The Experience Illusion

As a leader who builds and nurtures engineering teams, my desk sees a constant flow of resumes. I see bootcamp grads with fiery ambition, senior engineers with impressive project lists, and everything in between. But a pattern has emerged, a subtle trap that many talented developers fall into without even realizing it.

It’s the resume that boasts "ten years of experience" but lists five different companies, each with a tenure of about two years.

When I see that, a question immediately forms in my mind: Is this truly ten years of growth, or is it two years of experience repeated five times?

Think of your career as a complex system to be mastered. Some people learn the introductory mechanics, master the initial setup, and then, just as the system reveals its deeper, more challenging layers, they start over with a new one. They become experts in the first 10% of the process but never engage with the complex problems that lead to true mastery.

Too many careers in tech look like this. We jump from one environment to another, seeking the novelty of a fresh start, but we often leave before the real learning begins—the learning that only comes from navigating the consequences of our own decisions over time.

The Understandable Lure of a Fresh Start

The reasons for leaving a job are often perfectly valid. A dysfunctional team, a culture that stifles creativity, or a project that is fundamentally misaligned with your values—these are legitimate reasons to seek healthier ground. Sometimes, a change is not only warranted but necessary.

But often, the itch to switch comes from a different place. It comes from the messy middle.

The messy middle is that period after the initial excitement of a new job wears off. The codebase, once a pristine new world to explore, now reveals its dark corners and tangled histories. The architectural decisions you made with such confidence six months ago are now presenting unforeseen challenges. A feature you built is causing production issues, and now you have to be the one to solve it, to live with the consequences of your own work.

This is the point of friction. And it is precisely at this point that the allure of a new job becomes most powerful. Another company offers a clean slate, a new set of exciting problems, and none of the baggage of your current reality. The temptation is to leap, to escape the struggle.

But what if that struggle is the engine of your growth?

The Capabilities You Forfeit by Leaving Too Soon

Growth is almost always on the other side of adversity. The most profound capabilities are developed when you push through complexity, not when you avoid it. When you consistently leave a role before you have to grapple with the long-term results of your work, you rob yourself of the most valuable learning opportunities.

Here’s what you miss out on:

The Wisdom of the Full Lifecycle: You never learn the hard-won lessons that come from maintaining your own code a year or two after you wrote it. This is where you truly learn what makes software robust, scalable, and sustainable.
Seeing the Full Story Arc: You build the exciting "Chapter 1" of a project but leave before "Chapter 5," when the plot twists arrive and the original design has to adapt to new pressures. True expertise comes from seeing the whole story through to its resolution.
Developing Deep Influence: It takes time to build the trust and social capital needed to effect real change in an organization. Hopping every two years means you are perpetually the "new person," long on ideas but short on the relational runway to land them.
Forging True Resilience: By staying through a tough project, navigating a re-org, or refactoring a legacy system, you aren't just improving the codebase; you are tempering your own character. You are proving to yourself that you can handle the heat and see things through. That confidence is an invaluable professional asset.

How to Deepen Your Expertise Where You Are

So, how do you avoid this trap? How do you ensure you are truly gaining experience, not just repeating it?

Commit to Mastery. Instead of seeing your current job as a temporary stop on the way to something better, see it as the very place you are meant to be refined. What hard problem can you solve right where you are? What part of the system is broken that everyone is afraid to touch? Go there. Make it your mission to leave that corner of the world better than you found it.
Find the Meaningful Challenge. You don’t need to work at a world-famous company to do work that matters. There are significant challenges hiding in plain sight in almost every organization. Find a process that’s costing thousands of hours. Find a piece of tech debt that’s crippling developer velocity. Champion the cause to fix it. This is how you create a legacy—not by the logo on your resume, but by the impact you make.
Embrace the "Second Conversation." When the desire to leave strikes, have a "second conversation" with yourself or a trusted mentor. The first conversation is about frustration: "This is broken, and I'm out." The second conversation is about purpose: "Since this is broken, what is my role in fixing it? What can I learn by staying and wrestling with this problem?"

Ultimately, the value you bring to your team and the market isn't just a list of languages you know or projects you've touched. It's the story your experience tells.

A resume filled with two-year stints tells a story of someone who is great at playing the tutorial. It shows you can learn the basic controls and handle the initial challenges. But the world is full of people who can start things.

A career of earned XP tells a different story. It's a story of resilience. It proves you’ve navigated the messy consequences of real-world systems, that you've faced down the complex problems others avoid, and that you know how to get to the finish line. That is the kind of experience that is both rare and invaluable.

So when you look at your own career path, ask yourself what story it tells. Don't just collect tutorials. Start earning the kind of XP that can only be found on the other side of a challenge you refused to quit.