Freelancers vs. Entrepreneurs – The Jedi Edition

So, you are a freelancer. However, for some time now, you’ve been tempted by the idea of becoming an entrepreneur. You can envision all the fantastic benefits of making the transition, but you’re still uncertain. As it turns out, many others have faced this exact dilemma. Anakin Skywalker was one of them.

Although different terminology was used in that distant galaxy, the most respected Darth (entrepreneur) in the Star Wars universe was once in a similar position. Examining his transformation can assist you in your journey. But first, let’s delve into how this process truly functions.

Jedi Masters vs. Sith Lords

Let’s start by examining the differences between Jedi Masters (freelancers) and Sith Lords (entrepreneurs).

Jedi Masters

Being a freelancer is akin to being a Jedi; you undergo an apprenticeship, enhancing your skills by watching videos and tutorials, reading books, and practicing. If you’re fortunate enough to encounter a Jedi Master, you become their apprentice, and your growth accelerates exponentially.

As you grow more proficient and in-demand, you might consider hiring a virtual assistant to handle the basic, routine tasks associated with client interactions, promotions, and other miscellaneous duties – much like how Jedis utilize droids as assistants in battles.

R2-D2 serving the Jedi
Sith Lords

In contrast, entrepreneurship embodies the Dark Side. As an entrepreneur, you delve into the dark arts, have a higher propensity to dominate the world, and your path is likely to result in a more significant impact than that of a Jedi. You have little regard for outdated, dogmatic rules.

As articulated by Darth Bane (the inaugural Lord and consolidator of Sith Legions), the objective of a Sith Lord is to surpass and ultimately supplant his Master. This ensures perpetual evolution. Additionally, entrepreneurs acquire more toys.

The Sith Order

Why Anakin Became Darth Vader

As the Chosen One, Anakin Skywalker was prophesied to bring balance to the Force. In many of his internal struggles, he was depicted as a Jedi with aspirations of greatness – desiring to be the most formidable Jedi ever. Such ego-driven ambition inevitably leads to the Dark Side (akin to entrepreneurship)!

If you wish to helm your own business, you’ll need that very same ego-driven ambition. It’s also imperative to venture beyond your comfort zone and welcome uncertainty. Change is challenging, but just as Anakin ventured beyond his comfort zone to embrace the Dark Side of the Force, so must you.

Reflect on this: Do you recognize a hint of Anakin within yourself?

The Truth Behind Anakin’s Decision

Siths resemble entrepreneurs in their adeptness at managing resources. Most entrepreneurs are driven by a desire to nurture and provide for their families – the inception of business is rooted in the wish to care for loved ones.

However, here’s an insight: This drive predominantly originates from your ego. Your urge to care for others stems from a desire to ensure their well-being, so they remain by your side. Catering to your needs – be they romantic, emotional, or materialistic – is fundamentally self-preservation. That’s the essence of the dark side.

In a similar vein, Anakin’s allure to the Dark Side was fueled by his yearning for the power to safeguard his wife, Padme. He sought to master an immortality spell devised by Darth Plagueis (the financier of the InterGalactic Banking Clan and a Sith Lord).

Jedi Masters vs. Sith Lords (Continued)

Is there a significant distinction between Jedi Masters and Sith Lords? While Siths may appear malevolent, can we genuinely assert that Jedis are entirely altruistic?

The Jedi and the Sith are very similar.<span class="su-quote-cite">Chancellor Palpatine</span>

Have you ever considered that, at their core, Jedis, much like Siths, assist their loved ones primarily to bolster their self-worth, preserve their self-image, and ensure their loved ones remain close?

Freelancers and entrepreneurs are fundamentally alike. The distinction lies in the Siths/entrepreneurs acknowledging and reconciling with their nature. There’s a ceiling to earnings as a freelancer, limiting the extent to which you can assist all your loved ones. Recognize this, and your growth will accelerate, potentially leading you to become a Sith Lord.

I would rather earn 1% from 100 people’s efforts than 100% of my own efforts.<span class="su-quote-cite">John D. Rockefeller</span>

And one more observation: Sith Lords… attract a larger fanbase!

Darth Vader leading his droid army

Crossing Over to the Dark Side

Jedis often appear passive, primarily engaging in discourse. While their teachings may be rooted in noble intentions, they often yield limited tangible results in the real world. Jedis, akin to freelancers, are content creators. In contrast, Siths, resembling entrepreneurs, are business creators. A Sith Lord should possess a diverse skill set, spanning content creation, marketing, customer service, and recruiting adept Jedi employees.

For you to transition to entrepreneurship, you must exhibit the resolve Anakin demonstrated when he confronted fellow Jedi Masters. This doesn’t mean resorting to violence, but rather displaying unwavering determination, cutting ties, and forging ahead without hesitation. Abandon the habit of exchanging your time for money. Instead, channel the energy of your frustrations (perhaps stemming from ambiguous clients) to ignite your passion for business.

The Sith Code (Revised for Entrepreneurship)

Rule #1: Only Jedi Masters Can Become Sith Lords

Transitioning from a novice freelancer directly to an entrepreneur may not be advisable. Ensure that you’ve attained the stature of a Jedi Master before considering the shift to the Dark Side. This entails having a substantial financial cushion, preferably sufficient to sustain you for at least four months.

Rule #2: Understand How the Force Operates

Refrain from making the transition if you harbor reservations or feel unprepared. Such hesitancy can disrupt the Force’s equilibrium. Contrary to some beliefs, the Dark Side is untainted. It demands mental alignment. Ensure you possess the capability to guide and direct your employees, understanding their roles and expectations. Otherwise, the Force may reject you.

Rule #3: Sith Lords Value Networking

Having first established yourself as a Jedi Master, leveraging the connections you’ve cultivated during your freelancing tenure becomes more straightforward. Your existing clients, many of whom are already Sith Lords, will respect and support your entrepreneurial aspirations.

If you’re introverted and not inclined to change, perhaps remaining a Jedi is more fitting. The essence of a successful Sith Lord lies in networking and leadership. Exuding an aura of influence is crucial to harnessing the Force. If you’re reserved and resistant to change, reconsider the transition.


Embracing the metaphor of Jedis and Siths can simplify your transformational journey. Remember, Sith Lords are the true innovators. It’s widely accepted that a Sith Lord, when pitted against a Jedi Master of comparable prowess, often emerges victorious. This is attributed to the superior strength of the Dark Force. So, young Jedi, what’s holding you back?