From the Field: How I Ditched the 9 to 5 and Built a Business I Could Live With

Lori Benjamin

From the Field

My Story

I started working as a freelance content marketing writer after about 15 years of work in traditional marketing and advertising, mostly in the business-to-business software field. So, I come to it from a business rather than a journalism lens. Content marketing felt like an enormous (and obvious) breakthrough. For years, I’d been asked to write product-focused emails and online ads designed to interrupt busy people with a sales pitch. Now suddenly, I had clients who wanted to produce things that people would actually seek out and read. What a concept!

I discovered content marketing after leaving my ad agency job in the city behind and moving to an island about two hours north of Seattle and an hour by ferry from the mainland. Commuting was not an option. After five years of writing emails for Microsoft clients, I needed to update and sharpen my skills. It was 2012, and new ideas, voices, and technologies occasionally broke through the ad agency bubble, but were usually rejected in my commercial, business-to-business niche.

From my first Skype interview as an islander, it was clear I had a lot to catch up on. I began investigating marketing blogs in earnest, and found sites like Copyblogger, HubSpot, Seth Godin, Content Marketing Institute, and Convince and Convert. I had a decent portfolio, but not much for bylined articles, and I was competing against writers much younger than me. At first, all I found were clients asking me to work for less than minimum wage: To type fast and think very little.

Ultimately, LinkedIn turned out to be my most valuable tool. As an “early adopter,” I had started collecting recommendations around 2007—a great way to establish credibility in a field where almost nothing I wrote had my name on it. I began applying for any and every job I felt qualified for, no matter where it was based geographically. Unless the job description said specifically, “This is an onsite position,” I sent an application. If it seemed like a perfect match, sometimes I applied anyway, ending my cover letter with a polite, “I hope you’ll consider me as a remote candidate for this position or alternatively, for any project work I may be able to help you with.”

After a few months of this, I started picking up work that paid reasonably well. Within the first 18 months, I was making a decent living writing ebooks and ghostwriting guest blog posts on the very content marketing websites I’d been reading. I was over the moon.

The content marketer’s motto: Be helpful.

“Content marketing” is nothing new, of course. John Deere has been publishing its brand magazine, The Furrow, since 1895. Today however, every brand in the world is up against the overwhelming information overload that we all experience in our multi-screen, multi-tasked lives. Audience attention is the holy grail.

Because of the Internet and social media, the corporate decision-makers who’ve been my target audience for most of my career increasingly choose to do their own research, reaching out to sales only after they’re close to reaching a decision. It makes sense for software companies to offer insight and context as a part of that research conversation. Not many executives have the time or patience for traditional direct mail gimmicks and other interruption advertising tactics.

Marketing is an exciting field to be in now, because it’s changing so rapidly. It’s much more customer- and data-focused than it was even a couple of years ago—which means that good, effective work rises to the fore more consistently. Formats change constantly—in the past year, podcasts and video have surged. Virtual reality is on the horizon. But words will always be essential to communication, whatever the medium. If you’re a disciplined writer with a curious, creative bent and a basic understanding of business, you can make it work.

A few tips, for starters:

  • Take a creative writing workshop (or three). If I had a stronger technology or business education, I’m sure that would be valuable, but I cannot imagine a better preparation for my work than the many creative writing workshops I took in college and graduate school. Sitting in a room with my peers, I learned how to give and receive constructive feedback. To listen even when the critique I heard caused a spike in my blood pressure. To respond with thoughtful, creative rewrites that, as often as not, turned out better than the original. There’s more than one way of nailing it.
  • Choose unpaid work wisely. If you’re starting with no portfolio or experience, it may make sense to write for people who expect you to work for next to nothing. But it may make even more sense to write on a topic of your own choosing and develop credibility and a following that way. Go ahead and build expertise in an area with high income potential—but make sure you also feed your personal passions. That well of sincere interest and curiosity is where the best insights and writing come from.
  • You are your client’s voice. In high-demand fields, you can make upwards of $100 an hour as an established marketing writer, but never forget: Your client is in charge. Don’t like the feedback you’re getting? Take a deep breath and open your ears. Your work is not only about whether you can put together sentences that make people sit up and take notice. It’s most essentially about doing it in a way that accomplishes your client’s goals.
  • Professional courtesy is crucial. In building client and team relationships, you’ll find a collaborative mindset and a positive, pragmatic attitude much more effective than quick criticism or competitive maneuvering.
  • It’s okay to fire a client. There’s nothing worse than a client who doesn’t seem to respect your time and effort (unless it’s the client who flat-out refuses to pay at all). You will come across those people, unless you’re very lucky. Set your boundaries early, and keep a list of the qualities you expect from clients. Professional courtesy goes both ways.
  • You are the boss of you. Don’t feel like working? Think you can fudge that deadline and go skiing with your friends? As an independent consultant, you have a lot of leeway around when and how much you work. But if you commit to a deadline and don’t make it, you risk losing a client, pure and simple.
  • Print it out and proofread it before you hit send. Deliver a document full of typos and repetition, and your client will be predisposed to ripping it to shreds, metaphorically speaking. Read the print-out one last time before you send it. You’ll be amazed at what you didn’t catch onscreen. Aim for perfection, so your client can focus on the message rather than the misplaced apostrophe.
  • Client relationships are your lifeblood. When you work remotely, it can be hard to connect with people and maintain relationships. But one great connection can truly make or break your career. In my industry, people move from company to company constantly, which means two things: 1) My contact at Client XYZ could jump ship at any time and I could lose the business, and 2) My contact at Client XYZ could bring me many additional clients during her career. To develop a stable freelance business, treat people with respect and loyalty always. If you sense any issue, head it off immediately by reaching out personally.
  • Save your pennies. Every freelance business has its ups and downs—cycles of 80-hour weeks, mixed with ones where things seem eerily quiet. Make sure you build a good buffer to get you through the slow times. That way, you can relax and hit the beach, rather than checking your email every five minutes, praying for work.

Lori Benjamin writes for technology and marketing companies, mostly in the startup community. She has an M.A. in creative writing from Purdue University and a B.A. in English from the University of Redlands. Contact her at

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Media Innovation and Entrepreneurship Copyright © 2017 by Lori Benjamin is licensed under a Creative Commons Attribution 4.0 International License, except where otherwise noted.

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