Last week’s post about being “unemployable” really struck a chord.

E Major if I had to name it. 

Thick, raw, bluesy.

I appreciate all the replies. 

If you missed it, I wrote about all the “no resume” jobs I did after stand-up, waiting to find something new I could do to earn the money my family needed. 

Michelle and I had our first child (and a second one in the works) around this time. 

The life we envisioned for our family was not going to be funded by pouring drinks or pushing luggage carts. 

She and I agreed that it would be best for Michelle to be home with the kids in the early years, while I grabbed my spear and went hunting each day. 

If I was fortunate enough to choose my spear, it would have ink in the tip. 

I was running on faith that I’d find SOME way to earn money and have a career as a writer.

Maybe you can relate?

So, I enrolled in every college course I could that had anything to do with writing. 

I don’t remember the exact titles, but they were journalism courses at St. Petersburg College, and then the University of South Florida. 

Turns out you can only take a certain amount of elective courses before they force you to choose a major and pursue a degree. 

Kinda stupid if you think about it. But I guess I get it… class sizes and all. 

When I look back on that time, though, this is around 2000-2003, even though I had NO IDEA how to make money as a writer…

…I kept following the tracks and moving in the direction of my bounty.

The only thing I knew for sure was that sitting idle would cause us to starve.

So, when I talk with people who are where I was then, just discovering this amazing craft, wondering how to make a living with it, and often facing a life and career ‘reset’ as I was…

I can tell quickly who is going to make it, simply by applying a success-determining
effect I’ve come to recognize as… 


Those who have it will make it.

Those who don’t will have a much tougher road in front of them. 

I can teach you all the ways of getting paid and building a career as a copywriter.

But I don’t know anyone who can unteach lazy… or self-defeating… or victimhood… or a fixed mindset.

I didn’t recognize it at the time, but the reason I’ve had so many amazing mentors willing to help guide me in my career was because they recognized the momentum I was creating by always moving forward – even in blind faith.

It’s the same thing they had to do to make it. 

Takes one to know one.

Like a secret society of the determined who fight for each other. 

And here’s a cool bonus: all those shit, dead-end jobs will add to your unique DNA as a copywriter, because writers draw from every experience to persuade our readers.  


Even though those no-resume jobs sucked.

Even though bartending was not my destiny.

Even though a career in journalism didn’t add up.

And they ‘kicked me out’ of college.

I knew there was SOMETHING waiting for me out there. 

And I was intent on doing ANYTHING that would get me closer to it. 

Just like you’re probably doing right now.

In my decade plus as a freelance copywriter, I used every one of the lessons I learned in bartending, bell-hopping, stand-up, joke writing, script writing and journalism in ways I never could have imagined at the time. 

So when people ask me what I look for in a copywriter, I say: “HAND CRAMPS!” 

I can tell in a 5-minute conversation whether someone has the goods to make it as a copywriter by the amount of effort they put into learning the craft. 


Especially when they aren’t even sure they’re working on the right things, or how it will help them.

All they know is they LOVE how it feels to practice the craft, and the dream of becoming great at something they love is far greater than their fear of “wasting time.” 


Sitting idle, waiting for the answers to appear like magic is never an option. 

In fact, it’s a sin against the laws of nature, punishable by a life of failure and misery.

Be in the habit of DOING WORK that feels good.

Be in the habit of PURSUING your desire to be great. 

Be in the habit of DISCOVERING YOURSELF as the expert you will someday be.

I’m rooting for you!


P.S. I’m looking to work with 30 very specific people in January that want to take their freelance copywriting skills and earnings to the next level.

Here’s what I’m looking for:

  • You’re committed to working as a professional freelance copywriter…
  • You want my personal help to move past anything in your way right now…
  • You can commit at least 2 hours per week from the start of January 2022…
  • You are friendly and coachable…
  • You can keep a secret.

If that’s you, take a minute to fill this out and let me know a little about where you’re at with your freelance career.

I’ll be choosing people in the next couple of weeks…


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. 

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

PLUS: get fill-in-the-blank templates and word-for-word video scripts that instantly establish Know, Like and Trust with visitors to your site!


We will only send you awesome stuff