Freelance Writing Career Advice by Jay Vera Summer

How to get into freelance writing

My name is Jay Vera Summer and I’m a freelance writer. I enjoy engaging in a variety of types of writing, but writing content for brands pays most of my bills. My content niches are health and food. I also write reported articles, first-person essays, and fiction. In addition to writing for businesses and publications, I write and edit for my own websites. At, I give freelance writing career advice. At, I publish writing and art by people (like me) with chronic illness.

How was your university time?

My college experiences differ from many other writers’ college experiences, since I didn’t realize I could earnestly pursue writing as a career until a little later in life. Initially, I didn’t study writing or English in school. Instead, I obtained a bachelor’s and master’s in other fields. Years later, I decided to return to school and study writing.

First, I earned a B.S. in psychology, with the idea that I would go on to earn a Ph.D. after working as a research assistant for two years. During those two years, I became more interested in urban planning and public policy than psych. Basically, I wanted to help solve society’s problems. I ended up receiving a Master’s in urban planning and policy. I also started a Ph.D. program in planning and policy, then dropped out.

After years of working as a bicycle planner, I applied to MFA in creative writing programs. I’d spent so much time in the academic world that when I wanted to pursue my dream of becoming a writer, it felt natural to go back to school to learn about writing.

What’s ironic about this is, you don’t really need a degree to be a freelance writer. A degree helps, especially if you want to write about scientific topics, but it definitely isn’t a requirement. 

Why did you choose a career in Freelance Writing?

When I was a kid, I read and wrote all the time. I kept a journal of my thoughts and feelings. I wrote notes to friends at school and letters to pen-pals in other states. I read books, magazines, and the newspaper every day. 

I hoped that one day I would be a professional writer, too. As I grew older, people told me that writing wasn’t a real career path you could choose, so I dropped my dream and pursued a different path.

When I was around 30, I had what some people call their quarter-life or mid-life crisis (1/3rd-life crisis?). I didn’t want to settle into the life path I was on. I made many changes, one of which was quitting my job to pursue writing. Better late than never!

I chose to become a writer because I wanted to do work that felt meaningful and enjoyable. I didn’t want to spend the rest of my life wondering “what if” and regretting that I’d never attempted to pursue my dream of writing professionally.

What was your first job?

After graduating college with a degree in psychology, I worked as a research assistant. In that position, I recruited stroke patients to participate in a study on depression after stroke. I also conducted psychological and neuropsychological testing with patients.

Although my first job doesn’t appear related to my freelance writing career at a glance, it, along with every job I’ve had in my life, has helped. That’s what I love about freelance writing—as a freelance writer, you can draw on all of your past experiences to make your writing better. 

Although I don’t work with stroke patients or on psychological research any more, my first job helped prepare me to better understand health topics and read peer-reviewed medical writing. These skills improve my health-related content writing now.

How did you prepare for the interview?

With most freelance writing gigs, there isn’t an interview. Usually, clients want to see your writing. Instead of judging you by what you say in an interview, they read your cover letter, resume, and portfolio writing samples.

That said, I have had a couple clients request phone interviews. In those instances, I prepare by familiarizing myself with the client’s brand and website. If they already have some content writing online, I read it and take a few notes so I can reference it when we speak. This way, I show that I’m knowledgeable on their content and ready to make it even better.

How do you stay updated in your industry?

Newsletters! Writers love to write, so many of them have newsletters. I’ve learned so much from other freelance writers by subscribing. Some of my favorites are Opportunities of the Week, The Professional Freelancer, and  The Freelancer’s Year.

In terms of content writing in particular, HubSpot is the place to educate yourself and stay updated. The HubSpot blog is full of good advice. They also offer free certification courses (many of which I’ve taken). Their courses help you learn and give you a way to present yourself as an expert in content.

What’s your advice for people who want to become freelance writers?

Breaking into freelance writing requires hard work, but at the same time it’s one of the most accessible career paths available. If you’re good at writing and willing to learn, all you really need is a computer, an internet connection, and motivation. Everything you need to know is available online, for free. You just have to find it, then do the work.

My advice is to develop unwavering confidence and belief in your ability to succeed. Fellow freelance friends who provide support can help with this. There’s so much to freelancing that people with regular employee jobs can’t relate to or don’t understand. If you listen to their advice, you won’t freelance for long. 

Instead, find your “tribe,” as Seth Godin puts it. Follow freelance writers on Twitter and request them on LinkedIn. (I’m @jayverasummer on Twitter and on LinkedIn as well—feel free to add me!) When you immerse yourself in the writing world, it no longer feels like a faraway dream. When you see other people succeeding, you will learn from them and recognize you can also succeed as a writer.

Freelance Writing Career Advice by Jay Vera Summer

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