I’ll share something with you that I feel a lot of guilt and shame about: I’ve never been much good at pitching ideas as a freelance writer.
Or maybe it’s that I’ve never really tried, and therefore never really succeeded.
I’m not sure if people would know this about me just by looking at my clips. After all, I’ve written hundreds of pieces for at least a dozen sites and publications, interviewed many cultural icons, and published myriad newsletters and podcast episodes. I have done a lot of good work that I’m proud of—especially at staff jobs.
You see, it was never much of an issue for me to come up with ideas to pitch when it was my day job, and I had a boss and KPIs and weekly deadlines to worry about. I rose through the ranks at Time Out New York—from Things to Do Editor to Editor of the whole kit and caboodle a couple of years later—for a reason: I was ambitious, often asked for more responsibilities, and wasn’t afraid to try out new formats or cover off-the-wall events. And I’d talk to anyone. I wrote my first reported essay about trying out online therapy back in 2015, an idea that was all mine. And when my editor was looking for a sex and dating columnist, I told her I’d love to take on the challenge. Eventually, she gave it to me, and I wrote the Let Us Sex-plain column for two years.
So it’s not that I’m lazy (even though I call myself that sometimes) or that I don’t love writing and reporting (there are few things I love more) or that I don’t have good ideas (there’s a lot of published proof that I do). But when it comes to pitching my own ideas to publications that I don’t explicitly work for, I’ve always come up against huge creative blocks. And now I’m a full-time freelancer who needs to overcome all this to be successful. I’ve never quite been able to pin down the root of my resistance—maybe it’s fear of rejection (which you get constantly as a freelancer), or not being good enough to write for the publications I admire most. But whatever my psychic hangups are, I got a reminder of just how much they’re still holding me back recently.
At the end of 2022, I did my due diligence to get to inbox zero and I discovered that the dregs of my inbox were littered with years-old emails to myself with my own ideas—cryptic subject lines here, a couple of dashed-off sentences there, even which outlets to reach out to—things I had managed to scribble down and send off into the digital ether. But I never returned to tend to them. Instead, they sat in inbox purgatory. I read through old email chains from editors at popular publications asking me to pitch them or connecting me to their colleagues. They gave me a direct in, and I walked away. Even worse were the eager responses I found from story leads, sometimes from people who are Very Big Deals, that I just never responded to—a slap in my face as well as theirs.
It is devastating to think of the countless ideas I had during the nine years I lived in New York City that died between my ears.
All of those bylines that could have been mine. All of those missed connections. So much wasted opportunity. Yes, I’m being hard on myself, but this is tough love I need to hear.
This experience of seeing my ideas orphaned and discarded depressed me. What was my deal, anyways? Why was I dimming my own light? I used having a full-time job (where I had to pitch, write, interview, and edit every day) as an excuse not to pitch or take on outside creative gigs for a long time, which was half-true. I’ve never been a workaholic by nature (and I’m even less of one now) so I was disinclined to work more than my allotted 40 hours a week. But I did have leisure time in my 20s—I just invested it in partying and socializing instead of cultivating my creativity. I suppose I can’t fault my 20-something self for making fun her top priority.
But times have changed. Every day since I got laid off from my last full-time job in March 2020, I’ve slowly but surely kicked and screamed my way toward creativity. I decided to try—actually try—to be the writer I knew I could be. I wanted to live up to my own potential before I died, which in 2020 felt like it could be any moment. I finally bet on me.
And so many things blossomed. This newsletter gave me a place to worship my own ideas, then set them free with all of you. I ran with an idea for a podcast, and I made two seasons I’m super proud of, connecting with creatives I adore. And, out of financial necessity, I began to gather my courage and pitch my ideas. I got published in Marie Claire and Cosmopolitan and Pop-Up magazine and several other publications online and in print. Writing—both on the creative and corporate side—is now a main source of my livelihood.
When people ask me what I do I say, without hesitation, “I’m a writer.” It took years for me to get here.
So I’ve come a long way, and I’ve watered my own seeds. The me of three years ago would be very proud. But all of those dead-end ideas in my inbox served as a stabbing reminder of how much more I’ve yet to do—not because I feel I should, but because I want to. I have so much more to give and create, and my art has a space in this world. It’s up to me to carve it out.
This year, I chose one overarching goal for my creative life: to give my ideas the respect they deserve.
That means recognizing them when they bubble up, writing them down immediately, taking quiet time to contemplate, collecting them in a spreadsheet I return to often, my grotto of thingamabobs. My ideas need to breathe, and it’s my job to give them air. And then it’s my job to get them in front of the right editors and decision-makers who will help them reach the right eyeballs. That last part is crucial, and the part I’ve often failed to land in the past. No more.
Last week, an idea for a podcast came to me, emerging into my psyche like a lighthouse beam piercing the fog. I noticed it, latched onto it, gave it mental space right then and there. I wrote down some notes, thought about format. Then I called my friend Mike Kelton, who has his own podcast (Beyond, which explores the supernatural and is an absolute delight) to talk through the concept. He listened and gave excellent feedback, and I left the conversation with a rush of good feelings toward this nascent idea, bonding with this newborn vision skin-to-skin.
A new creative connection recently told me that she firmly believes that if the universe gives you an idea and you don’t do anything with it, it will give it to someone else who will. She learned of this concept of ideas as energetic viruses from the author Elizabeth Gilbert.
Gilbert has often talked about how she once halfheartedly worked on a novel set in the Amazon jungle, then set it down. One day, she discussed the novel idea with author Ann Patchett, who revealed that she’d been working on a novel set in the Amazon jungle with remarkably similar plot details: State of Wonder, published in 2011. They had never previously talked about their ideas to each other, never seen each other’s drafts, yet they ended up with matching key concepts. Gilbert maintains that the universe gifted her idea to someone else who would see it through.
This week, I received my own message from the universe.
My ambition has returned, and I’m motivated. I will keep developing my new podcast idea. But I am also doing some big thinking on how I can rebrand and reshape this newsletter so it can meet me and my creative process where I’m at now, rather than where it started almost four years ago (!). More to come on that in the future, once I’ve had some planning sessions with the HSC (Higher Self Committee).
For now, here’s one thing I know for sure: It’s finally time to read Big Magic: Creative Living Beyond Fear by Elizabeth Gilbert, a book that’s sat on my shelves for years. I’m ready, universe.
I LOVED Big Magic. Absolutely loved it. Big Magic reminds me of The Creative Act, Rick Rubin's book that I am reading right now, and both share the philosophy that ideas are germinating in the collective. And that when they land on us, it is indeed UP to us to decide if we will be the messengers! Thank you for this Jillian, meeting you and talking to you was the kick I needed to take my own book idea, and really invest my time and energy in it this year. (First step: finding an agent!)
Big Magic is such a game changer! I also found Artist's Way to be very helpful, as a fellow writer also aspiring to lean further into my creativity.