Wanna know what defines an entrepreneur?

It isn’t the “billion dollar” ideas…

Or the scrappy rebelliousness…

Or even the ability to create revenue.

Those things are inherent in most entrepreneurs, but also in wantrepreneurs – those who chatter about starting a business but never make the leap. 

To me, what defines an entrepreneur is the instinct for taking big gambles.

Not haphazard “roll of the dice” type gambles, that’s just a game of stats.

I mean the kind in Oxford’s second definition…

That “take risky action in the hope of a desired result” style gamble is a unique beast.

Want a good example?

Take a read of the “Amazon” section of Jeff Bezos’s Wikipedia page.

The first three chapters read like an edge-of-your-seat thriller, rife with perilous leaps of faith, doubling down on shaky concepts, and a multitude of chest-clutching, near-death moments. 

The only thing missing is an impromptu bullet-removing surgery inside a dimly lit warehouse.  

Your level of risky action may not be quite as… thrilling.

Mine wasn’t. But I remember it clearly as a defining moment in my life. 

Five thousand bucks to join a three-day intensive with Dean Jackson. 

I’ve since paid him (and others) triple that amount for a single day of consulting… but that first one was scary. 

Money was tight and my natural instinct was to hoard cash like a nervous squirrel feeling the first chill of winter.

But, something in me said to double down. 

I knew I needed a plan. 

I could either grab tightly onto what I had, or take risky action and hope for the desired result of growing my business in a new direction. 

Obviously it worked out, and here we are talking. 

But I’ve seen so many budding entrepreneur’s stand at that same crossroads and take the safer path. 

I never criticize their choice.  

But, it’s telling. And the results are predictable. 

The ones who clutch tighter either begin to shrink or fade from the scene completely. 

The ones who trust their instincts to go all-in on themselves prosper and thrive

But it isn’t just that they paid someone with the right experience to guide them (although good mentoring is a critical component of success)… 

… it’s the MESSAGE YOU SEND TO YOURSELF that causes the big shift from sideline viewer to in the game entrepreneur.

When you make the choice to double down, take a risk, and go all-in on yourself… a distinct voice from within whispers affirmations that you’ll otherwise never hear.

Kind of like when Siri answers a question you didn’t ask, except instead of creeping you out, it puffs your chest with pride. 

The voice I hear sounds a lot like Issa Rae.

Not sure why, but I like it. 

This year has been a global soul search-a-thon.

Nobody on the planet got to keep the plans they made the same way they made them. 

Which means entrepreneurs and their risky action taking selves had a massive upper hand.

At Copy Chief we were forced to cancel our live event. 

A six-figure loss in top-line revenue. 

The instinct to clutch tighter lasted about a minute before I realized what we’d gained by not planning, selling, and executing a major live event this year…

Tons of bandwidth for our team to make big improvements to our #1 product, the Copy Chief membership. 

So, we went to work installing…

  • A brand new Training Dashboard to help us teach better…
  • A brand new Community Forum to help us “commune” better
  • A brand new custom-coded Directory to help clients and copywriters connect better…
  • New web hosting to make it all run faster and smoother.

We even closed the doors to new members for the month of October to put all of our energy into the final touches. 

Risky action during a pandemic? 

To some maybe. 

But, I have no doubt that the investments we’re making now will keep us leading the industry for years to come. 

I can’t wait to show it all to you in November, once our current members are all moved in.

So, if you’re feeling stuck, or scared, or stymied by sameness… look for a risky action you can take and ask yourself…

“Am I a hoarder or a gambler?”

Get the answer from your gut, not your head. 

It’s important to be honest with yourself on this.

BTW, I’ve coached many people of both types… and both can have wild success, but in different ways.

If you’d like to know the different paths, ….check out this page here.

Rooting for you always.


Whenever you’re ready, here are a few other ways I can help…

Become a member of Copy Chief. It’s everything you need to sharpen your skills as a copywriter and build your freelance business – all with a killer support system at your back to help you do it. To learn more, check out this page here. 

Mark your spot on the Freelancer’s Journey Timeline. Moving forward in your freelance business starts with identifying where you are right now.  Go here to see the full Freelancer’s Journey Timeline and mark your spot. 

Find out what the best in the business do differently with 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. Tapping into their minds won’t cost you a thang – listen here.

The Amazing 60-Second Sales Hook That Creates An Instant Bond With Your Best Prospects…

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