost quit everything.
I had two client projects due. My full-time job had just rolled out a surprise deadline. And my partner gently told me, “I feel like I don’t see you anymore.”
I broke down. Ugly tears. Shaky hands. The whole thing.
What saved me wasn’t a productivity hack. It was permission.
Permission to pause. To rethink. To ask why I was doing all this.
Clarity: What a Side Hustle Really Gave Me
I thought I was building a side hustle for money.
But it gave me:
- Agency: The ability to choose what I worked on.
- Creativity: A space to experiment without corporate filters.
- Confidence: Proof that I could start something, even if it was small.
Not every project succeeded. Some failed. Some fizzled out. But I didn’t.
That shift in mindset made me revisit this gem: Freelance Freedom: Build a Side Hustle That Pays and Grows. It helped me separate identity from income. Growth from glamor.
Ask yourself:
If no one ever saw what I was building, would I still want to build it?
If the answer is yes, you’re on the right track.
Sustainable Hustling: Redefining Success
Success isn’t quitting your job tomorrow.
It might be:
- Making $200/month doing something you love
- Replacing your rent in a year
- Learning skills that make you anti-fragile in a changing economy
The key is sustainability. I created a weekly system that included rest, deep work blocks, and no-hustle Sundays. It’s not perfect, but it’s human.
Tools That Helped Me
In a world of noise, the right tools are your lifeline. Here are a few that made the difference:
- Notion for planning and tracking goals
- Toggl for time-tracking and staying honest
- AI writing tools to reduce grunt work (See: AI Tools for Remote Workers: Boost Focus, Cut Stress, Work Smarter)
- Calendly to make booking easy for clients
A Note on Money
Once I passed the $1,000/month mark consistently, everything changed.
I wasn’t rich. But I felt powerful.
I now had options. I could say no to toxic jobs. I could save for travel. I could invest in my next idea.
That was the moment I understood:
A side hustle doesn’t just make money. It makes space.
The Bigger Picture: Identity, Culture, and Choice
In many cultures, stability is king. Choosing a creative, risky, self-driven path can feel like rebellion.
My parents didn’t understand at first.
“Why are you working more for less?”
But over time, they saw the joy. The ownership. The self-respect. That mattered more than the metrics.
Sometimes, the most radical thing you can do is choose your own story.
Ask yourself:
What would your life look like if your side hustle wasn’t just about survival - but about becoming more you?
Last words:
If you’re dreaming of a side hustle, don’t wait for perfect.
Start clumsy. Start scared. Just start.
And if you’re already building, keep going. Take breaks, but don’t give up. Your side business doesn’t have to impress the internet. It just has to matter to you.
You might not go viral. But you might just come alive.
And that’s worth everything.
