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Upskilling as a Freelancer

Updated: May 1, 2020

My very first freelance project involved writing social media copy for a nonprofit. As Lewis Commercial Writing grew, we maintained social media writing as one of our deliverables. It was one of the easiest projects to land: everyone needs social media copy. 

But last year we finally cut it out. We began turning down projects to write social copy and haven't written for social (other than our own) since.


Why cut ourselves off from easy money-making opportunities? It came down to the trade-off, the opportunity cost.

Cutting out the busy work

From the start, social media projects had been busy work that helped us maintain easy cash flow. Busy work is fine for a season, but it eventually stops freelancers from landing larger, more challenging projects.

Admittedly, this was a fairly easy decision. We'd been ready to cut social media writing from our offerings for a while. But the second cutoff point we established recently was far more challenging.

Two weeks ago we told a prospective client, for the first time ever, that we no longer offer blog writing services to new clients. 

Again: What were we thinking? Why on earth would we turn down work?

Our reasoning comes down to a process I’ll call upskilling.

Upskilling: A promotion for the self employed

Upskilling is the willingness to leave behind lower-skill projects for those requiring greater expertise. As you improve as a freelancer, you turn down simpler projects to open your calendar for more challenging work.

This ensures two things. First, that we can provide higher-level value to our clients because we have the time and energy to solve larger marketing and business problems. Second -- and this part is key-- we face less competition.

The goal for every freelancer should be to continuously upskill. Each of us only has so much deep work to apply in a given week. Social media and blog writing, while relatively easy to learn, can drain as much creative energy as solving much larger creative problems. 

The upskilling trajectory

For many freelancers, upskilling really comes down to one thing. The key is that your upward shift—your retooling and upskilling process—is one of continuously replacing task work for idea work

Task work is everything we’ve already discussed: the projects every business needs and many freelancers can deliver on. Idea work involves higher-level, higher-value thinking (which is gained through understanding the systems at play when creating high-performing task work).

This process is natural in a corporate environment. It’s just moving up the corporate ladder: from helper to creative to manager to decision-maker.

This same upward momentum doesn’t happen organically for freelancers. We must force it by choosing to cut certain services and replace them with new ones. 

It might involve creating strategies for blogs instead of writing the blogs themselves or managing social media creators instead of actually creating the content. It ultimately involves solving larger business problems by understanding how systems work. 

To learn how systems work, usually you must endure the task work that comes with that system. 

Give yourself a promotion

It’s not easy to shift from task work to idea work. But upskilling is a natural way to scale a professional services business. In the world of freelance, you have to approve your own promotions. You don’t have a boss to take you from blog writer to content manager. 

You have to give yourself a promotion now and then, because no one else can do that for you. 


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