How Stacey Kelleher – Pino Said Goodbye To A 9-5 Schedule And Never Looked Back

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

Stacey Kelleher – Pino: Thanks so much Haris. I’m happy to share my experience as a freelance copywriter with your readers. Thank you for reaching out.

I developed a love of writing at a very early age, as soon as I learned how to read.  I would tap away on my grandmother’s metal typewriter for hours on end, writing short stories, poems, and letters. I never lost that love of writing I’m so grateful I’ve been able to channel it into a career.

After graduating from college, I landed a job in the marketing department of a well-known national retailer. This was my first “real job.” I didn’t know what to expect but I always seemed to gravitate to any of the jobs in the department that required writing: press releases, pitch letters, advertorials, speeches, etc. After a few months, I became the go-to employee for corporate copywriting projects.

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?

Stacey Kelleher – Pino: After working for the company for about six years, I found out I was pregnant with twin boys. I had every intention of returning to work after they were born, but my heart had other plans. Every woman knows what’s best for her and her family – and that is different for all of us – but I knew I wanted to spend these formative years with my children. After my daughter was born a year and a half later, I decided to take a few years off from working altogether.

As the kids got older and became more independent, I was itching to get back to work but leery of being saddled to a traditional 9-5 schedule. By now I was very involved with my kids school activities and sports and wasn’t ready to give that up.

Freelancing was the perfect solution. I could work when and as much I wanted. When I started freelancing, I was honestly a bit skeptical that it could make it work, but I was determined to create my own career path.  

Haris Halkic: Getting clients is one of the greatest challenges for freelance copywriters. What ways do you use to get clients?

Stacey Kelleher – Pino: I would say the first step to getting clients is creating a portfolio. Your credentials and resume don’t mean all that much if you can’t tell your client’s story. They want to see how you write. It can be as simple as a document with links to your writing samples or a more elaborate online showcase of your work.

For many writers, their work is very personal and they don’t feel comfortable exposing it to the world. If you want to make your samples available only to existing or potential clients, try a password-protected website.

If you’re just starting out and don’t have enough work to fill a portfolio, get creative. Contact family member or friends who own a business and ask if you can write or revise their press release, bio, or website copy. If it means working for free, don’t be discouraged. The exposure and experience is sometimes worth way more than a paycheck.

Try “moonlighting” as a freelancer while you’ve still got a full-time job so you have regular income while you’re getting your feet wet and gaining momentum.

With some writing samples under your belt, you’re ready to start exploring well-known freelance websites like Upwork and Guru to get some experience and build your confidence. There are many different reputable freelance job sites out there full of opportunities. I’ve had good luck with CraigsList as well.

Many small and mid-size businesses don’t need a full-time writer on staff, but they do need well written copy for the occasional bio or article. That’s where you come in. With the right client, one press release can turn into a long-term contract.

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

Stacey Kelleher – Pino: Unlike other skills or trades, I think writers work largely on instinct – much to the disappointment of my English professors. They know what sounds good, what flows, and how to shape a message.

That’s not to say that practice and training won’t help you improve your writing. Of course it will. Once you hone in on your niche, find out who’s doing it well and learn from them. There are countless online training courses available for every form of writing. And of course there’s Grammarly, Spell Check, and other wonderful tools to guide you along the way.

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

Stacey Kelleher – Pino: I can’t work with a lot of distractions, so I will silence my phone, close my calendar, and turn off the radio. It’s just me, my laptop, and a pen and paper.

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

Stacey Kelleher – Pino: Carol Tice is a wonderful resource for new and experienced freelance writers.  I’ve also learned a lot from the editors I’ve worked with over the years. As humbling as it can be to see your work come back with edits, your writing can always improve. Seeing it in a new way helps you to grow.

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

Stacey Kelleher – Pino: As a freelancer, I have the freedom to choose the work I want to do. I’ve turned down opportunities because they weren’t the type of writing I wanted to do, didn’t pay well, or the structure of the job just didn’t appeal to me.

With freelancing, I can grow my business as big as I want or slow it down to allow time for other important things – like family time.  

I love that every day is different. I write about something new on a regular basis and that’s allowed me to learn about parts of life I never would have been exposed to otherwise. And more than anything – I love that I can squeeze in a quick run whenever I need to de-stress.

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

Stacey Kelleher – Pino: During my first few years freelancing, I was not so great at managing my time. That left me with plenty of assignments pushed too close to their deadlines (and plenty of stress.) Now, I carefully plan out every week so that when Friday rolls around, I’m off the clock.

I strongly recommend incorporating some sort of schedule into your day. Designate a start time, include breaks, and plan to end your day at a reasonable hour.  Once your business takes off, it can be tough to turn off your work brain, but balance is so important. Even if you’re working from your living room couch, you can still burn out.

Haris Halkic: Are there areas you specialize on as a copywriter and if someone wants to hire you, what is the best way to get in touch?

Stacey Kelleher – Pino: Currently, I’m working primarily on SEO, articles and blogs for clients in the medical, legal, and hospitality sectors, but I’m open to new opportunities. My website is:


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