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According to MBO Partners, one in five freelancers have scaled to the full-time level generating six figures in revenue. That number is expected to climb, too, since so many freelancers are in high demand. But making that shift from freelance independent contractor to full-on CEO of your own business is not always an easy one. The good news is that many freelancers can break their bad habits and find scaling their business to be much easier than expected. 

Once you start to get traction in your freelance business, your mind easily turns to the possibilities of scaling. After all, you either started side hustling or jumped in full time because you wanted a flexible career that brought you good income, too. 

All too often, freelancers accidentally block themselves from things in their business that would help them scale effectively. After coaching and teaching hundreds of new and experienced freelancers, these are the common trends I’ve spotted as to what’s most likely to hold them back.

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#1 Bad Money Mindset 

Your connection to your feelings about money, worth, charging fair rates, and letting low-paying clients go can have a tremendous impact on how you show up in your business. If you’re not feeling confident about what you charge and how you charge it, you’ll balk on sales calls or let those late-paying clients get away with addressing their invoice weeks too late. 

Bad money mindset can easily show up for freelancers around all subjects, but money is a particularly sticky one. 

If you’ve internally logged away the thought that you have to work really, really hard to make your business a success, don’t be surprised when this shows up as a limiting belief.

If you’re concerned about out-earning a partner, family member, or business friend, this is a limiting belief that can cause you to self-block from higher earning potential. While these are just a few examples, taking control of your money situation and honoring it by charging fairly and keeping to good money boundaries can really help you uplevel much faster than you ever thought. 

#2 Continuing to Work with the Wrong Clients 

What got you here won’t necessarily get you there when you’re scaling your freelance business. It is absolutely possible to build a fully-booked or six-figure freelance business with the wrong clients. 

But that’s where you’ll get stuck. If you’re already clocking 60 hours per week on projects and the thought of taking on more client work makes you feel sick to your stomach because you’re so busy already, you’ve got the wrong clients. If all your time is consumed by the cheapest clients (and it almost always is) imagine the physical time and mental relief you’d get back by firing them and moving on. 

You grow as a business owner, and you can outgrow old clients who have not moved to the next level as you’ve improved your experience, work samples, business policies, and rates. Sometimes it’s the harsh truth that we have to leave behind some of the clients from the past to step into newer and better roles. I credit firing the wrong clients as a significant driver of going from $35k in revenue to $100k in revenue within one year. 

I credit firing the wrong clients as a significant driver of going from $35k in revenue to $100k in revenue within one year. 

#3 Not Getting Support in the Business

You probably have been the VP of every department in your own business up until now because there was no other option. You handle sales, marketing, client experience, project management, accounting, and more, don’t you? But if you want to take your company through the process of scaling, you’ll have to outsource and get support.

Support can come in three main forms: coaching, software/systems, and actual delegation to other people. 

With coaching, you’ll have someone to turn to as you need help thinking through the problems and fears you have at this new level. With software and systems, you pull away tasks that are time consuming and draining for you and replace them with automations and tools that handle it faster and easier. Do you really need to be hand-creating invoices with each new client or manually calculating your monthly revenue? No. With delegation to others, you can leverage the support of an admin or bookkeeper so that you stay focused in your own zone of genius getting clients and delivering client work. You could also consider Indy's tools like invoices, contracts, and proposals which make these processes simple and efficient.

Yes, you’ve been a solopreneur up until now. But that is no longer necessary once it’s time to scale and you can bottleneck yourself from being able to hit that level if you remain control-freak committed to doing it all on your lonesome. 

#4 Not Being Open to Pivoting 

Your next level might not actually look like more freelance clients or higher rates for your freelance services. It might be a second stream of revenue selling courses, books, coaching, physical products, digital products, or even an entirely new service.

It’s actually very common to get bored or burned out doing the same thing all the time and viewing your only method to fix that as adding more of the same. You’ve got to be able to get the mental space needed to step back and really tune in to your next step. If you don’t have that mental space yet, go back to the step above- what can you get off your plate so that you have more time and ability to serve in the role of true CEO? 

You could even zoom back up to the level of generalist or step into an entirely new niche as a freelancer if you wanted. Freelancers must constantly be aware of their own energy and passion for their work and also the demands of the marketplace. If you feel the need to shift, listen to it! 

Even though it’s not always easy to scale, what is easy is remembering that these blocks just call on you to be the fixer. It’s not your client’s fault or the market’s fault if you’re not seeing the returns you want- it might just be time to adapt and make needed changes.


Indy is here to help you in your freelance journey, from invoicing to contracting to proposals, we have the tools to make life easier as you scale your business.

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