After completing my contract with my last client, I revisited my Upwork account, eager to explore new opportunities. Finding clients has never been my strong suit, so I broadened my search across multiple freelance platforms. Since I was just starting out, I set my rates lower to gain traction. At the same time, I enrolled in a course on client acquisition and freelancing strategies to refine my approach.
I was fortunate to land my first client on my very first day. By the second week, another client reached out with an app project. At first, everything seemed promising, but as I delved deeper, I realized freelancing presented a unique set of challenges. Unlike traditional employment, where tasks are structured and objectives are clearly defined, freelancing often has ambiguous expectations. Project requirements can be vague, communication inconsistent, and priorities subject to change.
The Challenge of Communication
I always find it easier to communicate with just one person—usually the key stakeholder—because they tend to have the most apparent understanding of the project and its goals. However, in many cases, the person I interact with may not fully grasp the technical aspects of the steps required to bring their vision to life.
This creates a unique challenge: I often have to balance what I know is the right approach from a design perspective with what the client believes is right for their product. Design is inherently subjective—especially when it comes to visual elements. Unlike technical implementation, where there are best practices and clear solutions, visual design doesn’t always have a single “correct” answer.
The Complexity of Decision-Making
Another challenge I encountered was navigating the decision-making structure within companies. Many projects involve multiple stakeholders—a boss, a marketing manager, and a product manager. While my role as a designer is to execute the product vision, I am often excluded from key meetings where my designs are critiqued. This lack of direct involvement makes it difficult to iterate effectively and ensure that the final product meets the client’s expectations.
Psychologically, a product’s look and feel should establish a strong connection between all elements of the website or app. Consistency in colour, typography, spacing, and layout helps users navigate intuitively and feel comfortable. However, I suggested a unified visual approach in one particular project, only for it to be dismissed.
At that moment, I wondered: Should I just follow the client’s advice, even when it contradicts best practices?
When to Follow vs When to Push Back
If a client dismisses essential design principles, my role is not to argue but to educate in a way that aligns with their goals. Instead of saying, “This is wrong,” I’ve learned to frame it as:
- “A consistent design improves usability and makes navigation easier, which can lead to better engagement and conversions. Would you like me to show some examples of how this works?”
- “If we introduce too many different elements, it might confuse users. Would you be open to testing a more streamlined version first?”
This approach makes clients feel in control while subtly guiding them toward better design choices.
There are moments when I must accept the client’s decision and move forward, but I ensure that my recommendations are documented so that if issues arise later, they know where the decision originated.
Lessons Learned & The Road Ahead
Despite these challenges, freelancing on Upwork has been an eye-opening journey. It has taught me the importance of self-advocacy, clear communication, and setting expectations early on. I need to improve my communication with clients and stakeholders to navigate these obstacles. At the same time, I must recognize my boundaries and take ownership of my process—immersing myself in the user’s perspective, designing based on actual needs, and ensuring that my work is backed by strong reasoning.
While Upwork has been a valuable learning experience, I must explore opportunities beyond freelancing. The remote job market offers stability, collaboration, and long-term growth potential that freelancing sometimes lacks. Moving forward, I plan to balance both—leveraging freelance projects to sharpen my skills while keeping an eye on remote design roles that align with my long-term career goals.
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