Freelancing and The Future of Work

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Do you remember when freelancers were few and far between? It seemed like an unviable fad. “When are you going to get a real job?” freelancers were asked. Well, times have changed.

As of 2016, freelancers made up 35% of U.S. workers. That’s 55 million workers. They collectively earned $1 trillion in 2015. This group, defined as “individuals who have engaged in supplemental, temporary, project- or contract-based work within the past 12 months,” are a solid part of the U.S. workforce now. And their numbers will continue to grow.

The rise of the freelance workforce is one of the four major future of work trends that I focus on when I work with my clients to help them prepare what’s to come. Today, I am sharing five of my most popular posts on the topic. I talk about how to best manage freelance workers, explain a legal pitfall to avoid, and share stories from freelancers themselves.

1. Managing Freelancers: 4 Challenges and How to Face Them

In this post, you’ll find a roundup of some key issues to tackle when working with freelancers. Find out how to create a positive and collaborative environment for full-time and freelance employees, how to help freelancers meet their project goals and deadlines, how to manage efficient communication, and how to maintain organizational culture with freelance employees.

Follow this link to learn all this and more. 

2. Nine Unconventional Ways Freelancers Landed Gigs

According to a recent study by Upwork and the Freelancers Union, the most common places for freelancers to pick up work are friends and family (36%), professional contacts (35%), and online job platforms (29%) like Upwork,, Guru, and even Craigslist.

This breakdown spells trouble for some. American workers looking for projects on online marketplaces, for instance, are often competing with workers who live in countries where the dollar is strong. That means many foreign workers can accept far lower rates. If you can hire someone to transcribe an interview for $3 an hour, you aren’t giving that contract to a freelancer charging $15.

So where else can freelancers find work? Read the stories of ten people, who picked up gigs in some unexpected places.

3. Freelancers Are Ditching Cities for Rural America

Hans Hageman was living in a brownstone and making six figures as a nonprofit executive, but he wanted a different life. So he moved to Pine Island, New York (population 1,534), 55 miles northwest of New York City, but about as small-town as you can get and still within driving distance. “I only wish I had walked this path sooner,” he says. “In the changing world of jobs and work, I want my kids and the students I have taught to realize that the traditional path is dead.”

It may not be quite dead, but for many, that path does seem to be leading to different places, including far afield of urban employment hubs. To be sure, rural America has always enticed bold entrepreneurs striking out on their own, and people have long built successful, self-employed lifestyles far from cities. But the barriers to doing so are lowering—and fast. Just as throngs of “solopreneurs” are finding it’s easier and more cost-effective to work for themselves in Phuket or Belgrade than for a boss in New York or Seattle, some urban freelancers are likewise finding new incentives to resettle in rural areas in the U.S.

Read here to learn why these rural freelancers headed into the countryside, and what they say the main rewards and challenges have been.

4. A National Survey of the Freelance Workforce: America, Meet Your Future Workforce

Commitment Issues

It’s time to get to know your future workforce. One place to start is by understanding why they’ve walked away from the working world that’s been the norm for so long. It’s not easy to take the leap- what motivates them to freelance?

Read more to hear why people freelance in their own words.

5. Freelancer or Employee? How to Avoid Employee Misclassification

While learning how to effectively manage freelance workers is imperative, organizations also need to pay careful attention to how they are classifying their freelance workers and employees. Misclassification can be a one-way ticket to IRS and legal problems.

How can you be sure your worker is an independent contractor?

Read here to find out, and discover some familiar companies who learned the hard way.

Are you a freelancer? What are the major hurdles you face (if any)? Curious about trying to freelance? What holds you back? I’d love to start a dialogue. Leave a comment below, send me an email, or find me on Twitter.

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