The secret to successful freelancing: CEO mindset

Most people who launch a freelance career previously worked full-time for employers. Freelancing may have seemed a good option — or maybe an emergency need — after being “downsized” or quitting out of frustration or misery.

The lucky or conscientious among us made the transition gradually by building up their freelance work on the side of a full-time job before making the leap to full-time freelancing. 

But regardless of how you shifted to freelancing, chances are you started your work life as an employee. This means that the way of working you’ve become used to is to execute someone else’s priorities and directives. 

You may have been explicitly told what to do and how and when to do it. You may have had a bit more autonomy than that, but you were still in charge of delivering a small piece of a big puzzle that you had little say in creating. 

By and large, you were probably not able to exercise much control, creativity, or decision-making of your own. 

As such, you are likely used to maintaining an “employee mindset” — that is, working in a way dictated by others and that comes with very limited responsibility. You may have had responsibility for a small portion of your employer’s larger operation, and your control over your work life has been proportionate to that level of responsibility. 

When you become a freelancer, one of the biggest shifts you need to make in order to succeed is to transition from an employee mindset to a “CEO mindset.” 

As you may guess, a CEO mindset means that you’re in charge. No one will tell you how, when, or where to work. No one will tell you which things to pursue, which things to forego, or how to act on the priorities you choose. You are responsible for your entire operation, and your control over your work life is proportionate to that level of responsibility — as in, total. (And I don’t just mean in an ideal world; in some countries such as the U.S., tax authorities actually require you to have that autonomy to be classified as a freelancer.)

As you can see, there is a vast difference between an employee mindset and a CEO mindset. An employee mindset leans toward passivity and dependence, while a CEO mindset makes you by necessity active and autonomous.  

You will automatically make some amount of a shift to CEO mindset the minute you get your first freelance gig. Making your own decisions is part and parcel of taking on an independent gig. 

But too many people as they progress in their freelance careers stop with their mindsets lodged somewhere between employee and CEO.

Yes, they recognize that they need to make decisions, but they may seek out the most passive ways to do so. This in part explains the popularity of sites such as Upwork and Fivrr, which tend toward low pay but have the attractive-to-some feature of allowing freelancers to act as much like employees as possible.  

While the relative security provided by such platforms can be a benefit, it can also be a hindrance to your freelance career. In some cases, that sense of comfort you get from maintaining your familiar mindset is keeping you from making decisions that will catapult you into better and higher-paying areas. Even those who make a ton on Upwork, such as Morgan Overholt who recently joined me on the podcast, also find work in a variety of other places as well.

If you put more time and effort into striking out on your own to find your own clients independently through networking, trolling online groups, approaching potential prospects, optimizing LinkedIn, and other methods, you’ll have far more control over how your career progresses.

You’ll be able to transition into industries you want to work in but haven’t had access to. You’ll be able to raise your rates more easily and systematically. You’ll be able to pick and choose your client base more effectively.

This is all easier said than done; becoming your own CEO usually requires getting out of your comfort zone. Sometimes WAAAAAY out. Every day. Sometimes all day. You’ll experience self-doubt, impostor syndrome, stress, and even panic. You’ll tell yourself you should go back to the office. Or just chuck it all and move to a cabin in the woods. 

It can be very difficult to make the switch from employee to CEO, especially if you’ve spent years following orders. But if you stick with it and bear up under the pressure, you’ll ultimately come out with an exciting career you are proud of.

You’ll not only be proud of the career you’ve built but you’ll be proud of yourself for doing things that felt hard but you just knew were worth it. 

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