11 / Cultivating user confidence

Welcome to Issue 11!

When we talk about learning experiences, the conversation usually revolves around assessments, learning by doing, and the simple act of teaching the right thing at the right time. But there’s a crucial element that often gets overlooked: cultivating confidence.

I was talking with James Pacheco this week about his transition from finance to technology, and one idea stood out. As you gain experience, you also gain the confidence that you’ll be able to figure things out. That belief compounds. It creates a kind of superpower--the ability to learn anything if you set your mind to it.

Over the years, I’ve worked on a variety of educational and edtech projects. Too often, this part of the learner journey is missing. We focus on content, sequencing, and exercises, but not on building the confidence that sustains learning long after the course ends. If more educators and institutions prioritized this, I feel like the results would be phenomenal.

Now let’s apply that same lens to product experiences. Software is full of moments where learning is required: onboarding new users, rolling out new features, deprecating old capabilities. In practice, educating users is usually an afterthought. Very few teams consider whether their product builds confidence in the people who use it.

That’s why Linear’s documentation caught my eye this week. It doesn’t just explain how the software works. It lays out their philosophy, their approach to the problem space, and the meta-concepts you need to get the most out of the product. Reading it, I felt empowered--like I could learn, adapt, and grow alongside the tool. That’s not just education, that’s confidence-building.

Linear gets a lot of attention for its sleek design, but I think their real differentiator is subtler. They’ve managed to give users the belief that they’ll figure it out. And that belief keeps people coming back.

So as we build our own products this week, let’s explore: how can we go beyond tutorials and walkthroughs? How can we cultivate user confidence in a way that makes them feel unstoppable?

If you give it a try, please reply--I’d love to hear how it goes!

Let’s get Technically Lit,

Nick

Fresh content

A little something different

Continuing to hype up Linear, I really liked how they present their new quality series.