Everything I learned
as a professional planner.
I’ve spent the last year trying to find the perfect “system” as a freelancer. Then I came at the problem like a teacher.
A lesson in writing and life: Over-plan & be flexible.
I may have left the teaching career, but I have found a way to apply what I’ve learned as a teacher to my writing routine.
As a teacher, I truly do believe that you become a professional planner.
Little known teaching secret: There’s no playbook. No one’s giving us a schedule to follow, procedures, or even the curriculum sometimes - not really. We have a pile of resources that we use to build a plan.
We’re constructing that plan every week and tweaking it always.
Here are the two things I know about planning from having been a junior and high school English teacher:
Over-plan. Ever been caught in front of a room full of teenagers with nothing left to say or give them to do? Zero stars; do not recommend. I learned early on in teaching to ALWAYS over-plan. It’s always better to have more to do than what you actually have time to do. Overplanning isn’t just about not running out of stuff to do. It’s also about getting good at pinpointing what’s most important. Because you won’t get everything you want to get done in a day - or a week - but with overplanning, you’ll be able to start seeing what’s most important. So, no - you’ll never get to all of it - but you’ll accomplish what’s most important.
Be flexible. Ever have the most beautiful, carefully laid out plans for the day? And then, they do not happen? Might it be fair to say that our plans never go EXACTLY the way we plan? Teaching will teach you that plans are nothing but a blueprint. Many things will happen that we could not have planned for. So we get really good at crossing stuff out that doesn’t really need to happen, or pushing stuff off until the next day or week because… things have changed. They will always change. Get good at adapting - and revising the plan - quickly.
Perhaps the best part of being a freelancer is that you can have a sick day if you need it and then move things around to catch up, or you can be more productive on those high energy days and take the days off you need to recharge, without guilt. That’s why a rigid freelance schedule has never worked for me.
By overplanning and remaining flexible, I get the most out of my freelance work plan for the week.
Some things I’ve written recently:
This might be my personal favorite article I’ve written so far. That’s because I blended a first-person personal essay with real, in-depth research and closed it with a solid point. Oh - and it’s about Jolabokaflod, the Great (Icelandic Christmas) Book Flood.
By the way: this article was written for Hard Copy, and their podcast - Your Weekly Breakdown - was one of Apple Podcast’s Best of 2025.
Over the holidays, I had this thought about home becoming more novel after you move away and got to write about that for Insider.
I have always wanted to be a futurist but have little proof beyond my word** that I can actually predict future cultural trends. Sooo, I decided to prove it this year and made 8 predictions for 2026 that I’ll circle back to you this time next year.
**My son told me that all the girls are singing Djo at school… I’ve been crushing on Djo and Joe Keery for the last year, but after the last season of Stranger Things, he’s having a moment. He even took Taylor Swift’s 78 day streak at the top of the charts with him.
Here’s what I said about him on March 20, 2025: “So I think I have a creative crush on Joe Keery; I watched him in Marmalade (available on Hulu), which I do recommend for the unexpected charm, plot twists you don’t see coming, timely cultural commentary, and even the drive of a son’s love for his mom, but I also can’t stop listening to the two songs Djo, Keery’s band, has released ahead of their full album release, The Crux, on April 4th: Delete Ya and Basic Being Basic.”
What I’m reading/watching/listening to:
Reading: Here are 3 recent articles I read worth sharing:
I really liked these Everygirl ideas for reading goals this year…
Not happy news by any means, but awareness is so important; heat caused a mass mortality event of Flying Foxes in Australia. I have a real soft spot for bats and recently wrote about the Bat Houses at UF in October and again on Giving Tuesday.
Journalist Laura Jedeed conducted an experiment: how easy would it be to be hired by ICE? She was hired without a background check, inviting this important question: How many ICE agents have a record, such as domestic violence, rape, or crimes against children and other vulnerable citizens?
Watching: I’m leaning hard into my roots this (long) weekend…
The University of Miami is in the college football championship on Monday; I grew up in Miami as a Cane, but later grew into a Gator as an adult). IYKYK that’s scandalous. But this weekend, I’m taking my orange and green card out and rooting for my hometown and The U Monday night. Sure wish I was a UM student this weekend.
I followed Only in Dade before Marcello was on SNL… or had a special on Netflix !!?? I’m so happy for him - and for me - because I get to watch his special this weekend.
Rented Cuban Food Stories from the library - been dying to watch this for years, and I’m finally going to get to on my cozy, hometown-energy weekend. I have always found the history behind Cuban food fascinating, how they were able to work with what they were given in rations to make dishes that are still flavorful and cognizant of the culture before the dictatorship.
Listening: I’m listening to this gem from 1978 about a Russian dictator on repeat - it’s infiltrated both my son’s and husband’s brains - hashtag: sorry, not sorry? This song really captures the present vibe imo… “This man’s just gotta go!” declared his enemies.
And here’s a writing opportunity:
June Road Press is accepting poetry for an anthology until March 15, 2026. No submission fee; payment is in royalties.
And a prompt:
Make up jobs you’d love to have but don’t exist (yet).
Write on,
Ashley