How to be an antifragile strategist

Uncertainty is all we ever have. It's the strategist's trade to trade in helping decide in uncertain conditions.

But there are ways to find ways to thrive in it, not just survive it. That's where the work of Nassim Taleb comes in.

His work has been foundational to how i see the world. These seven simple ideas that may help you too.

1. Treat your strategy like prototypes, not performances

"Optionality is Promethean, narratives are Epimethean—one has reversible and benign mistakes, the other symbolizes the gravity and irreversibility of the consequences of opening Pandora's box."

Huge fan of optionality and its role in strategy. But with some exceptions, strategy by definition needs to be flexible to the context at hand. In other words, it needs to accept 'reversible and benign mistakes'.

Back in 2020, during the 'covid scenario planning' era of our lives, i learned this the hard way. All we had was a huge series of 'if this then that' options in front of us. Perhaps that's all we ever had, and we just took a while to get it.

So instead of it needing to be one big performance, consider prototypes instead. Beta versions of a thought which, although it may not be 100% right, it's not wrong either. But they should be specific enough that you can test them with your clients or customers. If sprints and prototypes are good enough for Google Ventures, they're good enough for us.

2. Don't start with ‘what's in it for us’, start with ‘what's in it for them’

"Thou shalt not have antifragility at the expense of the fragility of others."

This saying is from a former client of mine, but god damn if i ain't stealing borrowing it. It shouldn't feel like news for marketers or strategists, and yet it's so easy so lose perspective. This feels true now that i run my own studio, and can easily fall into 'max profit mode'. And surely, that plays a role (business without profit doesn't survive).

But there's always a short vs long-term game here.

You may profit in the short term from having it your way in a project, at the expense of others. But this might mean those folks don't return to you for repeat business – uh oh! This isn't about just loyalty, it's about having a product or service based on trust and value. So when thinking about whether you're value for money, always ask: what's in it for them? Everything else, invariably, follows.

3. If in doubt, treat digital channels like bricolage

"Bricolage is a form of trial and error close to tweaking, trying to make do with what you've got by recycling pieces that would be otherwise wasted."

One of the biggest dangers in marketing and strategy is we think too highly of ourselves. But we also don't give our audiences or the media they consume enough credit. For example, we debate endlessly whether an ad message should be about thing A, B or C. We can go to extreme lengths to argue the pros and cons of each.

Is it "here for you", or "here with you"? What a waste of time and money this can be.

Or, consider the alternative: put a little budget on A/B testing, and see what sticks faster. It seems basic, and yet why are we so afraid of doing small scale digital experiments? Especially if they can give us knowledge and confidence to make larger scale choices? Part of it is legacy processes, lead times, and not wanting to look like a fool – i get that. But what's foolish is to compromise time to market so you can be 100% sure of something.

This, of course, carries massive opportunity costs. And chances are, you'll just take longer to understand where you got it wrong. What if digital channels weren't built for efficiency, but instead for experimentation? The efficiency stuff just happened to be what they're really good at, as well.

4. Don't trade on ‘interesting’, trade on ‘important’

"We practitioners and quants aren't too fazed by remarks on the part of academics—it would be like prostitutes listening to technical commentary by nuns."

Are you as bored as i am about the seasonal / circular debates on LinkedIn? And yet, you and i know they are gonna come yet again, sometime very soon. Here's the thing: a lot of these debates might be a waste of your time. They're the bubble of the commentariat, who thrive on critiquing other people's work.

What i notice: people who ship work themselves couldn't give two shits about having hot takes. They're not interested in being hypothetical, they're doing the work they want to see, full stop. In simple terms, they care more about building than bashing. In what's important to do, not merely interesting to say.

This split, between interesting and important, is a useful shortcut for us too. It helps you filter through research, strategy statements, cultural references, the lot. Is this merely interesting, or is it important enough to carry implications? Once you filter your work through this lens, the job can become 10x easier, and less stressful.

5. Don't worry about what goes in, worry about what people take out

"For Tony, the distinction in life isn't True or False, but rather sucker or nonsucker."

I'm fond of saying that truth is often a moving target with an expiry date. I've also seen folks talk about how the truest ideas don't win, the most well communicated do. These thoughts riff on the idea of "suckers" vs "non suckers".

Suckers worry about being technically correct – what goes in. Nonsuckers worry about producing an effect – what people take out. And this, deep down, is the role of a strategist: to determine what comes out of something. So don't obsess with what goes into something, or what something should be. Obsess with what comes out of it, what something should do.

6. Be wary of more knowledge when what you need is confidence

"More data—such as paying attention to the eye colors of the people around when crossing the street—can make you miss the big truck."

We're all swimming in information, some of which is knowledge, very little of which is wisdom. Not because it's not any good, but because we don't know what to do with it. (Wisdom, as i see it, is knowledge applied in context).

In theory, LLMs can help with this, by accelerating research and synthesis. But only to a point, because you end up with overload again – different tools, same problems. We assume we need to read everything about a topic before we get a hunch about it. The hunch emerges after you start reading, but eventually there are diminishing returns.

There's a point after which another report or interview becomes noise, not signal. Because you start losing the perspective and distance you once had. In those cases, you don't need more knowledge, but confidence in the knowledge you have. And to instil this confidence in your clients too, who lost perspective way before you did.

This isn't an argument for how external advisors are smarter than clients, by the way. But what most clients really buy from an advisor is perspective, which is easy to lose. So don't worry about completionism bias on covering every single piece of ground. This may give you a perfect picture of a messy problem – no question. But it may also leave you with no more clarity on how to make a choice and move forward.

7. Accept criticism for what it is, an emotional indicator

"Criticism, for a book, is a truthful, unfaked badge of attention, signaling that it is not boring; and boring is the only very bad thing for a book."

There's a truth in that once you start getting critics, then you're onto something. Until then, all you can know is your work was forgettable enough to not be worthy of mention. I don't know why this happens in professional circles – possibly envy, jealousy, boredom. But there's a logic to how it's valuable from an effectiveness perspective.

Critics means free media. Free media means opportunities for salience. Opportunities for salience means you might end up in front of non critics. This is arguably the CK ad strategy: create sexual controversy, take it down, free PR. You exchange short term drama for media impressions, and a helluvalot of media impact.

So next time your thinking or campaign gets its share of criticism, consider why it might be. If it's born out of you having made a mistake (and you know you did), then fair enough. If it's a philosophical disagreement ("fandoms are a fad", yadayada), it might be a breakthrough.

Remember, the first job of advertising is to be noticed (and most ads aren't). A principle that can extend to any point of view you might have on your industry. The paradox of violent disagreement is someone cares so much they took time to respond. And that is often a sign you're onto something that truly struck a nerve.

Which is more than we can say for 90% of work out there, if not more.