Addressing the Freelance Wave

Written by Rob Miller on June 24, 2019

We are seeing an increasing number of freelancers in the United States and more change than ever in the freelance job market, as shown in this Upwork study. We have a dramatic shift in the labor markets where at one end of the spectrum we have millennials who demand a very clear work-life balance and at the other end, we have highly skilled baby boomers who are retiring but still want to stay intellectually challenged and busy. When you combine this with technology advancements, you have a convergence really driving the freelancer industry.

There are ways associations can address this wave of disruption and better accommodate the growing number of freelancers, and it doesn’t have to be complicated.


When looking to connect with freelancers, traditional methods such as using job boards, newspapers and recruiters are not the way to go. Instead, employers should look to new social tools where freelancers like to hang out. These tools are free. Obviously, many of these freelancers are looking at ways to be efficient so they’re going to look to free services. They’re going to try and build a brand for themselves on these tools, so that’s where you want to start. Tools such as LinkedIn and Facebook or even a service such as MindSeekers that hunts for candidates online and present them to employers are ideal sources. Although I think the best option is probably the dedicated online matchmaking tools for freelancers that specializes in associations and nonprofits such as

Associations also need to be more intentional about their planning their internal communications and daily work. Take the example of a meeting. You might need to set ground rules for that meeting such as you have to have an agenda, you have to send out connection information and you have to do it two days in advance. It could be as simple as those types of rules to modify the corporate culture and create an environment conducive for all members of the team being successfully included.

Another simple change organizations can make is get beyond email. As great as email is for one-to-one communication, it’s not a good collaborative tool. In fact, it’s not a good tool for long term organizational information because ultimately, what happens is that key information ends up in people’s inboxes. There are much better tools for collaboration such as Basecamp or Slack, which preserve, organize, and facilitate these dialogues. The decisions can be stored and processes can be put in place that quite frankly benefits the entire organization.


The Upwork study found that the number one concern for freelancers was being able to access affordable health insurance. Given that freelancers receive no benefits, this makes a lot of sense. I believe that national associations have an opportunity to consider providing various affinity programs including potential insurance to their members in their industries to address this concern, and remove a major barrier to their members pursuing their ideal work arrangement.

The Upwork research also found that freelancers were more likely to get professional education and found it more valuable than full-time staff members. Because the freelancer is trying to differentiate themselves from a fellow competitive freelancer, associations have a substantial revenue opportunity, if they can offer certifications, micro-certifications or certificates that would provide an avenue for freelancers to pursue and differentiate themselves.

Associations are in this very special place of trust; they have the trust of their members and the great industry they support. Associations should consider developing a marketplace where they can connect their industry with freelancers in a trusted environment. An example would be for the association to create an “industry-approved” professional services, which the freelancer and the industry would thus use to engage one another. Another example would be to create other training and articulate industry best practices. Associations therefore have a number of things that they can do to really provide value to freelancers and ultimately benefit their whole industry that they support.