Good mistake/Bad mistake

Newsletter #23

Howdy, friend! Here’s a small win I’d like to share: I’ve managed to workout every day since I started my COVID-19 streak. I hope you’ve been keeping healthy too.


I want to introduce the concept of good mistakes and bad mistakes. This is a tool I use a lot when coaching frisbee, and should probably use more in my daily work. Here are some benefits to this concept:

  1. Improve dramatically faster: I use it to direct players’ attention to the types of mistakes they should be making, versus the ones they shouldn’t. By shifting their focus to the right kind of mistakes, I’ve found players improve dramatically faster.
  2. Highlight what’s valuable and what’s a pointless time-suck: In business, you want to spend time doing high value work. Unfortunately, once you get good at something, it’s always tempting to keep tinkering. Unfortunately, tinkering and iterating tends to be a low value time suck with diminishing returns.
  3. Gain clarity on what’s actually possible: I don’t think people sufficiently explore the boundaries of what’s possible. If you held your breath for 30 seconds as a kid and tried again as an adult, most people will aim for 45 seconds because they’ve already mentally limited themselves. The reality is that if they aimed for 3 minutes from the get go, they’ll probably end up hitting 2 minutes on their first try. Unfortunately, most people don’t do this and hence have no idea what’s possible.

Here are some scenarios of good mistake/bad mistake

Earlier attempts at writing this post had me painstakingly defining good mistake/bad mistake. This is actually my 3rd full re-write of this post. And after 3 tries, I realised it’s easier for you to understand if I gave you tangible examples. So here goes:

You’ve received feedback that your presentations are long-winded and have too many slides.

Bad mistake: You go through your presentation with a fine toothed comb and decide to cut out 8 slides (from 87 slides). Your 1.5 hour presentation is reduced by 10 minutes. Nobody is particularly happy, but everyone can see that you tried.

Why this is bad: You’re still making the mistake of being long-winded, you’re just being a bit less long-winded. You’ve learnt nothing, and all you’ve done is mitigated the mistake.

Good mistake: Forcing yourself to present from 3 slides (including the cover) and limiting yourself to a 15 minute presentation. By going to this extreme, you make the mistake of being too brief and missing out important points. As a result, your boss tells you that you’ve missed out a crucial point.

Why this is good: This sounds bad, but it’s actually fantastic because you now realise your presentation has a total of 4 important points. In contrast, you originally thought you had 27 important points.You also realise that 15 minutes was too short, but 25 minutes would more than suffice.

Key takeaway: Good mistakes are an over accommodation of bad mistakes. Rather than chipping away at tiny incremental improvements, making mistakes on the other extreme lets you see where the boundaries actually lie. You learn much faster and can make huge leaps.

You’re trying to get better at playing the guitar. Specifically, you’re trying to move your fingers more quickly between the A chord and G chord.

Bad mistake: You try to move your fingers more and more quickly. You’re still having difficulty switching in time, but at least it’s getting faster.

Why this is bad: Much like in the previous scenario, all you’re doing is a less bad version of an existing mistake. Sure, it’s an improvement, but a minimal one.

Good mistake: You decide to completely re-learn how you’ve been holding the guitar. In doing so, all your chords become mistakes and it’s like you’re a beginner all over again.

Why this is good: You’re making mistakes that will take you to the next level in your guitar playing. It might feel like you’re moving backwards, but you’re actually laying the foundation for playing better overall.

Key takeaway: Good mistakes let you re-build foundations, allowing you to reach new heights. New levels usually require new foundations. Be willing to re-learn your foundations, even if it means making seemingly beginner mistakes.

You just got promoted and now have 5x more work.

Bad mistake: You work harder and faster. And end up making some mistakes in your work because you’re trying to do too much.

Why this is bad: Getting promoted is like levelling up. What worked for you at level 1, no longer works at level 2. Trying to tackle 5x the amount of work with the same amount of resources is just asking for failure, burn out and anxiety.

Good mistake: You decide to try your hand at prioritisation and delegation. You tell your boss what you’ll focus on and work with your team to delegate. It all goes horribly because it’s your first time. Your boss thinks you have no idea what the company’s priorities are, and your team thinks you have no idea how to manage.

Why this is good: I know this sounds awful, but don’t worry… You’ve correctly identified that your new level means new problems, which in turn means you need new skills to tackle those problems. You shouldn’t expect to immediately kick ass at your new level. Fortunately, courageously attempting to acquire these new skills is what’s going to have you kicking ass in no time.

Key takeaway: Good mistakes refocus on new skills that let you conquer new levels. What got you here, won’t get you there.

This shit is easy to say but difficult to do

People don’t like feeling like a beginner

It hurts your ego, and makes you feel like all your previous effort was in vain. Also, you’re worried that people think you’re lousier than you actually are.

People don’t trust in what they can’t see

Bad mistakes involve doing a bad thing slightly better. You can see what the slightly better version of a bad thing is. Therefore it’s tempting to keep striving just to make that small step forwards.

In contrast, it’s hard to map out a good mistake, or whether it’ll even work if you give it a go. It seems vague, you can’t be sure of the outcome, so you decide not to risk it.

I’m guilty of fixating on bad mistakes too

Here’s an example:

The last full service digital marketing campaign I ran, I fixated too much on Facebook and Google ads. We A/B tested the shit out of our ads, built funnels and optimised our lookalike audiences.

All this brought incremental change.

It also meant that bigger experiments like email marketing and SEO got pushed back because we kept finding small things that were easy to fix. We also consistently told ourselves these fixes were important or urgent.

Towards the end of the year (I worked on this for the whole of 2019), we started doing SEO and saw big improvements.

If only we had abandoned the small things earlier, in favour of making better mistakes by doing completely new experiments. A good mistake in this case would have been to try a new marketing channel (like email marketing) and have it fail on us.

2 things you can do to start applying good mistake/bad mistake

Articulating the good vs bad mistake

I do this when coaching. For example, if someone keeps under-throwing the disc (throwing it behind the receiver), I’ll tell them that’s a bad mistake and that a good mistake is over-throwing the disc (throwing it so far forwards that the receiver can’t catch the disc).

You don’t have to wait for a coach to articulate good and bad mistakes for you. You can determine what they are for yourself.

Keeping it nebulously in your head means you’ll never actually work on it.

Avoiding bad mistakes and encouraging good ones

Once I’ve articulated what a bad mistake is, I tell them that I never want to see them make this mistake, ever again.

I also constantly encourage them to make the good mistake. In fact, the more times they make the mistake of over-throwing the disc, the quicker they understand where the sweet spot actually lies.

Again, you don’t have to wait for a coach. Just encourage yourself. Also, tell other people (and your boss) what you’re doing, so that they can encourage you too.

Here are some good mistakes I’m working on

Finally, in the spirit of articulating and encouraging good mistakes, here are some good mistakes I’m working on.

I’m building a membership plugin called Member Hero. It turns blogs and newsletters into paid subscription sites, which lets independent writers earn money for the work they put out.

Here are some good vs bad mistakes I’m focusing on:

Bad mistake: Building for too long without getting feedback.

Good mistake: Building something quickly and having people tell me it sucks.

Bad mistake: Spending too long focused on one aspect of the business to get it perfect.

Good mistake: Dabbling in a bit of everything to get most things good enough.

That’s it from me. Let me know what good mistakes and bad mistakes you’re working on, and whether you found this dichotomy useful for learning and thinking about work.


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