Living the Writer's Life:
Jay Simon
By Mindy McHorse

Jay is an active voice in the Barefoot Writer Club,
housed with the AWAI Copywriting Insiders Facebook group.

After company cutbacks, Jay Simon decided he’d rather venture out on his own in a field he enjoyed. A tip from a friend set him in the direction of copywriting, and he jumped in with full intensity. His early dedication to learning the craft paid off quickly, and now he gets to be a hands-on dad to his young son, travel, and still bring in a healthy income. Enjoy Jay’s account of how he launched a writing career to love.

What did you do before you found copywriting, and how did you get here?

Jay went zip lining on a recent
family vacation to Costa Rica.

I was in finance. I was working for MetLife insurance company. Eventually the department I was in got shut down, so I was all of a sudden with no job. I really didn’t love finance, so I decided to venture out. A good friend of mine who was in direct-response marketing said, “Hey, you should definitely give it a shot.” So I signed up for the six-figure copywriting course, and the rest is history.

What kind of copywriting do you do?

I focus on email marketing and email consulting for some e-commerce brands and mostly coaches — coaches in the real estate niche and health niche — because I realized along the way that email is the engine for it all. And from learning email, you learn the funnel and how the leads get into the email and how things get sold. So now I’m mostly a consultant. If I have time to write the copy [for the project], I do. If I don’t, then I hire copywriters to handle the writing part for me.

I’d love to hear about how you got off the ground. What challenges did you face?

I’m a perfectionist at heart. So when I first started, I took the course three times. I read most of the AWAI newsletters. I wrote by hand some sections and also typed them out. One day I decided that I was like, You know what? I’m going to email a few of my close friends. One of them, he was in real estate, said, “Oh, sure. I was looking for a writer.” So I did the discovery call with him. He’s like, “There’s so much knowledge you have, I want you to share with my team.” We did a half day, where I presented some direct-response marketing concepts. That’s when I realized that the blend of consulting and teaching others meshed very well with writing.

Tell us a about what your life looks like now as a writer and consultant who’s in charge of his time.

It’s pretty good. I work from home. I have time to go to the gym in the morning for two hours. I come back. We live by the water here in New Rochelle, so if I want to take a long walk to clear my mind, I can just hit pause on my laptop, on my computer, and take a walk. I’m able to pick up my son every single day. Because I mean, once he was born, I basically also became the stay-at-home parent. My wife does go to work.

What are your goals and future plans for writing projects?

The lifestyle business that I have now is very comfortable. I don’t extend myself too much. I don’t really want to grow into a big agency. In 2022, I was going after one client to the next. And my friend said, “How much are you making now?” I’m like, “Well, I’m clearing over 15 grand a month.” He’s like, “This is fine. Take that money, do some other projects.”

I want to celebrate the fact that you’re happy where you are in your business. But there’s also the gift of flexibility, because if five years down the road you were to grow bigger, or maybe to pull down to part time, you have the choice.

Yeah, or you can travel. We went to Mexico in March, took my laptop with me. You work an hour in the morning and you can enjoy the resort. The lifestyle is real.

If you could go back and talk to that earlier version of Jay who was just considering copywriting, what would you tell him about what to expect?

Expect things to be harder than you think, but know that if you keep taking action, if you keep having conversations with people and building relationships, everything will be okay. That the ebb and flow is part of the process. You’ll have some times where it’s tougher than you think, but the reward is definitely, definitely worth it. And just to keep taking action, build a great community, keep talking to people and make a lot of friends.

Jay's Living The Writer's Life story was originally published in Barefoot Writer. To learn more about how you can start living your dream writer's life too, click here.

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