The future of freelancing (part 2)

Isaiah Trotter
4 min readDec 30, 2022

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Solving the problem of inconsistent freelance work

Despite all the solutions that are available to freelancers designers, and there are a lot (Upwork, Fiverr, Freelancer, 99Designs, Dribbble, Behance, TopTal, Working Not Working, Design Crowd, PeoplePerHour, Envato Studio, Guru, DesignHill…), how come there’s still nearly 600k freelance designers struggling to create consistency when all these solutions exist? I think it comes down to the simple observation that none of these platforms were built with the intention of guaranteeing work in the first place.

And I can prove that just by looking at some of the names. Toptal’s implies that they select from the top percentages (it happens to be 3%) of the talent pool that applies. 99Designs implies that clients can get access to a lot of different designs for a single project (from their design competitions. This deserves a separate post, but a system of design competitions is antithetical to guaranteeing work for freelancers. That’s fine because it was never the intention, but it’s worth pointing out.) Fiverr implies that you can pay $5 for work. PeoplePerHour implies you’re only hiring people on an hourly basis.

The underlying model for these companies is to merely give freelancers work by connecting them with clients who value cheap, or fast, or high quality, or high quantity of work, etc… That’s why it’s common place to see all these permutations of gig marketplaces. Just segment the clients into a particular niche of what they value, and it seems you’ll always find freelancers willing to do the work on those conditions, even if it hurts them. If freelancing as an industry is going to move forward, both freelancers and clients need a solution that gives them 10x the value they’re getting anywhere else. Somehow the biggest needs of clients and freelancers need to be synthesized into a solution that dramatically improves the quality of life for both parties.

Is guaranteed freelance work even possible?

There might be some hesitancy when you combine the word “guaranteed” with “freelance work”. It seems antithetical to the whole thing because, as more gig marketplaces come about, they largely follow the path set before them by previous companies. It’s as if the groove in the ground created by following the same path has become deeper and deeper. Consequently, straying from it feels unnatural. Is guaranteed work possible? I think it could be, but the resulting solution is going to look totally foreign to what’s currently out there. And that’s due to the fact that the underlying goal of the system (guaranteeing work) is an order of magnitude more difficult than the alternative (giving work).

Here’s a concrete example to illustrate what I mean. All the solutions out there were never designed to guarantee work in the first place. They act merely as facilitators. We can think of current freelancing platforms like gyms. Gyms are in the business of simply facilitating a place for you to work out in; they don’t guarantee results (gaining muscle, losing weight, etc…). Personal trainers on the other hand help you use that equipment to reach your goals. They are the ones who can help create the transformation in you, assuming you follow their instructions. However, there are currently no “personal trainer” type freelancing platforms to help guarantee consistent work for a freelancer, or guarantee long term business growth for a client.

This is the heart of where I expect the future of freelancing to go. It will become a transformational experience where freelancers and businesses come in at any level, and exit achieving their full potential. A lot more emphasis is placed on intentionally cultivating growth. And I think guaranteeing that work is the first step in providing the foundation for the long term success.

Making guaranteed freelance work a reality

Here’s one potential solution of what the future of freelancing could look like. This is just a concept though. I’m in the process of vetting this idea by testing with actual designers. So if you’re a freelance designer who wants some extra work, reach out to me; I could help you get some extra work while you help me test the hypotheses discussed in the video below.

The last article is going to consider the new market opportunities that arise after guaranteeing freelance work and income. This article will especially be helpful for CEOs of gig marketplaces who want to create a secure future for their company. That’s because these new opportunities, if solved in a particular order, seem to create a lengthy roadmap of continued growth. In short, I’ll be discussing how we could move up Maslow’s hierarchy of needs to first guarantee work (safety), then help freelancers establish connections with other freelancers and healthier relationships with their own families (belonging), help build confidence and mastery in their craft (esteem), and finally sending them off like a proud father when they no longer have a need for us (self-actualization).

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