The Freelancer vs. The Entrepreneur

The Internal Struggle

I’ve been freelancing for my entire professional career and The Entrepreneur in me has gritted his teeth the entire way.

He sat patiently as The Freelancer took his time making mistakes, honing his craft, and growing his roster of clients, knowing full well he would ultimately start his own company.

He knew all along this conventional model of exchanging hours of time for money wasn’t scalable. After all, there are only so many hours in a day.

What was The Freelancer to do?

Over the years, he had developed a specific set of skills that made him a fairly dangerous design practitioner. However, he knew it took much more to build and sustain a business as an entrepreneur.

After enough time went by, The Entrepreneur had finally had enough. He tapped The Freelancer on the shoulder and back-handed him across the face. Once he was paying attention, he squared up, looked him dead in the eyes, and said:

“You need to stop wasting your own time and turn clients into customers and users.”

The Freelancer sat there dazed after this rude awakening. From that moment on, he realized nothing would be the same.

It’s not that he wanted to stop working. In fact, quite the opposite. He simply wanted to buy more time to pursue work that gave him purpose, not just the work that paid the bills.

Knowing this, The Entrepreneur gave him two options:

  1. Find more work and hire people to complete said work, or
  2. Start creating products that solve the problems of your clients

The Freelancer paused and weighed his options. He knew in his gut he didn’t want to manage a team comprised solely of designers. He enjoyed interacting and collaborating with people from different backgrounds and disciplines.

Option #2 seemed like his best bet.

Since most of his clients were startups and entrepreneurs, he thought about their unique set of problems and how he could solve them.

Immediately, he noticed most of his clients dealt with the same issue:

How do you find others who share your ideas and have the skills you need?

While picking apart this conundrum, he slowly began to realize something:

He also shared this problem.

For years, he had formed deep connections with others by sharing and discussing ideas. These ideas became friendships, collaborations, and even partnerships.

However, with enough time, most of these relationships ended up as unproductive dead ends. After much reflection, the conclusion always sounded the same: these connections didn’t have the skills he needed or they didn’t believe in the idea. Either way, they couldn’t make progress together.

After meeting this realization head on, The Freelancer knew it was time to get to work. As he rolled up his sleeves with a newfound sense of purpose , The Entrepreneur appeared behind him with a smug look on his face.

He knew he had won the battle. However, like most entrepreneurs, he also knew the war was just getting started.


Does this sound familiar? Are you listening to your inner freelancer or entrepreneur? Please feel free to share your story in the comments below or on Twitter at @williamfrazr.

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