The Four Stages of Freelancing
(And How to Level Up)

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There are two types of freelancers: those who proudly call themselves freelancers and those who wouldn’t be caught dead using that term and prefer to call themselves entrepreneurs instead (but they’re often times still technically freelancers).

Because I work with service-based businesses, I’ve often wondered why that is. Today I want to talk about the different stages self-employed professionals go through and what needs to happen in order to take things to the next level.

Note: This is not a scientific study, but anecdotal. It’s based on my own personal experience being self-employed for nearly 20 years, mentoring countless others in my industry, and working with hundreds of clients.

Everyone’s journey is different and there are unique zigs and zags, so if you don’t fit neatly into a category it’s okay — I think you’ll find value in seeing the way others evolve in self employment regardless.

What’s the difference between a “freelancer” and “entrepreneur”?

Well, the dictionary defines them as:

freelance /ˈfriːlɑːns/adjective – self-employed and hired to work for different companies on particular assignments

Pretty straightforward.

entrepreneur/ˌɒntrəprəˈnəː/noun – a person who sets up a business or businesses, taking on financial risks in the hope of profit.

Not-so straightforward.

Every self-employed person is technically a business owner, and there are financial risks and hopes of profit. So what’s the distinction?

I think Seth Godin defines it best:

“A freelancer is someone who gets paid for her work. She charges by the hour or perhaps by the project. Freelancers write, design, consult, advise, do taxes and hang wallpaper. Freelancing is the single easiest way to start a new business.”

“Entrepreneurs use money (preferably someone else’s money) to build a business bigger than themselves. Entrepreneurs make money when they sleep. Entrepreneurs focus on growth and on scaling the systems that they build. The more, the better.”

I’ve realized in my work with clients that this is not a black and white issue: “entrepreneur vs. freelancer.” But in fact, there are different stages self-employed service providers go through…

Some freelancers aspire to evolve into entrepreneurs. Others want to reach higher levels of freelancing. It isn’t that one is better or more desirable than the other, it just depends on what you want.

Seth Godin describes himself as a “freelancer”… despite being a top marketing authority and author of countless books everyone in his niche can quote by heart, he still “does the work.”

The goal for an entrepreneur is to no longer “do the work” and that’s not for everyone and that’s… ok!

I know many creative professionals who find immense pleasure in the doing and have no desire to become a manager or to create products. 

I myself am a hybrid – I’m someone who loves helping people 1-1, but I also want to make money while I sleep. 😉 I spend every spare moment not working with clients on creating systems that bring in “passive” income.

So….what can we call someone like me? (Freelancepreneur? Can we make “freelancepreneur” happen?) 

But this isn’t about me. I’ve pondered this situation because I want to better understand how to help my clients level up and I know it all depends on where they’re at. So I sat down one day and created a chart to try and sort this out… and it wasn’t long before it was evident there were four distinct phases freelancers go through.

In each phase, there are common characteristics, problems, objectives, and opportunities and in order to level up, it’s helpful to know where you’re at and what you need to focus on to move forward.

Right then, so here’s how I see it…

Stage 1: Explore

In the explore stage, you’re transitioning from conventional employment to working for yourself. Or, maybe you’re right out of school and the thought of working for “the man” isn’t an option, so you set out on your own and look for clients rather than a job.

(Just a pause here to say HECK-YEAH-RIGHT-ON-YAY!)

You have marketable skills and expertise and you view self-employment as the path to living life on your own terms.

YOUR CUSTOMER

At the explore stage, your first order of business is to get clients — any clients — who need your skills. 

MARKETING

Your first move is to tap into your personal network and tell everybody about what you do. You also might use a freelance marketplace (e.g. Upwork) or job boards to get gigs.

Once you book your first clients, if you do a great job for them, they’ll tell other people about their experience and you’ll start getting client referrals. You’ll start building a portfolio, testimonials, and case studies and that will lead to more work.

But, you’re not in full control of who you attract and you don’t always feel 100% confident you know where your next client is going to come from. Because of that, you say yes to most of the opportunities that come your way.

You probably have some basic marketing assets — social media accounts, a website or portfolio, business cards, etc. But you don’t have much time or energy to do all that much with them. Mostly they exist so you can look profesh and so people have a way to find and get in touch with you.

You spend very little time doing marketing tasks and as much time as you can doing billable work.

PROFESSIONAL BOUNDARIES

At this stage, you may not have clear client boundaries and instead, are focused on making them happy (so you can get referrals). 

You’re likely learning lessons about all the ways clients can test your boundaries and struggling with things like scope creep, texts and phone calls on the weekends, and not getting you feedback or payment on time.

You probably commiserate about shitty clients with your colleagues.

YOUR OFFERS

If you are capable of doing it and somebody is willing to pay you for it, you say yes. You likely have a laundry list of services and deliverables on your services page and you create custom project quotes for each client or you bill by the hour for tasks you do for them. 

Leveling Up to Stage 2:

Start thinking about the work that really gets you into a state of flow. When you’re making money and feeling fulfilled in whatever it is you’re doing, what are you doing exactly? Think about ways you can be more specific in the way you talk about “what you do” — in your marketing messages and your 5-second pitch with people you meet — so more people start coming to you to do THIS work.

Think about who you enjoy working with most. What are their common characteristics? What about them makes the working relationship satisfying? Then, think about how you can get in front of MORE of these people.

Set boundaries and enforce them, this is important. In order to be efficient and profitable with what you’re doing, “people-pleasing,” going “above and beyond,” and “letting things slide” are not a good way to go about things.

Create good contracts, keep track of what you’re spending your time on and create some rules around that time, and don’t be afraid to say “no” when something doesn’t serve you.

And most importantly: Make time for marketing and market your business with consistency. If you are not planting seeds and building awareness and trust, you won’t be able to pick and choose who you work with and the type of projects you take on.

Choose a content type — written, audio, video, or visual (whichever plays to your strengths and comes easiest for you) and create as much as you’re capable of. Then, choose a social media platform and start showing up consistently. (Take this free masterclass to learn the five steps of getting customers on social media.)

If you’ve not been consistent with marketing, this is going to feel like a distraction from your billable work — but in order to level up, you need to put your own business on your priority list.

If this sounds like you, grab my Client Attraction Roadmap for tips that will help you get visible with your dream clients…

Stage 2: Master

You’ve been at it a while and you feel pretty confident this freelance thing is gonna to work out for you. (Hurrah!) You’ve learned some lessons and you’re starting to think about which direction you want to take things.

CUSTOMER:

You’ve had some experience working with lots of different types of clients and you’re beginning to notice patterns — some of your clients light you up and work feels effortless and others are a pain in the arse and more trouble than they’re worth.

You’re at the stage where you’re starting to get clear about who your IDEAL client is and who you DON’T want to work with. You start recognizing red flags and run the other way when you spot a “bad apple client.”

You may find that you’re most happy working with people from a particular vertical and you start to network with people from specific industries.

MARKETING:

Because you’re getting clearer about who your ideal client is and the type of work you want to do for them, you become more focused in your marketing messages.

You’re creating content designed to attract a specific type of customer and you’re showing up on social media consistently. You also take steps to make sure your content is discoverable in search — whether that means Google, YouTube, Itunes, or Pinterest.

PROFESSIONAL BOUNDARIES

You are beginning to understand that establishing and enforcing boundaries is a huge aspect of doing client work.

You have processes in place, you’ve established policies, and you work with contracts always.

You have a system for vetting clients — you know what questions to ask and what to look for before saying yes to the work.

OFFERS: 

Because you’re getting clearer about the work you want to do and who you want to do it for, you begin creating packages that describe this work. Your bulleted list of capabilities is replaced with more specific offerings.

The way you speak about your work starts moving beyond “WHAT” you do and starts focusing on “HOW” you do it — the benefits of your offers and the special sauce you bring to the table. (You create a unique value proposition.)

Leveling Up to Stage 3:

A lot of freelancers make a respectable living in stage 2 – in fact, you might coast here for quite a long time before even thinking about making a change. (I know I did!)

Just a word of advice about that: it’s easy to get stuck in the “it ain’t broke, so why fix it?” trap. But, things can EASILY change out there — your competition can change, your marketing platform algorithms can change, and you may find yourself in a situation where what always worked before doesn’t work anymore.

Make marketing a priority. Even if you’re so busy you think you don’t need marketing.

Also, this is a stage where burnout can easily creep up on you. If you’re not steering your business ship toward work that fulfills you, you may wake up one day and your exciting self-employment adventure feels more like a job you’d rather avoid.

If you feel BLAH, uninspired, exhausted, or you’re questioning what the heck you’re even doing… just know that this is just a signal it’s time to level up and everyone goes through it.

You may invest in courses and books and coaches to try to find your way forward and get unstuck — and while all of these things are good, and can even help you get the clarity you need, ultimately it will be up to YOU to take the leap.

What I have found is that people get STUCK trying to find answers outside themselves rather than having a good, honest gut check and accept what’s not working and create a clear vision for the future. I’ve seen people circle around themselves for YEARS and I’ve done it myself. 

Bottom line: moving past your stuck points at this stage is requires doing some serious mindset work and getting comfortable with going outside your comfort zone.

Think about the things you need to let go — whether tasks (yes, it’s time for you to hire a VA), clients, service offerings or something else. We all do things that aren’t serving us anymore (it’s a moving target!), and leveling up is as much about recognizing that as adding new strategies and tactics to the mix.

Most of all, work on feeling confident in your highest value — really get to the bottom of what that is and when you do, OWN IT.

If this sounds like you, take my free course!

Stage 3: Focus

This is one of the most EXCITING stages of freelancing and this is the stage I help people transition into in my work with clients.

When you’re ready to move past being an order taker and design service offerings that attract the right people to you to do the right work, you’re in the FOCUS stage.

You are focused on getting to the bottom of where your HIGHEST value is so you can create offerings that will reward you personally and financially.

You begin to design your marketing, offers, and messaging around your ONE THING. That one thing you want to get famous for and get people coming to YOU because for them, there can be no substitute — it has to be you.

This means you are operating in your zone of genius which means you’re fulfilled in your work and able to command more money in less time.

YOUR CUSTOMER

You are VERY specific about your target customer and you know everything about them. You know what keeps them up at night, you know what they desire, and you know what they need.

When you create marketing messages, you speak directly to them — you speak to their pains, obstacles, struggles and you talk about the transformation they want too… and you’re the one to help them get it.

MARKETING

Your marketing gets more focused and you are connecting the dots between your content and sales.

You create a value ladder (click to get my free Value Ladder Planner) so you’re able to attract clients on autopilot — they come to you because you have the solution they need and you’ve been building trust at every step off their journey.

The content you create revolves around you establishing your expertise and building authority… you might write a book, host podcast, write guest articles in high-profile publications, run webinars, give speeches.

You move beyond social media and focus hard on building your email list because this is land you OWN and it’s where trust and sales are won.

OFFERS

You narrow down your service offerings so you’re operating in your zone of genius and able to charge value pricing. You create systems and processes so you’re becoming more expert and more profitable the more you do this work.

No recreating the wheel with each and every client and no spending time doing custom proposals or doing the long, drawn-out sales process of back and forth emails and free discovery calls. You have a bullseye offer and people come to you for it.

You stop trading dollars for tasks and start selling solutions and pricing those solutions based on their value, not time spent.

(This is something I go into great detail on in my course, The Bullseye Offer Formula.)

You’re creating sales funnels that guide people to your offer using conversion tools like webinars, email sequences, and free courses.

You feel confident you know your client pipeline will aways be full and marketing becomes soooo much easier because you’re FOCUSED on who you are, who you want to attract, and where you’re guiding people to.

At this stage, you may create a product (digital course, book, etc.) to not only attract high-ticket clients, but to make additional, passive income.

PROFESSIONAL BOUNDARIES

At the FOCUS stage, your business becomes your #1 client. You know that every minute you spend serving clients 1-1 that you are not being compensated for is an opportunity cost for your business… spending that time on improving your processes, building products (if you want to), and marketing your business 1-many is how you’re able to make more money in less time.

You’ve got crystal clear boundaries in place and you know how to enforce them. You feel empowered to say NO. A lot. And you do.

And once you get a taste of being in full control of your business? You might not want to stop there… 🙂

Leveling Up to Stage 4

In order to transition from serving clients 1-1 to creating 1-many services or even digital products, it’s imperative that you become very protective of your time — you will need it to create systems that allow you to work more efficiently and profitably so you can devote a percentage of your time to marketing and product development.

Stage 4: Scale (Entrepreneur) 

At the SCALE stage, you’re ready to move beyond serving 1-1 to serving-many OR to charge much more for less time spent. You’re thinking about systems to become more efficient and productizing your offers.

CUSTOMER

Your target customer MAY shift here, and you’ll likely need a strategy for reaching more than one audience.

You may find that a customer who wants work done for or with them and is willing to pay premium pricing (Stage 3) is probably not the same customer who’ll sign up for a course or workshop so they can learn how to do it themselves. (YET.)

At the scale stage, you may need to recalibrate your thinking about your target audience to reach more people.

MARKETING

Your focus moves toward paid traffic, product and/or service launches, and setting up evergreen funnels. Your focus is on authority-building (getting famous for your one thing ramps up) and building your email list.

By this stage, you’ve got a pretty great marketing machine already in place, but you’ve got some gaps you need to fill. You’ll also focus heavily on watching your numbers and optimising every step of your funnel to maximise conversions (especially when you’re running paid traffic campaigns).

OFFERS

You’re creating processes around your bullseye services and “productizing” them so you can continue to charge more in less time or train others to implement.

It might also mean creating digital products (e.g. courses), hosting events (retreats, summits, live workshops, etc.), or growing your team — where you’re primarily in charge of generating new business and managing people who “do the actual doing.”

PROFESSIONAL BOUNDARIES

At this stage, your business is your #1 best client and your focus when serving 1-many will be on streamlining your customer service. You’ll create policies for things like how you’ll handle refunds or no-shows and outsource those tasks to your team.

Even if your goal is to stay a one-person business or keep your consultancy small, you’ll know when a task is better outsourced and where your time is most valuably spent.

Once you have a system to scale, the sky is the limit!

Conclusion

Freelancing, self-employment, entrepreneurship — whichever word feels right for you — is a journey. If you feel overwhelmed or if you’ve spent time comparing YOUR journey to someone else’s, I hope this has helped you realise that evolving from one stage to the next comes with a lot of moving parts and putting them together is a process.

When somebody brags about creating a multiple-six figure consultancy in their first six months, know that you’re probably not privy to the back story — the experience, resources, or marketing foundation they spent years establishing (and usually failures along the way too).

Like I always say, build your empire brick by brick and if you want to GROW, don’t try to leapfrog — take a look at what needs fixing TODAY and make one change at a time.

If you need some help creating your plan to level up, let’s chat!

If you have any questions, hit me up in comments!

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