A blonde woman with glasses wearing a blue top standing in front of a floral backdrop. She is Jennifer Romolini.
Image: Jennifer Romolini

‘Digital has made us more nimble, but also crankier and more anxious’

28 Mar 2019

From the world of glossy magazines to digital content, Jennifer Romolini knows a thing or two about adapting her career in an ever-changing world.

Because everyone is so vastly different, and each person’s career journey and experience can vary so greatly, there is never a one-size-fits-all method when it comes to the right or wrong way to go about climbing the career ladder.

In fact, there might not even be a ladder. It might just be you trying to achieve success in the way that is the most meaningful to you.

So, what do you need to know? What advice or journey will be relevant to you? What stories can you take solace from? Jennifer Romolini, who will be speaking at Inspirefest 2019, is a writer, editor and senior digital media strategist. She’s the former chief content officer of Shondaland.com and was also editor in chief of both HelloGiggles and Yahoo Shine. She was recently appointed the editor in chief of CannabisMD.com.

However, before she delved into the world of digital content, Romolini was part of the world of “big, fat, glossy, moneyed magazines”, an industry that doesn’t exist the way it once did.

“When I started in publishing we were literally marking up pieces of paper and turning them into proofs to hand to a printer to make a magazine. There was no real internet to be concerned about,” she said. “I’ve been lucky enough to adapt and adapt quickly in high-level digital media roles, to learn to game whatever social media/SEO/newsletters/paywall/pivot to headstands the business has thrown my way.”

However, that’s not to say that the transition wasn’t easy. Though Romolini said she loves writers and stories, she finds ‘content’ to be a much cheaper, faster, angrier beast than the calm, careful way words were handled in print. “I think if digital has made us more nimble, it’s also made us crankier and more anxious.”

But Romolini hasn’t stepped away from print altogether. In 2017 her book, Weird in a World That’s Not: A Career Guide for Misfits, F*ckups and Failures, was published. The book is an honest, sharp-witted, practical guide to help you get and keep the job you want – especially if you feel somewhat of an outsider.

“They say write what you know …” said Romolini. “In all seriousness, I felt there was a specific way that people like me – people who felt weird and outside and other, socially clumsy, just out of step with the room – were sabotaging ourselves,” she said. “I wanted to write a book to help misfits, one that said: ‘It’s OK, you don’t have to be like all the rest, you have value and can succeed just as you are.’”

When it comes to what people need the most help with, Romolini believes it’s getting them out of their own heads. She said people project all kinds of negative fantasies on situations, bosses and colleagues, and start painting a dark, ‘out-to-get-them’ world. “I’m constantly trying to help people I mentor or who work for me to base their decisions on objective facts and truth, not on the way their minds may have contorted reality.”

It can be hard to dish out career advice blindly because, as I said, it’s rarely a one-size-fits-all situation, and Romolini tends to agree. However, there are often small things that can work for a large number of people, and Romolini’s one piece of advice that she believes usually works universally is to take a breather before rushing into responses.

“Give yourself a beat before you respond to things – to emails, social media comments, job queries, Slack messages – and if that thing that you received made you feel angry or anxious or ashamed, multiply that beat times 100,” she said.

“We need to create more space for ourselves to think, to remember that we will not be rewarded for the speed of our reply so much as its smarts and thoughtfulness.”

She also said with the future of work moving away from the structured, corporate nine-to-five model and more towards the flexible gig economy, what is important for employees to handle in the ‘workplace’ will also change.

‘I wish I knew how bad I’d be at everything in the beginning’

“Instead of learning to manage a boss, office politics and climbing a ladder, you’ll have to become proficient at building out a client base and a solid reputation, keeping yourself to task, and holding yourself accountable, managing multiple projects, building a professional community and a foundation to your working life that’s not necessarily already provided for you by nature of a traditional office job.”

Romolini said she wished she knew to slow down, appreciate each job more and stop racing through, jaw and fists clenched. “I wish I knew how bad I’d be at everything in the beginning, how it was normal to produce utter garbage at first, so I could’ve been less hard on myself and less defensive with others,” she said.

“I wish I hadn’t been so desperately concerned over whether or not it would work out – which is a lesson I still sometimes need to remind myself about. Basically, it always works out unless you die, which is, I suppose, another way of things working out.”

Finally, I asked Romolini if she had any productivity tips that help her get through her working day. “Handwritten lists and an unhealthy dose of fear and self-loathing, though I’m trying to do more of the former and less of the latter.”

Inspirefest is Silicon Republic’s international event celebrating the point where science, technology and the arts collide. Early Bird tickets for Inspirefest 2019 are available now.

Jenny Darmody
By Jenny Darmody

Jenny Darmody became the editor of Silicon Republic in 2023, having worked as the deputy editor since February 2020. When she’s not writing about the science and tech industry, she’s writing short stories and attempting novels. She continuously buys more books than she can read in a lifetime and pretty stationery is her kryptonite. She also believes seagulls to be the root of all evil and her baking is the stuff of legends.

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