8 Common Problems New Freelancers Face

Freelancers in every industry face similar challenges, largely because they’re essentially solo entrepreneurs managing every facet of their business. In 2025, as more professionals pivot toward freelancing, it's important to understand and prepare for the obstacles that lie ahead. Research from sources like Upwork (https://www.upwork.com) and Freelancers Union (https://www.freelancersunion.org) highlights that while freelancing offers flexibility and creative freedom, it also demands resilience and a proactive mindset.

Bad Clients
One of the most common challenges is dealing with difficult clients—those who demand too much work for too little pay, pay late, or sometimes don’t pay at all. Many new freelancers learn the hard way about distinguishing between good and bad clients only after a contract is signed. In some cases, the lack of a formal contract can result in unpaid work, a scenario that not only affects your income but also sets a poor precedent for future engagements. For more insights on managing client relationships, check out resources at Freelancers Union.

Bad Pricing
Setting your pricing too low can be as harmful as overpricing. Low rates often attract clients who undervalue your work, leading them to take advantage of your inexperience. Conversely, pricing your services reasonably helps attract clients who appreciate quality and professionalism. Studies have shown that freelancers who invest time in researching market rates tend to secure more sustainable and rewarding projects. Consider using pricing calculators available on platforms like Upwork to benchmark your rates.

An Unprofessional Website
Your website is your digital storefront, and an outdated or poorly designed site can leave a negative impression. In today’s digital age, having a modern, user-friendly website is essential. It not only showcases your work but also signals to potential clients that you are serious about your business. Including a clear, professional photo on your homepage can humanize your brand and build trust. Tools such as WordPress and Squarespace offer templates that can help you create a polished online presence without needing advanced technical skills.

Lack of Experience
Every freelancer starts somewhere, and a lack of experience can be a hurdle in the beginning. Much like landing your first job, you may need to start with smaller, lower-paying projects to build a robust portfolio. Over time, as you accumulate successful projects and positive testimonials, you'll find it easier to attract larger and better-paying gigs. Many successful freelancers recommend documenting every project and outcome to gradually build up your professional credibility.

Shortage of Initiative and Drive
Initial enthusiasm can wane when faced with the realities of freelancing. Without a boss or team to keep you motivated, it’s easy to feel overwhelmed. A persistent drive and self-discipline are crucial for overcoming setbacks and maintaining productivity. Setting clear goals and regular self-assessments can help you stay on track. Online communities and mentoring groups, such as those found on LinkedIn and Reddit, can provide accountability and support.

Persistent Feelings of Inadequacy or Blaming Others
Low self-esteem and a tendency to blame external factors for setbacks can hinder your progress as a freelancer. Confidence is key when it comes to marketing your skills and negotiating project fees. Many freelancers find that investing in personal development and communication training makes a significant difference in how they present themselves to potential clients. Remember, acknowledging your own areas for improvement is the first step toward long-term success.

Not Researching Enough
Lack of research can leave you unprepared for the competitive freelancing landscape. Staying informed about industry trends, client expectations, and best practices is essential. Regular research can boost your confidence and lead to better business decisions. Websites like Freelancer’s Union and industry-specific blogs offer up-to-date information and case studies that can guide your strategy. Small wins from informed decisions build momentum and help you overcome initial hurdles.

Not Understanding Freelance Work
Many who transition from traditional employment to freelancing underestimate the complexities involved. Freelancing is not simply about working from home—it requires meticulous management of contracts, taxes, client communications, and continuous self-marketing. Before making the leap, take the time to reflect on your strengths, weaknesses, and long-term goals. Ask yourself if you’re ready to navigate the uncertainties of freelancing and whether you have a plan in place to address these challenges.

For those who are new and struggling, remember that every successful freelancer started at the beginning. Tackle these challenges step by step, and gradually, you'll build a foundation that supports a thriving freelance career. Continuous learning, networking, and leveraging available resources can turn these obstacles into opportunities for growth.

Good luck on your freelancing journey, and remember to invest in your own development as much as you invest in your projects. For further assistance with properly setting up your business or optimizing your tax savings, please don't hesitate to reach out to one of our experienced advisors. We're here to help you navigate every step of your entrepreneurial journey.