20 Common Challenges You Can Face in Growing a Freelance Business and Seeking Opportunities on Upwork and Practical Tips for Overcoming them

This post highlights 20 common challenges you may face when trying to grow your freelancing business and seek for more opportunities on Upwork plat form. Each challenge stated in this post is accompanied by a real-world example and a practical on how to overcome it.



Freelancing is a form of self-employment that provides you with the freedom to live anywhere  and deliver your services to clients all over the world with a reliable internet connection. Learn more here

Freelancing is doing specific work for clients without committing to full-time employment. Upwork says72% of U.S. freelancers state their main reason for freelancing is to be in control of their financial future. Examples of freelancing jobs include graphic designs, website building, data entry, proofreading and editing. See example here.

20 Challenges Freelancers can Face on Upwork

Here are 20 challenges freelancers face on Upwork, detailed with real-world examples and accompanied by practical tips for overcoming them.

1. Educational Bargaining

Challenge: Clients sometimes undervalue a freelancer's skills, seeking to negotiate lower rates, which can demotivate and undermine the profession’s standard.

Example: A graphic designer with five years of experience applies for a branding project with a budget of $400.The client counters with an offer of

Tip: Clearly articulate your value in your proposal. Include specifics about past projects, client testimonials, and how your unique skills directly contribute to the client's objectives. Set a minimum acceptable rate and stick to it, explaining that quality work costs more.

2. Competition

Challenge: With numerous freelancers vying for the same jobs, distinguishing oneself can be challenging.

Example: A content writer notices that for a popular job posting, over 100 proposals have been submitted within hours of the listing going live. How does one stand out among that many applicants?

Tip: Create an optimized profile featuring a professional photo, detailed descriptions of your skill sets, and a portfolio demonstrating your best work. Tailor each proposal, addressing the client's specific needs and incorporating relevant keywords that match the job posting, which can increase the chances of being noticed.

3. Finding Quality Clients

Challenge: Many freelancers encounter clients who have little experience and may not understand the work involved, leading to unrealistic expectations.

Example: A web developer is hired for a project but soon discovers that the client expects a complete website rebuild within a week, despite not having provided all the content or design specifications.

Tip: Qualify leads by looking for clients with verified payment methods, strong hiring histories, and positive reviews. Consider sending a message before bidding to gauge their experience and expectations. This initial communication can filter out potential issues downstream.

4. Time Management

Challenge: Balancing multiple projects, deadlines, and personal tasks can lead to burnout or missed deadlines.


Example: A copywriter takes on three projects at once but struggles to manage her time effectively, leading to late submissions and unhappy clients. Conversely, if she declines work, she could lose income.

Tip: Invest in time management tools like Trello or Asana to create a project timeline. Break larger tasks into smaller, manageable pieces and set dedicated work hours. Prioritize tasks based on deadlines and allocated workloads.

5. Client Communication

Challenge: Poor communication can lead to misunderstandings regarding project outcomes and expectations.

Example: A digital marketer submits a campaign proposal but fails to clarify the reporting process with the client. As a result, the client is unhappy with the lack of progress updates and assumes that no work is being done, causing tension.
Tip: Establish a communication plan with your clients upfront. Clarify preferred contact methods and frequency of updates. Use brief project summaries, recorded video messages, or visual aids as needed to ensure everyone is aligned throughout the project.

6. Maintaining Consistent Work

Challenge: Freelancers often face fluctuating workloads, leading to periods of high stress and uncertainty.

Example: A programmer completes a major project, only to find themselves with few new opportunities for months afterward, creating financial strain.

Tip: Proactively pursue new projects even when busy. Allocate specific time weekly for pitching or applying to new jobs and setting up automatic alerts for ideal job postings. Building ongoing relationships with clients can lead to repeat business.

7. Unclear Job Descriptions

   Challenge: Ambiguous job postings can lead to a mismatch in expectations between freelancers and clients, resulting in frustration and potential conflicts throughout the project.

   Example: A graphic designer applies to a job posting that states the client needs "creative visuals" for various campaigns, but does not specify the type of campaigns, target audience, or visual style. After the proposal is accepted, the designer learns that the client has a completely different aesthetic in mind, leading to multiple rounds of revisions and dissatisfaction from both parties.

   Tip: Before submitting a proposal, reach out to the client with targeted questions to clarify their needs. Inquire about their brand guidelines, target demographics, examples of preferred styles, and expected deliverables. By showing initiative and seeking clarity, you not only position yourself as a proactive professional but also ensure that both you and the client have a mutual understanding of the project scope.

8. Scope Creep

   Challenge: As projects progress, clients may request additional tasks that were not included in the original agreement, often without acknowledging that this will require extra time and resources from the freelancer.

   Example: A video editor is hired to produce a three-minute promotional video. Halfway through the project, the client asks for additional animations, voiceovers, and changes to the script, which were not part of the initial agreement. If the freelancer doesn’t address these requests promptly, they may find themselves overwhelmed and unable to meet the deadline.

   Tip: To prevent scope creep, include a clause in your initial contract that outlines how additional requests will be handled. Communicate clearly about any changes in the project scope, along with the associated costs and timelines. As soon as a client makes an additional request, remind them of the initial agreement and discuss how the changes could affect the project.

 9. Payment Issues

   Challenge: Inconsistent payment practices or disputes over payment can create significant stress and financial uncertainty for freelancers.

   Example: A freelance writer submits an article, but the client delays payment with various excuses. After several attempts to communicate, the freelancer finds it difficult to secure payment due to lack of a clear contractual agreement.

   Tip: Always work within escrow systems when available on freelance platforms. Ensure that payment terms are clearly defined in your contract before beginning work. Consider requesting a deposit upfront, especially for larger projects, to mitigate the risk of non-payment and establish a sense of commitment from the client.

10. Limited Networking Opportunities

   Challenge: Freelancers may find it more difficult to network and build relationships with industry peers compared to those in traditional office environments.

   Example: A software developer frequently works alone and misses out on valuable collaborations or partnerships that could arise from networking with other professionals.

   Tip: Take advantage of online communities and platforms where freelancers gather. Join relevant groups on LinkedIn or forums specific to your industry. Attend virtual meetups, webinars, and online conferences to connect with others. Building relationships in these spaces can lead to referrals, collaboration opportunities, and invaluable support networks.

 11. **Managing Client Expectations

   Challenge: Clients may have unrealistic expectations regarding timelines, deliverables, and results, leading to potential dissatisfaction.

   Example: A marketing consultant is hired to increase a client's website traffic by 50% within a month, despite the fact that such results typically require a longer timeframe. When those results aren’t achieved, the consultant faces criticism.

   Tip: Educate clients on realistic timelines by clearly explaining your process and the factors that influence results. Use previous case studies to set benchmarks and illustrate what can be reasonably accomplished. Regularly update clients on progress to keep them informed and engaged, reinforcing their trust in your expertise.

12. Working with Difficult Clients

   **Challenge**: Occasionally, freelancers encounter clients who are difficult to please, have unclear feedback, or exhibit poor communication styles.

  Example: A web designer is subjected to last-minute changes and passive-aggressive comments from a client, making it difficult to satisfy their needs and maintain a constructive working atmosphere.

   Tip: Establish a professional relationship built on mutual respect. Document all communications and decisions to reference if disagreements arise. If a client becomes too difficult, acknowledge your boundaries; it’s okay to suggest parting ways if the project is not a good fit after reasonable attempts to resolve issues are made.

13. Adapting to Client Feedback

   Challenge: Freelancers may struggle when clients provide feedback that is ambiguous, vague, or overly critical, making it hard to implement necessary changes.

   Example: A graphic designer delivers a logo concept based on the client's initial brief. The client responds with phrases like "I don't like it" or "Can you make it better?" without offering specific guidance on what they dislike or how to improve it.

   Tip: Encourage constructive feedback by asking targeted questions. For instance, you might say, “Could you specify which aspects of the design you don't like? Is it the color scheme, the font choice, or the overall layout?” This can help the client articulate their thoughts more clearly, allowing you to make meaningful adjustments that align with their vision.

14. Finding a Balance Between Multiple Clients

   Challenge: Juggling multiple clients and projects can lead to burnout, confusion, and missed deadlines if not managed efficiently.

   Example: A freelance consultant takes on too many projects at once to maximize income, but soon finds it impossible to allocate adequate time and focus to each client, resulting in poor quality work and dissatisfaction.

   Tip: Use project management tools or task lists to keep track of deadlines, deliverables, and client communications. Prioritize tasks based on deadlines and workload, and don’t hesitate to limit the number of clients you take on at any given time to maintain quality and service standards. Communicate openly with clients if you foresee potential delays; they will appreciate your transparency.

15. **Building a Personal Brand

   Challenge: Many freelancers struggle to establish a unique identity or brand that sets them apart from the competition.

   Example: A freelance writer competes with thousands of others on Upwork, finds it challenging to attract clients, and often loses bids to more visible profiles.

   Tip: Develop a strong personal brand by identifying your niche expertise and what makes your skills unique. Create a professional portfolio that showcases your best work and includes testimonials or reviews from previous clients. Use social media platforms to share valuable content related to your field, positioning yourself as an authority and drawing potential clients to you.

16. Handling Non-Responsive Clients

   Challenge: Freelancers may face difficulties when clients become non-responsive after an initial agreement, making it difficult to move projects forward or receive feedback.

   Example: A copywriter begins a project but after submitting the first draft, the client stops responding, leading to delays and uncertainty about how to proceed.

   Tip: Set expectations regarding communication frequency at the project's outset. If a client becomes non-responsive, reach out politely to check in. You might say, “I hope everything is well! I wanted to follow up on the draft I submitted and see if you had any feedback or further instructions.” If the client remains unresponsive, establish a timeline after which you will assume the project is complete and submit your invoice.

17. Dealing with Negative Reviews

   Challenge: Receiving a negative review can significantly impact a freelancer’s profile and future job prospects on platforms like Upwork.

   Example: A web developer receives criticism for a project that the client feels did not meet their expectations, despite the developer believing they delivered quality work in line with the brief.

   Tip: If you receive a negative review, respond professionally and considerately. Acknowledge the client's concerns and offer to discuss the situation further. This shows prospective clients that you are willing to engage constructively and learn from feedback. Consider asking satisfied clients for reviews to balance the impact of any negative feedback, thus improving your overall rating.

18. Understanding Platform Fees and Pricing Strategies

   Challenge: Upwork has a sliding scale fee system, which can affect freelancers’ pricing strategies and profit margins.

   Example: A freelancer is unsure how to set rates that remain competitive while still factoring in Upwork’s fees and ensuring sustainable income.

    Tip: Familiarize yourself with Upwork’s fee structure and factor this into your pricing. Consider what you need to make per hour or per project to cover those fees while still earning your desired income. Research similar freelancers in your niche to ensure your rates are in line with industry standards. Periodically review and adjust your rates as you gain experience and positive feedback.

 19. Staying Motivated and Focused

   Challenge: Freelancing can lead to periods of intense workload followed by slower times, making it hard to maintain motivation during downtime.

    Example: A freelance designer experiences a busy month followed by a dry spell, leading to feelings of self-doubt and decreased productivity during slower periods.

   Tip: Create a schedule that includes both work and personal activities, allowing for rewards and breaks during high-pressure days. Use slow periods to invest in personal development, such as learning new skills, refining your portfolio, or marketing yourself. Setting tangible goals can also help maintain focus, whether that’s reaching out to potential clients, submitting proposals, or updating your online presence.

 20. Maintaining Work-Life Balance

   Challenge: Freelancers often struggle to separate work from personal life, leading to burnout and decreased productivity.

   Example: A freelance writer finds themselves working late into the night and on weekends because they lack a structured schedule, eventually resulting in exhaustion.

    Tip: Set clear working hours and stick to them. Use tools like calendars to block out time for work while also scheduling personal activities and downtime. Communicate your availability to clients so they know when to expect to reach you. Prioritizing time for self-care, relaxation, and socializing can help maintain your mental health and overall productivity.

 By addressing these challenges effectively, freelancers can build resilient careers on platforms like Upwork and thrive in the ever-evolving freelance marketplace.

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