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Why Freelancing Is the Safest Path to Financial Freedom

Freelancing is becoming an increasingly popular career path. With the rise of the gig economy and the ability to work remotely in more and more industries, people are flocking in droves to freelancing as a way to gain greater control over their lives and finances.

However, the majority of those who do so seem to do it only as a way to escape the drudgery of the 9-5. Most freelancers I meet, even the ones offering the most in-demand services to the most lucrative niches, seem to have astoundingly low career expectations.

People see freelancing as a means to work independently and be your own boss. But people, even freelancers themselves, often see the best possible outcome to be a mid-five figure income, a ~20-30 hour work week, and a simple, quiet existence.

For many, this is all they could ever want. And hey, more power to them. But that’s not what I want, and it’s probably not what you want either. In this letter, I want to show you what freelancing can give you that so many fail to see:

A way to become financially free.

The Cashflow Quadrant

Before we begin, let’s introduce the concept of the Cashflow Quadrant, invented by renowned entrepreneur Robert T. Kiyosaki. The Cashflow Quadrant outlines the four areas where a person can earn income: E, S, B, and I.

An employee (E) earns money by working for a business.

A self-employed person (S) earns money by working for others on a contract basis, either hourly or for a fixed contract price. The key difference is that an S has multiple clients, where as an E has a single employer. The S is also responsible for paying their own taxes.

A business owner (B) owns a business that generates income for them. The business has its own employees, and ideally, will function autonomously without any input from the business owner. Kiyosaki classifies the majority of business owners who still play a role at their companies as employees.

The final quadrant is that of the investor (I). The investor owns various investments that produce returns, such as stocks, bonds, securities, real estate, and other interests. The investor doesn’t need to perform any tasks other than to put up money, shoulder the risk of losing it, and collect the returns.

It’s possible to earn income from multiple, or even all quadrants at one time. However, financial freedom exists almost entirely in the I quadrant. That’s not to say that one who earns money from multiple quadrants isn’t financially free. It’s just to say that in order to be truly financially free, your earnings from the I quadrant must be equal to or greater than the sum of your living expenses.

Further, it’s possible to begin earning income in any of the quadrants. They don’t have to happen in any particular order. But most of us will begin our journeys in the E quadrant.

The Cashflow Quadrant (created by Robert Kiyosaki)

Phase 1: Becoming an Apprentice Freelancer

For the vast majority of us, we begin our careers as employees being paid a wage.

I got my first job when I was 13 years old. I worked in a deli in a town with more cows than people. From there, I was employed continuously until I was 21, going through eight different jobs along the way. While it’s true that I earned relatively little money (as well I should have), I firmly believe that the lessons I learned about business, people, and life itself were imperative to my growth as a human. I definitely do not regret doing my time in the E Quadrant.

However, once I got my first taste of the S Quadrant, I was hooked.

When I was 16, I falsified my identity to get an account on Elance, now Upwork. I took a few contracts as a freelance writer. I also learned quickly that writing for a paycheck is WAY different than writing for my 10th grade English teacher. I got fired from one job and refunded another one. I didn’t have a single repeat customer, and earned only about $100.

However, I had earned that $100 from my laptop. I didn’t have to go into a place, I didn’t have to deal with customers, I didn’t even have to talk to my boss. I just had to send messages and write. Even though I sucked as a writer, it was an intoxicating concept.

I also intuitively understood that because I sucked now did not mean that I would suck later. I knew that success wasn’t a one-time event, but a process. Samurai Yamamoto Tsunetomo wrote in the Hagakure that success achieved before 40 was untenable, as the person did not have sufficient experience to manage their success. That’s why so many lottery winners go broke: Easy come, easy go.

With that in mind, freelancing is a great option for those who are willing to put in the time and effort to build a successful and sustainable career, and who value understanding over quick returns. As far as a first step into business goes, I don’t think freelancing can be beat. It’s low risk and high reward if you get it right.

What to expect as an Apprentice freelancer

I’m not going to go into how to get into freelancing. I’ve covered that in other articles that you’re welcome to read. There are also millions of excellent videos to watch on the subject (YouTube is your friend when learning a new skill).

However, once you get into it, you can expect to be an underpaid, overworked grunt. This is the Apprentice stage.

As an apprentice freelancer, you’ll be:

  • Working your day job (probably)
  • Getting paid for your work (but probably not very much)
  • Learning new things constantly
  • Getting comfortable talking to clients
  • Finding most of your work on platforms like Upwork and Fiverr

Your goals as an Apprentice freelancer are to:

  1. Gradually charge more for your work
  2. Build a strong portfolio that represents your abilities well
  3. Constantly hone your skills
  4. Get very good at finding work online
  5. Learn to write persuasively

Charge more for your work

It doesn’t really matter how much you charge at the beginning. My first Upwork contract only paid $50. It only matters that you get people to pay you so you get used to the idea of making money from your work. Raise your prices consistently as you become more skilled at your craft. My hourly rate went from $20 to $65 in the first year.

Build a strong portfolio that represents your abilities well

Obviously, I was FAR from technically proficient when I was a beginner. But I still had a portfolio that earned me clients. Think of it this way: some people need to hire a freelancer but can’t pay the rates that the experts charge. Those people look for the beginners. Whatever your skill level is at the moment, there is someone out there who will hire you.

Constantly hone your skills

Learning, studying, training and becoming better is your HIGHEST income producing activity when you’re a beginner. Level up your game as fast as you can. Work just enough to keep your bills paid, and focus every other second you have available on becoming worth more.

Get very good at finding work online

I started with Upwork. I still use it, though not quite as much. As an Apprentice freelancer, platforms like Upwork will be your bread and butter. This is where you find strangers to hire you before you’ve built a network. You can expect to send 10+ proposals to get a single message back. Further, you can likely expect to close 1 in 4 clients who message you back. It’s grueling, but it’s got to be done.

Learn to write persuasively

The vast majority of your jobs will start with a cold email, a DM, an Upwork “proposal” (more akin to a cover letter), or some other piece of written material. Learning how to be persuasive and write messages that get replies is a skill that will serve you for the rest of your life. Get VERY good at it as an Apprentice.

After a lengthy apprenticeship, likely anywhere from 2 to 7 years, you’ll wake up to find yourself a Journeyman freelancer.

Phase 2: Journeyman

For many, the Journeyman phase will be among the most exciting. It definitely has been for me. This is the part of your life where you quit your day job and transition into freelancing full time. If you don’t already, you’ll start putting time and attention into cultivating your online presence and gaining more attention.

A person can go from an absolute beginner to a highly paid professional in a very short amount of time. I consider myself to be at the tail end of my apprenticeship. Though it’s taken me five years, I know many freelancers who broke six figures after just a few years. There are even unicorns who make it happen in their first year, though this comes with many growing pains.

For most of us, though, the growth will be more manageable—but by no means less exciting.

For example, In 2018, I was charging about $500 per project. In 2020, right as the pandemic hit, I finally hit my stride as a designer and developer. I was suddenly able to charge around $3,000 per project. I wasn’t doing as many projects, as I hadn’t learned to find the clients who would pay my new rates. But I was still earning 50% more money in a third the time, seemingly overnight. It was revolutionary.

What to expect as a Journeyman freelancer

As a Journeyman freelancer, this is what life is like:

  • You’ve quit your day job (or at least are able to if you desire)
  • You’re putting money aside for taxes
  • You’re beginning to develop a personal brand
  • You’re charging more for your work than you ever thought possible
  • You’re getting repeat and referral clients
  • You’re relying less and less on platforms like Upwork
  • You’re earning enough money to live comfortably and pay all your bills

You also have some disposable income that you’re starting to invest in yourself. You might be:

  • Hiring lead generation services
  • Using paid ads (such as Google Ads, Facebook Ads, etc.)
  • Buying courses to learn new skills to help you grow
  • Hiring virtual assistants to do some of your more repetitive tasks

Once you’re well into Journeyman territory, you’ll find yourself at something that could very easily become a comfortable cruising altitude. This is the part where you’ve got a long-term job that could serve you adequately for the rest of your life.

However, most of us won’t want to stop there. There are other things that need to be attended to. For example, with many W2 jobs, you’ll get benefits such as health insurance and retirement plans. These things don’t come automatically when you’re a freelancer—you need to get them for yourself. In order to provide for these needs without compromising on your take-home income, it’s important to keep pushing.

Your goals as a Journeyman freelancer are to:

  1. Develop a niche and establish yourself as an expert in that niche
  2. Create strategies for finding your own high-value clients consistently
  3. Find an audience

Develop a niche and establish yourself as an expert

This one will happen automatically if you don’t take care of it yourself—and sometimes, that’s not even a bad thing. If your niche develops itself naturally, I don’t recommend fighting against it. If you find something that works, even if it’s not something you’re overly passionate about, you’re light years ahead of most other people in the game. Give your natural niche 80% of your focus. Save the remaining 20% for the things you are passionate about, obviously—but by focusing the majority of your time on where the money is, you’ll be able to live comfortably and attack the remaining 20% from a position of strength.

NOTE: It’s much easier to develop a reputation among a crowd of people who are likely to talk about you organically. That’s why marketing agencies contact me more often than construction professionals—because construction professionals spend their time talking about construction, not marketing. Marketing professionals spend their time talking about marketing and its related topics (including me). If you want to develop a reputation in a niche that’s not related to your line of work, target your messaging at the people in your niche who ARE related to your line of work. For example, the majority of my referrals from construction clients come from marketing directors that work for the company, rather than from those who own the businesses.

Create strategies for finding your own high-value clients consistently

As you evolve into a Journeyman freelancer, it’s important to reduce your dependence on freelance marketplaces and start finding your own sources of work. Eventually, you want to be able to rely exclusively on your own marketing efforts to keep your desk filled with projects. The most successful freelancers have multiple sources of work. That ability to diversify is what makes freelancing such a safe profession.

So as you grow, make sure to get your voice heard in places where it will stand out. For most of us, this means content marketing. Cold email campaigns, social media marketing, even direct mail. If you have a client who finds you on Facebook and visits your website, they’ll be 100% focused on you while they’re there. It doesn’t mean they’ll be guaranteed to hire you, but it does mean that you’ll have a much better shot.

Find an audience

Attention is your recession insurance. People get cagey when times are tough, especially around the unfamiliar. They’re less willing to click ads, they’re less willing to take cold calls or read cold emails, and they’re more suspicious of people they don’t know.

Your social media, email list and media presence is how you get past this. Become somebody that your audience recognizes, and you’ll instantly have a higher degree of trust than your competitors.

For example, it took me 10 weeks to go from 68 to 500 connections on LinkedIn. Once I hit 500 and my profile showed “500+ Connections” (the max your profile page shows), I added 150 connections in just a week. This happened because people saw that I had an existing network and felt more desire to be a part of it. Basic social proof.

A graph showing how weekly connection growth accelerated once I reached 500+ connections on LinkedIn.
Social proof: My weekly connection growth accelerated once my profile showed 500+ connections.

As a Journeyman freelancer, one can enjoy a great income, phenomenal work/life balance and a great degree of personal freedom. Freedom of time, location, choice, you name it. Freelancing offers many benefits to those who stick with it, such as the flexibility to choose your own projects and clients, the ability to work from anywhere, and the potential to earn more money than working 95% of traditional 9-5 jobs.

However, the path doesn’t stop there.

Beyond the level of the highly paid professional, or Journeyman, lies the realm of the Master.

Phase 3: Master

I’m a big believer in “fake it till you make it,” but regardless, I want to qualify this by saying that I am NOT a Master freelancer myself. I know a few of them, and aspire to join their ranks, but I’ve got a long way to go.

That said, here’s what being a Master freelancer looks like:

What to expect as a Master freelancer

  • You have a few employees or contract workers
  • You spend less of your time focusing on marketing and lead generation, as you have systems in place to automate them
  • You also spend less time focusing on fulfillment, as you have employees or contract workers who do much of the grunt work. You instead ensure that the final products that go out to clients are up to your standards.
  • You only spend your time working on the things that you are most skilled at.
  • You have multiple streams of income, at least some of which are almost fully automated
  • You have either embraced your online presence and have a significant following, or:
  • You have moved past the need/desire for an audience and have chosen to leave it behind.

You might argue that a person who fits this description isn’t even a freelancer, and in my opinion, you’re right. This is a person who has transitioned from the S Quadrant to the B Quadrant.


To really be a part of the B Quadrant (in my mind), one must be able to leave their business alone and have it run just as efficiently (or more efficiently) than when they were there. Kiyosaki himself qualifies a business as only being a B Quadrant business when it has 500 or more employees, but I don’t subscribe to that definition personally.

Your goals as a Master freelancer is to:

  1. Create income streams that run without your input

Create income streams that run without your input

As a Master freelancer, you’ll be at or near the top of your industry. You’ve worked for high profile people and companies, your work is highly visible, and you may have a certain degree of fame in your industry.

At this point, you value your time far more than your money. As such, you’re focusing on creating alternative streams of revenue that will keep your financial goals on track without requiring large amounts of your time.

Commonly, this means creating digital products like courses, books, software and similar assets. Your systems automatically deliver these products to the purchaser, and the purchaser uses the products without any input required from you directly. You have VAs in place to handle customer service and keep the business moving, allowing you to focus your time on whatever you want to.

However, the real high level players often work for royalties. The Master will create the product (often with a great degree of help from a publishing/management company), and then let others take charge of marketing and producing it. It’s true that they could likely make more money publishing their work themselves, but this would require a tremendous investment of time that they’re just not inclined to make.

Masters will also purchase revenue-generating investments with their money, such as stocks, bonds, gold, crypto and real estate. However, such topics of discussion are beyond the scope of this letter.

Alright, let’s recap.

As an Apprentice freelancer, you transition from the E Quadrant to the S Quadrant and begin earning your own way in life. This is where you learn your craft, get your first clients, and start learning what it means to be a business.

As a Journeyman freelancer, you’re a highly paid professional with a valuable skill. Your attention turns from just earning enough to survive to earning enough to genuinely thrive. You start to build a personal brand, grow your audience, and learn to find clients at will. It’s here where you become good enough at your job that you can largely choose how much you want to earn and how much you want to work.

Finally, as a Master freelancer, you’re able to become financially free. You do this by converting your skillset into income without having to add your time. You begin investing your money and time as an upfront cost rather than an ongoing cost. You have multiple streams of income and are virtually impervious to economic catastrophe. This allows you to focus even more of your time on the missions that really matter to you in life.

Best of all, the effort you put in to get to mastery has already given you ample money, time, and freedom. You were able to control your schedule, your clientele, and your income to a degree unavailable to almost every 9-5 job. See? They call it “freelancing” for a reason.

Final Thoughts

There is SO much money out there, and so many things you can do with it. This world is too big to explore in even fifty lifetimes, let alone the single lifetime you’re guaranteed.

If you’re struggling with a soul-sucking job that you hate, I literally cannot recommend highly enough that you get the hell out of it and take a shot at freelancing. Refer to the other letters I’ve written and take a fucking shot. Please. The only thing you need to do to be worthy of freedom is decide to take it.

If you’re an active freelancer, I recommend focusing on gaining and maintaining clarity. Look at what you’ve done, and think about where you’re wanting to go. Ask yourself if you have systems, processes and habits that are congruent with your goals. Make sure you have a way to make every day bring you 1% closer to your end state.

Stay hungry, friends. We are destined for great things.

—John Kakuk

I'm John Kakuk.

I’m a brand designer, web developer and marketer working with architects, engineers and construction companies. My purpose is to help others achieve the best versions of their businesses and themselves.

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