The Happy Path No One Mapped
The Startup Hired Me. Then They Fired Me. Here’s What I Wish I’d Known.
I’ve spent the last two weeks quietly unraveling in a role I thought I could handle.
I was hired as a Front-end Engineer to build the UI for a customer-facing portal at an AI startup. I thought I was doing what they wanted—stepping back, asking design questions, thinking through user flows. I sketched wireframes. I prototyped ideas. I pushed back on UX patterns that didn’t make sense.
But by the end of my second Friday, it became clear: what they wanted wasn’t thoughtful design. What they wanted was a fake-it-til-you-demo-it “happy path,” no questions asked.
I was let go that Monday.
These are some thoughts.
When Vision Replaces Communication
I was there for eleven days. That’s not poetic exaggeration—that’s a calendar fact. I got the offer on a Monday to show up the next morning. Two Mondays later, I was out.
Somewhere between day 3 and day 6, things went sideways. No one said a word until it was too late.
Everyone has a “vision” in early-stage startups. What they often lack is a shared language, any documentation, or even a basic list of deliverables.
I was interpreting feedback like a designer. They were expecting output like a factory.
That’s how effort turns into noise. It’s how someone who actually cared winds up feeling like dead weight; not because they failed, but because no one ever told them what success looked like.
What the Job Actually Was
They didn’t need a product thinker. They didn’t want to solve UX or product debt. They needed someone to take a Lucidchart and turn it into pixels: mocked. hardcoded. demo-ready.
That’s not a bad ask. But it was never communicated as the ask.
Meanwhile, the CTO assumed I’d take frontend inputs, wrap them in JSON, and call a v1 backend API (which, to be fair, did exist).
By the time I understood that, I’d already spent most of my energy solving the wrong problem. I’d done a lot of the wrong work for all the right reasons—and with the best intentions.
The Emotional Spiral of Misalignment
The thing about looking for a job for 435 days, and then getting let go less than two weeks in, is… well, of course you’re going to gaslight yourself.
You start to believe you were the problem.
You question your intelligence. Your experience.
You wonder, “Would someone younger, faster, smarter have nailed this?”
But the issue wasn’t my capability. The issue was that when everything is urgent and nothing is documented, even the right instincts look wrong.
In every team I’ve thrived in, caring, thinking, and asking questions were how you built trust—and built great products. But in some startups, those are the very things that get you tripped up.
I wasn’t stupid. I was trying to solve a product problem they thought they’d already solved—with a flowchart.
What I Learned (The Hard Way)
Never start without asking, “What does done look like?”
If no source of truth exists, build one—or escalate that it doesn’t.
Clarify whether this is a design opportunity or a delivery fire drill.
In chaotic environments, don’t assume that caring deeply will be rewarded.
And most of all: when there’s misalignment, speak early, speak clearly, speak again.
This Wasn’t a Failure. It Was a Flashlight.
I’m not writing this out of spite. I’m writing it as a marker for myself.
I didn’t rage-quit. I did my best to own any miscommunication on my part. I tried to go above and beyond to fix things, only to realize: they didn’t think anything was broken.
If you’ve ever been hired into a situation where everyone seems to know what’s going on except you?
You’re not broken.
You’re probably just the first person who noticed the gap.
And noticing the gap is the first step to doing better — for yourself, or for the next person who gets dropped in after you.
I’m curious how others have navigated this kind of disconnect. Have you ever worked in a role that turned out nothing like what you were promised? I’d love to hear how you handled it—leave a comment or hit reply.
Reminds me a little of one of my first jobs out of college, where the tiny startup I worked for had three founders, each of whom would often give me conflicting instructions. The lead partner was a brilliant visionary who was an amazing editor but incapable of giving actual initial instructions of what he wanted, so I'd be given the roughest idea of what he needed, go off and produce a polished version of it, and then get the most awful harsh criticism explaining exactly what I should have produced, usually with hand-drawn art of how it should look (but what he couldn't possibly tell me) in the first place. Things like "move this header one pixel to the right." Meantime, he'd tell me my priority was x, then y, then z, while partner #2 would tell me it was really y, then a, then b, then x, and so on. Took me a long time to learn to not take the criticism personally and to recognize that my time was best spent doing a VERY rough initial draft under the guise of "making sure I'm on the right track," since I knew it was psychologically impossible for him to think whatever I did on my own was actually right.
Lasted 18 months before I quit and went back to a tech support job. They were all shocked I was leaving and had no idea I'd constantly been worried I was about to be fired because I was always displeasing at least two of the three. I came back a year later to replace a mid-level manager under the condition that I only take direction from the lead partner. That was 27 years ago; I'm still there, now running the place, having outlasted them all.
You're right, you're not broken. There are too many places with people "in charge" who don't know what they're doing, don't know how to communicate, and don't know how to treat the people they retain. I'm sorry this happened, but it's on them, not you.