New Technology Has Sparked A Freelance Boom — Here’s What’s Coming Next

Uğur Kaner
Collective
Published in
4 min readMay 6, 2019

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The future of work is freelance. From graphic designers and web developers to delivery drivers and home cleaners, American workers are increasingly embracing the freedom and flexibility of freelance life. At the same time, talent-starved employers are taking advantage of the opportunity to hire skilled workers located all over the world, whenever they need their help. Already, there are 56.7 million Americans working on a freelance basis , according to Upwork, and by 2028, the company expects that 73% of all departments will have remote workers.

At the backbone of this shift is the rapid development of a host of communications and infrastructure technologies. That’s what lets a freelance writer continue working while backpacking through Vietnam and a Paris startup get computer engineering help from a talented developer based in New York.

But for these technologies to bring freelancers closer to their customers and colleagues, workers have to overcome a number of challenges in need of solutions — from their first day of business all the way through retirement.

When I was freelancing, I quickly learned how easy it is to ignore important things, such as forming an LLC, investing in a good bookkeeping tool or working with a professional tax preparer. Because these tools aren’t always immediately known to many freelancers, it’s often easy to put these things on the backburner. But the reality is, the sooner one has these tools and structures in place, the better, as it pays off in the long term.

How technology liberated workers from the 9-to-5.

When you think about it, it really is extraordinary how much technology has done to free us from our cubicles.

In the first decade of the 2000s, basic tools like high-speed internet, email and instant messaging made it easier for workers to telecommute, but it remained more effective to work with in-person colleagues and managers. Over the past decade, task-management and communications tools like Slack and Trello have empowered freelancers to work collaboratively without missing a beat. In fact, some studies now say that it’s more effective to work from home than in an office.

At the same time, sharing economy platforms like Upwork, Uber, TaskRabbit and Fiverr have enabled freelancers and clients to find one another. Whereas starting a freelance business once required workers to take a leap of faith into the unknown, today’s independent contractors can stride confidently into their new careers, secure in the knowledge that there are many accessible places to look for work.

The result is that more people are living their lives more freely, with flexible, remote working arrangements that allow them to take better care of family members, pursue meaningful hobbies and travel the world.

The next evolution of technology will make freelancing even more popular.

While technology has made it easier for people to go freelance, a variety of tools are still needed to help freelancers run more efficient businesses and live happier lives.

For instance, when you start a new job, you typically undergo an onboarding process with the human resources department that walks you through the various forms you need to fill out, as well as the basics of working at your new company. In many instances, onboarding software including Gusto, Zenefits and relative newcomer Rippling are used to smooth over the process.

But for freelancers, these sorts of tools are few and far between. Newly self-employed workers immediately face a maze of legal paperwork, unique tax filing rules and difficult corporate structure decisions to help them avoid common pitfalls such as opting to start as a Sole Proprietor (making them personally liable for everything) vs. an LLC or S-corp. Without the level of guidance afforded to W-2 employees, the process of becoming a 1099 is frequently more stressful than it needs to be. But with the right technology platform, freelancers could get the information and forms they need, right when they need them.

Once freelancers start working, they must also find fixes for the many benefits that full-time employers typically provide. Setting out on your own means finding your own healthcare and retirement plans, among other crucial benefits. For many freelancers, these barriers can even make it more preferable to stay at a full-time job they hate than to take the plunge into self-employment.

In addition to financial and health plans, some freelancers need help just getting paid for the work they’ve done. In the future, companies like DailyPay, a startup that supplants payday loans and Qwil, which gives freelancers instantaneous payment, will use technology and customer service to cut down on overdue invoices.

And when freelancers want to close or sell or business, they also need help tying up their legal loose ends so that they can move on to their next adventure. From start to finish, freelancers still need real help running their businesses smoothly.

Change is coming — is technology keeping up?

At the end of the day, the push toward a freelance world isn’t stopping anytime soon. As automation continues to make full-time work obsolete, workers and corporations will increasingly turn to flexible and part-time arrangements to complete the work that needs to be done. And if freelancers really are going to make up a majority of the population in the near future, then we’re going to need new technological infrastructure that can help them clear these hurdles.

Given the extraordinary power of technology to expedite and improve this transition, workers and innovators alike would do well to look toward the freelancing solutions of the future. As companies and workers flock to the freedom of freelance, those with the best technology tools will be the ones that come out on top.

Thanks for reading! While you are here, check out Collective — the platform we’re building for freelancers to start and run their businesses, while saving thousands in taxes every year.

Originally published on Forbes.

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Uğur Kaner
Collective

Engineer by training, designer at heart, product in craft. Co-founder Collective.com empowering business-of-one. Former @Memebox (YC W14), @Udemy