My 20-year freelance writing career has been an amazing journey so far. Here’s what I wish I knew as a writer 20 years ago.
Twenty years ago was a turning point in my writing career. It’s when my strictly news journalism career began evolving into my expansive writing career in food, parenting, journalism, personal essays and more that I built from there. Since then, I have grown from reporter to editor, author and college instructor. My work has been the key to entry into so many rooms. But the lessons I learned along the way are what ultimately helped me thrive.
I just wish I had learned them sooner. In 2005, a series of decisions changed the trajectory of my career. I wouldn’t understand how fundamentally that would be true for a long time.
I’d just had a baby — my son Will — and in the heady, hormonal postnatal period I shocked everyone when I quit my beloved reporting job to stay home and freelance. And then I quickly realized two things: I’d done the leap to freelance wrong (never quit until you’ve broken in!) and I couldn’t be happy without writing. That’s when I made the second shocking decision: I was going to be a food writer so I was starting a food blog while taking every writing assignment I could get.
It was 2005. Blogs were still new and relatively unknown. Moreover, it didn’t lend a direct path to income, so I was taking a massive leap of faith. It also didn’t help that I didn’t really know how to cook at the time.
When I think back to that time, I wish I could whisper so many things in my young writer ears. Here’s some of the most important ones:
Your Background in Journalism is an Asset, Not a Hinderance
This seems so obvious to me now, but at the time I didn’t see it. As I started inching my way toward writing for websites and magazine, I worried that my background in newspapers would make me an automatic no. My writing style was concise and wrapped around the transmission of facts. I often omitted or minimized that experience when I was pitching stories or talking to editors.
Now I realize I should have been treating my newspaper background as an asset instead of a liability and helping everyone else to understand why.
Choose a Speciality and Lean in Hard
Though I wanted to be a food writer, I didn’t want to just write about food. As I began building my career as a freelancer, I aimed to be the ultimate generalist. I took every assignment across every subject. From VoIP to human resources, user experience to digital marketing, pregnancy to food, health to hiring, I wrote a little of everything. It was years before I really zeroed in on specialities because being a generalist was a smart business move at the time.
However, hindsight is clarity. If I could advise my younger self, I would tell me to specialize in a few areas much sooner. Although in the short term it would have been harder, the long term benefits of being a known voice in specific topic areas far outweigh the temporary success.
Promote Yourself
It’s a funny thing: I don’t love talking about my work. It can feel like bragging, and I never want to do that. But promoting what you are doing is essential to career success. If you aren’t talking about your wins, who will?
If I could talk to myself 20-years-ago, I would tell her to learn how to self-market very early and do it often. You never know who might have a useful connection that could open a key door.
Some Areas of Life Will Be Off Limits
As a reporter turned digital writer, I have lived my life out loud for decades. From pregnancy on, I have written about my feelings, thoughts and so much more. And for awhile, I didn’t think there was anything I wouldn’t write about. But when it came time to separate from my ex-husband, a hard wall clamped down. Though astute readers saw through the lines of what I wasn’t saying, I realized there are parts of my life I wanted to be private. Since then, I have made similar choices around friends, family and my children.
Though I came to this realization naturally and when it mattered, I wish I could tell my younger self that it’s okay to set parameters on what the public knows. Moreover, I wish I could also tell that younger me to journal ferociously for myself. I’d love to have that window into what I was thinking — even if it wasn’t for publication.
Don’t Shy Away From Defending Yourself
One thing about the wild wild west of the internet that it took me decades to really accept: this isn’t like the newsrooms I came up in. The code of ethics that governed how journalists approach their work, and even how they interact with each other, doesn’t exist — not even now. And that means sometimes you have people jumping to conclusions.
Ultimately, you cannot control what people assume. You can only control how you respond. For a long, long time, I thought the best response was no public response. But these days, I realize that silencing myself was never the right thing. Responding publicly and directly — and not being intimidated by internet bullies — is the way to go. I so wish I could tell younger Sarah that.
Since quitting my full time reporting job at the New Haven Register in the mid-aughts, my career has taken me to places and segments of the industry I never imagined. I love what I do. And although hindsight shows us what we could have done better, it is the lived experience of this career and life that led me here. All of this is to say, I love my journey and I’m proud of it.
All the same though, I do wish I could predict the lessons I’ll wished I learned sooner when I reflect back 20 years from now.
So why that image for this post? It captures something that may not be obvious about freelance writing: it’s a constant hustle. You are pitching, writing and imagining new pitches all the time. That means you’re always going, always have a laptop near and always seeking the thing that will keep you alert. This image shows coffee (oh, sweet caffeine!), a sandwich (fuel for the body) and nearby laptop, a familiar scene for me over the last two decades.
