I Spent $675.92 Talking to Top Data Scientists on Upwork - Here's what I learned

My Search for Mentorship

You can either learn from your experience or the experiences of others. The former is slow and painful, while the latter is (relatively) quick and easy. This is why having mentors can help accelerate progress toward your goals.

While this all sounds great in principle, actually finding the right mentors is much easier said than done.

This was something I struggled with for months. It felt like my interests were too niche. I was (and still am) interested in the intersection of data science and entrepreneurship. While I found many data scientists and entrepreneurs out there, it was difficult to connect with those that identify with both categories.

However, after months of futile cold messages on LinkedIn, there came a turning point when I decided to transition my search off of LinkedIn and onto Upwork.

Entrepreneurs are on Upwork

For those unfamiliar, Upwork is a freelancing platform where clients post jobs, and freelancers apply for these jobs. I first interacted with Upwork as a freelancer back in grad school. However, I came in as a client in this most recent interaction.

As a client on Upwork, you can browse and book time with freelancers. As I explored the talent, I quickly realized there are serious data scientists on Upwork.

I’m talking about decades of experience and 6–7F revenues on the platform (and that’s just on Upwork). But the real kicker is any data scientist on Upwork is, by default, an entrepreneur (or at least closer to one than what you’ll typically find on LinkedIn). So it seemed I had found my niche mentors.

This kicked off a series of 10 calls with top data scientists on Upwork. I structured the calls in 3 parts: Past – how did you get started?, Present – how do you operate now?, and Future – where is this going?

I follow the same structure in this article to summarize and highlight key takeaways from these conversations. I hope this gives you some context and inspiration for what your data entrepreneurship journey can look like.

What got you into Data Science?

One of the most striking observations from these calls is that no two Data Science freelancer journeys were the same. Just to give a sense of this, here are the educational backgrounds of the 10 freelancers I spoke with Biomedical Engineering, Industrial Engineering, Biostatistics, Electrical Engineering, Computer Science, Finance, Physics, Data Science, Marketing, AI, Economics, Math, MBA, and DS Bootcamp.

Notice there are more backgrounds here than interviews, this is for two reasons.

Most had training beyond a bachelor’s degree, and
No 2 out of the 10 freelancers had the same exact training

The latter point is one of my favorite aspects of data science. It is a field that draws a wide range of perspectives and experiences, which makes for very interesting conversation and collaboration.

This is important to keep in mind when reading this article. The diversity in backgrounds extends to how freelancers operate and where they are headed. Put simply, different is the norm here.

How did you start freelancing?

While each freelancer’s start was unique, there was a common starting strategy that came up a few times. In the early days, many freelancers tended to have a strong focus on learning and reputation building.

There is more to data science freelancing than just the "hands-on-keyboard" work. Not only do you need to do data science, but you also need to sell yourself, juggle clients, manage your financials, etc.

A common way freelancers navigated this was to take on a (relatively) high volume of small projects in the early days. Not only does this provide several repetitions to learn from, but having a long list of successfully completed projects (with testimonials) creates credibility and makes it easier to get new clients.

While this "small-and-wide" strategy was great for getting started, it did not seem to be a common (or good) long-term strategy.

How do you operate now?

In keeping with the "different is the norm" theme, there was a wide mix of how these freelancers currently worked and got paid. Here are a few examples to give you an idea of this.

Freelancing full-time
Freelancing part-time while pursuing a side venture
Working full-time role while freelancing on the side
Full-time contract role (1099)
Transitioning out of freelance into a full-time role (W2)

This highlights the flexibility of freelancing. It allows professionals to tailor their work to what works best for them.

For those who were not seeking full-time work, it was common to limit the weekly time commitment for each client. 10 hr/week per client seemed to be a sweet spot, with a typical variation between 5–20 hr/week. With this time allotment, freelancers would typically have 2–3 clients at a time.

How do you get new clients?

There were 3 common ways the freelancers got new clients. The first and most common way was applying for contracts on Upwork or other sites.

The second way was via inbound leads (i.e. clients found them) on Upwork or other platforms. This occurred most often for those with a great reputation, a list of testimonials, or a strong presence on social media.

Finally, the third way (which was common for the most successful freelancers) was getting work from referrals alone. This seemed to happen when there was much more demand from clients than the freelance could supply (which also naturally drove up prices.)

Where is this going?

Each freelancer had a unique vision for their future. However, to make this more digestible, here I partition the long-term goals into 3 buckets.

Keep Freelancing & Scale Up Consulting Business

The first bucket includes the ones that can see themselves freelancing forever. They enjoy it, and it gives them a nice life. They work when they want, on what they want, with who they want, and where they want.

Also, in this bucket, I put the ones who want to scale up their consulting business. This tends to happen organically for those who have too much work than they can do alone and who enjoy project management. For many, this is as simple as having subcontractors that they work with frequently or even full-time employees.

Generate Passive Income & Build a Product-Oriented Company

Although freelancing provides tremendous freedom and can be lucrative, it still mainly consists of trading time for money e.g. I pay you an hourly rate to do a job. While this isn’t so bad, most would rather trade a little time for a lot of money e.g. you build a product once and sell it many times.

This is the second long-term goal bucket which lumps together generating passive income with building a product-oriented business. While these are technically different, they both can serve the same purpose: generating more value in less time.

Some freelancers planned to do this by creating online courses or other digital products. A handful of freelancers were actively building trading bots or other trading tools for personal use.

Others considered building software solutions tailored to mid-size companies or specific industries by leveraging their freelance experience and clientele. While I haven’t yet personally seen a successful realization of this latter idea, I am optimistic about it.

Transition to a Full-time Role

While freelancing offers flexibility and independence, some freelancers may eventually transition into full-time roles. Some even consistently cycle in and out of full-time roles. A few reasons for this from those that I interviewed were: you can make a bigger impact at an enterprise, more social interaction and collaboration, more certainty and income stability, greater opportunities for career growth, and a client becomes an employer.

My 4 Takeaways

These calls fulfilled the promise of mentorship that I was seeking in that they helped accelerate progress toward my goals. While it’s hard to say how things will turn out, I have a feeling this may be one of the best investments I made in my Entrepreneurship journey. I’m looking forward to putting these learnings into practice and continuing to build relationships with others in this space.

To wrap things up, here are the 4 key takeaways that I will keep top of mind for future freelancing endeavors.

Do good work so you can operate on reputation and referrals. If people come to you, you have greater leverage and optionality to help ensure the work and clients you take on are aligned with your goals.
Find a niche. Choosing a niche can help make you a big fish in a small pond. Here are some niches that came up in my interviews: finance, crypto, energy, OCR, LLM applications, and data strategy.
Form alliances across the tech stack. Data science work alone can be limited in its business impact and value generation. This is why forming relationships with other specialists (e.g. SWE, web dev, UX/UI, etc.) can help you provide greater value to your clients.
Develop a personal brand. Having a strong brand presence on social media platforms can make it easier to land Freelance contracts by giving you credibility. Additionally, sharing valuable content and showcasing your expertise can help ideal clients find you (as opposed to you having to find them).