Building Systems through Trial and Error

April 11, 2023

You might want some backstory on how I came to be this all-systems-go, organization-loving creative freak that I am. Because it wasn’t always this way.

I was laid off from my job at a luxury fashion and lifestyle public relations agency in November 2009, one of the many casualties of that particular recession.

(I was a bad fit at that company anyway, and you can imagine how much of a hit so-called luxury fashion brands were taking that time. Long story short, it was a huge relief.)

Before that, I really believed I needed to depend on some type of external structure to motivate me every day. I thought someone else had to tell me I had to have my butt in a chair by 9 a.m., to make me stick around with everyone else even though I had all my daily to-dos finished by 3 p.m.

rusty door reading "new bright idea" — Photo: Casey Barber

For the first time since graduating, I was completely in charge of my days and my time. And with so much opportunity-slash-unknownness, I freaked out.

I needed a budget. I needed a business plan. I needed to figure out how I was going to split all life duties and expenses with my husband while striking out on my own.

Turns out that building your own roadmap is not as simple as filling out an Excel sheet. But it does get you up a little earlier in the morning.

Trial and error

The honest answer to the reason why it took me from 2010 to 2020 to really make my systems gel is that I think technology finally caught up with what was going on in my head all this time.

With so many apps and pieces of software out there for you to budget, make lists, optimize productivity, keep track of your pets’ scheduled food deliveries, it feels like the world is finally making it slightly easier to get your shit together.

How have my systems changed in the past decade?

I used to plan our vacations using a three-ring binder, a Word doc for an itinerary, and a bunch of Mapquest printouts so we’d know where we were going.

Now I create my own itineraries in Notion (and in OneNote before that, and in Word before that), with every piece of information available with a touch on my phone.

I used to have a bunch of physical planners and calendars, painstakingly writing appointments and events on each one so my husband and I would literally be on the same page with our schedules.

Now I use Proton Calendar with automated reminders and bullet journals for handwritten backup. Yes, I still have calendar redundancies.

I started meal planning with a magnetic fridge whiteboard a week at a time, then upgraded to (guess what!) good old Word for my grocery lists, then turned that into a tabbed Excel sheet.

I’ve tried Evernote, Trello, Asana, and probably a bunch of other apps that have flown out of the transom of my mind over the years, and have finally hit on Notion as the one-size-fits-all solution for me.

Mostly because it’s not just for note-taking and it’s not just for productivity and planning, and it’s not just a glorified version of Excel.

It’s all those things and more, and if you’d like to go deeper, let’s connect on how to use Notion as your second brain.

Start where you are

With every iteration of my systems, I’m refining what I’ve been building and learning over the past decade. But it’s not possible to refine and learn unless you have something to start with.

It’s a winding road from a simple Word document to a fully-built-out monthlong Route 66 itinerary, but you gotta take the car out of park, to belabor this road trip metaphor.

So if you think it’s too late or impossible to make your mind less scattered and your life less emotionally cluttered, I’m here to reassure you that it’s not.

You just have to start somewhere. With one list, just one area you’d like to streamline. And if you don’t like the app or the format you’re using, then switch it up!

As a writer, I personally enjoy the redundancy of having a physical planner and calendar as well as a digital one. Maybe you need something similar.

Using trial and error with a few methods and strategies gives you insight into how the gears turn in your head. So you’ll be able to whittle down the most comfortable routines for you personally.

It’s not failure. It’s iteration. Remember that.

Sometimes talking it out with someone else as a sounding board is the most helpful option, giving you an objective view of what you’re trying to accomplish.

Schedule a creative strategy session with me and we can build a roadmap for working through your specific roadblocks or goals.