Life is going to throw all kinds of shit at us. 

That’s Life’s job.

Like a mean, but well-meaning, older brother…

It pushes our faces in the dirt often enough to make sure we learn our lessons along the way.  

So we can use the wisdom to do better.

Learn. Grow. Adapt.

And, ultimately, have better lives.

Business Life is similar.

With one big difference:

Where Life has unlimited ways to throw you off your game,
business challenges are actually quite predictable. 

The key to overcoming them, though, is being able to adjust to what Real Life is throwing at you along the way

That’s why it drives me crazy when another baby guru claims they have a “one size fits all” system for succeeding as a freelancer. 

I’ve personally coached hundreds of freelancers down the path to success and I can tell you: No two of them did it exactly the same way. 

Personal circumstances have to factor into the plan.

Because what works great for a single person living alone in their twenties, might be a total dead end for a single parent.

How an extravert with a big personality gets ahead can be the opposite of how an intensely shy data freak does it. 

The sales instincts of a former door-to-door salesperson are different from a former journalist. 

Then of course, you have KOLBE scores and the like that reveal why you can thrive in one environment and flame out fast in another.  

If the system you are following to succeed in freelancing is not working for you, it’s probably not your fault.  

It’s because the system is not flexible enough to adjust to your personal circumstances. 

Two years ago, I sat down and mapped out every phase of my journey as a freelancer. 

From struggling with what the heck I was going to do next in life after my comedy career ended (Phase 0)… to now running a recurring revenue business with a team of 27 people (Phase 7).


It helped me identify all the common patterns that a freelancer goes through in their journey. Which is why I call it The Freelancer’s Journey timeline. 

Once I mapped it out, my students were able to identify exactly where they were on their journey, and together we strategized what to do next so they could jump to the next phase. 

Amazingly, some freelancers have been able to achieve what
took me nearly TWENTY years and do it less than FIVE! 

That’s not a “weird trick” or a “shocking breakthrough”, that’s having a plan that adjusts to your strengths and minimizes your weaknesses. 

So, where are you on your journey right now? 

Are you Phase 1, just discovering the thing you’re good at and hoping to get paid for it? 

Phase 3, where you’ve been getting paid, but working too hard for too little money?

Phase 5, where you’ve been kicking ass for clients and need to start expanding into new revenue streams? 

Phase 7, where you no longer work with clients and are building sustainable income through intellectual property like books and courses?

Want help deciding? 

I put together a short questionnaire that will reveal the phase you’re in.

You can fill it out here to get a custom assessment of your phase in the Freelancer’s Journey. 

We’re doing these “by hand” right now, which means, along with my coaches in the program, I’ll be personally reviewing your answers and identifying your current phase. 

Then, Lolita, our community manager, will personally send you the result. 

Why are we doing it this way? 

Because we are in the first stage of building out a quiz funnel that will automate this process, and we want to make 100% sure that the information we put into it is accurate and based on REAL LIFE scenarios. 

So, we’re doing it the old fashioned way to start. 

Your answers and responses to your results will be our guide.

Essentially, you’re helping us get better at helping you. 

To say “thanks”, I have a special gift for everyone who fills out the survey. 

You can find your phase right here.

Let’s rock!



P.P.S Ready for more? Here are 3 ways we can go deeper… 

Tap into the #1 copywriting community and jobs board.

  1. Copy Chief has everything you need to sharpen your chops as a copywriter and build your freelance business – including the #1 jobs board in the industry.

  2. Learn how to level-up your freelance business quickly.
    Simply reply to this email to ask our Freelance Coaches any question you’d like about launching or growing your business. (These are real coaches, not sales people in disguise.)

    You can also click here to learn which of the 7 “Freelancing Phases” your business is in now. You’ll get the clarity you need to avoid getting distracted, so you can stop “winging it” and focus on the crucial “right now” problems to move your business forward.

  3. Listen to the Copy Chief Radio podcast. Every week we release a fresh new conversation with the top producers and change-makers in the world of marketing, copywriting, and business. 

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