Inside Scoop: Nearly A Decade of Freelancing on Upwork 🌟

Howdy datalancers 👋 

I’m really excited to kick off our very first community interview piece, included below.

Starting in September, I’m going to be interviewing more community members on their experiences and working on growing our community blog. Details at the end of the newsletter.

Onto the interview:

Interview with Anna: Insights from a Seasoned Upworker 🚀

Today, we’re excited to share insights from Anna*, a long-time Upwork freelancer who has navigated the platform for nearly a decade. She’s seen it all, from the early days to the recent changes. Here’s what I learned from our conversation:

^{*names have been changed to preserve anonymity of the community member, per their request}

Starting on Upwork: Building a Strong Profile 🌟

Danielle: What drew you to Upwork initially? What was it like when you first started?

Anna: When I first started on Upwork, I knew I needed to build a strong profile to attract clients. Think of it like booking a vacation spot—would you choose an Airbnb with no reviews? Most people wouldn’t. Similarly, clients are hesitant to take a chance on a profile with no history. So, I took on some simple, underpaid jobs at the start to build up my reviews.

Finding a Niche and Crafting Proposals 🎯

Once Anna had built up her profile, she focused on finding her niche—short-term, one-off data analysis projects. But she quickly learned that her approach to proposals needed to change.

Anna: One of the mistakes I made early on was writing proposals like formal cover letters. Over time, I learned that a shorter, more direct approach worked better. Clients are busy and sifting through dozens of proposals. My best results came from keeping it simple: "Hey, your project makes sense. Here’s what I would do: 1, 2, 3." Then, I’d suggest a time to discuss further. This approach respects their time and gets straight to the point.

Why Hourly Work? ⏰

Danielle: You mentioned you prefer hourly work on Upwork. Why is that?

Anna: With data projects, you often don’t know the full scope until you dive in. Clients might not fully understand the complexity of their data, and that makes it hard to estimate the time required. By working hourly, I can give an upper-bound estimate and adjust as needed. This ensures I'm compensated fairly, especially when projects expand beyond the initial scope.

The Changing Landscape of Contractor Platforms 🌐

Danielle: Have you noticed changes in platforms like Upwork, especially compared to other contractor services?

Anna: Upwork has definitely changed. When I started, sending a proposal cost just a few cents. Now, it’s all about "connects," which can cost up to $20 just to apply for a job. It's similar to how Uber was cheap when it was VC-funded, but as they’ve tried to become profitable, prices have gone up. Upwork seems to be following a similar path.

Danielle: So, the costs were more reasonable when they were subsidized, but now they’re focusing on profitability?

Anna: Exactly. But unlike Uber, on Upwork, you can put in a lot of money and never get a job. I’d hesitate to recommend it to new freelancers in 2024 because of this.

Advice for New Freelancers 💡

Danielle: What advice would you give to new freelancers considering Upwork?

Anna: Be prepared for upfront costs. You’ll spend money on each job you apply to, with no guarantee of being hired. That first job is especially tough—you need to convince someone to take a chance on a profile with no reviews.

Danielle: That sounds challenging for newcomers!

Anna: It is. Upwork might not be focused on attracting new freelancers anymore. They likely have enough money and freelancers from existing jobs.

Parting Wisdom 🧠

As we wrapped up, Anna shared some final thoughts on sourcing long-term contracts outside of Upwork.

Anna: Most of my long-term contracts come from people I worked with during my full-time job. Often, these are referrals from people who already know my work. For clients that are hesitant to spend money or think they need a full-time employee, I explain how hiring me part-time is significantly cheaper since they don’t have a full-time job’s volume of work.

Her focus is on companies with data needs that don’t require full-time staff—usually earlier-stage companies. This allows her to enjoy the freelancing lifestyle while only working part-time.

Thanks for taking the time to read!

If you’re interested in participating in an interview, or contributing to the blog, fill out this form and we’ll be in touch!

Cheers,

Danielle