How Emma Gannon Learned to Thrive as a Creative “Multi-Hyphenate” Freelancer

With her bleach-blonde hair, heavy-framed glasses and bold, bright clothing, 29-year-old Emma Gannon doesn’t have the air of someone who feels she has to conform to get ahead. And that impression is only confirmed by getting to know her better. She is a warm, lively, curious presence on her podcast, Ctrl Alt Delete, which boasts almost 5m listeners and counts Lena Dunham and Elizabeth Gilbert among its guests. In her 2016 book of the same name, she shares personal stories about growing up online, from sexts on Nokia phones to late-night chat room forays, all in the same tone she might take if she were talking to a trusted friend.

In other words, she remains authentic, letting the full force of her personality shine as she forges ahead in her career as a podcast host, broadcaster and author. In her second book, The Multi-Hyphen Method, she shares the secrets of how she has made this leap, and built a hybrid freelance career made up of multiple income streams. The emphasis is not on making stacks of cash by working around the clock, but on formulating a working life that’s actually suited to one’s own personal needs.

Now, with a new Skillshare Originals class, Gannon can add teacher to her list of accomplishments. While her most recent book describes how to turn the life you want into a reality, these classes take a step back and explain how to actually figure out your passion, purpose and path. On a recent, rainy London afternoon, she sat down with Skillshare’s blog to discuss all this in her familiarly frank and enthusiastic way. “I'm not interested in taking over the world,” she said. “I just want to do what I do and keep making it better.”

Did you always know that writing was what you were interested in?

Yeah, but I never thought I could have a job doing that. I wasn't one of those people who thought you could make money from being creative and I didn't know anyone growing up who had a job like that. It was like you had a job and if you want to do something fun on the side, do that.

I’ve had a full-time job at a PR company, I've worked at social media agencies. I've worked in classic nine-to-five office jobs for a long time. I had a blog, and I was fine with that. I thought you earn your money doing boring stuff and then you fuel your creativity on the side. I thought I'd always have a side hustle but I'd be happy because I can write and people can read it.

But then I started to understand the business model of having multiple income streams and I started making quite a lot of money, to be blunt, on the side. And realising that—I know being a freelancer isn't perfect and it’s not for everyone—but if you can make it work it is amazing. I was earning five times as much as my office job in less time. I think that's the reason I do what I do. I almost wanted to pass on the secret that you can make money working in different ways.

What was the first big step towards going freelance?

I started my blog in 2010 and then I got my book deal in 2016, so it was six years of writing most weeks and growing a platform that definitely wasn't overnight. It took ages. But that was definitely a turning point.

What lessons did you learn along the way?

People need to invest in themselves and look after themselves. And actually, the best way of doing that is becoming really skilled at things. If your company is taking ages to send you on a training program or it's taking two years until anyone's mentioned a promotion or no one's investing in you in the company, then there are ways you can do that on the side.

Sadly, it is extra work and that’s not something I love to endorse because I don't think everyone should have a side hustle. I don't think everyone should have to add to what's on their plate But at the same time, the side hustle can be something that helps propel you forward and you are doing that for yourself. You’ll always reap the reward of any skills you teach yourself. That’s why I love Skillshare. Everything you learn you get to keep, you can take it to the next company or put it into the next business.

Did you always have a strong sense of your "personal brand”?

I think people overcomplicate it and think that they need to have a pastel-coloured Instagram feed or something, that that's a brand. But I literally just think of it as 'Do people know who you are?' And that could apply to any job, like being a dentist and people thinking you're a good dentist. For me, it just meant ‘Can I get another job?’ and ‘Will people know my name?’

What challenges did you experience when you first started out?

I became much much better with money and budgeting. I cover that a tiny bit in the class. I'm not a financial expert but that was something that I had to really get good at. If you're on a salary, you don't need to think about it. Your tax comes out [of your paycheck], your [Social Security] comes out, you get it on the first of the month. One challenge for me was that I needed to know where every penny was, in case I didn't have any work for a month.

How did the podcast happen?

I'd written the first book, Ctrl, Alt, Delete, and I was very much done with writing about myself, but what I still wanted to do was to talk about the topics in the book: the internet, jobs, feminism, technology, mental health. So I thought the perfect thing to do is to interview people and I can just listen, and put it on iTunes.

I thought I'd do one eight-episode season and then think 'That was fun, I did a podcast.' but I’m now on my 200th episode and haven't missed a week in three years because it’s just so fun and pretty easy for someone who’s not very technical. It’s my favourite medium. It's so raw and natural and fun and quite forgiving and, yes, you need good microphones but you don’t need for it to be “This American Life” standard for it to be meaningful.

Did you have people helping you?

I started it doing it all myself. Again, that's why I like the link to Skillshare, because I taught myself how to edit my podcast through YouTube tutorials. I didn't have a clue, and it’s evolved so much over three years. Because I make money off it now I can invest back into it, so I can buy myself a good set-up. But at the beginning I bought two microphones off Amazon for about £30 and recorded it onto my laptop.

Now I still edit it myself because I love editing. I think editing is storytelling and I like putting the stories together from the audio. But I have a team who I work with now who manage the finances of it and also the guest booking and the logistics and responses and all of that stuff.

Is outsourcing and hiring people an important part of leveling-up your career?

I read a book this year by Paul Jarvis called Company of One, about how it’s really great to be a company with one person in. And that's what I am essentially. I have a management team now who I do work with but I don’t want to be a boss of people and I don’t want a team who I employ.

In the book, he makes the case that growth isn’t necessarily better, and isn't necessarily success. A million Instagram followers doesn’t mean you're better at your job than someone with 100 followers. I’m into the idea of ‘Stay at the size you want to stay at and make the money you want to make,’ but I don't like those people in suits who always tell you that you need to scale your business. Because that isn't always the best move for everyone and I think people can become quite unhappy when they have more people in their business. I'm not interested personally in taking over the world. I just want to do what I do and keep making it better.

What are your ambitions for the future?

I am a writer first and foremost but I really want to explore telling stories across different mediums. I feel that there's so much going on right now with Netflix taking over and Facebook Watch and all of these streaming services, and there are loads of brands who maybe want to work together [with me] to create a mini series around something.

I’m doing some work with the BBC [at TalentWorks, their new content department] at the moment. I think everyone’s trying to create cool stuff and for creators I think it’s a good time. Back in the day there were four TV channels. Now you can make things and have people put them out into the world. It's a really exciting time to be making things.

This interview has been edited for length and clarity. To learn more from Emma Gannon, check out her new Skillshare class, Discovering Success: 7 Exercises to Uncover Your Purpose, Passion & Path.

Cover image: still from Emma Gannon’s Skillshare Originals class.