When I joined my second startup as a full-time engineer, I noticed something interesting about how my understanding evolved. I spent over five years at VividCortex—a database observability platform similar to Datadog or New Relic—before moving to ShiftLeft, an application security startup. At VividCortex, I was deep into databases and observability. But at ShiftLeft, I had to learn the language of security from scratch. At first, I didn’t even know that some of the static analysis solutions we were building were possible. Terms like RASP, SCA, SAST, and DAST were completely new to me, and it took months to grasp their differences and trade-offs. Eventually, I understood why we chose SAST and what the name “ShiftLeft” actually meant.

Over time, I realized startup engineers go through three distinct stages of understanding:

Stage 1: Laying the Foundation
In this initial stage, you’re answering basic but critical questions: What exactly are we building? Who is it for? How are users actually using it? At ShiftLeft, this meant immersing myself in security terminology and learning entirely new concepts. At first, everyone around you seems like an expert, simply because they speak a language you’re still trying to decode. You’re mostly absorbing information and trying to get oriented.

Stage 2: Evaluating the Product
Once you’ve learned the fundamentals, you move into evaluating what’s actually built. Startups typically go through a period of rapid iteration to find product-market fit—experimenting frequently and discarding ideas quickly. As a result, the final product often contains engineering vestiges from earlier attempts. At this stage, if something about the product seems odd or confusing, you begin to realize it’s not necessarily due to your lack of understanding—maybe it just wasn’t implemented correctly. You become comfortable forming your own opinions. You realize not everyone is an expert, and some decisions were simply compromises or mistakes made along the way.

Stage 3: Achieving Enlightenment
After several years, you reach a point where your understanding goes beyond what already exists. By now you have deep insights into your customers, the product, and the broader market. You start to clearly see gaps, and you begin to form strong ideas about how things can be improved. This stage is about recognizing what’s possible, rather than accepting things as they are. It takes real depth—usually at least three or four years—to get to this level of understanding.

Takeaways
If you’re interested in solving hard problems and deeply understanding a space, you have to push through the first two stages. Without investing that time, your understanding remains shallow, stuck at the surface. Spending about four years at one company can give you enough depth to genuinely innovate and shape the future of the product. If you hop between companies every year or two, you might never reach the stage of true enlightenment—where you don’t just understand the problems deeply, but can actually start solving them.