When I quit stand-up comedy and got off the road, I was STUCK.

Ten years of driving all over the United States, sleeping in dingy motels, and talking dirty to strangers for laughs was incredible fun. 

But, when it was time for me to pull off the road and find a new line of work…

… I realized very quickly that comedy had left me woefully
UNEMPLOYABLE in the real world. 

I started doing stand-up when I was 18 and was on the road full-time by the age of 20, so aside from a few short-lived stints washing dishes and detailing cars, I had NOTHING to put on a resume.

And no amount of creative resume fluffing after a decade of telling jokes in hotel lounges makes you look qualified to do anything like a real job in the real world.

And I’m sure the bemused look on my face sitting across from anyone called a “Human Resource Officer” did nothing to convince them otherwise. 

Who was I kidding? 

I’d spent a decade skillfully avoiding anyone called “officer” — the last thing I wanted was to answer to one every day. 

Same goes for a “supervisor”, “manager”, or “boss”.

I knew how stupid it was for me to apply for a “job,” but I was clueless about how NON-JOB PEOPLE made money in the real world.

I needed to learn a new skill. 

Copywriting was years away. Hadn’t even heard of it yet.

So, I decided to try bartending.

Made sense. 

I’d spent a lot of time at bars and knew the culture, now I just needed to learn all the drinks.

So I went to school. 

No, not O’Malley’s Tavern to order “one of everything.”

Actual bartending school. The ABC School of Bartending.

Which, it turns out, is a major taboo in the bar world. 

Apparently “real bartenders” actually do get their education leaning on a plank of pine, sipping through every mix of every bottle.

Or, at least, they claim to… but I was… 

1) not that in love with booze, and… 

2) needed to find work – fast. 

Aside from the quick education, the thing that appealed to me MOST about enrolling in the ABC School of Bartending was their job placement service. 

To my surprise, I actually landed three different gigs from ABC. 

Each one – it turned out – more comically wrong for me than the last…

The bartending gig that still occasionally haunts a good night’s sleep was my very short stint at a high-end Chicago steak house where they prided themselves on their selection of port wines. 

NOT something we covered at ABC. 

NOR did the steak house bother to quiz me or educate me on the port wines. 

Ready, pour, aim.

I’ll never forget how ignorant and out of place I felt standing alone behind that elegantly marbled bar, in a stiff-collared black button-down, trying like hell to pretend I understood the foreign-sounding words people were saying to me. 

Customer: “two pours of the Quinta Valardo Adelaide…”

Me: “Uhhh, this one? With the round topper thing?”

The other jobs I got through ABC were less intense but equally wrong for me because they felt too much like… jobs. 

Uniforms, name badges, time clocks. 

What was this disturbing world of rules, and policies, and managers, and supervisors…?

Then I finally landed my best (and last) bartending gig through a friend of a friend who worked there. 

An old-school, blue-collar, beer-and-a-shot joint in Old Town. 

Now we’re talkin’. 

Finally somewhere I fit in. 

Good people, good jukebox, family-owned since the fifties… and not a port wine on the shelf!

I worked there for a couple of years and made decent money, all the while dreaming I’d find some way to earn a living as a writer.

I dabbled with screenwriting, joke writing, TV sitcom writing, and then journalism. 

I enjoyed them all, but the path to earning real money seemed heavily guarded by decision-makers and Catch-22 “experience required” scenarios. 

That’s why, when I finally discovered direct response copywriting,
my spine literally tingled.


For the first time, I found an industry where the rules actually favor the freelancer. 

If you can write decently well and adapt the psychology of selling into print, it is possible to…

– start earning money with little experience, and 
– deal directly with the person paying you… 

All the other writing jobs mean dealing with some twice removed gate-keeper with their own political power dynamics blocking you from the gig. 

In freelance copywriting, the only barrier to getting paid is YOU.

If you’re able to avoid the typical traps of trying to learn everything all at once before you feel “qualified,” the path is really quite direct.

To become a well-paid copywriter you need to…

    • Love writing
    • Embrace selling
    • Discover direct response copywriting
    • Develop a copywriting money skill that is in-demand
    • Use your special knowledge from other jobs, hobbies, or interests and apply it to your money skill
    • Study marketing from companies in your area of specialty
    • Create a portfolio of money skill copy samples
    • Position yourself as a specialist in your knowledge focused money skill 
    • Say hello to your future clients
    • Close deals
    • Work hard and deliver good work that gets results
    • Repeat until your calendar is full
    • Raise your fees
    • Enjoy funny looks from neighbors who can’t stand that you earn more than them tapping on your laptop in a coffee shop

If you take pride in your work, show up fully to meet your commitments, and can overcome the  “shiny object syndrome” that keeps you distracted from taking action… 

… then freelancing may be your ticket home.

Here’s to being well paid and proudly UNEMPLOYABLE!


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.

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