#35: Learning to Pivot as a Freelancer, with Jonathan Small

Today’s guest is Jonathan Small, an award-winning journalist and editor based in Los Angeles. He is the host of the podcast Write About Now, where he interviews successful writers about their journeys and what they’ve learned along the way.

He is also the founder of Write About Now Media, a creative consultancy group specializing in non-fiction writing, editing and podcast production. He is also editor-in-chief of Green Entrepreneur, which is a new website and print magazine about the cannabis industry that is published by the editors of Entrepreneur magazine.

Jonathan has had an interesting career, moving from editing major magazines in New York, including Stuff, Glamour and Fitness. Then, he moved to LA and got into film and video and later was the vice president of content for the Game Show Network and later the chief creative officer at DanceOn, a YouTube-funded dance and pop culture channel co-owned by Madonna.

Jonathan likes being his own boss and believes freelancers need to be self-starters and know how to organize their days. You also have to know when to give yourself a break and take time off of work.

Jonathan aims to structure his day each morning by saying things such as “I’m going to give myself three hours to work on this project today.” However, things pop up that are out of his control, so he needs to be flexible too.

When he needs to do deep work, he shuts down his email and internet tabs so he can focus. He also likes the advice to designate only a few times a day to look at your email inbox, instead of constantly looking at it all day long. He hasn’t embraced that approach yet, but he does try to flag important emails to get back to them later in the afternoon.

Having steady gigs, not pitching, is better for a sustainable freelance business. For a long time, Jonathan wrote the Ask Him Anything column for Cosmo magazine.

Now as a magazine editor he is seeing freelancers who are difficult to work with. Yeah, don’t be that guy. You can’t sustain your business by being difficult. Jonathan’s freelancer maxim: Under-promise, over-deliver.

You can advocate for yourself and ask for more money, but when the answer is no, you have to take it or leave it. Complaining about it only means that that editor is not going to hire you again and will not refer you to others.

Around 2000–2001 Jonathan was getting burnt out on magazines, so he pivoted and moved from New York City to LA to work with a friend who was starting a business in the film industry. He pivoted a few more times, to digital publishing, then video production and branded content.

It was helpful for Jonathan to learn new skills and be able to course-correct at various times in his career. Turned out that podcasting has been his favorite part of his career.

It’s hard to make a living solely pitching as a journalist nowadays. We’re no longer able to routinely earn $2/word at print magazines. On the flip side, there are a lot more avenues open to freelance writers, like podcasting, content marketing and creating blogs. Jonathan believes it’s important to establish your brand.

Jonathan started his Write About Now podcast through a digital marketing class assignment.

The podcast has morphed into a show where he interviews successful journalists and writers about their careers and what they learned along the way.

Podcasting combined everything he loves into one thing: interviewing people, creating audio, hosting, telling stories. Most of his listeners are aspiring writers, but about 30% of his audience are non-writers who just like hearing good stories.

On a recent episode, Mignon Fogarty, aka Grammar Girl, dove into grammar with him. That episode includes fun conversations about how Webster wrote his dictionary and the history of the semicolon.

Biz Bite: Run Your Content Through Grammarly


Write About Now website and podcast

Green Entrepreneur magazine

Jonathan on Twitter

Write About Now podcast on Instagram

Grammar Girl podcast episode

Jonathan on Grammar Girl’s podcast

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