Freelancing Secrets— w/ Jamie Brindle & Paul Mikhay
Chris Do argues that to achieve financial stability and creative freedom, you must stop acting like a freelancer and start thinking like a business owner.
Chris Do
Founder, The Futur™ · March 26, 2023
Art vs. Commerce: The First Conflict
There is a dangerous and romantic myth that saddles creative people. It’s the idea that to be a true artist, you must struggle. That commerce is the enemy of craft, and a client is an obstacle to self-expression.
This belief is a trap. It pits two necessary forces, art and money, against each other as oil and water. It is the reason so many talented creatives find themselves on a path to financial ruin, barely able to make a living.
During a live conversation with fellow creator Jamie Brindle, education entrepreneur Chris Do dismantled this false dichotomy. The tension isn't between art and making a living. The tension is in the confusion of roles.
Do you self-identify as an artist? A decade ago, Chris Do would have said no. “I’m a graphic designer,” he would insist. The distinction is critical.
“One of the greatest downfalls of graphic designers or people who are in the service industry is they think of themselves as artists,” Do explains. “Because what they see is the client is an inconvenience to them creating and self-expressing.”
This is a fundamental misunderstanding of your role. “The person who gives you a means to make a living to provide for you and your family and your loved ones is not a person that gets in your way,” Do states. “They enable you to live your life.”
To resolve this conflict, you must first accept two precise definitions.
First, art. The best definition Do has ever heard came from filmmaker Lana Wachowski. On a panel for her film Cloud Atlas, she defined it with elegant simplicity. “Art is an invitation to look at the world from a different perspective.” It is pure, it is personal, and it must be done on your own terms. Sometimes, there is no financial reward for it.
Second, design. For this, Do turns to a definition from Nobel laureate Herbert Simon, popularized by Marty Neumeier in his book The Brand Gap. A designer is one who devises a course of action to go from an existing condition to an improved one.
This definition welcomes everyone. If you help a client improve their business, their operations, or their communication, you are a designer. You are providing a service. Art can have a job, but that job is not your own.
When you are commissioned, you step away from pure artistry. Your agenda is no longer just self-expression; it is to solve a problem for someone else. Many creatives, particularly photographers and designers, view their commercial work as a stepping stone to gallery shows and pure artistic recognition. They try to inject their artistic self-expression into client work, only to be met with frustration when the client, understandably, has other goals. They don't want your unfiltered expression. They want their problem solved.
The solution is not to abandon your artistic impulse. It is to stabilize your life first. As entrepreneur Tom Bilyeu has advised, you need a foundation. Create a reliable income stream, perhaps one that becomes passive over time, and use that stability to fund your true art. Do not confuse the two roles.
The stakes are not just professional. They are deeply personal. Do tells a harrowing story of an artist friend whose wife’s father fell gravely ill overseas. The artist looked at his finances and realized he couldn’t afford a last-minute plane ticket for his wife to say goodbye. She never saw her father again, and the tragedy broke their marriage.
“Money doesn't solve a lot of things,” Do says, his voice tight with emotion. “But it does buy a ticket for your wife to go see her parent before she dies. And that's really important to me.”
You cannot think about self-actualization when you cannot pay your rent. The artistic impulse must be served, but not at the expense of your basic ability to function and care for the people you love.
The Power of a Label: Freelancer or Business Owner?
Words are not just labels. They are the code for our reality. They shape our self-story, our actions, and how others perceive us.
As author Ronald J. Baker writes, “All transformation is linguistic. If we want to change the culture, we have to change the conversation.”
Do applies this principle directly to the world of independent work. The word most people use, “freelancer,” comes with baggage. For many, it evokes an image of poverty, of someone just scraping by between “real” jobs. It feels transient and unserious. The term itself is a linguistic trap.
The origin of the word is even more telling. As pricing expert Jonathan Stark points out, the term “freelance” comes from the Middle Ages. It described a mercenary, a “free lance” or sell-sword, hired to fight a war they didn’t believe in. The connotation is one of a hired gun with no stake in the outcome beyond a paycheck.
For Do, the definition is precise and has significant implications for how you operate. A lack of clarity around this term is causing widespread confusion and limiting the potential of millions of independent creatives.
A freelancer is one who sells their time. This is the fundamental distinction. When you are a freelancer, you are paid for the hours you work, not the work you get done. The business model is rooted in time as the unit of value.
Here are the defining characteristics of a true freelancer:
- You are selling time. Your rate is typically hourly, daily, or weekly. The client is buying your presence and your labor for a set period.
- You cannot delegate fulfillment. The client hired you. If you brought in an assistant to do your work while you drank coffee, the client would be justifiably upset. The expectation is that your hands are on the tools.
- You often work on-site. While remote work has blurred this line, the traditional freelance model involves showing up at the client’s office and working like a temporary employee.
- You are not responsible for the business functions. Sales, marketing, contracts, and project management are largely handled by the client. You show up, do the work, and submit a time sheet.
There is nothing wrong with being a freelancer. It is a valid way to work, and large agencies are built on the backs of talented freelance labor. The problem arises when you are operating as something else but still calling yourself a freelancer.
The next stage of evolution is the Independent Business Owner. This is not a freelancer. This is an employee of one. You are a business, and you must act like one.
The shift is primarily psychological before it becomes operational. You are no longer a hired hand. You are a strategic partner. Here are the traits of an independent business owner:
- You are selling value. Your price is based on deliverables, outcomes, or the value created for the client, not the hours it takes you. This is a core principle in value-based pricing.
- You are free to delegate. The client does not care who does the work, how it gets done, or how long it takes. They care that it meets the promised standard. You are a business, and businesses have teams and processes.
- You are responsible for all business functions. You manage marketing, sales, proposals, contracts, invoicing, project management, and customer service. You are the CEO, CFO, and COO.
- You are an equal partner. Author and designer Kevin Finn refuses to call the people who hire him “clients.” He sees it as a business-to-business relationship. He is not a vendor; he is a partner. This reframes the power dynamic entirely.
When you approach a lead from the perspective of a strategic partner, you immediately stand out. You start asking different questions. “How are you measuring success for this project?” “Where are the goal posts?” These are not questions a typical freelancer asks. These are the questions of a business owner invested in the outcome.
The Ghost in the Machine: How to Let Go of the Work
For many creatives, the biggest hurdle in transitioning from freelancer to business owner is letting go of the work itself. The identity of a “maker” is strong. The idea of becoming a “telephone designer,” as one of Paul Rand’s critiques of Kyle Cooper put it, who just phones it in and tells others what to do, feels like a betrayal of the craft.
This is another limiting belief. We do not expect Phil Knight to stitch Nike shoes. We do not expect Elon Musk to build our Tesla. We do not expect Gordon Ramsay to flip our burgers. Why do creatives hold themselves to a different standard?
Do’s own career provides a powerful lesson in making this transition early. Just a few months out of school, after a brief stint freelancing, he realized two things about himself: “I’m really lazy and I don’t like to work by myself.” So, he started hiring his friends from school to help him with the work.
He was working for the legendary design firm R/GA, led by Kyle Cooper, which had just changed the industry with its groundbreaking title sequence for the film Seven. The demand for talent was immense. Do began working remotely, and soon he had a small team of three people working with him.
He didn’t tell the agency. He just delivered the work of three people at the rate of one. Project after project, he built trust and a reputation for incredible speed and quality. The day rate kept increasing with each new project, to the annoyance of one producer.
Finally, Do walked into the office one night to show Cooper the latest work. After getting approvals, he took a breath. “I just want to let you know something,” he said. “I didn’t do all this work.” Cooper was initially offended, accusing him of ghostwriting. Do’s response was simple and direct. “Did it ever occur to you how I was able to do the work of three people in a day?”
Cooper paused. And he understood. The conversation was over. Do was not being paid for his time. He was being paid for the output, for the result. His ability to build a team and a process was a feature, not a bug. He had stopped being a freelancer and had become a business.
The key, as Jamie Brindle points out, is maintaining the standard. “You go to a Gordon Ramsay restaurant, you’re not pissed that Gordon’s not back there flipping the burgers,” Brindle says. “You assume that Gordon has hired the right people to do it to his standards.”
If you delegate work and the quality drops, that is not a failure of delegation. It is a failure of leadership and management. You made a promise to the client to deliver a certain level of quality. It is your responsibility as the business owner to ensure that promise is kept, regardless of whose hands are on the keyboard. Fail to do that, and your brand is tainted. You cannot build a business on broken promises, a lesson crucial for anyone interested in growing a creative agency.
The Soloist's Scale: Growing Without a Team
But what if you don’t want to be a manager? What if you genuinely love doing the work and have no desire to run a team or an agency?
This does not mean you are doomed to a capped income. It simply requires a different strategy for scale. You can remain a party of one and still dramatically increase your earnings and freedom.
The first and most powerful lever is your price. The only way a solo practitioner can make more money is to increase their rate. As Brindle explains, a rate increase is not just about making more money; it’s about buying back your time.
When you are too busy with client work, you have no time for business development. This leads to the dreaded feast-or-famine cycle. You work frantically on three or four projects, they all end at once, and you spend the next few months desperately trying to find your next meal. A rate raise is designed to strategically lose your lowest-paying clients, freeing up your calendar to consistently find better ones.
As Do puts it, price is a function of supply and demand. Your job is to increase demand while simultaneously decreasing the available supply of you. This involves two non-negotiable actions.
First, get good at your craft. “The premise is always you got to put time into your craft,” Do insists. Too many people hear “charge more” and think it’s a magic trick for the unskilled. It’s not. You must be able to deliver on the promises your high price makes. Put in the hours, develop your skills, and have proof of your ability.
Second, specialize. The entire point of positioning is to reduce or eliminate competition. When you are one of one, you are non-fungible. You have no competition. There is only one person who can do the work the way you do it, and that person is you. Your rate is your rate. The market does not get to dictate it. This focus on uniqueness is a key component of building a powerful personal brand.
Beyond raising your rates for one-on-one services, solo practitioners can scale in other ways:
- Productized Services. Create a version of your service with a defined scope, process, and price. You build an assembly line for a specific offering, allowing you to deliver it more efficiently and at scale without custom proposals for every client.
- Digital Products. Monetize your expertise. If you’re a colorist, you can sell LUTs. If you’re a designer, you can sell templates or courses. This allows you to decouple your time from your income entirely, creating a new revenue stream that complements your client work. This is how you can truly begin to build wealth.
Hunter, Farmer, or Fisherman? Your Lead Generation Identity
Once you’ve defined your role and your offering, you need a system for attracting clients. Not all methods of lead generation are created equal, and choosing the wrong one for your personality is a recipe for burnout.
Do breaks down the approaches into two primary archetypes: the hunter and the farmer.
The Hunter operates on outbound sales. This is the world of direct outreach, cold calls, and networking. The hunter stalks their prey, follows tracks, and hopes for a big kill. It can be incredibly exciting, an adrenaline rush that comes with landing a massive whale of a client. But it’s also dangerous and unpredictable. You feast for a while, but then you enter a long period of starvation, living off the last kill while you hunt for the next.
The Farmer operates on inbound marketing. This is the world of content, community, and reputation. The farmer tills the soil, plants seeds, and nurtures them over time. It is not sexy. It is not instantaneous. A farmer who fails to water their plants will starve. But it is steady and predictable. Fruit will come, not right away, but in season. This long-term mindset is at the heart of effective content strategy.
The key is brutal self-honesty. “I’m an introvert,” Do admits. “I don’t like sales. I’m not built for that.” He knows he is a farmer. Trying to be a hunter would be a struggle against his own nature, competing against people biologically wired for the chase.
Your purpose is to understand your unique set of skills, your personality, and your strengths, and to maximize them. If you’re a four-foot-five basketball player, you can play the game, but you will likely get destroyed by someone who is seven feet tall. They have a physical advantage. Play the game you are built to win.
Jamie Brindle adds a third archetype to the mix: the fisherman.
The Fisherman operates in defined marketplaces. This is the world of platforms like Upwork or other job boards. It gets a bad rap, but it can be a highly effective strategy if approached correctly. These platforms are a pond full of people who are actively looking to do business. The key is to know which fish you’re trying to catch and how to bait the hook. Brindle’s agency found a lucrative niche doing animation for other agencies on Upwork, landing clients worth hundreds of thousands of dollars over time.
You can pursue all three strategies, but you must understand which one is your primary driver and align it with who you are.
The Final Distinction: Content vs. Collateral
For many creatives today, the “farmer” model of inbound marketing means one thing: creating content. They see successful YouTubers and Instagrammers and think, “I can do that. I already do this for my clients, why not for myself?”
This leads to another critical confusion: the difference between creating content and creating advertising collateral.
In his seminal book Permission Marketing, Seth Godin writes that the internet was the first mass communication medium not originally designed to sell ads. Radio and television were built for that purpose. But now, we have taken this incredible platform for connection and turned it into another channel for disruptive advertising.
Many creatives who think they are “doing content” are just making ads for their services in disguise. This is not content. This is collateral.
The hunter uses social media to find and close leads. The farmer uses social media to build an audience and a brand over time. It’s a completely different mindset. One is transactional; the other is relational. One is about short-term sales; the other is about long-term trust.
Brindle notes that when he and his wife started their social media presence, they made a conscious decision. They were not talking to potential clients. They were talking to their fellow practitioners. They were building a community, not a sales funnel for their agency. The byproduct of that expertise could then be used to create digital products and scale their business in a new direction.
This is the ultimate evolution. It begins with a choice. Define your role: artist or designer. Define your business: freelancer or owner. Define your strategy: hunter, farmer, or fisherman.
Be honest about who you are and what you want. The words you choose will create your world.
Choose them wisely.
TRANSCRIPT
Enjoyed this? There’s more where it came from.
Get insights on creativity, business, and design from The Futur.
You can unsubscribe anytime. By submitting, you agree to receive communications and to our Privacy Policy.
“Every emotion that you have is coded with words.”
— Chris Do
Key Takeaways
Subscribe
Details
- Length
- 1h 28m
- Views
- 33,635
- Topic
- FREELANCING