Introduction

A really common failure mode that I observe in myself and others is to get stuck and then give up. To be working on a problem, or trying to generate ideas, find it hard and stop looking. I find that this goes hand-in-hand with the far larger problem of being trapped within your preconceptions - to notice the obvious solution to your problem, the obvious life path ahead of you, the obvious thing somebody in your role should do, and never realising there can be anything more. I think this is a really big problem, because the world is large and complicated. The space of possibilities is enormous and the ability to search beyond what’s obviously visible is really valuable for noticing when you are wasting motion.

I think these problems are, at their heart, a lack of creativity. I think creativity is an incredibly valuable skill and, importantly, a learnable skill, not an inherent trait. This is a skill that I still suck at, but I’ve improved a lot at over time, and this post is my attempt to outline the approach that’s worked best for me.

This is obviously a useful skill in settings like doing art and research. But I’ve found it useful in a wide range of areas in my life. A few highlights:

Solving personal problems
Giving advice to others
Solving the small problems I run into when doing work
Finding ways to have fun
Finding projects I feel excited about

5 Minute Timers

I think there are two main insights here:

Generate then filter ideas

I’m a massive perfectionist, and I find it easy to slip into the failure mode of generating the perfect idea. This is incredibly unhelpful, because this is paralysing in practice, and means I struggle to come up with anything. Any weak and half-formed ideas are discarded before they can be fleshed out into something worthwhile
This is an example of a general failure mode - trying to both generate and filter at the same time.

I find that these involve very different parts of my mind - generating ideas should feel free-flowing and diffuse, while filtering should feel constrained, directed and focused. And these different mindsets can’t be activated at once, so in practice I’m either neglecting one or rapidly switching between them

This especially applies when it comes to any decision that feels scary or overwhelming - eg thinking about life decisions

And this is super, super bad, because often the scariest thing is something unknown and fuzzy! By making the unknown feel clear and concrete, often it’ll feel a lot easier to pursue, so this leaves me stuck in a catch-22.
For example, I was recently considering the idea of taking a gap year, and feeling a bit overwhelmed by the idea. So I decided to sit down for an hour, and generate a list of 50 different things I could do in that year. This was a really useful exercise, and would’ve been completely impossible if I’d spent that hour overwhelmed by the thought of actually doing any of them

Hard does not mean impossible

A common failure mode is to feel stuck and give up. This is completely understandable! Feeling stuck is unpleasant and hard, and pushing through it takes willpower
But, in practice, while it may feel like being stuck means something is impossible, all it really means is that something is hard. This is important, because the solution to an impossible task should be to give up, while the solution to a hard task is often to just keep trying! This is a super common and subtle error, and it’s important to notice it in the moment
I’ve found that overcoming this gets a lot easier with practice - it’s difficult to make yourself continue on a task that feels impossible and fruitless, even if you know it’s all in your head. Only after having some genuine successes can you begin to change how you feel about this.
More generally, I find that overcoming this is a key subskill to becoming a person who Actually Does Things, and to do anything particularly interesting or unusual. If it’s something that most people don’t or can’t do, then there will normally be some kind of mental barrier in the way. And while it’s valuable to know your limits, you should try to know your true limits, not the cached thoughts of what you think your limits are.

Of course, as with any insights that take willpower to apply, the solution is not to try harder, it’s to systematise them! And my main tool here is to notice every time I want to be creative, set a 5 minute timer, get a blank document up or a piece of paper and generate solutions until the timer goes off.

This is one of my favourite life hacks, for both sounding so ridiculously simple that there’s no way it actually works, and being incredibly useful in practice. This lets me implement both insights in a super low-willpower way! I spend the full 5 minutes generating and, because I’m under a fairly sharp time limit, it’s easy to remain focused. This means my mind rarely wanders, and I can maintain the mental distinction between generating and filtering, there isn’t enough time to get distracted like that! And it forces me to continue past getting stuck, because it’s only for 5 minutes! If I really need to, I can just sit there for 5 minutes staring at a blank piece of paper. But, in practice, I always come up with something.

Further, this is something you want to be systematised - it should be a reflex. I try to always have a physical timer within arms reach (I recommend this style for great visuals) to make it as easy to do as possible (I also like the ability to say “Alexa, 5 minute timer”). And I’ve cultivated the habit of noticing any time I feel stuck, or out of ideas, or when I’m doing anything remotely important, and starting a 5 minute brainstorm. The fact that it’s 5 minutes, specifically, is pretty arbitrary, 4 or 6 minutes would work equally well. The point is to have a single default time, to minimise the activation energy of setting one.

Even though I’m fully convinced that 5 minute timers are awesome, an embarrassing amount of the time I still notice myself complaining about or dwelling on a problem without having spent at least 5 minutes trying to solve it! And I also notice this a lot in other people, to the point where one of my favourite questions to ask people is “have you spent at least 5 minutes thinking about this problem?”. 5 minutes is such a short amount of time, that I don’t think your answer to that question should ever be no. I think a great social norm, if you ever notice this failure mode in yourself or somebody else, is to set a 5 minute timer and have both of you think about the problem. (Anyone reading this has an open invitation to ask me this question if you ever think I’m not trying hard enough!)

Frankly, I find it somewhat depressing that anything as simple as this is so useful. And I think it’s reasonable at this point in the article to feel skeptical. So, if you do, I propose a test: Set a 5 minute timer, and make a list of problems in your life - things that annoy you, things you want to work on, things that could be better. And then, go through that list, and cross off any you’re confident you’ve spent at least 5 minutes of focused time trying to solve. If you’re anything like me, you’ll have an embarrassingly long list left over. I’d be pretty curious about what happens if you try doing a 5 minute brainstorm for anything left.

Alternate sources

Another great source of creativity is using other people! As Nate Soares notes, often the advice that feels obvious to me doesn’t feel obvious to somebody else, and vice versa. We all have our standard toolkits, and ways of seeing the world. And these vary a lot between people! Asking people for advice or suggestions is almost universally useful when you want to expand your horizons of possible ideas. I’ve lost count of the number of times someone has given me a suggestion they thought was obvious that I’d never have come up with, but seemed instantly insightful when I heard it.

You can also use 5 minute timers in groups! Whenever I’m part of a group discussion, I think it’s extremely useful at the start to set a 5 minute timer, and have everyone generate ideas on their own, and then share. It’s super easy to get anchored on other people’s thoughts, and this ensures we can start out with a wide range of

Conclusion

I think being creative is a really useful skill. And that if you aren’t setting 5 minute timers for yourself, you’re missing out on some incredibly low-hanging fruit. Cultivating this habit has significantly increased my ability to be creative, and come up with ideas I missed on the first pass.

More generally, it’s difficult to notice in the moment to start a 5 minute timer. I think it can be useful to practice and explicitly develop the habit! I find it pretty consistently useful to try it on open-ended, introspective prompts (in, eg a weekly review). So, if this article has resonated with you, here are some examples I’ve found useful. I recommend picking a prompt that seems fun to you, and spending the next 5 minutes thinking about it! After all, the best time to start a new habit is right now.

What am I procrastinating about?
What am I stressing unnecessarily about?
What’s a mistake I’m currently making?
What’s something really awesome I could do today?
What obvious ideas am I currently missing?
What’s something nice I could do for somebody else?
What are the coolest things I’ve learned recently?
What’s my biggest bottleneck?
What am I currently grateful for?

Finally, if you’ve gotten through this entire article, and it doesn’t feel relevant to you. That you can’t come up with areas of your life where you’d like to be more creative. Then, well, that in itself feels like a lack of creativity. I’d be pretty curious to see what happens if you set a 5 minute timer, and try to generate places you could use these ideas.