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Freelance Will Not Be the Future Unless We Build Bridges Today

February 20, 2021
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Earlier this year, I was at a pitch session for the LAUNCH Accelerator preparing to pitch my company, GigLoft. There, my cofounder and I were talking to different guests about our vision and how we saw the future. When I mentioned that freelance is the future, another founder of a freelance marketplace told me that he thought we were wrong. I couldn’t believe this. This person runs their own freelance marketplace but they don’t think freelancing is the future!? Well, it sure got me thinking.

Months later, I decided I agree with him. In the current state of freelancing, I am also convinced that freelancing isn’t the future. The reason for this is because freelancing is so damn hard! If someone decides they want to freelance full time, they have a long way to go before they can make it as a full-time freelancer. The problems seem never-ending to someone wanting to just get started.

Friction areas when wanting to freelance

Marketplaces have never been busier

The “easiest” way to get clients for freelancers, which is marketplaces, is becoming harder and harder to find any success with. With Upwork now charging for connection requests, it’s clear that there is more supply than demand, and this is bad news for new freelancers wanting to get a spot on these platforms.

Getting paid on time and correctly is still an issue

Another reason freelancers sometimes don’t make it is because they get screwed by clients who take months to pay, or who never pay at all. The risk of taking on work and deferring payment until the work is done makes freelancers weary and often shuts down the opportunity for them.

Benefits are still a mess

Freelancers don’t have an employer to give them health insurance and a 401k plan. This is a huge friction point. Freelancing is hard enough, it’s less worth it without any benefits, Everyone needs benefits and unless you’re under the age of 26 or have a significant other who has a plan you can get on, it’s very challenging to find a good health insurance plan.

The “way in” isn’t clear

If you haven’t freelanced before, chances are you wouldn’t be sure on what the first steps would be to start doing it. There is no standard way to become a freelancer, and this makes getting in confusing. With so much advice on the internet, it’s hard to know who to trust or what steps to take first.

Will freelancing ever hit critical mass?

All of these reasons are why there is an argument that freelancing will never hit critical mass. Even so, the demand for freelancing is apparent: 47% of millennials tried freelancing in 2018, but only 11% of Americans freelanced full time.

This shows an obvious gap in the market, and Generation Z is seen to be even more prone to freelancing, as they grew up as digital natives. Additionally, I feel like I know more than 50 people my age who all have started a digital agency in the last decade.

The younger generations want to freelance, but the infrastructure to enable millions of people to successfully start freelancing isn’t there yet. So as it currently is, freelancing isn’t the future. But, it will be the future if we build bridges today that address the big roadblocks mentioned above. Luckily, there are companies in the early stages that are addressing these challenges.

Together, they will all make up the bridge needed to help freelancing cross enter into the mainstream.

A few companies are building the bricks that millions will stand on tomorrow.


In a world where contracts are opaque and not always guaranteed, there needs to be a platform that streamlines freelancers' payments in a safe way for both parties. Deel is building this platform, which gives potential freelancers the number one quality needed to jump in: peace of mind that they will get paid for their work.


At GigLoft, we’re playing a major role in bringing freelancing into the mainstream. GigLoft U is the only modern learning experience teaching creatives to create a successful freelance career around your unique skill(s). We’re tackling the “unknown” factor of launching a freelance career—there is a path to follow, and GigLoft supports you along the way.

Our first cohort of students just graduated, a majority of whom found clients while enrolled in the GigLoft U program. These people represent the average skilled creative who wants to freelance: current students, recent grads, and mid-career professionals, all of whom wanted to star their freelance careers. These are the types of people who will create even more economic impact if the bridges are built to eliminate the friction!

It takes a village

Freelancing won’t hit the mainstream organically. It’s going to take the efforts of the three companies listed above + dozens more filling in gaps that increase friction to start freelancing. If these companies didn’t decide to tackle the growing problems for independent contractors and freelancers, then the founder I talked to at LAUNCH will be right—freelancing won’t be the future.

But with a dedicated effort from a small group of companies tackling core problems freelancers are presented with, we can cross the chasm and help more people find joy and happiness in their work through freelancing.

Hopefully soon, everyone can #workanywhere.

Mat Sherman is a Co-Founder of GigLoft, a school and community that makes freelancing predictable, collaborative, and rewarding.

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