How This Messy Journey Started
Okay, so back in early 2015, I felt stuck. Real stuck. My office gig just felt… grey? And my Virgo brain was screaming “Systems! Order! Meaningful Work!” every damn Monday. So I decided enough was enough. I grabbed a cheap notebook – seriously, the dollar store kind – and wrote at the top: “WTF Am I Doing? Fix This NOW.” Felt kinda dramatic, but hey, it worked.
Actually Putting Pen to Paper (Old-School Style)
First thing? Staring down what sucked. No sugar-coating. I scribbled:
- Job: Bored out of my skull, felt like a paper-pushing robot.
- Skills: What skills? Felt rusty AF.
- Dream Job: Fuzzy. Something “helpful,” maybe “organized”? Useless.
- Freak-outs: Daily, about money, being stuck forever, wasting time.
Seeing it all dumped like that? Brutal, but man, it cleared the fog. Then came the Virgo Overdrive. I mapped my week like a drill sergeant:

- Monday/Wednesday: 7-8 PM – Google the heck out of “jobs Virgos are good at.” Spoiler: Lots of admin, HR, writing stuff. Saved links (remembered “no URLs,” just notes!).
- Tuesday/Thursday: 7-8 PM – Annoy people. Literally. Emailed three friends in fields I thought might fit (healthcare admin, project coordination, technical writing). Asked them: “What’s your actual day like? What sucks? What rocks?”
- Saturday Morning: 9-11 AM – Brainstorm attack! Looked at notes from the week. Compared what sounded good VS what sounded like hell. Highlighted anything that made me think “Huh, maybe?”
The Hard Part: Making Myself Do Stuff
Talking was easy. Doing? Not my jam. My inner critic screamed “YOU’LL FAIL!” every time I opened my laptop. So I tricked myself. Tiny wins. Like, “Today, you just update ONE bullet point on the LinkedIn profile. That’s it.” Did that for days. One sentence here. One skill added there. Felt pointless, but it built momentum.
Biggest hurdle? Applying. Even for stuff that kinda fit. I’d write a cover letter, stare at it, rewrite it, hate it, delete it… damn near burnt out before hitting send. Broke it down:
- Step 1: Found ONE job post I liked 70%. Printed it.
- Step 2: Used a marker pen and physically highlighted keywords in the job duties (like “organize,” “analyze data,” “communicate clearly”).
- Step 3: Went to my messy resume. Hunted for ANYTHING that matched those words. Even tiny tasks. Scribbled on the resume where I could add those keywords.
- Step 4: Rewrote JUST THOSE BITS on the computer draft. Didn’t touch the rest yet. Told myself: “Just make these bits match.”
Took hours for that first one. Felt inefficient. But it worked. Got an interview!
The “Success” Part (Wasn’t Overnight!)
Success wasn’t landing the C-suite job. Nah. Success looked like:
- The Notebook: Filling it with messy, honest thoughts.
- Applying: Finally hitting “Submit” on that first terrifying application.
- Interview: Surviving one without puking (almost did).
- The Win: Getting an offer for a Coordinator role at a small education non-profit mid-year. It used my love of systems (yay, spreadsheets!) and helping people. Not fancy. Paid less than my old soul-sucking job, but felt RIGHT.
The biggest lesson? Using my Virgo love of steps and analysis against the anxiety paralysis. Breaking everything – the fear, the research, the applications – down into dumb, tiny, doable actions. No magic formula. Just stubborn, step-by-step grunt work, plain as oatmeal. And honestly? Still kinda messy today. But it moved me.
