How to go from freelancer to CEO

The leap from freelancer to CEO is challenging but immensely rewarding.

Albert Einstein once quipped that it is impossible to solve a problem from the same level of awareness that created the problem. By the same principle, your business will not evolve if your mindset stays the same.

Many of the entrepreneurs I’ve worked with over the years got their start providing a service to clients. This is one of the quickest ways to get momentum because overhead is low and all you need these days to make six-figures from a cafe in Paris is a laptop, a smartphone and a strong Wi-Fi signal .

But new challenges arise once you begin making more than $100,000 per year. At $10k to $20k per month, you fall into the “quicksand.” The more you kick, the harder it feels like you have to tread just to keep your head above water.

You’re exhausted and doing all the work inside the business, even though you know you need to get help. You can’t maintain this pace forever and it’s already starting to show in your work.

You now have an important decision to make: are you going to remain a freelancer, or will you make the leap to CEO? If you choose the new path, the journey will be challenging but immensely rewarding. To do so, you’ll need to make some radical mindset shifts.

Here are three key principles you need to internalize in order to go from freelancer to CEO.

1. Performannce, not hours.

CEOs get paid for how well their system performs, not how long they spend inside of it. Freelancers trade time for money and find themselves trapped in a house that will collapse the moment they stop laying bricks.

As soon as they stop working, the money stops coming in. That’s the description of a job, not a business. When every dollar you make is tied to the amount of time you spend working, it prevents you from living your life.

This is not the CEO way. CEOs, on the other hand, leverage other people’s time to create money.

The CEO doesn’t “work” for money. There are tasks and “work” involved, but the CEO’s income is dependent on how well she has designed her systems, people and processes. If the system is efficient and scalable, it can make exponentially more money as the organization and demand for the product grows.

Think of it this way: in the beginning, your business is a system that harvests your time and energy into profit. This works at a small scale, but your time and energy are finite, so at a certain point you max out (if you try to overextend yourself, that’s when you burn out).The real issue isn’t your work-ethic or productivity – it’s how you have (or haven’t) designed the system. If you’re curious, I went deep into business system design and processes in a recent 4,200-word article.

There is no direct dollar-per-hour amount that can be assigned to a CEOs work because their work is the culmination of every piece of the system they’ve engineered to create the product.

They are getting paid for results driven, not tasks completed. CEOs are composers orchestrating a symphony that is their company and money is music to their ears.

2. CEOs know their numbers and manage their resources like a pro.

If I asked you what your profit margins are, could you tell me? What if I asked you about your closing ratio, how much of your gross revenue is dedicated to operating expenses or what your average customer value is?

Most freelancers do not know their numbers. Period.

Freelancers are used to having their personal and business finances mixed together. They see the money they make as theirs to spend and do so with free reign. (I’m not criticizing. I used to be like this, too.)

This way of thinking is the root of “broke millionaire syndrome.”

CEOs realize that money is fuel for the journey. To steer the ship in the right direction you must look at your company objectively. And the numbers never lie.

Not knowing the numbers in your business is like flying a plane with no instrument panel. You’re headed somewhere very fast, completely blind. Not good.

Numbers are what allow you to track performance against goals, hold yourself and your team accountable and spot weaknesses before they become big issues. CEOs know their numbers. Do you?

If you don’t, I recommend starting with Mike Michalowicz fantastic book Profit First as a way to get comfortable with this fundamental aspect of running your business.

3. CEOs know that their job is to elevate others to leadership.

Most freelancers are used to being the “go-to” for solving problems and have learned to depend on themselves. Because, let’s face it, most people suck at their jobs.

In basketball, freelancers would be the ball hogs. They live by the saying, “if you want something done right, do it yourself.” This mindset is initially a strength because it creates momentum and fast action which leads to results. But over the long haul, the “do it all” approach to the business game hampers the freelancer because it doesn’t allow them to put others in a position of leadership.

You don’t need to be the only superhero inside of your company. You should focus on hiring superheroes. This means allowing people to step up and make decisions on their own, teaching them to make the right choices based on the values everybody in the company shares.

When your team knows what to do without asking, can make important decisions and implement action plans without having to clear every little detail, you’ve truly created leaders. Leaders still make mistakes, but they also take personal responsibility for those mistakes and can be counted on to learn from them.

A great CEO learns what Gino Wickman calls “delegating and elevating.” They realize that they are very rarely the best person for the job, they can’t wear all the hats or be everywhere at once. So rather than focusing on doing the work themselves, they focus on selecting the right person to do the work and allow that person to lead.


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