Embracing Difficulty

17 May 2026

Difficulty is often a sign you should be doing something more, not less.

Years ago, I was on a team that deployed their code once a week. These deployments were painful, frequently spanning hours of tracking down noisy alarms and running sanity checks, and the release process quickly became the most dreaded part of an oncall’s duties.

Amidst all that frustration, one of the principal engineers in the org started advocating for us to deploy more. This was not a popular position to take. At first I was annoyed, concluding that they must not be aware of just how painful this process was to make a recommendation so out of touch with reality. But as I came to understand their reasoning, I began to love the idea.

Their argument was that you have two choices when faced with a situation like this: shy away from the difficulty by avoiding the situation, leaving the problems to fester and allowing your fear to become entrenched, or embrace the difficulty by doing it more.

By embracing the difficulty, you start to learn more about why the task is difficult. You develop the context required to make improvements and simultaneously cultivate the motivation required to execute them.

With this mindset we switched to daily deployments and eventually full continuous deployments (i.e. dozens per day). The surprising part for me was that it didn’t require much planning of how to do so successfully; simply by doing it more frequently, we built the skills and knowledge necessary to do it better. We were forced to remove friction from our tools rather than tolerate it as an infrequent inconvenience. Noisy alerts became obvious when we saw the same ones go off every day. While an up-front analysis would’ve found many of the same improvements, we got the same result in less time with less effort just by doing.

In the decade since, I’ve applied this approach to all sorts of things. It’s a wonderfully relevant principle to many tasks in software engineering. With some nuance it might be a useful approach to the rest of life as well.