The 4 Stages of Freelancing Explained | Part 1

In this episode of Freelance Cake, Austin L. Church discusses the moonlighter and hustler phases of freelancing, shining a light on the motivations, challenges, mistakes, and questions at each stage, as well as the main breakthrough and financial goal for each.

December 29, 2023
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Disclosure: This episode is sponsored by CrowdHealth, and also includes affiliate links which means I may earn a commission if you make a purchase through my link. All opinions are my own.

You’ve surely heard of the corporate ladder, but what are the career progressions for freelancers? Those of us who sell creativity in some form usually freelance part-time at the start, and those who stick with it eventually think, “Hey, why shouldn’t I be one of those people who make money while they sleep?”

In this episode of Freelance Cake, Austin L. Church discusses the moonlighter and hustler phases of freelancing, shining a light on the motivations, challenges, mistakes, and questions at each stage, as well as the main breakthrough and financial goal for each.

Whether you're reflecting on your current stage or aspiring to reach new heights in your freelancing career, this episode offers practical insights and guidance.

This episode is the first of two parts, and in the next installment, we'll explore the lifestyler and diversifier stages of freelancing. Don't forget to tune in for that one as we continue peeling back the layers of the freelancing journey.

Key points

  • Stages of freelancing (01:53)
  • Moonlighters overview (02:49)
  • The motivations for moonlighters (03:44)
  • The challenges for moonlighters (04:39)
  • The questions for moonlighters (05:50)
  • The main breakthrough for moonlighters (06:13)
  • Hustlers overview (08:29)
  • The motivations for hustlers (10:34)
  • The challenges for hustlers (11:10)
  • The questions and breakthrough for hustlers (12:39)
  • The main financial goal for hustlers (13:39)

Notable Quotes

  • "The main breakthrough for moonlighters is growing confidence in their ability to win projects and deliver outcomes while managing other responsibilities."
  • "The main breakthrough for hustlers is setting smart strategic prices that reward your skill, efficiency, and expertise."



[00:00:00] Welcome to the Freelance Cake Podcast. I'm your host, Austin L. Church. The goal of this show is to help full-time, committed freelancers get better leverage.

[00:00:13] As the sworn enemy of busyness and burnout, I have no desire to see you work harder. Instead, I reveal the specific beliefs, principles, and practices you can use right away to make the freelance game more profitable and enjoyable. So chill out and listen in, because the best is yet to come.

[00:00:35] This episode of Freelance Cake is brought to you by CrowdHealth. Healthcare in the US is complicated, confusing, and highly personal. Insurance premiums, deductibles, and copays can get really expensive, especially for freelancers and consultants who don’t have an employer paying for anything.

[00:00:54] Case in point, here’s what a UX consultant wrote to me in an email: “My biggest headache is currently health insurance. It’s so expensive for a family of 4 with 2 self-employed parents. Really tough.”

[00:01:08] That is exactly why my family of 5 switched to health-sharing. Over the last 9 years, my wife and I have been through 2 births, a broken arm, 2 surgeries, emergency room visits, MRIs, allergy shots, and a disability diagnosis. Get this, we’ve saved over $60,000 in out-of-pocket costs without sacrificing our quality of care.

[00:01:32] If you’re not familiar with healthcare crowdfunding. I hope you’ll take this opportunity to educate yourself. I’ll drop some links in the show notes, or you can head straight to and use code “freelancecake” (that’s just one word) to get 3 months for $99. Go to

[00:01:53] You've surely heard of the corporate ladder, but what are the career progressions for freelancers? Based on hundreds of conversations with freelancers and consultants, I've noticed four distinct stages in the journey.

[00:02:09] First one, moonlighter. Second one, hustler. Third one, lifestyler. Fourth one, diversifier. Each stage or progression comes with its own distinct set of motivations, challenges, mistakes, and questions.

[00:02:26] I encourage you to just listen slowly through this episode and consider where you currently are. Take special note of which stage, breakthrough, or financial goal resonates with you right now. Better yet, record what resonates with you in your journal. You'll want those insights to help you make decisions.

[00:02:49] Let's start with moonlighters. Most freelancers I know start part-time by picking up freelance projects here and there while holding down another job. I use the word “job” here loosely to mean not just full-time employment but an entirely different set of obligations that consumes most of their time and attention.

[00:03:11] A designer may have a salary at a digital agency and create album covers and t-shirts for bands at night. A high school English teacher may pick up book editing projects during the summer. A stay-at-home dad may homeschool his kids and shoot 10-15 weddings a year.

[00:03:30] Here's an unusual one I heard recently: My friend Matt's dad served as a senior pastor at a church but several months a year, he'd put on his CPA hat and prepare tax returns. Go figure.

[00:03:44] The motivations for moonlighters will be familiar to most of you. Here are three of them: testing the waters with this whole freelancing thing, making extra money on the side for fun, for bills, or for a big purchase, having creative freedom when a 9 to 5 job doesn't scratch that itch.

[00:04:06] It's worth noting that moonlighting can start by accident and that the business may grow organically and stops and starts. For example, you start sharing your illustration projects online and Aunt Barb surprises you with a direct message. She asks, “Can I pay you to create a holiday card for my recruiting firm?” That single project paid for all the gifts you bought that season and woke you up to the possibility of side projects.

[00:04:39] Moonlighters have several main challenges. Here are three of them: finding projects, finding time and energy to complete those projects, and juggling the responsibilities that come with managing a business. The same small loaf of minutes must feed many mouths. Of course, plenty of moonlighters figured out and a large number are content to keep this side hustle on the side. Moonlighters don't need many tools because you don't have many projects or tasks to keep straight at any one time.

[00:05:18] The common thread among mistakes moonlighters make is a muted sense of urgency, undercharging because you don't rely on the income, inefficiency and sloppy process because you don't have a tight production cue, more casual attitude toward building the brand and business because who suffers if you have a weak web presence or out of date portfolio or you forget to ask for testimonials, referrals, and repeat business.

[00:05:50] The questions, fears, and insecurities for moonlighters vary with the person, but here are some of the more common ones. You ask, what's the next most logical step for my business? Or how do I break into full-time freelancing? How much should I charge? Where do I go from here? Am I doing this right?

[00:06:13] The main breakthrough for moonlighters is growing confidence in their ability to win projects and deliver outcomes while managing other responsibilities. The main financial goal for moonlighters is socking away cash in an emergency fund useful for its own sake in stabilizing one's personal finances, but also important for runway if you ever were to go full-time freelance. After another quick word about our sponsor, I'll keep going with this.

[00:06:48] Healthcare crowdfunding is a model a lot of people in the United States are still unfamiliar with. Basically, instead of submitting your medical bills to an insurance company, you send them to other people and those people pay a share of your bill. Then when they have medical bills, you reciprocate.

[00:07:07] And thankfully, there are health-sharing memberships like CrowdHealth that facilitate that whole process and make it easier and even support the process with some really good technology.

[00:07:18] So you continue to go to whichever healthcare providers you prefer, you negotiate often significantly lower bills because you’re cash pay or private pay and then everyone benefits because instead of all of the inefficiencies and extra costs of the insurance industry and insurance companies, you just bypass that and you crowdfund your medical bills.

[00:07:46] So if you haven't already, go check out CrowdHealth. Go to On the home page, you can learn more about the model and I do want to reiterate that my family has had a crowd-funding healthcare membership for nearly 10 years now. We're huge fans of this model because we've saved conservatively over $60,000. So again, go to, put in promo code “freelancecake” (all one word), and you will get your first 3 months for $99. That's it. All right. Now, back to this sweet, sweet slice of Freelance Cake.

[00:08:29] Next up is hustlers. Eventually, some moonlighters decide to take flight into full-time freelancing. The reason is often a growing dissatisfaction with a full-time job, the pay, the coworkers, or a slimy supervisor.

[00:08:47] Other folks get pushed forcibly out of the 9 to 5 nest. When I lost my job during the great recession in 2009 and suddenly found myself freelancing

ull time. I had two choices. The first was flap desperately to stay aloft like a drunken buzzard or sink like a stone.

[00:09:10] I always had an entrepreneurial bent but I didn't see it in myself until I was in my late twenties. Each of us is an iron filing caught between two magnets. I tried the more conventional path first and the safety, security, and predictability of a regular paycheck appealed to me.

[00:09:32] Eventually, the other magnet – mastery, autonomy, and purpose, or MAP a la Daniel Pink's Book Drive – eventually that second magnet won the tug of war. No one to answer to, no soul-crushing meetings, or icky performance reviews. Glorious freedom!

[00:09:55] Well, not quite. Every career path has its own set of problems. As a newly self-determined freelancer, I didn't have to listen to my old creative director remark on the holes in my genes. It's called style, sir. You might explore it?

[00:10:12] But that didn't change the fact that I had only $486 to my name. So when I got laid off, in four short days, I went from, “I really ought to save more” to “Ra ra ra!” That's the noise you make when your rational mind overloads with panic.

[00:10:34] The motivations of hustlers are etched into my memory with the acid of painful firsthand experience. What were those motivations? Finding more and better clients (that is, more budget and creative license), selling nondifferentiated services like copywriting and design, pretending I have a clue or you have a clue you know what you're doing, trying to be “competitive” with your prices, making enough money to pay the bills, serving clients well.

[00:11:10] Freelancing isn't some neat experiment anymore. It's survival. Once the external scaffolding of a team boss and routine disappear, we see the challenges we're really dealing with. It's easier to hit a deadline when you receive a grade in college or don't want to get fired. But when the small red cartoon devil version of your boss isn't hovering over your shoulder and telling you to get back to work, you may find yourself with even worse coworkers who live in your mind.

[00:11:44] These coworkers include overthinking, perfectionism, procrastination, second-guessing, imposter syndrome, and the biggest turd of them all: scarcity mindset.

[00:11:58] When you are a hustler, mistakes abound like beatles on a dung pile. All the mindset traps I just mentioned, shoddy contracts or none at all, offering every service like a one-person band or a bodega, undercharging because you tell yourself you can't afford to lose a project. Well, that's scarcity mindset. Weak boundaries with clients and enabling their bad habits along with your own. Nonspecialized work with weak or no positioning. “You have a pulse? Sure, I'll take your money.”

[00:12:39] The burning questions for hustlers or these lit-up arrows pointing to breakthrough are as follows: How do I depend less on referrals? How do I get a grip on my marketing? How do I make more money without simply working longer hours? How do I raise my prices without losing all my clients? How do I specialize or niche down? The main breakthrough for hustlers is setting smart strategic prices that reward your skill, efficiency, and expertise.

[00:13:13] Higher prices can and should coincide with a pivot from charging hourly to charging flat fees. The secondary breakthrough comes through establishing what I call a morning marketing habit that makes you less dependent on referrals and much more likely to get the clients you most want because you're going after them.[00:13:39] The main financial goal for hustlers is paying yourself as much or more after tax as you made with your salary at your last full-time position in beginning to fund certain specific lifestyle goals.

[00:13:56] Okay, that's a wrap for the moonlighter and hustler stages. My podcast producer, Jason and I, decided to break this episode up into two shorter episodes. The next one is going to touch on the lifestyler and diversifier phases of the freelance journey.

[00:14:17] So tune in for that episode and if you already know that you're in this moonlighter or hustler phase, go ahead and take out your journal, set aside 15 minutes, think more carefully around the next breakthrough you need based on what we covered today.

[00:14:37] Okay, see you in the next episode.

[00:14:41] Hey, before you go, a quick reminder, be sure to check out the business redesign group coaching program. It's fundamentally about revenue design and lifestyle design and it's based on the $300K flywheel framework that I have developed over the last 15 years of trial and error and nearly $2 million earned as a creative entrepreneur.

[00:15:04] Instead of feeding more and more time into the business machine, you can join me and other like-minded freelancers and consultants as we learn how to think like a CEO, not a technician, stack up the right advantages, and find our income lifestyle sweet-spot. Go to to learn more about business redesign and apply. My friends, the best is yet to come. See you in the next episode.


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