I spent years working near complex technical systems without touching them, convinced they belonged to someone else. It took running my own messy, real-world operations to realize the only thing I’d been missing was permission.
I’ve been thinking a lot about permissions lately — not the file-system kind (chmod +x, access controls, the tiny switches that determine what can run), but the quieter internal ones we grant ourselves without noticing.
1. The Line I Didn’t Know I Drew
For most of my adult life, I stayed adjacent to deeply technical work without ever crossing fully into it. I ran products, built companies, partnered with engineers, influenced systems… yet in my mind, there was an invisible line around “real” engineering.
I could advise it.
I wasn’t supposed to touch it.
The odd thing is that I used to touch everything.
2. The Early Clues Were Always There
As a kid, I edited the binary of a floppy-disk game called Petz to create new dog breeds, without any sense that this was “advanced.” On our family Macintosh, I explored every mysterious utility I could open. At a friend’s house, I treated her dad’s Linux terminal with the reverence normally reserved for museum artifacts — thrilling, mysterious, and absolutely something I wasn’t meant to type into.
I wasn’t afraid of breaking anything; I just sensed I was entering a space adults believed belonged to a particular kind of person.
Somewhere between childhood curiosity and adult professionalism, that attentiveness hardened into hesitation. You absorb enough subtle signals — how math is framed in school, the implied divides in early workplaces, the cultural habit of sorting people into “technical” and “creative” — and eventually you internalize the idea that systems have gatekeepers.
3. Reentering the System
My shift back into technical work wasn’t dramatic; it arrived almost incidentally.
The systems inside my business grew more complex, and suddenly there wasn’t anyone else to solve the thorny problems.
A fulfillment issue would appear that forced me into API docs.
A strange inventory behavior demanded understanding how data moved between platforms.
A barcode discrepancy threatened an entire workflow and required me to inspect logic I had never intended to own.
A webhook misbehaved, and I’d find myself tracing the path of a request from one system to another, watching where it bent.
None of this was theoretical. It was operational, urgent, and very real. And because these systems were mine, the work stopped feeling off-limits. The command line — which I’d treated for years like a velvet-roped area of the tech world — became a tool. A quiet, direct place where I could finally see how things actually worked.
Once I stepped over that internal threshold, something shifted. The more I allowed myself to touch the inner machinery of my systems, the more natural it felt. Not easier — just clearer.
Sometimes the biggest technical shift isn’t a new skill.
It’s the moment you stop standing outside the fence.
4. Capability vs. Permission
All of this made me realize that we talk constantly about capability — what people know, what they can build, what they’re trained for — but we rarely talk about permission.
Permission is softer, but it shapes everything.
Permission to explore a tool even when you’re not sure you “belong” there.
Permission to try something before you’ve earned a title.
Permission to enter spaces that have been culturally framed as not “for you.”
Permission to stay curious even as an adult.
Permission to let your hands move across systems you used to only observe.
Permission turns intimidation into curiosity.
Curiosity becomes competence.
Competence becomes confidence.
Confidence eventually becomes fluency.
5. Where I Am Now
I’m still learning every day. I still reread error messages. Still hit bugs that humble me. Still cross-reference documentation twice.
But the relationship has changed. These systems aren’t foreign anymore. They’re places I’m allowed to be — places I can move around in.
Sometimes the most meaningful technical shift isn’t a course or a certification.
It’s simply granting yourself access.
— LW
Shaped with the help of AI as an editor and thought partner. The ideas, experiences, and lifelong commitment to em dashes are entirely my own.