You Need To Talk (The Silent Conversation About Your Freelance Business)

by Kevin

in Copywriting,Freelancing

Talk_To_MyselfThanks to everyone who completed the Freelance Copywriter survey last week. Some very revealing stats so far. I’m going to post the results and share some of the most important lessons I’ve learned about things like…

– The best type of clients to work with (better pay, less hassle)
– How to quickly move “up the chain” in our small but widespread community of copywriters
– The best and worst possible ways to approach clients and colleagues you want to work with
– The incredible two-word fix to stop undervaluing your own skills

If you’re a working freelance copywriter and haven’t filled out the survey yet, feel free to join in here: Freelance Copywriter Survey

Quickly though, have you noticed? There’s been a spate of “high level” consulting courses duking it out in the marketing universe lately. Some look really good, others are vomit.

Maybe you joined one. If so, good on ya. (I hope it was one of the better ones.)

In my experience, there’s no faster way to jump start or accelerate your career than with a solid mentor. Especially for a freelancer just starting out and possessing more talent than connections.

I studied copywriting for over a year without a clue how to find my first client. In hindsight I realize I wasn’t actually looking for clients at all. That’s because the idea of charging someone for my copy when I had NO IDEA whether it was any good or not paralyzed me with fear.

It wasn’t until I lucked into discovering that an old comic friend, Vin Montello, was also learning to become a copywriter that things changed.

Unlike me, Vin had developed the cojones to go out and sell himself. He’d dogged it out for years as a comedy writer in the murky waters of Hollywood. Out there you learn quickly that writing talent is only half the equation. If you want to get (and keep) work, it’s hustle or die.

So I learned to hustle, that was step one.

Quick funny story from those early days: Vin calls me and says, “Hey man, there’s a guy on Fortin’s board looking for someone to write an autoresponder series. You should bid on the job. You have more talent than half the people bidding now, just go for it.”

I said, “Thanks man, I’ll go do it right now. One question though… what’s an ‘autoresponder’?”

Yes, I was green as Kermit’s ballbag back then, but you know what I did? I sat down at the kitchen table and wrote an email series about a made up golf product (I don’t even golf, and this guy was in the romance niche), turned it into him with my bid. And guess what…

The guy had me arrested!

Kidding. Of course the guy hired me or this story would completely suck.

Important things was, I had my first paying client. I promptly moved into the corner booth of my local Panera and worked my ass off on those emails for a week.The client loved the emails, made money with them and then recommended me to more clients. I’ve never been without a client since.

A few months later I quit my job with the fat salary and the red alert stress levels and never looked back.

Were there some “oh shit!” moments along the way when I was sweating the mortgage payment? For sure. But something always came through and I built my career brick by brick. Gig by gig. Connection by connection. Mentor by mentor.

These days I’m known as one of “the expensive guys” and my calendar stays booked solid 3-6 months ahead. If that sounds like bragging then you’re looking at it all wrong.

The fact that I stay so booked actually says more about the desperate need for good copywriters than it does about my mastery of the craft. Plus, there’s nothing unique or special about what I did to get here. Anyone who is willing to dedicate themselves to the writing and the hustle could have a thriving career as a direct response copywriter. I can spit out the names of at least 10 people that have done the same or better. Sometimes much better.

So does that mean you should follow the same path I did? No.

Here’s my latest revelation when it comes to succeeding as a freelancer (and why it’s very hard to find a qualified mentor to guide you where you want to go): at some point, early in your career, you’ve got to sit back and take personal inventory.

Take a long walk and have a brutally honest conversation with yourself. And I mean, literally have a conversation. Speak both roles of you and your the true friend in this world you can trust with your darkest secrets, which is also yourself (don’t foolishly put this trust in any other human). Just talk it out just like you would with someone else… and (important!) call bullshit on yourself when necessary.

The goal is to discover what you genuinely love about your freelance biz, and which parts are getting you stuck. The parts you love are easy, but the ones keeping you stuck might surprise you – if you’re truly honest with yourself.

This is a breakthrough moment exercise. If you’re eager to reach the next phase of your freelance business, you’ll do this. In fact, you won’t be able to avoid doing it now that you’ve considered it.

And no, I DO NOT want you to post your revelations in the comments section. This is deep personal stuff. Some of it isn’t easy to admit or accept. So, if you go into it planning to share, you’ll start putting filters on your honesty.

This is just for you.

In the next post, I’ll talk about what to do with this new stuff you learn about yourself. It’s the secret to making more money, gaining more respect and most importantly, achieving balance in your life as a client-wrangling freelancer.

Stay tuned,



Raymond Duke October 17, 2013 at 4:20 pm

Thanks for the read. I needed to hear this to affirm what I’m about to do. I sent you an email about it because the reply was rather long.

Kevin October 18, 2013 at 11:11 am

Raymond, your email is packed with wisdom and high-level self-awareness.

You’re more than welcome to post it here if you choose. I’m sure lots of readers would get value from it.


Nick Brighton October 17, 2013 at 4:36 pm

Hey Kevin,

Intriguing post as always. Hope you’re well man. I won’t share anything personal here, but I can tell you that I’ve already done this, and I’ve already come to my conclusions – I think. I know what’s holding me back, and what’s keeping me in the game… and it’s a tumultuous grumble that echos around my conscious mind on a daily basis. Keep rockin on man, your occasional posts and emails give me a real lift and remind me why I love what I do.

Kevin October 18, 2013 at 11:12 am

Great hearing from you, Nick. Really appreciate your words, brother.

Simon James October 17, 2013 at 10:09 pm

Hi Kevin

What conversation do you have with yourself if you’ve never written copy for anybody else and therefore don’t already have a freelance biz to love parts of (or get stuck by)?


Kevin October 18, 2013 at 11:06 am

Hi Simon,

Think about baseball.

I know you’re playin’ but seriously, critical thinking and internal deep dives are key for any biz.

I’m focusing on my freelance copywriter brethren for this series, but any entrepreneur can gain a ton from it.

To quote Robert Plant: All will be reveeeeealed….

Matt O'Connor October 18, 2013 at 8:31 am

Great post, thanks Kev. I always love hearing other copywriter’s adventures on their way to “the top”.

And “green as Kermit’s ball bag”? That’s a keeper.

I miss Fortin’s board, that was a great resource way back when.

Kevin October 18, 2013 at 11:07 am

I miss it, too, Matt. What an incredible board.

Thanks for the note. I bet your rise up story is a zinger.

Let’s share soon.


Tony October 18, 2013 at 10:05 am

Hi Kevin,
This is a bitchin’ head swivelling post. I love the take away of self-talk. I think writing stuff down and arguing with yourself (not in a freaky omg he’s lost it way) but on paper.

Kind of letter- to -self private writing session will get you closer to your real self, and unearth any wussing-ness you may unwittingly be harbouring or whatever fear you have floating around in the dark recess of your mind which may often not seen the light of day without you getting up- close and personal. Can’t wait for the second instalment.


Kevin October 18, 2013 at 11:09 am

Spot on, Tony. “wussing-ness” haha. If I had a time for every time Carlton said to me, “quit being such a pussy and do it!”

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