Freelancers vs. Entrepreneurs – The Jedi Edition

So you are a freelancer. But for a while now, you’ve been tempted by the idea of becoming an entrepreneur. You can imagine all the great benefits of making the switch, yet you’re still not sure. As it turns out, there have been many others who have had to face this exact same problem. Anakin Skywalker was one of them.

Although a different terminology was used in that galaxy far, far away, the most respected Darth (entrepreneur) in the Star Wars universe was, at one time, in a similar place. Studying his transformation can help you with yours. But first, let’s take a look at how this really works.

Jedi Masters vs. Sith Lords

Let’s begin by taking a look at the differences between Jedi Masters (freelancers) and Sith Lords (entrepreneurs).

Jedi Masters

Being a freelancer is much like being a Jedi; you go through an apprenticeship, growing your skill by watching videos and tutorials, reading books, and practicing. If you are lucky enough to come across a Jedi Master, you become his student and your growth increases tenfold.

As you become more powerful and sought-after, you might have the option of hiring a virtual assistant to do the basic, routine work needed for client interaction, promotions, and other miscellaneous tasks – just like how Jedis employ droids as assistants to aid them in battle.

r2 servant to jedi

Sith Lords

Entrepreneurship, on the other hand, represents the Dark Side. Being an entrepreneur, you study the dark arts, are more likely to rule the world, and your destiny will probably lead you to a more astounding impact than that of a Jedi. You couldn’t care less about dogmatic, archaic rules.

The purpose of a Sith Lord, as stated by Darth Bane (the first Lord and unifier of Sith Legions), is to outgrow and eventually overthrow his Master. As such, constant evolution is assured. Plus, entrepreneurs get more toys too.

the sith order

Why Anakin became Darth Vader

As the Chosen One, Anakin Skywalker was foretold to be the one who would bring equilibrium to the Force. In almost all of his inner tumultuous dialogues, he was portrayed as a Jedi who wanted more – to be the greatest Jedi who had ever lived. That sort of ego-driven thinking can only lead to the Dark Side (of entrepreneurship)!

You will need that exact same ego-driven thinking if you want to run your own business. You’ll also need to step out of your comfort zone and embrace uncertainty. Change is difficult, but Anakin also stepped out of his comfort zone to embrace the Dark Side of the Force.

Now ask yourself, do you see a bit of Anakin in yourself?

The Truth Behind Anakin’s Decision

Siths are like entrepreneurs; they know how to manage money. And almost all entrepreneurs have the drive to take care and provide more for their families — the birthplace of business is the desire to take care of others.

But I’ll tell you a secret. You should know that this desire actually comes from your ego. You want to take care of others because you want them to be safe and healthy so that they can always remain around you. Feeding and satisfying your needs – whether they are romantic, emotional or materialistic in nature – is essentially fending for yourself. That’s how the dark side works.

Similarly, the real reason Anakin was drawn to the Dark Side was that he craved the power to protect his wife Padme by learning an immortality spell created by Darth Plagueis (banker of the InterGalactic Banking Clan, also a Sith Lord).

Jedi Masters vs. Sith Lords (Contd.)

Are Jedi Masters and Sith Lords really so different from each other? Although the Siths are seemingly evil, are the Jedis truly selfless?

"The Jedi and the Sith, are very similar." – Chancellor Palpatine

Don’t you realize that deep down, Jedis, just like the Siths, help loved ones just because they want to feel good about themselves, maintain their self-image and keep their loved ones close by?

Freelancers and entrepreneurs are basically the same. It’s just that Siths/entrepreneurs admit and come to grasp with their nature. There’s a time limit to what you can earn by working as a freelancer, and you won’t be able to help all your loved ones. Understand this and you’ll grow much faster and eventually become a Sith Lord.

"I would rather earn 1% off 100 people’s efforts than 100% of my own efforts." – John D. Rockefeller, a well-known real-life Sith Lord

Oh and one more thing, Sith Lords… have more fans!

darth vader

Crossing Over to the Dark Side

Jedis are weak, and do nothing but talk. Their teachings, while sometimes full of good intent, create less results and less impact in the real world. The Jedis / Freelancers are content creators. The Siths / Entrepreneurs are business creators. A Sith Lord must know a bit of everything, from content to marketing to customer care to getting awesome Jedi employees.

As for yourself, to cross over to entrepreneurship, you have to do it like Anakin did, kill fellow Jedi Masters… or just be determined, sever all ties, and never look back. Kill your instinct and habit of selling your time for money. Use the Force of your anger (against confused clients) in favor of your circumstances to fuel your passion for business.

The Sith Code (Revised For Entrepreneurship)

Rule #1: Only Jedi Masters can become Sith Lords

There’s no point in being a junior freelancer, only to quickly change trains and try to become an entrepreneur. Make sure you are a Jedi Master before attempting to cross over to the Dark Side; have a decent living capital that is enough to last you 4 months.

Rule #2: Understand how the Force works

Don’t cross over if you have doubts or feel you’re not ready for it. You’ll only cause disturbances in the Force. Unlike what some might think, the Dark Side is pure. You need to be mentally congruent with it. Make sure you can dominate and lead your employees and you’ll know what to ask of them. Otherwise the Force will spit you out.

Rule #3: Sith Lords love networking

By first being a Jedi Master, it will be easier for you to make use of all the connections you’ve gained while working as a freelancer. You’ll have clients (who already are Sith Lords) that will respect you and help you in making the leap.

If you are not an outgoing, extrovert person, remain a Jedi. The key to becoming a succesful Sith Lord is networking and leadership. You’ll need to have an aura of influence. That’s how you make use of the Force. If you are shy and you know you can’t change, don’t even make the leap!


If you can really mentally use this metaphor of Jedis and Siths, you’ll make your evolution that much easier. Oh, and keep in mind that we Sith Lords are the real creators. It’s a well-known fact that a Sith Lord will easily win a battle with an equally powerful Jedi Master. That’s because the Dark Force is stronger. So what are you waiting for, young Jedi?

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