When I was asked to contribute a piece to a series I was working on for Financial Pipeline on career advice, I laughed it off. The people we were speaking with were at the top of their fields, having grown, managed and hired for several financial companies worth billions of dollars.
As a writer and journalist who ran her own freelance business (and editor of this site), I wasn’t sure what I could possibly have to add. But the thing about successful careers, especially now, is that they come in all shapes and sizes – and often, they take turns we never expected.
That seems like a good place to start.
Be honest with yourself about what you love and what you value
I have a clear memory of being 12 years old and reading an interview in Rolling Stone magazine and thinking – this is what I want to do. The idea that talking to interesting people, learning new things and writing about them for a job seemed too good to be true. It was a moment of complete clarity – which I proceeded to ignore every chance I got. Writing didn’t seem like a real job. It wasn’t something I was taught to value. It wasn’t practical. I lived on the edge of that dream – initially majoring in Psychology and minoring in English in my first year of university (I switched halfway through), looking for jobs that involved writing but weren’t about writing, getting a master’s degree in literature but still thinking I should get a job in business. It wasn’t until I met a TMU journalism professor that I was able to envision writing as a job – journalism seemed like a “practical” way to write, and to make a difference. I loved every minute of working in news and covering politics and business – and that allowed me to start a freelance career when my kids were little, and to, 10 years after that, finally begin writing fiction.
Use your network and make a plan
Networking is crucial for any career, but for me, it was reaching out for coffee chats with people I knew while still working at The Canadian Press that set me up to launch my freelance business. Some talks were just to find out about the different places I could try to work with; others were about how feasible this was. Several of the people I spoke with informally became or led to my first clients. I spent one year working full-time while my kids were one and three, while going for coffee chats and working on the side to prepare for the transition to full-time freelancing. Once I was clear that there was a need for the writing, interviewing, editing, media training and consulting skills I was offering – and enough leads and work lined up to take a calculated risk – I jumped in. That planning and networking meant I had a roster of clients from the start – and I’ve worked steadily ever since.
Be open to your career looking different than what you imagined
My job looked different from that of my colleagues and involved working from home before remote work was widespread. For an ambitious, straight-A student who loved getting gold stars, that was a hard shift. I no longer worked within the buildings that housed Toronto media. My previous office had been at the Queen’s Park Press Gallery; now it was a desk in a corner of my living room. People used to be impressed when they heard about my job, but now they were just confused. And I wasn’t breaking stories that led national news – I was writing profiles or handling projects for companies outside the media. But I was also meeting a lot of amazing people and working with increasingly high-profile clients. I learned all kinds of things I never would have before, and began taking on a larger role in shaping content strategies for several clients. The work I’m doing now is engaging, challenging and uses a lot of the same skills I would if I were still working in traditional media, or as a managing editor at a newspaper. It doesn’t carry that title, but it’s just as meaningful.
Ignore the haters
That lack of title, however, can come with a lack of respect – mostly from people who don’t know me or my work, and whose opinions I really shouldn’t care about. But those voices – internal or external – can be hard to ignore. I used to spend a lot of time explaining to people that I used to have a real job. I’d list my credentials, past titles and university degrees because I thought it would amount to something people could understand. As a journalist, you spend a lot of time trying to convince people who don’t want to talk to you to do so. You get good at it. But that’s easy compared to the feeling you get when you tell people you work for yourself, especially when you have young kids. People dismiss you pretty quickly. It used to bother me, to be miscast in that way. But I’ve gotten to live my life in the way that I’ve wanted – working with amazing clients doing meaningful work and raising my kids with the level of presence I needed so that now that they’re teenagers, they still come to me with their problems and tell me about their life – even when it’s something they don’t think I’ll want to hear.
Stay curious, stay flexible and embrace the chaos
Things worked out well for me, but it wasn’t always easy, and it was often messy. I plan well, but I’m also good with uncertainty and chaos. There is an element of faith in jumping into anything like this, and you have to be able to adapt. I was practical – I took the time to save, research, line up clients and set timelines. There was a path and a window for this thing to work. I never burnt any bridges. I took on some work I didn’t love. Sometimes I took on too much work. I made mistakes and I learned from them. I explored new opportunities; I learned new things to write about subjects I never had before. I kept talking to people, and kept my overall goal in mind: to stay in my field, to write for a living, and to have the flexibility to be there for my kids. Over time, I was able to have steady clients, to be choosier about what work I took on. I work more than full-time hours. But I do it on my schedule. I stayed open to opportunities, and even though I thought I may go back to full-time work or grow the business more once my kids were older, in the last few years, I found myself gravitating towards creative writing. Writing a novel is a dream no younger version of myself would even dare admit to having – but this version of me knows it’s a dream worth pursuing – and has been using everything she’s learned so far to make it happen.
Someone told me early on to look for what success meant to me, not to other people. I’ve never defined success in the traditional ways others often do – big title, big money, expensive stuff. If that’s what makes you happy, absolutely go for it. But if it isn’t, be honest with yourself.
Not everyone will get it, but 12-year-old me would be thrilled to know where I ended up, and that’s more than enough.
