Startups | 3 min read

Finding the right challenge

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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 tried 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. The same is true for 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. In the 1970s psychologist Mihaly Csikszentmihalyi explored the concept of “flow”, 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 about its application in game design. A lot has been written on the concept and its application in many disciplines from 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, and the difficulty of the game can increase as their skill level advances. If the difficulty level of the challenge exceeds the skill level of the player they can become anxious. If it’s too easy they can become bored.

Flow sits between boredom and anxiety

The “flow” zone

However, not all players are equal. 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.

The flow zone is different depending on the skill level of the player

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.

The three ways to feel challenged

1. Increase your skill level in an area of existing expertise

This requires finding challenges that will build 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 really 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 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 wary 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 challenges to develop new skills, you’ll undoubtably find yourself on a hamster wheel.

Are you looking for a new challenge in your career? We’re hiring!