My first two weeks on Upwork as a Digital Strategist and Web developer: Things to keep in mind.


In the burgeoning world of remote work and freelancing, platforms like Upwork have become a gateway to countless opportunities. But diving headfirst into this pool without a clear strategy could lead to quick burnout and fruitless endeavors. To shine brightly in this competitive space and ensure you get the most out of your Upwork experience, it’s essential to approach it methodically and strategically.

In this guide, we will explore four fundamental steps to ensure you embark on your Upwork journey the right way: Crafting a robust management plan, defining and showcasing your services, meticulously building your profile, and leveraging your external network. These will equip you with the right tools and mindset to kick-start your freelance journey on Upwork effectively.

And hey, I am no Upwork expert (yet), but in my first two weeks, I’ve achieved some amazing results. Thus far, I’ve received a rising talent badge, apparently given to only 5% of freelancers, and I’ve already onboarded my first client. Read on to see what allowed me to reach this far in just two weeks.

1. Craft a Robust Management Plan

Bird’s eye view of my management process diagram. From lead to a delivered project.

The first step towards a successful freelance journey on Upwork is developing a detailed management plan. Starting without a well-defined strategy is akin to navigating through a dense forest without a map; it’s easy to get lost amid the workload and responsibilities. A comprehensive plan will guide you in handling projects, meeting deadlines, and providing a level of service that will impress your clients and pave the way for future opportunities.

To implement this effectively, productivity and project management platforms can be a game-changer. For instance, ClickUp, my tool of choice, can be tailored to accommodate various workflows, helping you manage projects seamlessly. It allows you to track deadlines, assign tasks, share files, and even integrate with other tools you may need. This kind of platform can greatly enhance your ability to deliver on your promises and maintain a high level of service.

2. Define and Showcase What You Offer

As the old saying goes, “If you stand for everything, you stand for nothing.” This wisdom holds true in the freelance marketplace as well except for some particular cases. Understanding your core skills and competencies is the key to marketing yourself effectively when getting started on Upwork. Customers appreciate hiring experts, so, it’s always beneficial to highlight your strengths in specific areas. Your initial aim should be to garner a reputation for excellence in your chosen fields. This way, you can establish a solid foundation, build your credibility, and then branch out to showcase your versatility.

Upwork recognizes the multifaceted talents its platform hosts, offering the ability to create a General profile as well as two specialized profiles. These can be curated to reflect specific skills and services, ensuring you present yourself in the best light for each potential client. But be mindful: the more services you offer, the more time and effort your profile needs to maintain its credibility.

If you’re someone who excels in multiple fields, you’re not alone. It’s possible to be a Jack of all trades without spreading yourself too thin. The key lies in demonstrating a proven track record in each skill you list. So…

3. Invest Time in Your Profile

Snapshot of my profile’s public view

“First impressions last.” This is especially true for your Upwork profile, your primary tool to leave a lasting impression on potential clients. A stellar profile goes beyond a well-written biography and a professional photo. It’s about showcasing your skills, experiences, and accomplishments in a way that truly resonates with your target clients.

But remember, a great profile doesn’t happen overnight. It requires thoughtful crafting, consistent updating, and a lot of patience. Don’t skimp on detailing your past experiences, completed projects, and unique skills. Make sure to include samples of your work if possible. Regularly updating your profile to reflect your most recent work can also help demonstrate your growth and active presence on the platform. This investment of time and energy will undoubtedly pay off when clients start to notice and appreciate the depth of your capabilities.

4. Leverage Your External Network

While Upwork is a fantastic platform to find new clients, it’s equally essential to leverage your existing network. Just as in traditional businesses, referrals and word-of-mouth are powerful tools in the freelance world. Clients with whom you’ve built a relationship outside Upwork can be encouraged to contract and process payments through Upwork, boosting your profile’s reputation. Also, reach out to your network and get testimonials on past projects. We all have someone we’ve collaborated with or worked with in the past that can fairly give us that boost that a testimonial provides.

Snapshots of testimonials on my Upwork profile

This technique has served me well. Just two weeks after setting up my profile, I onboarded my first client through this approach. I’m eagerly waiting to see how the success score from this job will factor into my overall rating, and I’m hopeful that I can earn the Top Rated badge by the end of summer.


Navigating your freelance journey on Upwork may seem daunting at first, but by approaching it strategically and methodically, you can turn it into a rewarding experience. Remember, the path to success on Upwork isn’t about being the quickest. It’s about consistency, quality, and understanding the dynamics of the platform. Stick to these principles, keep refining your approach, and soon enough, you’ll find yourself thriving on Upwork.

Connecting with Me

Embarking on the freelance journey is not a solitary pursuit; it’s about forming connections and partnerships that enable growth and success. And, this article would not be properly finished if I didn’t include a bit of a sales pitch ;)

If your business is seeking a transformative shift through technology, grappling with operational inefficiencies, or yearning for a stronger online presence, you don’t have to look further. I’m Diego, and I specialize in propelling businesses into the digital sphere through web development, digital transformation, and prop-tech innovation.

From developing modern web applications with JavaScript, TypeScript, React, Next.js, and Tailwind CSS, to optimizing property management software, I blend creative problem-solving with deep industry expertise to deliver solutions that exceed expectations. My toolbox extends to intelligent automation tools and productivity optimizers like Google Workspace and ClickUp, enabling your business to achieve operational efficiency and growth.

But beyond the expertise and tools, my commitment is to build a partnership with you. My approach is rooted in understanding your objectives and working in unison to deliver results that go beyond the ordinary. So, whether you’re looking to automate your operations, enhance your online presence, or unlock the potential of property management software, I’m here to make it happen.

I invite you to explore my Upwork profile, where you can dive deeper into my services and past accomplishments. And if you’re ready to discuss how I can help elevate your business to the digital stratosphere, don’t hesitate to reach out. Let’s connect, share ideas, and together, we can carve a path to your business transformation.