What it takes to “make it” as a freelancer

by Kevin

in Copywriting,Freelancing

Excellent feedback on the last post about going deep with yourself to figure out what it is you really love about your freelance work…

… and which parts make you wander the backyard naked mumbling to yourself.

I received a good amount of personal notes from freelancers and small biz owners across the spectrum all saying they “needed to hear this”.

Amen, brothers and sisters.

Life gets lonely in the bubble. Many of us feel isolated. It’s rare to connect in a meaningful way with someone who understands what we do — especially in the “real world”.

Think about it… most of your neighbors and relatives still think websites are built by magic nerd elves and remain convinced that a free trial of anything is a scam of Madoffian proportions.

One of my real world friends recently told me how much he enjoyed certain free guitar instruction videos on YouTube, then quickly added, “I mean, they’re only posting them to try to get you to sign up for the ones you have to pay for.”

I asked if he had looked into their service. “No!” he said, “I’m not falling for that.”

Yes, as marketers it often feels like we’re living in the Land of Misfit Toys. But, honestly, would you want it any other way?

We all arrive to this strange land from different paths, but also share some traits that bond us, like…

  • Fierce independence (difficulty playing well with others)
  • Above average intelligence (fueled by an eagerness to learn)
  • Generous hearts (and willingness to share what we’ve learned) and…
  • Empathy for others (even idiots)

I love meeting marketers and copywriters at industry events, everyone has an incredible story about what led them here.

Short aside: I’ll be at Joe Sugarman’s event this weekend in Vegas with John Carlton, Jon Benson and Joe Polish. Every one of them generous beyond reason with their knowledge, and still humble enough to remain eager learners. One thing that always impresses me about marketing conferences is how many “gurus” you see sitting and taking notes during the presentations. It’s easy to assume these guys don’t need to learn any new tricks, but the majority of them are furiously scribbling notes. And if they are out in the lobby chatting, it’s usually about some serious next-level ideas they’ve got brewing. So, if you’re in Vegas this weekend, please stop me and say “hello.”

Point is, no matter how “big” you get in this business, it’s not likely to change who you are now. Fame and money will only exacerbate your personality traits. (You don’t often hear of a marketing guru described as “kind of a douche.” They tend to be universally loved or hated.)

That’s why having “the talk” with yourself is so crucial to your success. You are who you are. We all have our strengths and weaknesses. Discovering the role you will play at a premium level is critical to your success and your client’s expectations.

Take a guy like Jason Moffatt. He’s brutally honest about who he is (an old school hustler with a heart of gold) and what he should and should not be doing for money. Jason is great at a lot of things. I think of him first as a master communicator. J-Mo could easily write the follow-up to How To Win Friends and Influence People, and I’d be first in line to buy it…

… but he’d be terrible as a freelance copywriter. (And, of course, the first to admit that.)

That’s because it takes a certain kind of bizarre co-dependency to succeed as a freelance copywriter. In the foreword I wrote to John Carlton’s updated edition of his Freelancer Course I called it, “the sickness.” Meaning, you have to be relentless enough to master the art of high conversion sales writing, disciplined enough to meet hardcore deadlines, amiable enough to get along with clients, and flawed enough to offer up your rare talents to others for a fractional portion of the pile of money your copy will help earn them.

On paper it seems really stupid. And to some it is. Hence why so many great copywriters eventually stop accepting clients and become their own best client, writing for their own products.

So why do we do it?

For some of us it’s a comfortable fit (you can make fantastic money without any of the hassles that customers and affiliates and a staff bring with them)

For others it’s a stepping stone on the path to their own brand of inf0 gurudom (what better way to learn the process than by being involved at a deep level?)

And for all of us it’s a calling. We write because we are writers. My favorite statistic from last week’s survey was that only 25% thought their writing skills needed work. Copywriters are confident writers. We have to be because there is no hiding from the quality of our work. Earning the title “Best Seller” on Amazon can be achieved with simple listing strategies… earning it with a direct response campaign means you kicked holy ass!


So, if like the survey says, your writing skills are solid and your selling skills are solid, what is holding you back the most?

This is where things get interesting. Most said it’s better leads and connections, but I think success really comes down to confidence in our ability to deliver big for clients… and getting comfortable with bragging a little when we do.

There are other issues, too, like the type of client you are attracting (the 18% of you working with “larger companies” must be masochists) and our odd inability to write worth a shit for our own pitch pages… but at the end of the day, it’s about confidence.

You know the #1 question I get from new freelancers is the same one I had when I was starting out… in fact, it’s the one burning question that caused me to hunt down John Carlton and ask it to him directly.

I had to know the answer.

I’ll share the question, the answer and the simple tactic I used to bring in a flood of new clients at the height of my “rent check” desperation in next week’s post.

For now though, jump into the comments and share your best horror story of attempting to explain “what it is you do” to people in the “real world”. It’ll be good therapy for us all.

See you there,



lawton chiles October 22, 2013 at 11:42 am

I used to reply that I wrote sales copy…or that I was a copywriter and people would go on about trademarking stuff.

So now I tell them I write ads or am in advertising.

It’s funny to see their reactions when i say that I’m in marketing vs. advertising.

People tend to have a poor view of us marketers but love us and get all intrigued
when we say we are in advertising.

It’s a funny world. I wouldn’t trade what I get to do though. Or the folks I’ve
met and befriended along the way.

Nick Brighton October 22, 2013 at 1:04 pm

Total resonance again Kevin. This job is lonely as can be. It’s hard to keep motivated when most of your clients send you gigs via email (repeat clients anyway.) At best, a quick Skype call which is still pretty detached from the real world.

Isolation can cause suck the confidence out of you like a vacuum. You don’t really see what you’re doing for others, or what others think of you, or how other copywriters are getting fired up or working their assess off… so you kinda have to imagine, or most likely forget. Or just ramble on blog comments.

And then there’s the clients who occasionally come along and massacre your work, or try and haggle you on price, chipping away at your confidence again. You gotta find some inner strength.

Then there’s those weeks – or even months when you’ll hit burnout and feel like all your skills and experience are pouring out of holes in your brain. That’s always fun.

And to top it off, people STILL don’t understand what it is you do. Not even your closest family. But why? There’s nothing complicated about the job description of a copywriter. So why do we struggle to explain it? Copywriting might not be a common occupation, but neither is marine biology… and do you think those marine biologists are sweating it every time someone asks what they do?

I’m starting to sound like a whiny brat, but I wouldn’t change a thing. Copywriting the only job and skill I’ve had that I’ve reached expert level – and enjoyed consistently for years. Besides, I sometimes have nightmares about being back in employment and that’s enough to keep me in check ;)

Lauren February 13, 2014 at 1:29 pm

Great post Kevin and I’m with you all the way here Nick. Having just jumped ship from the corporate world to go it alone as a freelance copywriter my biggest issue is the isolation factor (along with finding clients but that’s another story we’re all familiar with). However, for me, the radio is proving to be my big friend. I find a debate or news/info channel online and have it playing quietly in the background while I work. I don’t actually listen to it but it feels like there are people somewhere around talking away while I focus on my writing. For the moment that’s my salvation, along with making a point of walking to my local coffee house and working there for a couple of hours on days when I feel really isolated. My back up is my Spotify list – played loud. Great to know you’re all out there and feel the same at times.

lawton chiles October 22, 2013 at 1:57 pm

Right on Nick. I feel the insecurity at times as much as the next guy. The home runs feel great though :)

Glad to know I’m not alone in the world.

James Clouser October 22, 2013 at 3:06 pm

I’ll never forget the interview that got me into music school.

The Director of Admissions became visibly bothered, threw up his hands and said: “I don’t get it with you musicians. You seem like such a quiet, subdued individual. Yet, Todd [my mentor] tells me that you had him on the edge of his seat during your audition. How’s that possible?”

My reply was that I become a different person when I’m playing. I feel the same way when I’m writing copy.

Maybe it’s the artist’s dilemma? The duplicity is even more of a paradox among copywriters. We’re supposed to be salesmen, for crying out loud!

I’m only a rookie in this business, but just getting this far has been an eye-opening experience from a personal development standpoint. Like Lawton said, glad to know I’m not alone.

David Raybould October 22, 2013 at 3:41 pm

Nice post Kev. Is there any way we can set up some kind of membership site just for me? Where
I pay and you deliver this stuff directly to my eardrums in your dulcet tones?

I want KROG FM on demand, damnit.

Very cool to see you blogging more, by the way. Enjoying it.

My weirdest “so what do you do?” moment:

Talking to the singer of a band I’d known in London back in my slacker days. This was years ago, when I first started making some noise as a freelancer (and getting paid as such).

Hadn’t seen him in a while and he asked me how I’d gone from being a lowly paid bartender to living in one of the nicer parts of town in just the few short years since we’d last met.

I explained I’d started a business working with website owners helping them make more money by writing their ads.

And he flat out didn’t believe me. Kind of poo-pooed my answer. Asked if I was into drugs or something illegal, or if I’d had a rich relative die.

Funny, but he wasn’t kidding.

Wild right?

Yes, wild. But it puzzled me for years. Why would somebody react like that?

When I look back now, I know exactly why (and there’s a lesson here for every freelancer).

It was because I wasn’t CONFIDENT in what I said. I fumbled my words and fidgeted around… I clearly wasn’t comfortable answering him. And because it looked like I was lying, he assumed I was.

So why wasn’t I confident? Why was I fumbling my words?

Because he’d asked me the fabled “Most Difficult Question In The World,” aka “The Question Of Death.”

Why does that one question strike fear into even the most capable writers? Guys who are able to stare down a million dollar control without breaking a sweat crumble at the mere idea of having to explain their job to somebody.

I wasn’t confident for the same reason none of us are the first hundred or so times we answer that question.

For some reason (maybe the same one that makes some of us co-dependent, and DEFINITELY the same reason our own pitch pages are so hard to write), copywriters attach a lot of significance to what people think we do.

It’s like we NEED their acceptance. We need them to see how cool our jobs are, to understand the
near-mythical magic powers we have.

We’re looking for their approval on some level, I think. Or at least a hearty “attaboy!” for throwing off the shackles of working for the man and doing something under our own steam.

I’d been freelancing for quite a while before I realized that was the reason I felt more tongue-tied than a 13 year old boy at a Victoria’s Secret model wrap party whenever somebody asked me what I do…

… and that realization instantly flushed those feelings out of my life, pretty much forever.

These days, I’m not too bothered if people understand what I do. I no longer have that same need for acceptance, or experience those verbal diarrhea moments when somebody does ask.

In fact, a lot of the time I just make stuff up for my own amusement.

My favorite response right now is “I’m a facilitator. I facilitate money into people’s bank accounts”.

I’ve also told people I rob banks and smuggle cocaine from South America.

Funny thing is, you get basically the same responses either way. And I think that’s a lesson in itself.

Obviously, if you’re introduced to somebody you’d like to work with, do what’s necessary to make them understand the explosive value you’ll deliver in return for your suitably exorbitant fee.

But anybody else?

Fuck ’em. Don’t sweat it, fellow freelancers. Be proud of what you do. Don’t worry about the fact that people don’t get it. They never will.

Delicious post Kev, thought provoking.

-David Raybould

Kevin October 22, 2013 at 9:46 pm

Killer post, David. Great point about people being as willing to believe and outrageous lie as the truth.

Unfortunately most people who ask me are parents of other kids at school and much as I’d love to, I can’t bring myself to go all Hunter S. Thompson on them with the answer. The fun part is that they still don’t get it, even though I feel like I’ve got my rap down.

I say, “I work with entrepreneurs to sell their products online.” Then let them ask questions if they’re interested. They typically do, but sometimes just the word “entrepreneur” fries a circuit.

I appreciate you popping in, buddy.


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