“Clients are the hardest to find when your skills are the weakest.” – Holland Webb

Haris Halkic: Hi Holland, thanks a lot for agreeing to share some tips on copywriting and your background. Let’s start with how you got started in copywriting? Please tell me more about your story.

Holland Webb: Thank you for inviting me. Writing was my dream from way back because I loved to read. As a kid, I sat with my nose stuck between the pages of a book and my imagination fully engaged.  When I was a teenager, I had dreams of being the next Michener or Clavell, traveling the world and writing powerful novels set in fascinating locations.

Instead, I took a graduate degree in international public policy and then went to work for an INGDO (international non-governmental development organization). I spent most of my time there writing proposals, reports, fundraising letters, and marketing pieces. That job built the foundation for a copywriting career although I didn’t realize that was happening at the time.

Starting in 2009, I sat out the Great Recession by teaching English in Guatemala. My writing skills didn’t improve much, but my grammar did. And so did my ability to communicate with people who lived outside the international development bubble where I’d spent my working life.

Over time, I realized that I wanted out of the insular community of nonprofits and schools I was writing and teaching for, so I joined a content marketing agency as an editor and writer.

While the work was unbearably tedious, the senior editors did a great job teaching me how to write for B2C brands. Their editorial feedback was gold, and when I was able to go out on my own, I carried it with me to my own clients.

Today, I mainly serve as an education content writer focused on higher education marketing and editing for edtechs. I will, however, write anything that isn’t illegal or immoral and that has a paycheck attached to it.

Haris Halkic: How did you transition to freelance copywriting from your previous job? What’s your best piece of advice for someone who is employed and wants to become a freelance copywriter?

Holland Webb: My first freelance client was a former employer, the INGDO I mentioned earlier. Their copywriter had just taken a full-time gig with another company, and they asked me to write for them about 20 hours a month. Since I knew the agency, the donors, and the field work, it was a great place to start. I didn’t have to read through an idealized customer profile before sitting down to write a piece. I could rely on my intuition for a lot of that, and train my focus on boning up on the fundamentals of good content writing.

Working full-time for an agency was a big help, too, since it made me understand an agency’s expectations and relationships with its clients not to mention the value of having professional editors review my work.

My advice? Once you’ve developed social proof with clips and references from your part-time freelance work, it’s much easier to launch a full-time business.

Sharp skills, deep knowledge, a big network, and experience in selecting good clients can help you be successful as a freelancer. Get those things while you still have a regular paycheck to cover your monthly expenses.

Haris Halkic: Getting clients is one of the greatest challenges for freelance copywriters. Could you tell me more about how you get clients?

Holland Webb: 

Clients are the hardest to find when your skills are the weakest.

Let’s face it, the barriers to entry in this profession simply don’t exist. Slap the name “copywriter” on your LinkedIn profile, and you’re in. And unfortunately, many people with poor writing skills are marketing themselves as copywriters causing agencies and businesses to be very shy about working with an unproven asset. Once you can demonstrate that you know what you’re doing, however, the work is much more plentiful.

Remember, though, the quality of your clients is as important as how much work they give you. Before you jump at a client who is waving work at you, make sure they’ll treat you well and pay you fairly. Some agencies take advantage of new but talented copywriters. Don’t let that happen to you.

To get great clients, you’ve got to build great skills. Only then should you start showing those skills.

An online portfolio and an active LinkedIn account can help you do that. Cold applications to open posts get about a 0.5% positive response in my experience, but having said that, I should add that I secured both my top-paying client and my longest-lasting client that way.

Once you have a client or two, ask them for referrals. That’s the easiest and most effective way I have found to get new clients. Let me put in another plug for LinkedIn here, too. I get a lot of business just by being active on the platform.

Haris Halkic: How did you learn to write copy? Are there teachers, books or resources that you can recommend?

Holland Webb: I learned to write copy by writing copy then having editors cut it until it bled. I never took a class, read a book, or joined an online forum. I did have years of grant writing under my belt as well as experience in oral storytelling. That reminds me that I can recommend Donald Miller’s book A Million Miles in a Thousand Years, which is a fresh look at the art of storytelling.

Haris Halkic: How do you prepare for a writing session?

Holland Webb: Put my butt in a chair and my fingers on a keyboard.

Seriously, there’s no way to write except to write.

Procrastination is a deadly enemy we all contend with, but in the end, the only way to slay it is to write quality product that you turn in on time.

Haris Halkic: Who’s your favorite copywriter or piece of copywriting?

Holland Webb: My favorite copywriter is Dorothy Sayers who worked at S.H. Benson’s advertising agency in London during the 1920s. She’s the one who came up with the slogan “It pays to advertise.” Sayers also wrote this little jingle for a Guinness beer ad that featured a toucan: If he can say as you can, Guinness is good for you, How grand to be a Toucan, Just think what Toucan do.

She went on to write a popular series of detective novels, including one called Murder Must Advertise about a copywriter who was murdered in his advertising agency. Today, Sayers is still well known for her radio plays and her heavy intellectual work on feminism, theology, and social commentary after getting her start as a copywriter.

Haris Halkic: In your opinion, what are the greatest advantages of being a freelance copywriter? What makes this lifestyle so special?

Holland Webb: In an agency, the boss stands between you and the client, serving as a buffer. When you’re on your own, the stakes are much higher, the wins more satisfying, and the losses more educational.

I relish the freedom to work when I want, deal with my own clients, take responsibility for my own mistakes, hear praise directly from the client.

I also like taking naps during the day, working late at night when I want to, and taking time out to talk to people like you. One day, I want to try out the digital nomad lifestyle I keep hearing so much about.

Haris Halkic: What one daily habit has contributed to your success more than any other?

Holland Webb: I keep a color-coded to-do list, and I love checking off items or changing their colors when I accomplish something.

Haris Halkic: If someone wants to hire you, what is the best way to get in touch?

Holland Webb: Carrier pigeon. I also have a website, www.hollandwebb.com, and I’m pretty active on LinkedIn, Twitter, and Facebook. Or you can email me the old-fashioned way at hollandlylewebb@gmail.com.

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