We tend not to say ‘I told you so’ because we know it’s a frustrating and pedantic thing to hear. Not that it isn’t a rightful position to find yourself in: When you’ve confidently shared a prediction, that gets ignored, only to be proven correct. That right to say ‘I told you so’: Denied.

Worse still though is not saying ‘I told you so’, but knowing the recipient knows that you could: To be thought of as a frustrating pedant when all you did was share a prediction, that was ignored, that then turned out to be correct. Tripple fail.

The saddest part is that the intention of most people in a position to say ‘I told you so’, is that they’re trying to help. People don’t seek not to be listened to when they’re sure about something, nor do they want to be frustrating. They’re just soul who’s intentions are good…

An example predicament (indulge me for a moment): Someone suggest that you go on holiday (they have a nice idea so +1 point to them). You love the idea (no points for that).

They suggest Greece, because it’s nice AND they’ve found a deal you can afford, in November (another +1 points for continuing such a nice idea with such good research and intentions).

You are pretty sure that November is the start of the rainy season in Greece. Really, pretty sure.

Option 1: You say you’re sure it’s the rainy season in November (-1 points for being a downer on the nice idea). They say ‘it’s Greece! It’s always hot. And even when it rains it’s just heavy and short’. You try again and suggest either saving longer for something better next year or going away for a weekend in you’re own country (-1 point for continuing to be a downer and having less exciting ideas).

You give in to their optimism because you want to believe it, and fear losing any more points. Total so far: Them +2. You -2.

You go on the holiday. It rains. A lot. It’s not a good holiday. Not awful but not really memorable. A bit disappointing.

Whether or not you now say ‘I told you so’, you get a further -2 points. Because they know you could say it. And maybe they feel you didn’t try hard enough to explain ‘rainy season’ more clearly. They, get another +1 point for trying. At least they tried to make a good time happen.

Final score: Them +3. You -4! Damn you, you frustrating pedant. But, backtrack a bit, Sliding Doors style, and you’re still at risk…

Option 2: You think it’s the rainy season, but say nothing. Holiday turns out the same. This time they get +1 for trying and because they had no idea it was the rainy season and feel awful for their mistake (hope+guilt scores high).

You get no points at all because you did nothing to help with anything. All you get is the crappy holiday and worthless secret guilt, yuck, which is worth -4 points, at least. Final score: Them +3. You -4!

Damned if you do, dammed if you don’t. How to get around this occasional Cassandra Cures? How can we more successfully express our predictions and recommendations?

In my reckoning, there are three possibilities of never being in the position of having to say ‘I told you so’:

1. Building so much trust that everyone just listens to you and your predictions. Realistically though, this route is either a long and lonely road toward falling from a very high place, or full blown megalomania.

2. Finding a super NLP-like way to get everyone to do what you think is right, while believing it’s their own idea. You risk never getting credit for anything, but at least you’re in a world where everything is just as you think it should be. This is the ’These aren’t the droids you’re looking for’ method, so sadly only really useful for Jedi and those with slight delusions of grandeur (come on, you actually think you’re right all the time? ALL the time?).

3. Finally, and genuinely, there is preemptive empathy and regret: Being conscious that your steadfast prediction will result in a frustrating outcome for all, and instead, expressing that you hope your prediction is wrong, and that you’re on the side of optimism.

This technique can even result a sort of win-win situation: If you’re wrong, then your fear was luckily just overcautiousness. Phew. Thanks for caring and being concerned.

If you’re right, you’re not a frustrating pedant, you’re just another party that wishes you weren’t right, and you’re able to compassionately share in the misfortune of your comrade. You end with a genuine hate to say ‘I told you so’.

But, being genuine is the crux here. This ‘technique’ is about being a mensch. That frustrating pedant potential will shine through if you don’t actually care and if smugness and schadenfreude is detected.

Haters say ‘I told you so’. If you find yourself in a position of having to say it, or wishing you could, then you weren’t being helpful in the first place.