HOSTED BY Kevin Rogers


EP 222: Freelancer’s Journey: Anna Iveson – Delivering your best work – Even if you think you aren’t ready.

CCR222 - Anna Iveson
Copy Chief Radio

EP 222: Freelancer’s Journey: Anna Iveson – Delivering your best work – Even if you think you aren’t ready.

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In This Episode

Landing your first few gigs as a freelancer can be an exhilarating combination of intense excitement and gnawing fear. 

It’s natural to be nervous… after all, you want to deliver great work your client will love… but there can be a whole new set of internal fears that come leaping forward the minute a client says “yes”.

“Am I ready for this?”
“Will I embarrass myself?”
“Is it too late to reverse the deposit and back out?”
“I wonder if my therapist can fit me in on Thursday?”

It’s normal… and kinda hilarious once you’re past this phase and realize everything turned out for the best… but that doesn’t make it any less distressing when you’re going through it.

In this Freelancer’s Journey episode of Copy Chief Radio, Kevin talks with Anna Iveson, a wildly in-demand copywriter from the UK.  

Anna is no stranger to the exhilaration and intense anxiety that comes with starting a new freelance career.

After taking the leap from occasional blogger and stay-at-home-mom with three kids, to courageously agreeing to write an entire launch sequence for her very first client in three weeks…

Anna’s suddenly become so in-demand that when she raised her prices it triggered a bidding war for her services…

So how did she do all this – and survive to tell about it?

In this episode, Anna goes deep on the start of her career and her first few harrowing client experiences…

The times when she was afraid to make the wrong decision in a new situation…or say the wrong thing to a prospective client and lose the gig… 

And what led her to trust her instincts even when self-doubt was pounding at the door.

There are a lot of subtle nuggets in this episode that touch on the humanity of being a freelancer… 

And why that humanity is not only appreciated by clients… but sought after.


  • (12:50) Anna and Kevin go deep on their first brutal client experiences, and reveal why “one gig cannot break your career.”
  • (15:45) How Anna won her first client by boldly answering a question that most freelancers dread.
  • (24:34) How to part ways with a client like an absolute pro.
  • (29:00) Anna reveals why regularly having her copy ripped to shreds was the best learning experience she could ever hope for.
  • (32:15) Think copying controls is boring? Here is a simple twist that breathes new life into those controls and kicks up your copy skills.
  • (40:00) Why waiting until you feel “qualified” to take on a task is an illusion that only sabotages you from getting to work and finding success…


Plus… whenever you’re ready:

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