“I do most of my writing in the morning, so I’ll get up, have a coffee … and by 8 a.m. or so, wander up to my desk and start working. Unless it’s a day where I say — screw it. It’s beautiful out … I think I’m going to play some golf or take the dogs for a long walk.”
— Paul Hollingshead, Six-Figure Freelance Copywriter

paulsImagine going from one job to another, never making much money, never really feeling on track. 

Then, imagine jumping ship from that nightmare into the kind of life you’ve always dreamed of … a life where you’re commander of your own time, where you can live by a Florida beach or in the splendor of Vermont’s many seasons, where you get flown around the world to meet fascinating people, play golf, and encourage others to follow their dreams. 

Meet Paul Hollingshead, whose story is what most writers dream of (and what many copywriters go on to experience). He went from stocking grocery store shelves to earning an average of $300,000 a year writing persuasive letters in a dynamic and ever-changing industry. 

It all started when Paul answered an ad in the newspaper for a company looking to train someone in direct-mail copywriting. He threw himself into studying everything he could and practiced his writing relentlessly. The effort paid off, as his first project brought in over a million dollars and launched his career. 

Paul went on to co-found American Writers & Artists Inc. (AWAI), now the publisher of Barefoot Writer. He’s well-known for his consistent ability to pin down a conversational tone while discussing complex subjects, products, and services. Paul is also well-known for his generous advice and support of writers new to this world. As you’ll soon discover, he shared quite a bit of that guidance when we connected with him from his home in the Vermont countryside, including the biggest challenge writers face today and the most important thing you can do to ensure career-long success. 


Hundreds of new writers have been inspired by your story of going from stocking grocery store shelves to life as a six-figure copywriter. But if you hadn’t seen that ad in the newspaper … what might you have gone on to do instead? 

It’s hard to say. I didn’t really have any marketable skills. I only graduated high school and had taken a few community college courses. But I always found a way to make some kind of living, either in sales or jobs I got through contacts. I’m not exactly a go-getter, but I am resourceful. I always find a way. But the grocery store job … that was a low point, for sure. 

Did you always enjoy writing, or was copywriting the first time you’d ever considered the idea? 

My older brother, whom I’ve always looked up to, is a highly respected fiction writer. And my father was a politician who wrote columns for the local newspaper. And my mother was always writing something. So I guess writing was in the family. Problem was, I was terrible in high school English — but even so, I always kind of thought I would write some day. One of the courses I took at community college was journalism and I was pretty good at it. Good enough that I got a job at a local newspaper writing about community sports. Pay was dismal, but I wasn’t good or focused enough to make the leap to “serious” journalist, so I wound up getting a job in ad sales, where the money was slightly better. 

How long have you been a working writer? 

I think I got one of my first projects with Agora back in 1996, so coming up on 20 years now. Might have been 1995. I’m terrible at remembering years. 

What projects do you have in the pipeline? 

Right now, I have three projects on the go — all for the same financial client. One is a front-end project about investing in private companies. One is a back-end “lifetime” letter where we sell all the group’s services for a flat fee. And the other is another front-end that offers a special report for $5. 

What’s the hardest part about writing for you? 

That’s an easy one. Coming up with the main idea — something that’s new and fresh and will really captivate the reader the way it has to today. 

The big challenge copywriters have — the biggest in my view — is that we’re always selling something that’s been sold a million times before. The worst reaction your reader can have is — “Oh, I’ve seen this before. I know what it’s about.” So your biggest challenge is making something old seem new again. If you can develop a knack for that, you’re golden in this business. 

What’s the easiest part of writing? 

I’m not sure there’s a part of the letter that’s the easiest. I’ve learned that if it’s too easy, you might not be doing enough work to get it right. But I will say — if you have that great idea before you start writing, then your letter, project, or whatever you’re working on will go a whole lot smoother than if you’re trying to execute a bad idea. 

What’s the most unusual writing project you’ve ever worked on? 

Years ago, and I’m not sure how … I think it was when AWAI was taking on outside clients for some reason, I was asked to write a letter on a “business manners” book by Letitia Baldrige. I thought, “If I can sell complicated trading systems, surely I can sell a business etiquette book capable of giving up-and-coming executives an edge on their competition.” Turns out I was wrong. Not only did it bomb — the company said it was the worst performing letter they had ever tested. I had been writing for two or three years then and had had some good success, so it was a real wake-up call for me. I felt terrible. But now that I’m thinking about it, I’d love to try that letter again. With 17 or so years under my belt since, I could probably make that letter work. 

That would be interesting to test! Tell us about your non-writer side … like what music do you enjoy?

What, are we on a date here? Music … well, I’ve been a pretty big Springsteen fan since I was a teenager. Darkness on the Edge of Town had just come out and I was hooked. One of the best times I’ve had in recent years is taking time to get to Springsteen concerts with my son who’s now in his late teens. That’s one of the nice perks about being a freelance copywriter — you can just hop on the road for a week and follow a band around a part of the country. And in the case of Springsteen, at least, be able to afford some pretty good seats on StubHub. But other than Springsteen, Bob Dylan, Barenaked Ladies (I used to see them in local bars growing up in Toronto), Neil Young, John Mellencamp, Elvis Costello, Jack White, Alanis Morissette, The Clash, Radiohead come to mind. I tend to gravitate to storytellers. Musicians with interesting lyrics. 

That story appreciation is obvious in much of what you’ve written. What’s not obvious is why you chose to move to Vermont from Florida? 

I’m from Canada, so it was all about the heat — and the lack of changing seasons. I loved everything else about Florida — the easy living, the tax benefits, and being close to Katie [Yeakle], Mark [Ford], and all the people I got to know well down there. But at the end of the day, I’m a northerner and Florida just wasn’t my thing. 

And what have you come to love about New England? 

As far as living in New England, it’s really beautiful up here. Summers are great, autumn is fantastic, and the winters are crisp, fresh, and picturesque. There are no crowds, no traffic jams, and you can always get a parking space or a seat in a restaurant. We picked this specific area of Vermont for the schools. And it’s paid off. Mike, my son, has had a great experience going to school here … is doing great academically and has lots of wonderful supportive friends who have pretty much all grown up together. 

That said, I do come from the city and do miss the energy of a Toronto or a New York sometimes. So one of the nice things about where I am in Vermont is I can just get on the train and be in NYC in two and a half hours. 

What kind of habits do you have when you sit down to write? Any rituals? 

No, not really. I do most of my writing in the morning, so I’ll get up, have a coffee, some breakfast, read some news, do the NYT Crossword Puzzle, and by 8 a.m. or so, wander up to my desk and start working. Unless it’s a day where I say — screw it. It’s beautiful out … I think I’m going to play some golf or take the dogs for a long walk. 

When you meet up-and-coming writers who want to do what you do, what advice do you give them? 

A lot of the new writers I talk to are really into the preparation stuff — doing the programs, finishing the courses, getting signed up for a membership program, getting business cards, and whatnot. And that’s all great.

But the most important thing you can do every day is write. Even if you’re not sure what you want to write yet. Just find something to work on and write. Maybe it’s an ad you came across. Look at what they’re selling and take a crack at writing your own letter about it. Who cares if it’s terrible at first? As much as I hate clichés — Mozart didn’t sit down to the piano and rattle off Piano Concerto No. 23 in A (I had to Google that, by the way). He had to play for hours and hours to be able to do it. So if you’re not writing every day — how are you going to get better at writing?

What would you recommend for the time-strapped new writer with big goals?

I always suggest this — divide your day (or however much time you have to work on copywriting) in to three parts. If you have three hours at night to work on this — spend an hour on coursework, spend another hour reading and studying successful promotions. And then spend the final hour writing. If you do that consistently, everything will work out.

In your opinion, what’s more important — a positive attitude, or regular writing practice?

Regular writing practice. No doubt in my mind. Because if you’re studying and writing every day, you’re bound to get better. And that alone will create a positive attitude.

What’s a typical day like now, compared to life before you found writing?

Well, my previous job was a long time ago, but as I recall, it was pretty simple (and quite depressing). I’d get up, shower, put on my Publix-issued polo short, my coral-colored apron, and drive to the grocery store … punch in and start stocking shelves.

Now? Well, I told you a little bit about how my day starts. But basically, I like to write in the morning when my mind is the freshest. I’ll write until about noon and pretty much stop. I’ll have lunch … maybe do a quick workout downstairs or go for a walk. Afternoons, I’ll answer some emails or go into town and get some things done. I also like to schedule any conference calls in the afternoon, after my writing, so I make myself available for those. If I’ve had a particularly rewarding morning of writing, I might take the rest of the day off.

Now, there have been days where I’ve gotten on a roll and written right through my noon cutoff time. That’s good too, because not only is it fun to write when everything is working and falling into place … but because you’ve really had a productive session, you feel good about things at the end of the day.

So there’s a lot to be said for having a solid writing routine, agreed?

Yes. You feel much better about yourself when you write every day and you look forward to writing the next day. That’s big because it makes you more productive.

What tips can you share for avoiding writer’s block?

Always try to end your writing day knowing what you’re going to write the next day. That way, you’re eager to get started writing and you’re not sitting there wondering what to write. If you write until you don’t know what you’re going to write next and just stop for the day, you’ll have a much tougher time getting started the next day. Does that make sense?    

Absolutely. For you, what’s the very best part of Barefoot Living?

It’s all Glicken to me. Just the freedom alone is a huge gift. Knowing that, so long as I’m not too far behind or on a tight deadline, I can take a few days off and travel … there’s no better feeling.

What other “life bonuses” do you get to enjoy thanks to life as a copywriter?

In my line of work — financial publishing — we’ll often have meetings and events in some pretty special places … and we’ll combine them with golf events, skeet shooting, fantastic meals, concerts, and so on. And of course, all expenses are paid. And just the fact that you’re constantly surrounded by these smart, creative people — and have free access to all their knowledge, resources, and time is pretty amazing.

fourBut perhaps the best Glicken ever is the fact that every year, Katie and the AWAI team fly me down to Florida and pay me to talk to AWAI members about copywriting while I buy them drinks at the bar. Could there be a better job for four days of the year?