7 Challenges Every New Online Writer Faces (And How to Conquer Them)

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If you’ve ever posted a picture online and added a caption or commented on an online thread, you’ve written online. And it doesn’t get much harder than that! Not even if you’re writing online to earn.

While there’s an undeniable thrill to embarking on a career as an online writer, the journey isn’t without its unique challenges. From choosing a niche to finding consistent work, these obstacles are commonplace in the early stages. But don’t worry – with the right strategies and mindset, you can overcome them and thrive as an online writer.

The Roadblocks to Success: Challenges Faced by New Online Writers

It’s important to acknowledge that the challenges faced by online writers who write primarily for income can differ from those who write primarily for expression. We’ll explore the unique joys and challenges of writing for passion in a future post. Here, however, we’ll delve into the seven hurdles you’re most likely to encounter as you launch your online writing career.

Challenge 1: Choosing a Niche

trying to choose a freelance writing niche while doing deep work

As a new online writer, the world of potential topics can feel exhilarating… yet overwhelming. Some of the hurdles you may face include the following;

  • The Paradox of Choice: With endless possibilities at your fingertips, making a single decision on what to focus on can feel paralyzing.
  • Balancing Passion and Profit: You may have passions that don’t seem lucrative, or find yourself pulled towards profitable writing niches that don’t spark your enthusiasm. Understanding how to navigate this tension is crucial to a sustainable writing career.
  • The ‘Generalist vs. Specialist’ Dilemma: Should you cast a wide net with your writing or target a specific niche? There are benefits and drawbacks to both approaches, and your decision might evolve.


While there’s no single “right” answer, consider these strategies to guide your decision:

  • Pursue Your Passions (Within Reason): Writing about topics you are interested in will make the process more enjoyable and help you maintain your momentum. Consider how you can make your passions viable, even if they aren’t immediately profitable.
  • Utilize Your Existing Skills: What unique knowledge or experiences do you possess? These can set you apart as a writer and lead to niche opportunities.
  • Conduct Market Research: Which topics are people interested in? What are businesses and clients willing to pay for? Identify gaps in the market that align with your strengths.
  • Start Broad and Narrow Down: It’s okay to experiment with different topics before finding your primary focus. Over time, you’ll gain clarity on what you enjoy and what resonates with your audience.

Challenge 2: Building a Portfolio

building a portfolio of relevant online writing publications as an online writer

Which came first: the chicken or the egg? New writers face this exact kind of scenario when starting. Clients want to see samples of your work to trust your abilities, but how do you land those first clients without samples to show? This frustrating cycle leaves many writers feeling trapped before they even begin.


This challenge isn’t just about having a blank slate, there are other things to consider:

  • Limited Experience: Even if you’ve dabbled in writing, you might not have published samples that truly demonstrate your current skills.
  • Quality vs. Quantity: Do you focus on polishing a few outstanding pieces, or aim for a variety of samples, even if some lack that extra finesse?
  • Owning Your Work: Client work is often confidential, so how can you use it to strengthen your portfolio without breaching agreements?


Don’t despair! Here are strategies to break out of the chicken-and-egg dilemma and build a compelling portfolio:

  • Strategic Guest Posting: Target reputable blogs or publications within your niche and pitch them well-crafted guest articles in exchange for a byline and a link to your website or portfolio.
  • Personal Blog or Platform: Launch your own space (blog, Medium page, etc.) to hone your voice, showcase diverse writing styles, and experiment with topics you’re passionate about.
  • Volunteer Your Services: Offer your writing skills to non-profits, local charities, or small businesses in need. You’ll build experience and gain samples you fully own.
  • Repurpose Existing Content: Don’t underestimate the power of polishing older work, such as college essays or thoughtfully crafted social media posts, to demonstrate your writing potential.
  • Showcase Your Process: If you lack published work, create samples highlighting your approach. Produce outlines, conduct research, and draft partial pieces demonstrating your methodology and attention to detail.

Challenge 3: Finding Consistent Work (especially as a freelancer)

my self editing technique in 4 steps after getting consistent work

Freelance writing offers tremendous freedom but also the constant hustle of finding new clients and projects. The income fluctuations and unpredictable workload can feel stressful, especially for those new to self-employment.

Here’s a closer look at the difficulties:

  • Feast or Famine Cycles: Periods of overflowing work may be followed by stretches of frustrating silence, making budgeting and financial planning a challenge.
  • Pitching and Networking: Constantly pitching yourself to potential clients and building a network takes time and energy away from your writing.
  • Client Acquisition Rollercoaster: The excitement of landing a new client can quickly be dampened by the time and uncertainty involved in the search for the next project.
  • Balancing Freedom with Stability: Many writers thrive on the flexibility of freelancing, but the lack of inherent job security can be a source of anxiety.


While there’s no foolproof way to have a full client roster at all times magically, these strategies will put you on the right path:

  • Diversify Your Client Sources: Rely on a mix of job boards, freelance platforms, networking in niche communities, and cold pitching to broaden your search and reduce reliance on any single source.
  • Build Client Relationships: Focus on providing stellar service to current clients. They offer repeat work and may even refer you to new opportunities.
  • Explore ‘Hybrid’ Opportunities: Consider exploring in-house agency roles or full-time positions as a starting point. It provides steady income while building your network and skillset.
  • Pursue Retainer Clients: While one-off projects are common, seek clients willing to offer retainers for recurring work, creating more predictable income streams.

Challenge 4: Mastering Self-Promotion

self promotion by an online writer

As an online writer, you are your own biggest advocate. However, many writers struggle with the notion of self-promotion, feeling uncomfortable putting their work out there for scrutiny. These may be due to;

  • The Introvert’s Dilemma: Naturally introverted writers may find networking and selling their services challenging.
  • Fear of Rejection and Self-Doubt: Submitting pitches or promoting your work creates vulnerability and the possibility of rejection, triggering self-doubt and hesitation.
  • Identifying Your Value: New online writers often underprice their services or struggle to articulate why a client should choose them over others.
  • Finding the Right Platforms: The abundance of social media and online platforms can be overwhelming. Where should you be focusing your promotional efforts?
  • Outbound Marketing Discomfort: Cold pitching, where you proactively reach out to potential clients, might feel intrusive or intimidating to many new writers.


  • Shift Your Mindset: Instead of viewing self-promotion as bragging, think of it as offering value and connecting with potential clients who genuinely need your skills.
  • Build a Strong Online Presence: A professional website or portfolio and thoughtfully curated social media pages provide a foundation for clients to discover you.
  • Leverage Testimonials and Case Studies: Highlight positive feedback and project successes to demonstrate your competence and build trust.
  • Practice Your Pitch: Have a clear and concise “elevator pitch” ready to confidently introduce yourself and your services.
  • Focus on Client Needs: Approach potential clients by highlighting how you can solve their problems, rather than simply listing your skills.
  • Mastering Cold Pitching: Research companies, personalize your pitches, and focus on providing value upfront to increase your success rate.

Challenge 5: Imposter Syndrome (fueled by rejection)

imposter syndrome for online writer

Imposter syndrome is a pervasive feeling of doubt and inadequacy, even when faced with evidence of your skills and accomplishments. It’s particularly common among writers, often exacerbated by the inherent subjectivity of the craft and the potential for rejection.

Here’s why it’s particularly challenging for new writers:

  • Internalizing Rejection: It’s easy to take a rejected pitch or a negative critique as a sign of your lack of talent, rather than as part of the process.
  • Comparison Trap: Social media and online communities can fuel doubt as you see the successes of other writers, often without the full picture of their struggles.
  • Negative Internal Narratives: Many writers have a harsh inner critic, focusing on flaws and minimizing successes.
  • Lack of Experience: New writers haven’t yet built up a strong track record of achievements to counterbalance self-doubt when it creeps in.


  • Recognize Your Accomplishments: Celebrate even small wins and keep a list of positive feedback to refer to when doubt arises.
  • Reframe Negativity: Challenge your inner critic and replace self-deprecating thoughts with encouraging statements focused on growth.
  • Community and Support: Build connections with other writers who understand these struggles and offer support and validation.
  • Focus on Progress, Not Perfection: The goal is not to eliminate self-doubt but to manage it so it doesn’t hinder your progress.
  • Understand Rejection: Rejections are almost inevitable. Learn to view them as opportunities to improve your pitches or find better-suited clients.

Challenge 6: Writer’s Block

empty writing pad due to writer's block

Every writer, new or experienced, faces the dreaded blank page at some point. Writer’s block manifests in different ways: a lack of ideas, feeling uninspired, or a sense of paralysis despite wanting to write.

Here’s a breakdown of why it’s particularly tough for new writers:

  • Pressure to Produce: Early on, you might feel immense pressure to generate consistently good work, which can exacerbate the frustration of a creative block.
  • Fear of Judgement: Worrying about the quality of your writing, especially when you’re still establishing yourself, can stifle your creative flow.
  • External Stress and Burnout: Life circumstances, overload, or lack of proper self-care can lead to mental exhaustion and make focusing on writing difficult.
  • Lack of Established Routine: New writers might not yet have routines that support their writing and help circumvent creative stagnation.


While I have a few strategies to combat writer’s block, I’ve written extensively about the topic and believe this post offers even more valuable guidance: Writer’s Block 1

Challenge 7: Time Management & Procrastination

The freedom of freelancing is a double-edged sword. While liberating, it demands excellent time management skills and the ability to combat procrastination. A lack of structure can hinder productivity and potentially jeopardize client deadlines.

Here’s a breakdown of why it’s particularly challenging for new writers:

  • Distractions Abound: Working without a traditional office environment means facing numerous distractions, from social media to household chores.
  • Lack of Clear Boundaries: The line between work and personal life can blur, leading to procrastination or burnout from constant availability.
  • Underestimating Project Time: New writers often inaccurately estimate how long writing tasks will take, leading to missed deadlines and rushed work.
  • Procrastination Habits: Pre-existing procrastination tendencies become even harder to overcome with less external accountability.


  • Set Working Hours: Create a dedicated work schedule and stick to it as closely as possible. This establishes a work/life balance and sets clear expectations.
  • Minimize Distractions: Eliminate digital and physical distractions during dedicated writing blocks. Use website blockers and notification settings to your advantage.
  • Time Blocking: Break your workday into chunks with designated tasks (research, writing, editing) to maintain focus and track progress.
  • Pomodoro Technique: Work in focused bursts of 25 minutes, followed by short breaks. This combats fatigue and promotes focused concentration.
  • Break Projects into Manageable Tasks: Overwhelm often fuels procrastination. Create smaller, achievable tasks to reduce the mental barrier to starting.
  • Accountability: Find a writing buddy, mentor, or online community to share your goals and provide support to stay on track.


Building a successful online writing career is an exciting challenge filled with rewarding opportunities. It’s also a journey that involves navigating some common obstacles. By understanding these challenges and developing proactive strategies, you’ll be well-equipped to overcome them and build a sustainable and fulfilling career.

If you found value in this post, we encourage you to:

  • Share the Knowledge: Help other aspiring writers by sharing this post on your social media platforms or in your writing communities.
  • Stay Connected: Subscribe to our blog for ongoing resources, tips, and inspiration to support your continued growth as an online writer.


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