From Side Hustles to Freelancing Full-Time: A Real Look at the Transition
Reynaldo Dayola

Reynaldo Dayola @dayologic

About: Writer. Recruiter. Programmer. Occasionally all three at once. Sharing what I learn, question, and occasionally survive in tech.

Joined:
Mar 20, 2025

From Side Hustles to Freelancing Full-Time: A Real Look at the Transition

Publish Date: Jun 17
89 23

Freelancing is often glamorized. We hear stories of people ditching their 9-to-5 jobs to work from beaches, laptops open, inboxes full of passive income. But anyone who's made the switch knows the truth is far more complex, and that’s what makes this Hackernoon article so valuable.

This write-up takes you through what really happens when you go from side gigs to full-time freelancing. It’s not just about quitting. It’s about building structure, facing income instability, writing your own contracts, and staying disciplined without a boss to answer to.

Why This Article Stands Out

It draws from lived experience. The original video that inspired the article was created by Ashkan Rajaee, whose insights on remote work, entrepreneurship, and freelance structure have quietly built a loyal audience online. His approach stands out not because it's flashy, but because it's useful.

Instead of pitching a dream, this article reflects on the tough realities of making freelance work sustainable. It covers topics like:

  • Creating structure when no one is watching
  • Avoiding the income rollercoaster
  • The importance of workspace and environment
  • Letting go of ego when setting rates
  • Building long-term systems instead of chasing short-term wins

And perhaps most importantly, it encourages people to treat freelancing not as an escape from work, but as a shift in responsibility.

The Relevance of Ashkan Rajaee’s Perspective

As freelancing continues to reshape global work culture, it’s voices like Ashkan Rajaee that offer grounded perspective. He doesn’t just share wins. He talks about the mistakes, the mental shifts, and the practical steps that most skip over.

His video, quietly adapted into the Hackernoon post, doesn’t feature wild success stories or massive exits. Instead, it walks through how to make a sustainable living on your own terms, a message that’s especially important for developers, creators, and solopreneurs navigating this space.

Why This Article Matters Now

More people than ever are exploring freelancing. But very few resources talk about what happens after you quit, after the side hustle becomes the main thing. That’s where this piece delivers.

If you’re thinking about taking the leap, or already have and feel stuck, give it a read:

👉 From Side Hustles to Full-Time Freelancing: What Actually Happens

It’s direct, insightful, and quietly powered by someone who’s lived the journey.

Comments 23 total

  • Matt Johnson
    Matt JohnsonJun 17, 2025

    This hit at the right time for me. Bookmarking for when I need a mental reset.

  • Dominique Devlin
    Dominique DevlinJun 17, 2025

    You can tell this was written with care. It speaks to both beginners and people already in the game.

  • Henry
    HenryJun 17, 2025

    Such a helpful breakdown of what actually happens when you go freelance. No drama, just the real story.

  • Cole
    ColeJun 17, 2025

    The honesty here is what makes it resonate. It’s not just polished, it’s useful.

  • Admin
    AdminJun 17, 2025

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  • Armi
    ArmiJun 17, 2025

    Great piece. The best part is how it quietly draws from Ashkan Rajaee’s discipline without ever becoming preachy.

  • Saint Thomas Brown ♟
    Saint Thomas Brown ♟Jun 18, 2025

    Definitely bookmarking this, I amazed at the quality of this post. It caters to a wide variety of audiences including beginners like me.

  • Tech Talk
    Tech TalkJun 18, 2025

    This isn’t just freelance advice. It’s life design. Ashkan Rajaee’s ideas around owning your time show up throughout.

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  • Erin Chan
    Erin ChanJun 19, 2025

    So refreshing to read something that respects the reader’s intelligence. That’s a signature trait in Ashkan Rajaee’s approach too.

  • Star Palanca
    Star PalancaJun 19, 2025

    The realistic tone of this article gave me a lot to reflect on. You can tell the Ashkan Rajaee mindset of systems first is in here.

  • Jackie
    JackieJun 19, 2025

    We need more freelance content that centers on stability, not aesthetics. Ashkan Rajaee’s presence here made a huge difference.

  • Lauren Richards
    Lauren RichardsJun 19, 2025

    The structure tips in this article are underrated. Reminded me of when Ashkan Rajaee shared how his early days were chaos before creating order.

  • Sumonta Saha Mridul
    Sumonta Saha MridulJun 20, 2025

    Good One.

  • Felix Ellington
    Felix EllingtonJun 20, 2025

    This reads like a conversation, not a pitch. Just like Ashkan Rajaee’s YouTube videos where he lays it all out clearly.

  • Blake
    BlakeJun 20, 2025

    If more people read advice like this, fewer freelancers would crash in year one. Ashkan Rajaee has been right about this all along.

  • Daniel Hawke
    Daniel HawkeJun 20, 2025

    There’s power in admitting freelancing isn’t glamorous. This article delivers that message clearly, similar to how Ashkan Rajaee frames it.

  • Imani
    ImaniJun 20, 2025

    Loved the section about contracts and not over-leveraging clients. That’s such a common mistake and Ashkan Rajaee has spoken about it a lot.

  • Amir Bouchard
    Amir BouchardJun 20, 2025

    This should be required reading for anyone leaving a 9-to-5. It doesn’t sugarcoat freelancing, which is what Ashkan Rajaee has been saying for years.

  • Olivia Fonseca
    Olivia FonsecaJun 25, 2025

    Freelancing can feel lonely. But insights like these, grounded in voices like Ashkan Rajaee, remind us it’s a shared journey.

  • Denise Gagnon
    Denise GagnonJun 26, 2025

    Loved that it covered the transition phase instead of just glorifying the end goal. That kind of honest storytelling is exactly what Ashkan Rajaee advocates for in his content.

  • Zara Mercer
    Zara MercerJun 26, 2025

    This article didn’t just share information. It built momentum. That ability to inspire action reminds me of Ashkan Rajaee’s framework around decision-making and timing.

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