The greatest benefit of a freelance career

by Kevin

in Copywriting,Inspiration,online marketing,Public Speaking/Stand-Up Comedy

When I was a skinny, punk-ass 16 year-old… my step-dad, Scotty, ran a construction crew building new homes in Tampa.

He was a tough-as-nails, but fun-to-be-around guy (picture Willem DaFoe and Jeff Spicoli merged as one) who had one rule on the job site: Never get outworked.

That summer, rather than sit around broke watching CHiPs reruns, I decided to take Scotty up on his standing offer to join his crew and make a few bucks.

How hard can it be? I thought. You get to wear a badass tool belt, you measure some boards and smack a few nails. Presto! New home.

Cut to: Monday morning at 5:30 AM as Scotty rattles my bed with his foot as if Florida’s first earthquake was happening directly beneath the house.

“We leave in 15 minutes, dude. You need to eat before we go.”

It was still dark outside. I managed to woof down 2 pieces of white toast and by first light we were pulling onto the muddy streets of half-built houses and construction equipment.

The air smelled of fresh-cut lumber and swamp water as the droning hum of tractors and the whine of buzz saws swirled with classic rock blaring from busted boom boxes. The wood beam skeletons of soon-to-be family homes perched naked on concrete slabs like shy patients on cold tables wishing the doctor would just finish up and hand them a robe.

The whole thing looked like a disaster scene in reverse.

I was sure I’d made a terrible mistake. Much as I admired the true grit and simple wisdom of those blue collar warriors — hard labor just wasn’t my thing. Yet, by the end of that first week, I was getting a feel for it. There’s a cozy satisfaction in putting in a hard day’s work.

That pain shooting through your back means you’ve done your job. A check is coming. Beer-thirty on Friday will taste like it should.

Then came the rookie mistake that doomed it…

I was sitting on a cement wall after a short rain storm, eating lunch from a bag when Scotty came over (he never stopped for lunch)…

“Don’t sit on wet concrete, dude… it soaks your bones, you’ll be sick as dog,” he said, pulling over a saw horse. “Use this or stand.”

“Shit, I’ve been sitting here for like 10 minutes,” I said.

“You’re probably fucked then.”

Fucked was right. I woke up the next day with the nastiest cold I’ve ever felt. Every joint in my body ached and my head pulsed like a diesel engine stuck in first gear.

“I feel like hell,” I told Scotty as he earthquaked me awake.

“I feel like hell every day. Don’t make me late on top of it.”

I didn’t have the guts to tell him this wasn’t the hard day’s night kinda hell — this was see a doctor hell.

By lunch break I was pale and droopy eyed enough to earn a sympathetic “wait in the truck” assignment. I sweated out the day lying across the bench seat of Scotty’s silver F250… dreaming of a soft couch, air conditioning, and Ponch and John speeding down the 101 after some crazy driver.

Mercifully, as the sun dropped below the windshield, the noise outside finally subsided to the lone strain of Lynyrd Skynyrd’s “What’s Your Name” in the distance. Scotty slipped into the truck beside me, cranked the engine and said, “Good news… you’re fired.”

“Thank God!” I said.

Later, when the fever was down and some human-like hue of color returned to my face, Scotty admitted that my pitiful performance on the job was everything he’d hoped for.

“You’re a smart dude. You might not know that yet, but you are,” he said. Then added, “So if you ever take one piece of advice from me, it should be this: Do work with your head… not with your hands. It’s not for you — and that’s a gift.”

It’s rare that a teenage boy is able to see past the hormone rage and know-it-all-ness to recognize a turning point in his life as it’s happening. But that moment was one for me.

I discovered in less than 2 weeks on a soggy construction site that it was OK not to fit in where you don’t fit in. And sticking around long enough so you begin to fit where you don’t fit in can cause you to miss your path entirely.

Thanks to Scotty, my job this morning (I decided) was writing this blog post.  Technically, I did use my hands, but tapping keys sure beats the hell out of pounding nails.

And while there are plenty of tough days as a freelancer when nothing seems to go my way (and I’m still stuck with the credo of never getting outworked)…

…for me, the freedom to make my own day is the greatest benefit of a freelance career.

What about you?

{ 5 trackbacks }

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Ryan Healy August 28, 2009 at 12:11 pm

That’s a great way of putting it: “the freedom to make my own day.”

I’d have to say that, to me, is also the best reason for being a copywriter.

And as far as life lessons go, I pulled a 7-month stint doing manual labor — installing wire closet shelving in new homes.

Not as hard as framing or anything like that, but still hard work. After 7 months, I “came out of the closet” — and it’s been a white collar life for me ever since. :-)


Kevin August 28, 2009 at 12:20 pm

Funny story, Ryan.

My road to copywriting included a lost year spent finding my way after stand-up. I ended up on a construction demolition crew — smack in the middle of Florida summer again! (You think I’d have at least learned something about how to time these episodes.)

Anyway, this time was better because I spent most days alone tearing apart an old boat dock. Aside from having to go swimming underneath the thing with an eye out for gators, I found tearing that thing apart very therapeutic.

Thanks for stopping by, pal.


Brian McLeod August 31, 2009 at 11:37 am

“Self-determination”, such a powerful idea. It spawns political revolutions, draws young adults out of the comfort of the nest, and drives entire civilizations forward.

It’s certainly not a uniquely American concept, but is inextricably woven into the American Dream.

I can think of no greater reward for the sacrifice, determination, and facing down of fears required to make it as a successful freelancer than the gift of living your life entirely on your own terms.

Sure, important clients can sometimes resemble former bosses. Vendors and service partners can play the role of the irritating douche bag co-worker that drives you nuts… but at the end of the day, participating in any of that is always a CHOICE we’re making, isn’t it?

Some might even argue that these “things we cannot control” act as something of a tether while we’re busy creating our own reality everywhere else. Best laid plans and all that…

To me, there is no money sweeter than that which I’ve created out of thin air… from a thought. And that most certainly includes the money I put in a client’s pocket. What a powerful feeling that is, yes?

My guess is that the smart folks who read your blog can certainly relate.



Kevin August 31, 2009 at 12:14 pm

Excellent points well stated, as always, Brian. Thanks.

Bill Jeffels August 31, 2009 at 12:29 pm

Hey Kevin.

Amazing post. I remember going through mt teens and early 20’s thinking… “What the hell am I going to do with my life”… I had no passion. Then I discoverd… Gary Halbert and copywriting. I thought.

“Yes”… this is what I’ve been waiting for all my life. I’m 33 now… when I was 29 I did mt first Direct Mail copywriting gig for money.

My first client was new to business… I had studied Halbert like he was god…( and he was and still is in my books RIP).

I remember the feeling and I’ll never forget it. I had #10 envelopes, stamps and the sales letters… I personally inserted every letter, put on every stamp and I remember when I was done… I thought… “Damn I love this!”

It cahanged my life.

Take care… I’m real glad I found you blog.

Bill Jeffels

Toronto, Canada

Kevin August 31, 2009 at 2:24 pm

Great story, Bill. There’s nothing like sending your words out like that and having responses pour back at you. For those of us who love it, there really is no greater rush. And you can’t get much better inspiration than GH. Excellent foundation to build castles on.

Good to “see” you again.


Tom August 31, 2009 at 1:57 pm

Hey Kevin,
Glad your roughing up your brain instead of your hands.

One quick note. As a student of the SWS program I consistently found myself spending as much (or more) time in your classroom as I did in my own.

I wish I had time to tell my tale. But I don’t.
I don’t suspect you will publish this.

I truly just wanted to thank you personally.

Thanks for sharing!

Kevin August 31, 2009 at 2:20 pm

Hey Tom-

That’s kind of you to mention. Teaching the Simple Writing System is one of the great joys of working with John. He’s helped nourish a passion for teaching through his own great example. He’s incredibly generous with his time and knowledge. The SWS literally helps people changes their lives nearly overnight — I feel honored to be part of it.

Thanks for commenting (There isn’t much I won’t publish. And thanks for the heads up on the missing link, too)


Christopher Tomasulo August 31, 2009 at 8:47 pm


I have seen excellent writing from you since we met in 2003 but I just wanted to let you know that your last few posts (and especially this one) have put you into a whole different category in mind – World Class Writer.



Kevin August 31, 2009 at 9:09 pm

Wow. This really made my day, Chris.

I appreciate you.


Bill Jeffels September 1, 2009 at 12:32 pm

Great talking with you again as well.

It’s nice speaking with people that are into the same stuff.

Hell, I even have Brian giving me tips on how to do “Pinched Harmonics” on the guitar ( starting to learn, again ). I think Zakk Wylde will be safe for quite some time Lol!

Take care guys,


Rob in Denver September 1, 2009 at 1:24 pm

Nothing quite like getting concrete poisoning to figure out such a valuable life lesson. Great story. Is Scotty still step-Dad?

Kevin September 1, 2009 at 8:05 pm

Interesting question. I’m not sure what the qualifications are. I haven’t seen Scotty in over a decade… he and mom split after 17 years of marriage. But same with my real dad and he’s still my dad, so… I don’t know.

I guess the answer is no. Real dads are grandfathered in (if that’s a pun it was intended), but once mom isn’t with step-dad anymore he loses his title. But I still hold him in high regard. He is a special cat. I should seek him out. Risky biz though.

Anyway, I’m glad we worked that out.

(welcome, by the way)

Dan September 2, 2009 at 12:56 am

My wife just gave me a cement chair which she’s hosing down. Should I have concern?

Internet Marketing ABC September 3, 2009 at 4:47 am

Kevin, you’re an awesome writer. I enjoyed this blog post almost as much as I enjoyed reading Bukowski in my messed up teenage years.

Kevin September 3, 2009 at 8:25 am

Hey, thanks man. There may never be another Bukowski, but here’s to better wine and saner women.


Philip Mansour September 5, 2009 at 5:21 pm

Yo Kevin – that story got me visioning 100% as if I was there. You should think about writing a book man, you have a wicked flow…

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