The Four Freedoms of Entrepreneurship

Everyone wants freedom, but not everyone is willing to pay their dues to attain it. Freedom comes at a price.

The ancient Spartans fought the Persian Empire to protect their freedom and 300 Spartans willingly died at the Battle of Thermopolyae to preserve it (and I watched the movie 300 about 50 times when it came out on Blu-Ray).

The United States fought the British empire in the American Revolutionary War to win its freedom, and 25,000 revolutionary soldiers died during the 8-year war to attain it (and I watched the movie the Patriot with Mel Gibson about 20 times when it was showing on the closed-circuit movie channel at my college).

Today, many employees want to win their freedom from their employers, become entrepreneurs, and start their own business.

Wanting freedom is a universal human desire, but attaining it is the hard part. To become an entrepreneur and start your own business, you are attempting to achieve freedom from corporate employment.

What price are you willing to pay?

The Freelancer Freedom Wave

The number of independent freelancers has exploded in recent years and according to Forbes by 2027, 50.9% of the US working population will be freelancing.

From that article, it's clear that employees are starting to realize they can jump the ship and win their freedom by becoming a freelancer, consultant, or agency and providing a professional service. Often times, they make more money by providing the same service they once provided to their employers. But this freedom also comes at a cost.

If you want to quit your job and become an entrepreneur, it's not as easy as just saying, “I quit! I'm free now.”¬†Even for those that are currently freelancing, consulting or own an agency business, many continue to work tirelessly in pursuit of the freedom they initially desired. Instead of their service-based business becoming their agent of freedom, it's become just another boss to serve.

So, how do you attain entrepreneurial freedom?

The Four Pillars of Entrepreneurial Freedom

There are four pillars to achieving freedom as an entrepreneur, and each is interrelated with the other.

  1. Finances
  2. Work
  3. Location
  4. Lifestyle

It's almost like an equation.

Freedom = (Finances + Work + Lifestyle) ÷ Location

One of the most impactful pillars of entrepreneurial freedom is location. Where you live often determines how much income you need to support your lifestyle. It also impacts what type of work you can achieve, impacting the final two pillars of freedom.

There is a big difference in expectations between living in Chiang Mai and San Francisco (trust me, I have lived in both cities). Be mindful of the environment you choose. It impacts everything.

To escape the cubicle nation, you need to have the finances to support that vision. Without the financing to support your endeavor, it's only a matter of time before you head back to the cube farm. Beyond having the finances to support your freedom, you need to think about how the work you provide either hinders or supports your vision of entrepreneurial freedom. Is the work you provide rare and valuable to those you serve?

Your¬†lifestyle¬†will be impacted by where you live, what work you do, and how much money you make. Sometimes to achieve entrepreneurial freedom,¬†you have to make sacrifices in your lifestyle. When everyone is partying on Friday night, are you working on your “freedom” business or are you out¬†having a good time?

Earning entrepreneurial freedom has a price. It also takes time. If you want the freedom to do the work you love, be financially independent, and support your lifestyle, then it's going to take time.

Freedom is expensive to achieve but worth the effort to attain.

It's Saturday 8:07 pm as I write this to you. I could be watching television and relaxing. Instead? I was thinking about you and decided to write this post.

In my own way, that's how I exercise entrepreneurial freedom. I can work how I want, when I want, and from wherever I want. This post is going live while I'm on a remote fishing trip in Canada. I took off a week without the certainty of the Internet being available. That's entrepreneurial freedom.

In this post, we will be going in-depth on the four freedoms of entrepreneurship.

1) Financial Freedom: Spartan or Athenian

In the pursuit of your own version of freedom, you need to clarify what financial freedom means to you. This post contrasts two different viewpoints on financial freedom and poses the question of which viewpoint you should adopt.

2) Freedom of Work

Not all work is created equal. As you progress in your career as an entrepreneurial agency owner, the work you do has a geometric effect on your financial freedom variable. You'll discover the #1 question you need ask yourself so that the work you do helps you achieve freedom.

3) Freedom of Location: A Tale of Two Locations

I've lived in both Chiang Mai, Thailand and San Francisco, USA. Both cities are conducive to attracting entrepreneurs, but for very different reasons. Should you live in a cheap city as you bootstrap your business or should you live in an expensive city with a high cost of living to force yourself to execute faster? Read on to discover the answer.

4) Freedom of Lifestyle: The Way of The Entrepreneur

Entrepreneurs set their own schedules, priorities, and goals. Employees are told they need to be at their desk from 9-5, what their work priorities are, and what goals to meet at the next annual performance review.

The lifestyle of an entrepreneur is self-directed. The lifestyle of an employee is prescribed. Learn about these and many more differences between entrepreneurs and employees.

Financial Freedom: Spartan or Athenian?

Financial freedom is probably the number one most sought-after milestone for anyone who jumps into freelancing, consulting, or owning an agency business.

But there are two mindsets when it comes to financial freedom and knowing which mindset resonates with you is key to achieving your own entrepreneurial freedom.

The Spartan Mindset of Frugality

Frugality means living a simple life. It means you have a budget and you need to count the pennies carefully, so you don't overspend. It means you have a fixed amount of money to spend, and you need to control your impulses to not purchase all the things you want, instead focusing on fiscal austerity.

The ancient Spartans were the epitome of frugal living. They ate what they needed, trained to survive, and dedicated their life not to seeking pleasure in life but becoming the best warriors the world had ever seen. Training to become the best warrior was the end-all-be-all and leading a simple life was good enough.

If you approach life from a minimalist point of view, then this type of financial freedom mindset is for you. It's the type of financial freedom advocated by Mr. Money Mustache and his leagues of Mustachians. You, in essence, limit your consumption to achieve financial freedom.

The opposite of the Spartan mindset, of course, is the Athenian mindset.

The Athenian Mindset of Abundance

Abundance, on the other hand, is the opposite of frugality. It means exploring life to the fullest. It means you indulge in the things you love because you can. It means increasing the amount of money flowing into your finances so you can support doing things you enjoy outside of work and your other responsibilities.

The ancient Athenians were the epitome of abundant living. They sought to expand their territory and spread their way of life. They valued beauty, music, literature, drama, and art. In Athens, you could pursue an education in science and art versus the Spartans who only cared about military training. It was Athens that gave us Aristotle after all.

If you approach life from a “live-life-to-the-fullest” point of view, then this type of financial freedom mindset is for you. It's the type of financial freedom advocated by I Will Teach You To Be Rich by Ramit Sethi. You purposefully¬†engineer a business that supports your lifestyle endeavors so you can do things you want – whenever you want. You work hard to build a business that replenishes your finances so you can do the things you want because it's fun or makes you happy. You don't restrict your consumption to achieve financial freedom, instead, you create massive value for those you serve via a business that constantly replenishes your financial accounts.

Spartan or Athenian?

Before you set out to attain financial freedom, you need to decide what financial freedom means to you. Be clear about your mindset.

Does financial freedom mean living a Spartan or Athenian life?

If you've chosen the path to become an entrepreneur, chances are you'll be living both lifestyles at some point. To lead an abundant life you sometimes have to start as a Spartan and be frugal. As time passes, and your business takes off, you can trade the Spartan life for an Athenian life.

I have gone through both phases during my entrepreneurial journey. There have been years of Spartan times, where every available resource went into building my business. There have been times of abundance, where my businesses provided outsized value to my company, my employees, and my customers.

For many of us, financial freedom comes from owning a business that generates revenue to support your lifestyle, location, and work-life balance.

So are you a Spartan or an Athenian?

Freedom of work

Your Work Trajectory Is Non-Linear

Like everyone else working in digital marketing, I studied computer science in college.

Say what?!?

Yes, I studied computer science in school, NOT marketing. In fact, I've never taken a single marketing class in my life. And it's not just me.

Every digital marketer I've ever hired at my agency did not formally study digital marketing in college. Many had degrees in liberal arts like English or Psychology, while others had degrees in Biology, Accounting, or Finance.

But it wasn't just my agency…

On my Jumpstart Podcast, I interviewed many agency owners, digital marketing experts, and other subject-matter experts and I noticed that same trend.

Most successful marketers naturally gravitated to digital marketing not because they studied it, but because they had an insatiable curiosity for what digital marketing represented and the potential to make a contribution to the industry.

In fact, most of the digital marketers I know have technical, mathematical, or scientific backgrounds with little formal marketing training.

Let your career find you

By studying computer science in college, I already had a predisposition and sincere appreciation of the importance of numbers.

Today, digital marketing is heavily data-driven and understanding how numbers and marketing models work are a prerequisite for succeeding in any digital marketing campaign.

I never intended to become a digital marketer…

But I fell in love when I saw Google launch Adwords and then Google Analytics.

I saw that digital marketing was a numbers game (it still is).

So I took a chance and experimented.

Fast forward to today, and I'm known as a PPC and Analytics expert.

Digital marketing chose me not the other way around

An opportunity presented itself, and I had a natural predisposition to this type of work.

When you're young in your career, you assume you have a choice in the work you will do.

The thing most people assume about their career is that it's a linear path, it's not.

You might find yourself gravitating toward a different field of expertise because it's intuitive to you.

It's like that scene from the movie Goodwill Hunting where Will tells Skylar:

Will: Beethoven, okay. He looked at a piano, and it just made sense to him. He could just play.
Skylar: So what are you saying? You play the piano?
Will: No, not a lick. I mean, I look at a piano, I see a bunch of keys, three pedals, and a box of wood. But Beethoven, Mozart, they saw it, they could just play. I couldn't paint you a picture, I probably can't hit the ball out of Fenway, and I can't play the piano.
Skylar: But you can do my o-chem paper in under an hour.
Will: Right. Well, I mean when it came to stuff like that… I could always just play.

Pay attention to the areas of work where you can just play.

Let your work choose you, not the other way around.

When you force your career, you feel frustrated, stressed, and miserable.

Achieving Freedom of Work

Of course, letting your career choose you isn't enough if you want a career that brings you freedom.

It's basic economics.

Where there is a lot of supply, there is little demand. Where there is little supply, there is A LOT of demand.

It's a cardinal rule of economics.

What's more valuable; a single piece of coal or a diamond?

We all know the answer.


Coal is a dime a dozen, but diamonds are scarce.

It's the same when it comes to the work you do.

Is your work rare and valuable?

Is the work that you do rare and valuable to others? To your clients? To the marketplace?

The answer to this pivotal question is the key to your freedom of work.

Because when you do work that is rare and valuable to others, your finances reflect that through higher revenue and profit margins.

This is one of the biggest reasons why I tell all my Agency Jumpstart students early in the program that they need to start thinking about choosing a niche. But I also let you know that you will often need to work providing many services to at least 10 clients before the niche chooses you.

When you specialize, you become more valuable to your clients. Because you are now that rare agency, freelancer, or consultant that can accomplish the work that few others do.

If you want to achieve freedom via work, you need to focus on work that is rare and valuable to your audience.

Let the niche/career choose you and then focus on finding what's rare and valuable about the work that you do.

A tale of two locations

Enter San Francisco: Accelerating my Timeline of Action

A few years ago, after quitting my day job, I moved to San Francisco and holy cow – it was an expensive city to live in!

Moving to San Francisco forced me to accelerate my timeline for building the business behind Jeffalytics. If it hadn't had been for living in San Francisco, then PPC Course, my first flagship course would never have been born.

It was because San Francisco was such an expensive city filled with ambitious people looking to start and grow their own startup that I became inspired to accelerate the timeline for my own business.

It's like Warren Buffet says:

‚ÄúIt‚Äôs better to hang out with people better than you. Pick out associates whose behavior is better than yours and you‚Äôll drift in that direction.‚ÄĚ

In my experience, that's 100% true.

When you do this, you start picking up the behaviors, mindset, and ambition of the people around you through osmosis. Moving to San Francisco accelerated my timeline for launching my first online course.

The expenses of living in San Francisco inspired me to take massive action faster because if I didn't take action, the expenses of living in San Francisco would have caught up to me. Either I took action or the expenses of the city would be too much, and it would be game over. Back to the bold north for me.

Moving to an expensive city like San Francisco led me to accelerate my timeline of action so that I could build out my company faster and truly achieve entrepreneurial freedom via a business that generates monthly recurring revenue.

Enter Chiang Mai: Keeping Expenses Low

Here's the funny thing – after only a year in San Francisco, I became nomadic in 2015. I've been traveling full-time ever since. One of the places I lived during my journey was Chiang Mai, Thailand.

Chiang Mai has great food, smart people, and it is insanely cheap to live there.

I saved lots of money while living in Chiang Mai, but there were times that I felt a sense of loss of ambition as I worked on my business.

With a cost of living so low, there was less drive to grow the business. With ends met, it's easy to spend more time enjoying oneself than working full throttle on growing your business.

Necessity is the mother of invention, and with your basic needs met in just a few days of work, it's easy to find other distractions to fill your time.

Expensive or inexpensive: Which one is right for you?

Like many nomads, I'm still trying to find the perfect balance. Both of these experiences continue to influence my future choices of location.

If you are just starting off in your entrepreneurial journey, then it makes sense to control expenses then living in an inexpensive city like Chiang Mai. If you want to grow your business massively, you might eventually choose to live in a city that will level up not only your ambition but also accelerate your timeline of action.

If you are just starting off in your entrepreneurial journey, then it makes sense to control expenses then living in an inexpensive city like Chiang Mai. If you want to grow your business massively, you might eventually choose to live in a city that will level up not only your ambition but also accelerate your timeline of action.

Much like the other forms of entrepreneurial freedom, there are solutions for every step of the journey.

Have you ever lived in an inexpensive city? What about an expensive one? How did it impact your business?

The way of the entrepreneur

The Currency Of Freedom


Independent Consultants.

Agency Owners.

At the core of each role is entrepreneurship.

Those who start their own ventures and sell their¬†own work (or as Seth Godin says “art”) do so for one reason:¬†Freedom.

No one quits their cozy 9-5 job to start their own business doing more of the same.

Could you imagine taking all that risk but still doing the same work routine where you clock in, get coffee and sit at your cubicle replying to emails?

Or to¬†continue with the same work banter complaining about clients or other employees (“sounds like Keith's got a case of the Mondays!”).

When you give up on receiving a steady paycheck every two weeks and a 3% annual salary increase in the name of freedom, you've officially made the jump into entrepreneurship.

The core of all four freedoms is entrepreneurship.

Entrepreneurship is the currency of freedom for those of us dissatisfied with the status-quo.

The Lifestyle Of An Entrepreneur Versus An Employee

Look up the word “lifestyle” in the Merriam Webster dictionary and you'll find the following definition:

Lifestyle (noun) – the typical way of life of an individual, group, or culture

Any choice you make in business brings on an associated lifestyle. But that's where the similarities end.

Entrepreneurs set their own schedules, priorities, and goals.

Employees are told they need to be at their desk from 9-5, what their work priorities are, and what goals to meet at the next annual performance review.

The lifestyle of an entrepreneur is self-directed.

The lifestyle of an employee is prescribed.

The way of life of an entrepreneur is about creating unique value that only you and your team can produce. It's about putting your name out there in front of hundreds, thousands, and maybe millions who are waiting to reject your “art”, your venture, or your project. All in¬†the hope of finding your true fans before the money runs out.

The way of life of an employee is about getting that next paycheck, maintaining a stable lifestyle, and minimizing risk.

Entrepreneurship = Lifestyle Of Risk

If you're an entrepreneur, then you embrace the risk of rejection as part of your lifestyle.

The entrepreneur knows that at any time they can fail, or be rejected.

But it only takes one success to erase thousands of failures.

Thomas Edison knew it when he famously said:

“I have not failed. I've just found 10,000 ways that won't work.” – Thomas Edison

The greatest entrepreneurs are those who learn from their failures and move forward until success becomes inevitable.

Yet even when financial success does come, entrepreneurs love the work so much they still do it.

Work As A Way Of Life For Entrepreneurs

Most entrepreneurs, even after they've achieved financial freedom, still work every day.

Mark Cuban is worth over $3 billion dollars and yet his “morning meditation”¬† is¬†his work.

“Business is my morning meditation. Business is what I like. I get up and I work immediately. I love doing this” – Mark Cuban.

For an entrepreneur, work is essential to freedom. Because your work aims to make the world a better place.

Even when an entrepreneur strikes it rich, many of them will work, work, and work.

Work is not a chore. Work is a lifestyle.

The lifestyle of an entrepreneur buys a whole lot of freedom, but the drive to work never goes away. That means living a life facing failures, rejection, and naysayers as you forge forward to the life you envision.

The mansions, Lambo's, and other toys are just byproducts of getting things right after thousands of failed attempts. The byproducts of having the discipline to deliver work every day, and the desire to make an impact on the world.

That is the way of the entrepreneur. That is the freedom we all seek.

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