If you’ve read this blog before, you’re likely familiar with Jonathan Rick’s powerful ghosting and freelancing insights, which he shares regularly on the GG blog and on his own site. As you might expect, he steered his Featured Writer conversation away from himself and more in the direction of actionable advice for our benefit. Explore his insights below.
1. Tell us about your writing journey. How did you begin writing, and how did you break into the industry? When did you know you could make a career out of it?
My mom was a high-school English teacher who always encouraged me. Never underestimate the power of praise.
That support sustained me in high school, but it wasn’t until college that I began to see myself as a writer in my own right. As a result, I launched an opinion column for the school paper and landed an internship at Time magazine in New York.
After I graduated, I pursued journalism, but soon realized that I preferred to opine rather than report. So I applied for an internship at the Cato Institute, a think tank in Washington, D.C. I assumed I’d get to write about foreign policy, which was the subject of my senior thesis in college.
Cato had other ideas.
They saw my résumé and stuck me in the media-relations department. Initially, I was devasted: Couldn’t anybody edit an op-ed? It turned out I had a talent for this work — and what was initially an unwelcome decision set in motion the trajectory of my career.
Long story short: After my internship ended, I landed at a political-advocacy nonprofit, then a PR agency, then a management consultancy, before hanging out my own shingle. Freelancing full-time was a risk, but it’s proved to be one of the best decisions I’ve ever made. And I count my lucky stars every day that I’ve been able to make a living doing what I love.
2. Tell us what you can about your career doing writing for hire — speechwriting, ghostwriting, freelancing.
Using these formats (and more), I’ve ghosted for everyone from Cabinet secretaries and CEOs to celebrities and students. I relish the challenge of working with smart people to channel their vision.
3. Have you had any especially memorable client experiences — good and bad? (No need to name names unless you’d like to.)
About five years ago, a CEO hired me for a “reputation recovery” campaign. In short, when you Googled her name, several negative articles appeared, and she wanted to repair her digital front door. To this end, I proposed that we publish a series of thought-leadership op-eds.
She embraced the idea and quickly wrote up a draft.
It was terrible.
What’s worse, in emailing it to me, she CCed a colleague, who replied-all: “This looks great! Jonathan, What do you think?”
I was in a tight spot. Should I tell the truth, or should I go along to get along? I called a friend, a fellow ghostwriter with decades of experience, who gave me two priceless pieces of advice:
1. Clients hire consultants for our expertise. If we don’t provide them that, then we’re not doing our job.
2. I should make whatever edits I think are needed, but instead of saying, “I rewrote this,” I should say, “I made a few tweaks.”
It turns out my friend was exactly right: The client had no pride of ownership and was wholly receptive to feedback. I’ve since made candor a cornerstone of my business philosophy.
4. What does your writing routine look like? How do you stay productive and overcome blocks?
As anyone who works from home will tell you, deadlines are your best friend. This is especially true for writers, who excel at procrastination. So whether the deadline is self-imposed or assigned, urgency helps me focus.
As for those so-called blocks, here’s a fun story I’m stealing from my fellow Gotham ghost, Mike Long. Writers are so creative that we’ve invented a fancy concept for good old procrastination. We call it “waiting for the muse.”
This is ridiculous. In no other industry is it acceptable for people to daydream and lollygag because they’re waiting to be inspired. Imagine yourself lying on the operating table when your surgeon strolls in and declares, “I can’t operate today — I have doctor’s block. Let’s try again tomorrow.”
The reason you’re laughing — the reason this silly scenario never happens outside a writer’s head — is because nonwriters power through their excuses. Sure, everyone has a day when you don’t wanna wake up. But most people don’t let existential dread bog them down. They view their craft not as something that can be done only in a perfectly quiet room, with the right keyboard and a comfy chair, but as a job.
As Roger Ebert puts it, “The muse visits during the act of creation, not before. Don’t wait for her. Start alone.”
5. What’s your best piece of advice for someone looking to be a full-time writer?
You’re here for candor, so let me be frank: Freelancing is tough. It’s tough from a financial perspective: You’re always hustling, and you eat only what you kill. It’s tough from a psychological perspective: You don’t get a paycheck every two weeks, nor do you have coworkers to socialize with every day. And it’s tough from a productivity perspective: You have to be super disciplined and organized without the aid of a boss.
So my first suggestion is to ask yourself if any of these constraints is a deal-breaker. If so, there are workarounds: You can pay yourself a salary, join a coworking space, give yourself a daily to-do list. But the fact is, Freelancing full-time isn’t for everyone.
That said, working for yourself is a helluva lotta fun. If you want to give it a go, I’d recommend four tactics:
1. Diversify Your Income
I write and edit; I do digital marketing; and I deliver workshops. Those are all separate streams of revenue. Many freelancers have a similar structure — with the goal that if one practice is slow, another is busy.
2. Land an Anchor
Almost all my colleagues have what’s called an “anchor” client, which is a client that makes up a sizable percentage of your income. Better yet, some have several anchors. So make it a priority to find a company or even individual with whom you can establish a long-term, retainer-based relationship. Not only will you gain cash flow; you’ll also gain confidence to decline low-paying opportunities you might otherwise chase.
3. Take Time Off
As a freelancer, you’re pretty much always on the clock. That’s unhealthy and can beget burnout (which the WHO just recognized as a legitimate medical diagnosis). So make it a point, every once in a while, to take time off from your phone, your computer, even from conversations about work. I know, I know — easier said than done. But here’s the upside: You’ll return recharged, refocused, and thus more productive.
4. Always Be Networking
Think about all the people you’ve come into contact with over the years: Roommates, teammates, childhood friends, college friends, work friends, friends of friends, colleagues, bosses, interns, employees, significant others, relatives, neighbors, doctors, your favorite bartender. You never know where a lead can come from, and so never be afraid to sell yourself, to make folks aware, gently, of how you can help them. Rejection is inevitable, but if you’re in this business for the long haul, you need to take the long view.
Do you have a story idea? Pitch it to us below, and we’ll work to match you with a writer like Jonathan who can help you bring your vision to life.