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The 3 Best Ways To Graduate From “Simple Freelancer” To A “True Entrepreneur” With Multiple Income Streams

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Feeling like you've hit a ceiling in your freelancing career? Ready to take the leap into True Entrepreneurship but unsure where to begin? You're not alone, and I've got the perfect resource for you!
I recently recorded a podcast episode all about what it means to graduate from freelancing.
This episode is tailored for creative freelancers like you who might feel stagnant or limited in their current roles and are seeking new challenges, broader impact, and diversified income streams.
In this episode you’ll discover:
  • The six levels of freelancing
  • What it takes to master the “agency model”
  • How to build your “offer ladder”
  • Creating tools for your industry
  • And more…
If you're ready to explore the idea of transitioning from freelancer to entrepreneur, this episode is a must-listen.

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[00:00:00] Brian: Hello, and welcome to the six Figure Creative Podcast. I'm your host, Brian Hood. If this is your first time listening to the show today, first of all, welcome. This podcast is for creative freelancers who want to earn more from their creative skills, and you wanna do that without selling your soul. That sounds like you.

[00:00:12] Brian: You're in the right spot for my returning listeners. So glad to have you back. I've got an awesome episode planned today. This isn't a topic that I've kind of been avoiding talking about because it's only relevant to what I would consider a small percentage of the listeners. but it's a really important topic that very few people ever really talk about.

[00:00:26] Brian: So I wanted to have an entire episode dedicated to what I call graduating from freelancing. It's when you've hit that a hundred thousand dollars a year mark. For some people it might be multiple six figures a year, and you've hit this plateau where you've tapped out what you can do. Everyone hits this at a different limit, but there's only so much work you can do as a freelancer before you just hit that upper limit.

[00:00:44] Brian: For me, it was about 180 to $200,000 a year as a freelancer doing audio production or music production.

[00:00:50] Brian: and what can happen when you hit this limit is that we start feeling satisfied. We start getting complacent. We start thinking too small. We start thinking, alright, I have arrived.

[00:00:58] Brian: I am successful now. And if you [00:01:00] aren't there yet, maybe you're somebody who's at the beginning of your journey right now and you haven't quite hit that six figure mark or that part where you feel like you've plateaued out, you will eventually hit this. So it's still good to know what your journey will end up at at some point. and a lot of freelancers, they fall into this trap and it's a wonderful place to be. It's still a trap. It's where you have a seven figure skillset stuck into a six figure opportunity.

[00:01:18] Brian: And I've just seen this time and time and time and time again. I've seen this from close friends.

[00:01:23] Brian: I've seen this from acquaintances. I've seen this from my own peers. I've seen this from people that I know of, that I don't know personally. And it's always a very similar path. they spend years honing their craft. They work their way up the ladder. They do all the right things. They get their careers to this point, and then they just plateau.

[00:01:39] Brian: Many of them end up just coasting for a long time and they start to feel stagnant. I think as human beings, we're just meant to progress in some way to feel like we're always moving forward towards something new and.

[00:01:49] Brian: That's why most video games have this level progression system, especially RPGs, because we just like to have the sense of progression in our lives. And it's like if you were playing the same level on a video game over and [00:02:00] over and over and over again, every day, it would get old. It would start to feel stagnant, and you would start to question whether or not you're doing the right thing.

[00:02:07] Brian: So my hope for this episode is that it spurs some of you ahead that might be in this position where you really aren't. Reaching the impact that you could reach if you were able to move outside of your very limited bubble that you're in right now, that you've worked yourself into Because I've seen people who spend 20 plus years building a name for themselves, building out that T-shaped skillset as a freelancer that I talked about on episodes. 235 and 236, where I talk about the full stack freelancer. all of those amazing relationships and that network that you've built up. But in the last five, 10 years, you probably have started to felt stagnant a bit. And if you're happy with where you're at, by the way, if you're happy doing the same thing over and over every day, even if you've hit that upper limit and you're completely satisfied, that's not who I'm talking to.

[00:02:46] Brian: If that's you and you're the type of person who can do that and feel fulfilled and satisfied and feel like they're not wasting an opportunity or not moving towards something that they should be doing if, that's you move along, But this is for those people who feel that sense [00:03:00] of a deeper calling from what they should be doing, and they want to maybe.

[00:03:03] Brian: Entertain the idea of what might be considered graduating from freelancing.

[00:03:08] Brian: This is where you start to stretch and work those entrepreneur muscles. And if you do this for the wrong reason, This is literally what I talk about at the beginning of every episode. You're earning more at the expense of selling your soul.

[00:03:19] Brian: We don't want that. but if you do it for the right reasons, then I truly believe you're stepping into your calling.

[00:03:24] Brian: every one of us have a different thing that we're called toward All creatives are called towards something. And I cannot think of a bigger waste of talent and skill and experience Than to not step into your calling as a creative. And if you do step into your calling and it happens to be graduating through freelancing and you're like me, where you wanna have, you're honestly a D H D, and you want to have your fingers in all the different pies and have a bunch of different funnel along the way, then there's a few benefits that come from this.

[00:03:49] Brian: If you do make this step.

[00:03:51] Brian: The first is if you're wired like me, there's more fulfillment in this, just like video games where you feel like you're constantly leveling up and you need that sense of progression to feel satisfied and fulfilled. [00:04:00] That's the first part, because you're gonna have a lot of new experiences all along the way as you're completing this graduation.

[00:04:05] Brian: And then the second part is, You're gonna experiencing new challenges all along the way. ' cause I am a problem solver by heart, by trade. That is my secret sauce. That is my skillset. That's the thing that I think sets me apart from a lot of people, is I look at every pain point that I have as a problem that needs to be solved, that excites me.

[00:04:21] Brian: But the second thing is, there's more impact involved with this. I remember back when all I was doing was freelancing and I was working with one to two clients at a time. There's not a lot of impact with that. I'm affecting the lives of one to two people, now I've diversified in a lot of different areas and we'll talk about some of those and what, ones might make the most sense for you.

[00:04:37] Brian: But I have much wider impact right now because what I do touches hundreds of thousands of people, maybe millions, definitely millions over the last decade compared to just working with one to two clients at a time as a freelancer.

[00:04:48] Brian: Much bigger impact. So if that sounds interesting to you, let's dive into this. I've got three different methods for graduating. From freelancing. I. And before I get into those, I want to do a quick refresher on an episode we did way back [00:05:00] in the day on episode 185 and 186. It was called The Six Levels of Freelancing.

[00:05:05] Brian: the reason I want to talk about this is because, If you try to do this graduation step before you're really ready for this, it's gonna be more pain than gain. so let me quickly recap those six levels and then we can talk about where graduation fits into those six levels. The first level is the yes mode freelancer. That's when you're in yes mode. You're just starting out. You're saying yes to any project that comes across your plate, just to gain experience and build your portfolio. Level two is the generalist. That's what we call the butt in seat. That's the person who's doing a lot of different things and they just, their butts in seats in different areas and they're still trying to figure out what their niche is gonna be. Level three is traction. That's when you start to actually gain traction in one of those areas you've been exploring while you're in level two, the generalist area, you start to make a part-time income from that.

[00:05:45] Brian: Level four is the pro, that's the full-time person. That's where you start to go deep in one of those areas where you're a specialist.

[00:05:50] Brian: Level five is the six figure freelancer. That's the person who's found a way to greatly monetize a skillset in some niche or some market or some industry, and earning a substantial living from their [00:06:00] income. And then level six, only after you've passed that six figure freelancer mark.

[00:06:04] Brian: Level six is graduation. That's where you have graduated from, freelancer to entrepreneur. So this episode is dedicated to that sixth level. It's all about what to do once you've gotten past level five and you fill that pull or that calling to graduate. This is a completely optional step. I cannot stress that enough.

[00:06:20] Brian: this is not me saying that every single freelancer who's ever hit six figures has to graduate, I'm not even saying that those who graduate are better than the ones who don't.

[00:06:29] Brian: I'm just saying this episode is for those of you, if you felt that, pull that, draw that calling to something bigger and for you better. again, this is not quote, a better path for everyone. It's only a better path if you fill that calling.

[00:06:41] Brian: So let's talk about those three options for graduating from freelancing. The first, and probably the most obvious one is the agency model and the reason this is more obvious is because you're just taking what you are already doing as a freelancer and you're scaling it up through a team.

[00:06:55] Brian: there's a reason there's 50, 60 something thousand agencies in the US alone. It's because [00:07:00] this is a very common path towards scaling up and getting out of that plateau that you hit as a freelancer. Solo freelancers can only take on so many projects at a time before the roster's full. So a way to get past that is to start hiring a team underneath you to fulfill on those projects. So, for example, in my recording studio, I had a hard cap on how many projects I could do per year. so the way to do the agency model would be to actually hire out people underneath me to do all of the projects. Very difficult to do in that niche.

[00:07:26] Brian: However, I believe there's always a way to make it work. It may not be the best way to do it. It may not be the best industry for it, but somebody has likely already done it.

[00:07:34] Brian: So if you go back to episode 125, way back when we were called the six Figure Home Studio. There's an episode called How to Build an Online Recording Studio that employs 30 plus Engineers. It was an interview with a guy named Joe Wadsworth. he runs a, site called the Online Recording Studio,

[00:07:48] Brian: which is essentially an agency model for music production. So he's built a team of audio engineers. He's got the marketing engine to bring in enough clients to fill all the calendars of those people. And he makes a ton of money doing [00:08:00] this.

[00:08:00] Brian: So if you're gonna go with this route, this is a great time to review the book. the E-Myth or the E-Myth Revisited by Michael Gerber.

[00:08:06] Brian: And he talks about those three types of people or the three personalities. There's the manager, the entrepreneur, and the technician. you're a freelancer or you're a creative, you're almost always just the technician. That's the creative. That's the one who's doing the work in the business.

[00:08:19] Brian: When you move out into an agency model, you're gonna be much more the manager and the entrepreneur.

[00:08:25] Brian: and that's because as an agency, you're gonna hire and build a team underneath you to actually do the work, all the technical work. So you need to be great at hiring. You need to be great at leading. You need to be great at managing, at setting expectations, at holding people accountable for what they say they're gonna do, which is a totally different skillset than just a freelancer.

[00:08:42] Brian: Just a creative. On the other side of things, you have to be the entrepreneur as well, because in an agency, you're steering a much bigger ship. As a solo freelancer, you can just make decisions on the fly, and the only person you have to bring along for the journey is yourself. If you decide to pivot and go another direction by yourself, that's easy. But when you start building an [00:09:00] agency and you have a team underneath you, you have to make decisions with more people in mind, and that creates the need to be a better entrepreneur, to not just make snap judgements, to not just make.

[00:09:09] Brian: Half-assed decisions to change things all of a sudden.

[00:09:11] Brian: So that's option one. That's the agency model. That's one way to graduate from freelancing and build up to the seven figure, multiple seven figure of business. Matter of fact, I was listening to a podcast earlier where someone had built a $500 billion per year agency. I. Which is insane to me.

[00:09:26] Brian: But for many creatives, that's a big step. It is very difficult to just go from a, a solo freelancer and creative to all of a sudden being inspired and want to build a big agency. Usually, if you're gonna do that, that's already top of mind for you.

[00:09:39] Brian: That's something you likely had in mind from the very beginning, or you worked in an agency, you've seen how they work and you come out of that wanting to start your own. so that leads us to option number two when it comes to graduating from freelancing, and that is becoming a teacher or a coach.

[00:09:51] Brian: This is more and more common over the last three to five years, I'd say. You've probably seen. Tons and tons of stuff online about how to do this. You've seen so many people talk about this, but this should [00:10:00] not be ignored because so many of you are so great at what you do and you've gotten to where you are because of your skillset.

[00:10:06] Brian: That moving towards the coach or educator side of things might be the national next step for you. This isn't for everybody for sure, but this is for some types of people who have a great personality and a great desire to be a teacher. so let's take a step back for a second and let's look at something called the offer ladder.

[00:10:20] Brian: This is something we talked about on past episodes before, but if you look at the typical offer ladder, there's three tiers to this offer ladder. There is the done for you tier, and that means that you are doing the work for the client. That's just the general freelancer agency model where someone's coming to you with a problem that needs to be solved.

[00:10:36] Brian: or they have a goal they're working towards, whether it's they need their wedding photoed or they need a new website created, or they need their album produced, or they need new headshots, or they need new visuals for, their influencer brand.

[00:10:48] Brian: I don't know. done for you means that you do the work for them. That's the top tier. It's usually the most expensive. That is the general freelancer or agency model, the service-based business The second tier, the one below that is called [00:11:00] done with you. and that's where instead of you do the work for them, they're doing the work, they're responsible for doing it all, but you're guiding them through the process. This is more about the coaching side of things. So if you are.

[00:11:10] Brian: Helping someone take better head shots, you're helping someone. I don't think the wedding photo industry is really gonna move to the done with you option, so we can ignore that one. But if you go towards, like the music production's a very common one where you're guiding an artist through learning how to self-produce.

[00:11:24] Brian: I.

[00:11:24] Brian: Or you're working with certain brands or small business owners on building their own websites from scratch, et cetera, et cetera. This is called done with you, where they're doing all the work, but you're guiding them through the process.

[00:11:33] Brian: Maybe giving them feedback, Where you're helping them get past roadblocks. Maybe you're giving them little nudges to get things done through accountability.

[00:11:40] Brian: then we get to the bottom of that offer ladder, and that's do it yourself. D i y. This is where you're more of a teacher than a coach. A coach helps them do things. A teacher just says, here's how to do it now. Go figure it out on your own. So this is where you get courses. books kind of fall into this category, but this is where you're just saying, here's how to do the thing. Good luck. Good luck in [00:12:00] Godspeed. this is arguably the most difficult way to make this transition, especially if you don't have any other experience with education or teaching or building a, base of clients.

[00:12:09] Brian: Because the business model here needs to be just as sound as it was when you were freelancing The two metrics that matter the most for this or freelancing is how many clients do you have in a year? And then how much is each client worth? On average, your A A C V average annual client value or average annual customer value If you're doing.

[00:12:25] Brian: Selling courses, you consider 'em customers versus clients, but how many clients do you have? How much are they worth? Whether you're a freelancer or you're offering coaching, or you're doing courses, if you choose this path of being a teacher or coach or consultant, You still have to have sound business fundamentals, and that means you still need to understand client acquisition just like you would whether you're a freelancer or not. Generally speaking, done with you and do it yourself where you're doing coaching or courses in the education space, because this is more scalable.

[00:12:52] Brian: you have to build a new skillset usually around either content marketing, where you're building some sort of organic source of. [00:13:00] Leads and sales. So that can be social media, short form, long form content on YouTube. It could be a podcast like this, or you have to start learning how to be a marketer a bit online with using paid acquisition strategies.

[00:13:11] Brian: You could also do things like affiliates. There's a lot of other strategies you could use to grow this beyond the scope of this episode, but that's the second option for graduating from freelancing and moving to that next level is doing the teaching or the coaching? A k, a, the do it yourself. D i y teaching or done with you coaching side of things where you're walking them through a process that you've developed. By the way, I hadn't even talked about my myself in this, but this is what I do, and have done. This was actually the first thing I ever did to graduate from freelancing. In 2015, I launched a mixing course. I was mixing heavy metal music, and then I launched a course called From Shit to Gold. You've probably heard me talk about this before, if you've listened to the podcast.

[00:13:44] Brian: and led to about 30 to 40% of my income that year from a course that I launched, like the third quarter of that year. So it was like, I wanna say September-ish. Around that time

[00:13:53] Brian: I launched this course and it still accounted for a, very large chunk of my income and that was the first time I'd ever stepped towards [00:14:00] the graduation from Freelancing Steps.

[00:14:01] Brian: So I've launched multiple courses and then now I actually do coaching. So I did it a bit backwards. I did the course thing first, and then I did the done with you, the coaching thing, which is what I help with now. I help creatives and freelancers get more clients through client acquisition strategies.

[00:14:14] Brian: So now it leads us to option three, what I call selling shovels. If you've ever heard of there's a quote I'm gonna butcher here, but it's something like, in a gold rush, you wanna sell shovels or sell tools, something like that.

[00:14:26] Brian: And this is again, an opportunity that many freelancers and creatives could move into. Because they're in a unique position to understand themselves a k a, their clients if they're selling to themselves more than anyone else. And so when you're selling shovels, you are selling essentially the tools of the trade.

[00:14:42] Brian: What are the things that are gonna help people like you to the outcome that they want. this is something else that I've done. I've released two software products. One is called File Pass. It's file sharing and collaboration and paywalls for the audio industry so that when you send files to your clients, they can't download them until they pay you.

[00:14:58] Brian: They can collaborate and leave timestamp [00:15:00] comments on all the files. Wonderful platform. It's done very well, but I launched that in 2018 or 2019, and that was a tool for the industry.

[00:15:08] Brian: I also have easy funnels. that is a website and funnel builder with email marketing software built in and appointments and scheduling everything that a freelancer would need in order to run their freelance business. That is available as well. That's another tool that I sell that helps the industry that I understand, because I grew up in this industry.

[00:15:23] Brian: I know freelancers inside and out. I know what they need. I know what they hate. I know what they like. I know what they don't like. I know what they think they want, but they actually need,

[00:15:29] Brian: now I've developed software to help with that. So there could be certain software that you could develop depending on your skillset or partner with people, which is what I do. I'm not a developer, I don't know, code. Partner with people to help develop the software for your industry and then bring it to them.

[00:15:43] Brian: I've also seen people launch hardware, which is very difficult to do from what I understand. I've never gotten into physically manufacturing a piece of hardware and then trying to sell it. That sounds like a nightmare to me. But I have seen it done especially in the audio industry, I've seen people launch pedals and gear, whether it's guitars or guitar pedals.

[00:15:59] Brian: I've seen people [00:16:00] create.

[00:16:00] Brian: Compressors and preamps. There's a lot of boutique gear that people are releasing now, especially in the audio space, and I would imagine certain industries, again, every niche is different, but certain industries would have hardware opportunities, especially if you are drawn towards that world. Again, these are just all options that you have as a freelancer.

[00:16:16] Brian: Depending on your skillset and desires. I would imagine that most people are not interested or capable of developing manufacturing. Sourcing and, selling hardware. So the third option when it comes to selling shovels or tools is digital products. This is much easier to do, especially if you already have these things created.

[00:16:33] Brian: this is usually one of the first transitions I see people start to make when they're, graduating out of freelancing into a more scalable business. So it might be that you were selling templates that you've already developed, Like videographers. They have lutts, they sell. or you'll see people that are selling contracts.

[00:16:46] Brian: Anything that can be delivered digitally, that is a valuable asset, that is a tool to help that person get to the outcome that they want is a viable way to do things. Now, keep in mind that. There are two different ways you could go with this. This is really [00:17:00] important to understand who are you trying to sell these to?

[00:17:02] Brian: Because a lot of people, when they make tools or sell shovels, they're selling it from people just like them, other freelancers, and they're moving into that world where they're helping people just like them. That's one path you can go. Option two is to sell tools or shovels or software or hardware to the types of clients you've been serving so far as a freelancer.

[00:17:20] Brian: So looking back on my past as a heavy metal drummer turned heavy metal music producer. Which path did I choose? Well, If I was going down the serving the clients that I've been serving, I would've developed software and courses and coaching for for heavy metal musicians, right?

[00:17:35] Brian: That wasn't the path that I went. I went for people like me. I was selling mixing courses for people who were interested in heavy metal mixing, so I went that route. Either way, there's no right or wrong there. It's just as long as you know who you're targeting that's going to greatly affect, you build this income stream it doesn't make sense if all of your marketing assets you've built up so far as a freelancer. Are all targeting, let's just say small business owners, but then you launch digital products for [00:18:00] other designers or other photographers or other videographers.

[00:18:02] Brian: It just doesn't make sense. On the other side of things, if you've been posting content on social media or building a mailing list of people like you and building masterminds of people just like you, the other photographers out there, the other music producers that are out there, then it makes perfect sense to launch products, whether it's coaching, consulting.

[00:18:17] Brian: Shovels hardware, software to those types of people versus the clients you've been serving. So again, no right or wrong answer here. It's just a matter of which one makes the most sense for you. Which one are you drawn towards? And which one do you think has a bigger opportunity to help you step into what you feel like your calling is so that you are able to make a bigger impact with your skillset.

[00:18:36] Brian: one other kind of important note about option three when you're selling shovels, is you don't actually have to create your own here. This is a secret that most people don't understand. You can actually become an affiliate for your favorite products and services.

[00:18:47] Brian: I've done this for years. If there's a certain tool that I love and that I recommend that I use myself, I can recommend that tool to other people. And anyone who goes through my unique affiliate link to sign up for that tool, I get a commission for that. [00:19:00] It's a wonderful way to monetize an audience in a way that serves all three parties.

[00:19:04] Brian: It serves the tool because they're getting customers. It's serving the customer because they get a tool that they wouldn't have otherwise being able to access or even know about. And it serves me because I get a commission or a kickback when I recommend people to that tool.

[00:19:16] Brian: so if you want to sell tools, you can just find ones that work well in your industry and start promoting those tools to people that trust you, that already want your recommendation. And the larger your following is the bigger of a piece of pie That is, because I see people with hundreds of thousands of YouTube followers, they've graduated from freelancing, they've built a massive following, and they make tons of money selling other people's tools as affiliates.

[00:19:40] Brian: So this is a path you can go down. You do not have to be the one that creates the tools. So those are the three options for graduating. I wanna give you a bonus. Fourth here. But the first is a recap is the agency model. That just means you hire a bunch of people underneath you and you start to scale up the amount of clients that you can serve through other people.

[00:19:56] Brian: Option two is the teacher or the coach. That's where you're exploring the [00:20:00] done with you option or the do it yourself option by teaching or educating or coaching people through the same outcome that you would've otherwise done for them. but you're not doing the work.

[00:20:09] Brian: You're helping them do the work. Option three is to sell shovels in a gold rush. You wanna sell the tools, you wanna sell the shovels. There's an option there, whether you're creating them yourself or you're partnering with companies as an affiliate to sell their tools to your audience. But bonus option four is the approach that I've taken.

[00:20:25] Brian: It's the hybrid approach. That's where you take bits and pieces of each of the three options, and you create your own unique approach in whatever order that you want to do.

[00:20:34] Brian: What is most appealing to you right now? What makes the most sense for you right now? What are you most drawn towards and what does your skillset make the most sense to do right now?

[00:20:41] Brian: It might be that you wanna be a teacher, you wanna sell courses, and you start to build your following on one of the platforms out there, whether it's TikTok or Reels or YouTube or a podcast, or you start to build a mailing list through paid ads. And all along the way you're promoting an online course.

[00:20:56] Brian: But once that course launch is done, or once you get that course out into the world, you start to [00:21:00] sell other tools. So now you're incorporating a bit of option three in there where you're selling the shovels. You're not creating your own software, you're not creating your own tools.

[00:21:07] Brian: You start to partner. as things start to pick up, you start to offer coaching along the way. And then maybe because you have enough money, you can start to develop your own software, or you start to release other tools like templates. Again, you can mix and match here however you want. But at the end of the day, this is a way to multiply yourself, multiply your skillset into a bunch of different new, fun, exciting areas for the freelancer, who feels like it's maybe time.

[00:21:29] Brian: To start testing new waters and graduate from being just a freelancer, which again, there's nothing wrong with being just a freelancer. I'm putting just in air quotes. Freelancing is a wonderful craft. It's a wonderful business. It is awesome. But when it comes time to graduate from that and you feel like you're butting up against this wall trading dollars for hours doesn't really gel well with you anymore, and you wanna become more of an entrepreneur, then these are your three options.

[00:21:51] Brian: If you are interested in making this shift, I am more than happy to talk to you about it, to maybe help you out along the way. I help a few people who are kind of in that graduation phase right now, where [00:22:00] they're exploring new and amazing things, and that's actually been some of my more successful coaching clients are the ones who have made the shift from freelancing to coaching or courses or something else.

[00:22:09] Brian: But again, if you're interested in this, you can just go to six figure creative.com/coaching.

[00:22:13] Brian: can start the application on that page and then we'll be in touch with you if it makes sense. So that is all for this week. Again, a topic that I is near and dear to me as somebody who is very much the entrepreneur and I love getting my hands in all different areas of life and business, exploring new things.

[00:22:28] Brian: If you understand the Enneagram, I'm an Enneagram eight with a seven wing, and if you don't know what that means, it's okay. It just means that my wing, the thing that's really close to me in the personality side of things, the seven is the one who wants to experience all the things and wanna do all the new and fun and exciting things.

[00:22:43] Brian: That's the. A d h D side of myself that naturally comes out in business that's why I have too many businesses, to be honest with you. again, that's all we have for this week. Thank you so much for listening to the six Figure Creative Podcast.

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