One of the patterns I’ve noticed consistently throughout my career is that the most valuable things I’ve done: building teams, entering unfamiliar markets, learning new technical disciplines, leading through ambiguity, were things I was genuinely bad at when I started. Not mediocre. Bad. And for a long time, I confused that early failure with a signal that I was on the wrong path. It took years of accumulated experience to realize the opposite was true: the difficulty wasn’t a warning sign, it was a defining feature of the thing’s value. If something meaningful could be done well from the start by most people who attempt it, then by definition it wouldn’t be rare, and rarity is a significant component of value.
Why Easy Things Are Low-Value Things
This isn’t a motivational platitude; it’s an economic reality. If you pursue something where a large percentage of people succeed early and often, you are entering a crowded space. The barrier to entry is low, which means supply is high, which means the value of doing that thing well is compressed. Think about it in terms of hiring: if you’re looking for someone who can do something that ten thousand other people can also do competently, you have enormous leverage as a buyer of that skill. The person doing the work has very little leverage. Conversely, if you’re looking for someone who can do something that almost no one does well, the dynamic inverts entirely. The person with the rare skill commands the room.
This has practical implications for how we invest our time, both personally and as leaders guiding others. When I see engineers gravitating only toward tasks they already know how to do, I understand the impulse: it feels productive, it feels safe, and there’s a satisfying rhythm to executing well on familiar ground. But I’ve found that the long-term cost of that comfort is stagnation. The people who become truly indispensable, the ones who grow into architects and technical leaders and CTOs, are the ones who repeatedly chose the harder, less certain path and endured the discomfort of being a beginner again and again.
- If the success rate is high from day one, the skill is likely commoditized or soon will be
- If almost no one can do it well initially, but the thing itself is worth doing, you’ve found something worth investing years into
- The early failure rate is not a bug: it’s the filter that keeps the field uncrowded
Failing Repeatedly Is the Curriculum
There’s a psychological trap that catches many talented people: they succeed early in their careers at things that come naturally, and they build an identity around being someone who succeeds. Then when they encounter something genuinely difficult, something where failure is frequent and progress is slow, they interpret the struggle as evidence that they’re not suited for it. I’ve watched this happen with brilliant engineers who move into management for the first time and feel lost, or with strong individual contributors who take on cross-functional leadership and suddenly can’t rely on their technical fluency to carry them. The disorientation is real, but the conclusion they draw from it is wrong.
The truth is that repeated early failure is the curriculum, not a sign that you’ve enrolled in the wrong course. Every difficult skill I’ve developed, giving hard feedback, making decisions with incomplete information, communicating technical risk to a board, involved a long period where I was conspicuously not good at it. What made the difference was staying with it, reflecting honestly on what went wrong each time, and making incremental adjustments. This is closely related to the idea that our discomfort with difficult leadership moments often signals that we’re engaging with something important, not that we should avoid it. The discomfort is information, but it’s not a stop sign.
- Early failure does not mean misalignment; it often means you’ve found something worth mastering
- Identity built around effortless success becomes fragile when real challenges arrive
- Improvement comes from honest reflection after each failure, not from raw repetition alone
Love the Process, Not Just the Outcome
This is where the old advice to “do what you love” reveals its actual wisdom, which is often misunderstood. The point isn’t that you should only do things that feel pleasant or come easily. The point is that when you genuinely care about the domain, when the work itself is intrinsically interesting to you, you can tolerate the long, unglamorous stretch of being mediocre at it. You can even enjoy that stretch, because the process of learning, of struggling, of slowly getting better at something that matters to you carries its own deep satisfaction. If the only thing sustaining you is the expectation of a successful outcome, you will quit long before you reach mastery, because the outcomes in the early phase are almost uniformly discouraging.
I’ve seen this play out vividly in how different leaders approach strategic thinking. Some treat it as a box to check; they go through the motions because the role demands it, but they don’t find the puzzle inherently compelling. They plateau quickly. Others are genuinely fascinated by the interplay of market dynamics, organizational capability, and timing. Those leaders keep getting better year after year, even when their early strategies fail, because they’re drawn to the thinking itself, not just the results. The failures teach them something they actually want to learn. Over time, this compounds into something rare: a leader who is both deeply experienced and still genuinely curious, still improving.
The ultimate insight here is simple but easy to forget in the noise of quarterly goals and performance reviews: if you invest years becoming great at something that was genuinely difficult to learn, you end up holding something rare and valuable. If instead you optimize for early success and comfort, you end up competent at things that many people are competent at, which is a much weaker position. The difficulty is not the price you pay for eventual value; the difficulty is what creates the value. Learning to see it that way, and to find meaning in the struggle itself, may be the most important shift a leader can make.
