Finding the right challenge

What does it mean to be challenged? I’ve found the greatest satisfaction in life comes from times I’ve pushed myself to try something new, or something I didn’t think I could achieve and then succeeded at it. This sounds like a truism but facing and overcoming challenges isn’t actually always the hardest part. It’s finding the right challenge to build your skills. I’ve learned this from building products, it’s often harder to identify the problem than to solve it.

Before digging into the ways to feel challenged, consider first what it means to be challenged. Psychologist, Mihaly Csikszentmihalyi explored the concept of “Flow” in the 1970s, this is “a state of concentration so focused that it amounts to absolute absorption in an activity”. In his research, he found that the skill of an individual and the difficulty level of the challenge can create different emotional and cognitive states. When these are matched at the right level for the individual, they can experience a state of Flow. We’ve all experienced this when we get so engrossed in a task that hours pass without us noticing, often described as being “in the zone”.

I first encountered this concept when reading it’s application in game design. There’s been a lot written on the concept and it’s application in many disciplines form sports to the workplace, but I’ve found it’s application in games to be the easiest to understand.

The crux of the concept is quite simple. If the difficulty of the challenge matches the skill level of the player, they can get into a state of flow, where the difficulty of the game increases as their skill level advances. If the difficulty level of the challenge exceeds the skill level of the player, they can become anxious, and if it’s too easy they can become bored.

The “Flow” zone

Not all players are equal, however. Experienced players want the difficultly level to be higher than their skill level to feel a greater challenge, while novice players want to feel a sense of achievement and require an easier challenge.

Different “Flow” zones for different players

By understanding this, we can begin to think about the types of skills we want to build, identify challenges that will allow us build those skills, and match the difficulty of the challenge to both our skill level and player type.


There are three ways to feel challenged.

1 — Increase your skill level in an area of existing expertise. This requires finding challenges that result in building depth in an existing skill you want to master. In these challenges you’re already a hardcore player, and it’s important that the difficulty of the challenge is right for you. Consider the level of your skill and look for opportunities that will challenge you enough in that area to actually level up.

2 — Build a new skill in an unfamiliar area. These challenges are about broadening your skillset. It doesn’t mean trying just anything new, but being selective about what new skill you want to learn, and finding a challenge that helps you build it. Remember, in this new area you’re a novice player, and it’s important to find challenges that will build your skills at the right pace.

3 — The illusion of a challenge — workload. It’s easy to be confuse being challenged by your workload with being challenged by your work. Even the simplest tasks can feel challenging if there’s too much to do. This will feel like furiously running on a hamster wheel. It’s the worst type of challenge. You work hard but effectively build no new skills. You can experience both anxiety and boredom but little satisfaction.


Think about ways to be challenged in the first two and be aware of the third. As you set goals for yourself, think about the skills you want to build, and view the opportunities in front of you through that lens. Without being deliberate about seeking out the challenges to develop new skills, we’ll undoubtably find ourselves on the hamster wheel 🐹 🎡.