Taking the Risk and Anxiety Out of An Often Broken Professional Freelance Marketplace

Leah Jewell
6 min readFeb 7, 2023

The gig economy is huge and growing and everyone is impacted by it in one way or another. Hiring contractors, freelancers, and contingent workers is expected to be a $455 billion global industry in 2023. Transportation (Uber, Doordash, etc) and asset sharing platforms like (Airbnb) make up 88% of that that total . Professional services, which can include research, data entry, design, writing, building websites, and more, make up 3.8% of the global gross dollar volume of gig revenue.

The gig economy is expected to grow at such a rate that the majority of the U.S. workforce will be made up of 58 million freelancers by 2027. Continued fiscal tightening within corporations, a growing demand for remote work, and the need to access new and different talent pools to get work done will all contribute to the growth or professional freelance services.

Setting aside transportation, asset sharing platforms, and home improvement marketplaces, people have primarily three routes to choose when thinking about freelancing a professional service:

  1. Find an individual on a professional marketplace (UpWork, Fiverr, Catalant, TopTal, etc)
  2. Find a larger team off-shore to handle bigger, recurring work.
  3. Turn your full-time roles into remote gig work- ie: Google has more freelancers (54%) than permanent workers (46%)

There are pros and cons to gig work from the perspective of the company trying to get work done and the individual delivering the work.

Individuals report many different reasons why they choose freelancing. including:

  • Flexibility
  • Extra income
  • Control of schedule/ be your own boss

The cons are also well documented and real. They include lack of stability, impact on company culture, and lack of insurance. For many people, the pros outweigh the cons and/or freelancing may be the only option on the table.

Professional gig work, even for entry level work, is most accessible to adults who have already cultivated a network and portfolio, and even then it can be tough to break through to get “clients.” This is even more challenging for students. Three-in-ten 18- to 29-year-olds have ever earned money through an online gig platform- mostly through ride sharing. Entry level professional services, like online research, data entry/cleansing, user testing, and sales lead qualification are all categories of work students have the skills and desire to do, but accessing this entry level gig work remains challenging, if not impossible for students. Some of the challenges for students include:

  • Don’t know about professional marketplaces in order to sign up.
  • Don’t know how to articulate “gigs” and/or figure out tiered pricing options needed for online marketplaces.
  • Don’t have experience to get noticed in a sea of professionals- even if the work itself doesn’t require specialized experience.
  • No network to pull on to get started with a few gigs.
  • Don’t know how to scope the work- something most professionals learn how to do with experience and practice and is required on freelance platforms.

19 million college students represent a population of untapped talent for short-term work, and a way to build a companies talent pipeline in the future. They are not well-served or accessible in the professional gig world as it exists today. Companies would benefit with better access to this skilled, motivated freelance talent pool.

From a company perspective, there are many benefits to hiring freelancers including:

  • Extra help when needed- especially with open jobs outnumbering people looking for full-time jobs.
  • Faster deliverables
  • Affordability
  • Access to a larger, more diverse talent pool
  • No long term commitment

Most companies have a mix of success and horror stories when it comes to working with freelancers. Whether you’ve had good or bad luck, one thing is true- finding and working with freelancers is often harder than it should be, even with digital marketplaces connecting buyers and sellers. The biggest challenges are:

  1. Picking someone- It’s not hard to find someone, but it is a major pain to sort through all the options. It’s easy to type in a keyword related to the work you need to get done (online research, graphic design, etc) but when you are presented with hundreds, if not thousands, of possible candidates, you find yourself spending hours wading through a sea of qualified 5 star freelancers. Who do you pick? Which one best fits your needs? How do you distinguish the candidates?
  2. Needing a team of people- Marketplaces are set up for you to find and work primarily with one person. What if you have a big work project, or recurring work, and having a team of people would help get your work done faster? Now you are really stuck.
  3. Pricing- Deciphering all the different pricing models and tiers can be confusing and the “fine print” is different for each person. Sure, it looks like the work starts at $20 but actual requirements don’t always sync up and the price is usually much higher.
  4. Communication- Restricting communication to a platform can be challenging and time consuming. Sometimes you can simply get something done faster and easier with a call or a video chat.
  5. Scoping work- Anyone who has tried to scope work knows it’s hard and takes time. If you aren’t specific, you won’t get what you need. Responsibility lies on the business to get this right and think through every detail. A freelancer can help unpack your requirements but a lot gets lost in translation and the back and forth can really eat up time during the day.
  6. Risky- Even with experienced people, you may have so many iterations that you either end up taking more time than you have, paying more, or giving up because the end result doesn’t match what you needed.
  7. Off- shore- Leveraging a team of people off-shorte to do large/recurring work has its own complications- time zone, language, knowledge of your business/environment, training, and managing people/turnover. It’s often the choice for affordable work, but these challenges often add to cost and time.

Not everyone has a bad experience with freelance marketplaces or off-shoring. However, finding people to do work is still challenging and risky. And when you have to spend tens of hours finding people, scoping, and managing the work, it’s no surprise people get frustrated, sometimes to the point of paralysis and not being able to move forward. Work doesn’t get done and/or existing employees get handed extra work they don’t have the time, expertise, or desire to do.

If you are one of the 70% of small-medium sized businesses who use freelancers or a larger company looking to get more work done because you can’t fill your positions, here are a few ways you can take the risk and anxiety out of freelancing:

  1. Get help with scoping– Come to the conversation with a good idea of the specifications of your work. Why are you doing the work? How will you use the work? What type of work? How much? What are the components? Do you have examples of prior work to use as a guide? Good scoping decreases the risk of bad or unacceptable work on the back end. Use a company/person who will help you with scoping to help save you time and ensure you cover all the unanticipated details you may not be thinking about.
  2. Move beyond the 1 to 1 match– Most people think about hiring one person to do a small, discrete project. However, you can get more work done if multiple people can work simultaneously. This is harder to do with marketplaces focused on matching you to one person. Larger companies tend to go off-shore to leverage teams of freelancers. If you are a small to medium sized company who doesn’t have the time or infrastructure to set up training and relationships abroad, or if you are a large company who runs into the off-shore challenges listed above, you can try companies with U.S. based workers, like Work Simplr, to scale the work you need done with any size team of freelancers. Most importantly, companies like Work Simplr leverage qualified U.S. students to do the work, which keeps the pricing competitive with off-shore options.
  3. Get help managing freelancers– Although still time consuming, it’s possible to manage one person on a small task. It’s much harder to manage a team of people. Let’s face it, the last thing you want to do is off-load work and then spend all your hours training and managing freelancers! to make sure the work is done on-time, accurately, and thoroughly, look for companies who provide a turn-key solution to managing the work.
  4. Get a guarantee- Ensure you are working with a person/company who will guarantee the work they do without charging you extra money for changes/revisions (as long as they fall within the original scope of work– another reason why scoping is critical!)

Challenges aside, leveraging freelancers can be a great way to get work done, and not just for small one-off projects. Everyone will experience the gig economy in one way or another throughout a lifetime of work. It’s important to continue to look for ways to improve the experience for both employers and individuals.

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Leah Jewell

Bridging the gap from school to work. Passionate about helping students. Co-Founder of Work Simplr- an on-demand workforce powered by students