Side Hustle Diaries: What I Learned After 12 Months of Hustling

After a year balancing IT projects and side hustles, I share lessons, tips, and insights to help you start online work-from-home gigs with confidence today.

1. Choosing the Right Side Hustle: Quality Over Quantity

Listening to Curiosity, Not Hype

Early on, I made a classic rookie mistake: I chased every trending “online work from home” idea I saw. I signed up for a dropshipping course, tested out print-on-demand, and even tried creating stock photos to sell. Spoiler alert: most of those flopped. The lesson? Don’t blindly follow headlines. Instead, ask yourself:

  • What skills do I genuinely enjoy using?
  • Which tasks can I sustain without burning out?
  • Is there a real demand especially in the IT or tech space for what I want to offer?

For me, the sweet spot turned out to be freelance DevOps consulting and creating small automation scripts for local businesses. It wasn’t glamorous, but it played to my strengths and kept me energized.

Listing My Options

To narrow things down, I made a simple table (on a spreadsheet) listing potential side hustles, their entry barriers, and estimated monthly income. Here’s a simplified example of what that looked like:

Side Hustle Idea

Skills Required

Initial Cost

Estimated Monthly Income

Freelance DevOps Consulting

Linux, AWS, CI/CD

$0–$50

$500–$1,500

Creating WordPress Plugins

PHP, JavaScript, PHPMyAdmin

$10–$100

$200–$800

Teaching Python Online

Python, Presentation Skills

$0–$100

$300–$800

Selling Stock Photos

Photography, Photoshop

$100

$50–$300

Dropshipping E-commerce Store

Market Research, Shopify

$20–$200

$0–$500

Remote IT Support (Part-Time)

Troubleshooting, Communication

$0

$200–$600

Gradually, the first three row items emerged as “best side hustles from home” for my skillset especially since demand for DevOps expertise and coding tutorials remains high in 2025.

 

2. Juggling Work from Home and a Full-Time Job

Establishing a Routine

Balancing a full-time IT job with side projects was, without exaggeration, a dance. At first, I tried to hustle after the workday ended, but my brain hit a wall by 7 PM. So, I experimented with waking up at 5:30 AM. That early-morning window (while everyone else was still asleep) turned out to be golden productivity time. I’d grab a coffee, open my home office, and dedicate two focused hours to my side hustle before clocking into my main job.

On weekends, I blocked out 4–5 hours for deeper work like recording Python tutorial videos or coding DevOps scripts. The key was respecting these blocks like calendar appointments. Whenever I allowed myself to “just check email real quick,” those side-hustle hours melted away.

Maintaining Boundaries

One unexpected challenge was the overlap of tasks. When an urgent support ticket popped up, it was tempting to tackle it right away even if I’d planned to work on my freelance script. Eventually, I learned to set clear boundaries:

  1. Dedicated Work Hours: My main job from 9 AM to 5 PM was untouchable by side-gig distractions.
  2. Morning Hustle Hours: 5:30 AM to 7:30 AM for side projects no exceptions.
  3. Family Time & Rest: Evenings were reserved for winding down, spending time with loved ones, or just binge-watching a show without guilt.

Over time, protecting these windows became second nature. And those pockets of dedicated effort were crucial for steadily growing my side hustle income.

 

3. The Learning Curve: Skills Gained (and Lost)

Sharpening Technical Skills

When you commit to side hustles, you quickly realize how much there is left to learn. A year ago, I’d never set up a CI/CD pipeline from scratch now I routinely automate deployments for small businesses. Every freelance gig became a learning opportunity:

  • Automating with Bash & Python Scripts: Most local clients needed batch data processing or basic server monitoring. Building small Python utilities taught me clean coding practices.
  • Exploring New Cloud Platforms: Beyond AWS, I dipped my toes into Azure and Google Cloud Platform for one-off projects. The exciting part: comparing how each service handles networking or serverless functions.
  • Improving Communication Skills: Explaining a complex technical concept to a non-technical client in plain English? That skill got sharper every single week.

Facing Burnout and Skill Decay

On the flip side, pushing too hard led to a scare last February: I started feeling drained and unfocused. My one-week vacation didn’t help; my mind felt so tired that writing even a small blog draft was a chore. That’s when I remembered skills can decay if you don’t rest. I scaled back my side hustles from eight hours a week to five and noticed improvements almost immediately. Rest became part of my skill-building journey.

 

4. What Worked (and What Didn’t)

Successful Experiments

  • Building Mini-Tools for Local Businesses: Instead of chasing high-paying but highly competitive gigs, I focused on neighborhood shops that needed simple inventory-tracking scripts. They paid $100–$300 per project, but the turnaround time was quick, and I learned about client management.
  • Teaching Python 101 Workshops: A local co-working space invited me to teach a “Python for Non-Techies” workshop. I charged $20 per seat and sold out a 15-person class. This not only brought in $300 but also introduced me to other side hustlers looking for collaboration.
  • Writing Technical How-Tos on Medium: Instead of blogging on my personal site, I wrote a few in-depth guides on Medium about setting up Docker containers. Some articles got decent traffic, and I earned $50–$100 per month in Medium Partner payouts.

Dead Ends and Pitfalls

  • Print-on-Demand Merch: I spent a weekend designing geeky T-shirts, set up a Shopify/drop-shipping flow, and… sold exactly zero items. My friends still laugh about my “AI Meme King” shirt that never took off.
  • Stock Photography: I invested in a better DSLR and spent two weekends shooting IT-themed stock photos (think: “developer typing on a laptop” or “coffee cup by code editor”). It took months to sell even one image. The lesson? Niches matter my photos weren’t unique enough.
  • Affiliate Blogging Without Focus: I tried writing “Top 10 Coding Laptops” just to get affiliate commissions. Without domain authority or proper SEO, the article drifted into obscurity. I learned that a blog needs genuine expertise, not just affiliate links.

 

5. Building Community: Finding Accountability Partners

The Power of a Supportive Circle

One of the most surprising elements of this journey was how critical community turned out to be. After a few months of solo hustling, I felt my motivation dip. Then I stumbled onto a small Slack group for IT side hustlers. Suddenly, sharing small wins or venting frustrations felt refreshing.

  • Weekly Stand-Up Calls: Every Friday afternoon, our group would hop on a quick 15-minute call and share one thing we achieved and one challenge we faced. Even if it was something as small as “I fixed a production bug under pressure” it felt like a victory worth celebrating.
  • Open Source Collaboration: I met two folks who were also building automation tools. We decided to collaborate on an open source GitHub project for server monitoring. Pooling our skills made development faster, and the community recognition boosted our confidence.

Accountability Drives Progress

Knowing that someone would ask me, “How many DevOps scripts did you deliver this week?” made me less likely to skip my morning hustle hours. Over time, I repaid that accountability by helping newer members of the group, suggesting podcast episodes or sharing short code snippets. This sense of giving back reinforced my commitment and kept my own hustle engine running.

 

6. Getting Paid: Pricing, Invoicing, and Taxes

Setting Prices That Reflect Value

Pricing was always a sticky point. Initially, I undercharged sometimes as low as $15/hour for freelance work because I feared clients wouldn’t pay more. After six months, I took a hard look at market rates: for a DevOps consultant with a few years of IT experience, $40–$60/hour was reasonable. I made a spreadsheet to track:

  • Hours spent vs. deliverables
  • How competitors priced similar services
  • The value added (time saved for the client)

Once I bumped my rate to $45/hour, I still landed clients. In fact, some respected me more for charging what I was worth.

Invoicing and Taxes: Staying Organized

At tax time, I almost panicked because I’d saved receipts in random folders. Lesson learned: create a dedicated “side hustle” folder in Google Drive, then back up monthly statements. I switched to using a simple invoicing app that auto-generated PDFs, tracked paid vs. unpaid invoices, and reminded clients after 30 days.

Since I was in India, I also consulted a tax advisor on how to report extra income from online work from home. A modest 15% advance tax applied, but because I maintained clean records, filing my returns was relatively painless.

 

7. Balancing Passion and Profit: Staying Motivated

The Joy of Small Wins

One of my clients once sent an email:

“Your automation script saved me about two hours of tedious manual work every day. Thank you!”

Reading that made my whole week. It reminded me that beyond the extra paycheck, side hustles brought real impact. Whether it’s a blog reader sending a “Thank you for this tutorial” message or a local shop owner praising an inventory tool, these small wins kept me going through tough weeks.

Avoiding Burnout

Around month eight, I hit what I call the “side hustle slump.” My main job was unusually demanding during a big project release, and my side gigs piled up. I felt drained both mentally and physically. Here’s how I recovered:

  1. Took a 10-Day Break: I scheduled no side-hustle work, no blogging, nothing. Just a short family trip to the coast.
  2. Revisited “Why” Statements: I pulled out my old notes “I want to learn cloud automation,” “I want to help small businesses,” “I want to earn freedom.” Rekindling the original motivations gave me fresh energy.
  3. Set Realistic Goals: Instead of aiming for $2,000/month side income, I reset the bar to $800–$1,000. That felt doable given my workload.

 

8. Looking Ahead: What’s Next After 12 Months?

Scaling Up (Or Knowing When to Pause)

Now that I’ve crossed the 12-month mark, I face a question: should I scale up or slow down? My DevOps consulting client wants me to build a small team to automate similar tasks for multiple businesses. This could become a mini-IT agency. But I also have a budding interest in launching an online course on “Automating DevOps with Python.”

For anyone reading this, the takeaway is simple: scale when you have stable processes, clear demand, and enough bandwidth to delegate. If not, it’s perfectly fine to pause and consolidate what you’ve learned.

Advice for Your Own Side Hustle Journey

  1. Start with What You Know: If you already have IT skills, explore “online work from home” gigs that leverage them. You’ll learn faster and build confidence.
  2. Protect Your Time: Early mornings or designated weekend blocks can become sacred hustle hours if you treat them like nonnegotiable appointments.
  3. Join a Community: Whether it’s a Slack group, a local meetup, or an online forum, accountability and shared knowledge are invaluable.
  4. Embrace Small Wins: A $100 gig that teaches you a new skill is often more valuable than chasing a $1,000 contract in an unfamiliar niche.
  5. Stay Flexible: Trends change what’s a hot “best side hustle from home” today might fade next year. Keep learning and adapt.

 

Conclusion: Your First Step Is the Hardest, but Also the Most Rewarding

If there’s one overarching lesson from my year of side hustling, it’s that growth seldom happens in comfort zones. Juggling an IT career with side gigs meant I missed a few Netflix marathons and early weekend lie-ins. But in exchange, I learned new cloud technologies, expanded my network, and built an extra income stream that still supports small local businesses today.

So if you’re on the fence, ask yourself: what stops you from taking that first step? Whether it’s a line of code, a quick tutorial, or a simple spreadsheet to list your ideas start somewhere. Your 12-month “diary” of lessons, triumphs, and yes, even failures, will become the story you can’t wait to share. And who knows? Maybe someone out there will read your “Side Hustle Diaries” next year and feel inspired to begin their own journey.

Ready to start? Block out your prework hours tomorrow, jot down your top two side hustle ideas, and commit to a 30-day experiment. You’ve got this.


sidehustles

1 Blog posts

Comments