The Best Worst Mistakes of my Life

I cocked-up my Cambridge interview. You know the ones (no, I didn’t either) where candidates who look good enough on paper (in my case, for a philosophy Masters) need to also look good enough in person. Well, having long harboured (completely unfounded) aspirations to attend ‘Oxbridge’ this Aussie country kid was about to come good and she cocked it up — possibly my worst error of judgment in my academic philosophy education.


Because it in fact turned out to be the best of my ‘worst’ mistakes to date. And it heads quite a line of jolly good-bad mistakes so far in my academic life. Such as taking all of my first and a bit years of undergrad of ‘not giving a toss’ combined with ‘just could not be bothered’ to realise I was never going to be an engineer — well not one that gave a toss or could be bothered. Then, by some cosmic accident, never knowingly done philosophy, I signed up to major in it. And not to disappoint it took quite a lot of my own know-it-all, smart-arse, and being-a-dick mistakes to properly figure out how this being a philosopher business works.

‘Congratulation — you’re a screw-up!’ you shrug. ‘Aren’t we all?’

‘Yes! Yes, indeed,’ I say, ‘and it’s so very important that we all are.’

Luck, mistakes, and lucky mistakes, unlucky ones too, along with plain getting it wrong are much maligned. However, that is just another mistake — the worst.

Our desire for hard-earned perfection is insatiable, eternally striving to ‘not put a foot wrong’. No wonder we’re all exhausted. But it actually means we just miss out on putting our foot in any place of real value, like in our mouth, down the wrong path, or in sight of shooting ourselves in it. Instead we should get more closely acquainted with wrong-footedness. Embrace our mistakes because they are the only way to find out what is genuinely worth knowing, having, being.

Last time, in my attempt to defend and show how to approach philosophical expertise, I mentioned that luck and accident will dictate your first encounters with philosophy. And my suggestion for navigating this situation is to choose wrong, repeatedly. So we had better become good at this choosing. As there are better and worse ways of being a screw-up, here are some of the better.

Do it.

Although I have previously argued against it, there is massive pressure to look smart. It seems like our only options are to say something impressive or nothing at all. Our fear of appearing stupid is so strong that when we are truly puzzled and desperately need to say so we tend to go with the nothing at all — which is properly stupid. There is another option.

Do ask the obvious question, always. It is probably not so obvious, rarely anything ever is in philosophy. And even if it does turn out to be obvious, that doesn’t make it stupid. It is only a stupid question if you already know the answer or are not genuinely interested in it. As only those trying to impress (i.e., the know-it-all, smart-arsed, dicks) who ask things that they already know yet don’t really care about.

Keep asking until you are satisfied with the answer. The first answer is not always the obvious, right or best, especially for you. Remember you are asking to allay your puzzlement. There is no point just going with whatever comes out before you have understood it. Of course, such satisfaction is hard to get. It is unlikely to happen in one philosophical conversation. That is why being a philosopher is a life-time gig.

Do it on purpose.

We do many things by accident, by mistake. However, the most informative occasions can be those where we go wrong by choice. Now, I am not recommending you turn idiot, masochist, or criminal. Just that, since we rarely get things right the first time, we try new things out in a conscious and reflective way. That is, to consider ‘I wonder what would happen if…’ before ‘oh, I didn’t expect that to happen’; and afterwards to think about ‘so, what went on, here’. (This compliments the imitation that I have previously discussed.)

Admit it.

The scourge of perfectionism is that even when you cock-up, you need to look like you haven’t. We then spend much of our time pretending. Pretending ‘it is this other person/thing’s fault’ or ‘I meant to be that way’ or ‘insert your nonsense here’ While, it would be quicker and exceedingly better to simply admit it. Then you are able to gain something from it. For if you never genuinely acknowledge where you go wrong, nor think about why, you cannot learn from it.


Persistence is important. But make sure it is the right kind. Unthinking repetition of the same bad idea won’t make it a good one. Whereas, reflecting on your past attempts in order to improve your future ones is the best route to the right idea.

Be lucky.

We are very caught-up with being entirely self-made, making it by hard graft alone. Although we knock it, nevertheless, so much of our lives is dictated by luck and accident. Where, when, and to who we are born, the school we are educated, the first philosophy we read. It seems silly then to completely forsake our luck. Be careful, while you are obsessed with toiling away your best chance might be passing you by. Instead, I suggest be open to what your lucky encounters might bring — it might be beyond what you could imagine working on your own.

Lastly, be safe.

To openly make mistakes, and admit to them, makes you very vulnerable. To do it well requires safe places and people to support you. The world of philosophy has a culture of ruthlessness, which makes places where it is safe to fail hard to find, yet not impossible. Start small. As I began this blog — go for a coffee, have a conversation, cultivate a trusted philosophical friendship, then you can confidently reveal ‘I don’t understand.’

Well, I missed out on Cambridge. Honestly, I still have no idea what they wanted, only that at the time I was not it. To repeat, lucky. Because it meant I unexpectedly ended up with something much better —  an institution, supervisor, and research topic that is best for me. See, I’m getting the hang of this getting it wrong.


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