Oh, hi friends!
I just realized right now that this year is my 10-year freelance anniversary.
That’s, um, wild.
Looking back on this last decade, I wrote about travel, personal development running, The X-Files, and small businesses. I edited for a luxury fashion magazine, a music weekly, a food website, and of course Money. I ghostwrote newsletters, covered conferences, wrote podcast scripts.
I pitched many stories that were rejected by editors (one of which I just realized I incorporated into Do It Today six years after first pitching it — nothing is wasted). I wrote for $150 an article and $2 a word. I was ghosted by an editor who refused to pay my invoice (it was $400) and have waited eight months to get paid less than that.
But looking back on my Excel sheet of stories and invoices, I’m proud of this mish-mash of opportunities and periods of growth and, if I look really hard, I can see an actual arc. Moving away from covering culture to (trying to) create it. Turning down assignments that don’t sit well (for money reasons or people reasons or if they simply didn’t make sense for me in the moment). And, sometimes, using all that extra space in between — the space not taken up my office politics or drama — to explore new mediums, genres, skills.
Scarcity mindset would not have allowed me to last 10 years. There was always something new on the horizon.
I was inspired to reflect on this after talking with Tim Herrera, a creative and energetic and inclusive editor and now freelance genius, who I really wish I had in my ear 10 years ago. He runs Freelancing with Tim, a newsletter and education platform for freelance writers and self-employed folks. Our podcast chat reminded me how hard it is to take a big leap. But how you can also find good people to help you.
Here’s Tim:
“So I think anybody who's considering leaving a full-time job for freelance life or self-employment, whatever it may be, spend time, on nights, on weekends, developing some thing, whatever it may be, whether it's just making contacts, generating story ideas you wanna pitch as a freelancer, building a newsletter audience, whatever it is, have some thing that you can rely on and turn to once the paycheck stops coming.
When folks kind of jump out into the freelance life without having some thing, I think can be really scary. And I think that's where a lot of the fear and anxiety comes from. When folks talk about wanting to go independent but not really knowing how to do that I think having that plan really softens the landing and can position you in a way that you don't feel the stress and anxiety of, ‘Oh shit, I just left a job.’”
You can listen to our conversation on Spotify, Apple Podcasts, or wherever you get your podcasts.
And I hope you remember to celebrate your anniversaries — the ones that might signal who you were before, and you are now.
And you should sign up for Tim’s upcoming workshops on pitching, contracts, writing personal essays, and more — so much value there!! We appreciate you, Tim!