The 7 Dark Elements of Pioneering Leadership

Pioneering leadership brings about many wonderful things—the key of which is enduring relevance. You can read more on that in my book.

Not in my book, though, are my thoughts on the shadow side of pioneering leadership. Because everything has it’s shadow side.

Let's see how blessedly cursed you are.

1. You frequently experience discontent

Most of us are familiar with the phenomenon of ‘constructive discontent’. If you’ve ever set a goal, you’ll have created a form of constructive discontent—a discrepancy between your current state and a desired future state. Your attempts to reduce the discrepancy between these two states is what gives rise to progress. And progress is glorious. 

But unlike simply achieving goals, hitting targets or making incremental improvements upon previous performance, if you’re cursed with a pioneering spirit there is no victory. There’s always more that can be done, new things to learn, and better paths to discover. Success is fleeting—progress: infinite. 

This can be incredibly fatiguing. After all, constructive discontent is still a form of discontent. You are still comparing the present state against a more ideal future, and comparison is a fantastic way to catalyse unhappiness. Left unchecked, it can wear away your wanderlust—the very thing that sparks to urge to explore and pioneer.

Mindfulness mitigates this. The m-word. I still have a heap of work to do for myself in this area*. I find Rohan Gunatillake’s approach to be very useful, particularly for those seeking mindfulness within a digital world. He’s the creator of the Buddhify app and the author of This Is Happening. Many have also recommended that I read Tara Brach’s Radical Acceptance. Stoicism is also a thoroughly useful philosophy to explore. Oliver Burkeman’s The Antidote: happiness for people who can’t stand positive thinking is a useful primer, as is this very deep post from Tim Ferris. And of course, there is a stack of science to support a daily ritual of gratitudes—the ability to appreciate the relationships you have, the lessons you have learned, and the progress you’ve made.

*Oh bless, constructive discontent again.

2. You don't make quick decisions

Others might see you as indecisive, but really, you like to think thoroughly: to mitigate cognitive bias and maintain optionality—the ability to avoid being locked into any singular course of action, so that you may adapt your plans as you obtain new information. 

To pioneer is to explore—to keep all options on the table, and to avoid collapsing possibility into a singular defined path.

Of course, decisions must be made, as choosing to not choose is still a choice. Pioneers just might take a little longer to decide, rather than rush in blindly, or default to the familiar.

Transparency mitigates this. The more frequently and openly you share your thinking, the more others can appreciate the implications of the choices you need to make. Rather than keeping it all within your head, keep an active and open journal, or share your updated thoughts via an internal comms platform (like slack). When you do make decisions, frame them as experiments. You don't need to wait for clarity or certainty—this will allow you to proceed without conviction (and make meaningful progress without robbing your ability to pivot or adapt when needed). 

3. You struggle to 'dumb things down'

And nor should you! Nothing is simple. And nothing is right or wrong, black and white—everything is grey. Things are complex.

But unless they’re with you on the journey, it can be hard for people to keep up with you—to grasp the complexity as you do. And to be fair, the curse of knowledge is a known cognitive bias. 

People want simplicity; to be reassured of their own world view—but you struggle to provide this reassurance. Rather than placating them with platitudes, you seek to provoke new and better thinking. You hold yourself and others to a higher standard of thinking: one that ruthlessly questions assumptions and biases, and one that sees people see more.

Thought leadership mitigates this. If you’re pioneering, your job is to shine a light on the path for others. You’re the vanguard—nay: the avant garde. Matt Church (the founder of Thought Leaders Business School) recently wrote an article on the inside job of thought leadership—which is particularly apt for any pioneer. It was Matt that helped me learn how to ‘smarten ideas down’, rather than dumbing them down.

4. You constantly feel like an imposter

Any moment now, someone will call you out. They'll point to this heretical new thinking of yours, and denounce you as the fraud you are. You'll then be escorted from the building.

This imposter syndrome is not a bad thing—in fact, it’s quite common. And self-doubt can be a good thing

But it’s still a thing.

As Oliver Burkeman writes: the more you rise and develop as a leader, the more likely you are to have other successful colleagues to compare yourself to. Of course, you’re comparing your internal thoughts with their external front. You can’t see their insecurity, and as such, your insecurity is amplified. If you’ve got the Pioneer’s Curse—if you’re inclined to lead through uncertainty, with no map to rely on—then this will only be amplified hugely. 

Vulnerability mitigates this. Naturally, you’re familiar with Brené Brown’s work. A good pioneering leader doesn’t pretend to have all the answers. Rather, you take a more antifragile approach—you're comfortable being 'found out', because it enriches your thinking. You know it is better to be caught having pioneering thoughts, than to be caught having no new thinking at all.

5. You're incredibly unproductive

You struggle to pursue tasks that only perpetuate the status-quo. And then, when busyness hits you, you're bad at it. You don't 'thrive' under external pressure, and you aren't anywhere near as efficient as you could be.

You are at your best when you're doing deep work—but this can appear lazy to others. Deep work, as Cal Newport puts it, is cognitively demanding work that requires you to focus (without distraction) and apply skills that are hard to replicate. It's deep work that produces the things that matter most in this world.

Delegation mitigates this. You need to play to your strengths. Not everyone can pioneer all the time. In fact, for the vast majority of work, we need people who are efficient—otherwise nothing would get done. We need people who are operationally magnificent—otherwise we'd burn too much energy in un-leveraged effort. Play to your strengths, and work to the strengths of those on your team. If you don't have a team, outsource the things you suck at. If you can't do that, batch-process busywork so that you have uninterrupted make-time.

6. You're the black sheep in the boardroom

It’s a tough gig being a pioneer. You're the one challenging the status-quo, and it's making everyone uncomfortable.

Good! Comfort breeds complacency, which catalyses our collective decline into irrelevance. Pity the fools who think otherwise. We need to be uncomfortable. But that doesn't mean people are going to like it.

You want to be progressive and make clever happen, but everyone else just wants to be productive, and make shit happen. What's more, they resent your crazy new thinking, because it just means more work and change for them.

Diversity mitigates this. Why is it just you who is the black sheep? Are you on an all male panel, perchance? Can we bring some other perspectives into the mix? Not more black sheep no. And certainly no more white sheep. But why not a purple sheep? Or a tangerine sheep? Let's get a rainbow flock happening. Because if you care about quality thinking, you care about diversity. To do otherwise is an anathema to meaningful progress. 

7. Everything takes longer

If you have the Pioneer's Curse, you cannot fathom doing something that doesn't contribute meaningful progress. You're not so good at replicating, recycling or reproducing stuff that has been done before. Everything has a touch of the bespoke, because the context is always shifting, and your thinking is always evolving.

This is partly due to the curse of curiosity. I sometimes envy those folks who can become bored (not really; not at all). How simple their world must be. But if you're afflicted with curiosity, it can be insatiable. 

As Nicholas Nassim Taleb says: "Curiosity is antifragile, like an addiction, and is magnified by attempts to satisfy it." There are so many wonderful tangents to explore, so many opportunities to widen the keyhole perspective we have in life. And so, if you're cursed with a pioneering spirit, everything takes longer.*

* It's probably thanks to a combination of curiosity, constructive discontent and an incredibly healthy relationship with self-doubt (elements 1–5 above) that makes these museletters so long. 

Constraints mitigate this. You need to play this like a progressionist, not a perfectionist. This means actively seeking constraints.* Future-pace possibilities, and work out the critical path for your missions and projects—remembering that the further into the future we go, the fuzzier things become. 

* I tend to treat deadlines as amusing hypotheses begging to be disproved—but I've learnt to dial up the pressure they provide. 

And then, get comfortable releasing versions of your work, rather than waiting to ship a perfect, final piece. Everything is a draft. Combine this with a trio of the other mitigators mentioned above—thought leadership, transparency and vulnerability—and you'll be able to make meaningful progress (even if it's not perfect).


Of course, the wonderful things about pioneering far outweigh the 7 dark elements above. You’re never bored, the progress you make is meaningful, and you are infinitely more likely to sustain relevance and make a lasting difference in this world.

It’s a harder path, but it’s worth it.

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