A good friend of mine sent out an email the other day on ‘leadership’ versus ‘salesmanship’.

I wanted to edit this post a little before throwing it up here, but unfortunately it’s 2:30am already so here’s his email verbatim:

Hey friends,

You’re getting this email because we’ve had a intelligent and meaningful conversation at some point about leadership, or some aspect of leadership (e.g., charisma, trust, being a ‘visionary’). I wanted to send this email out to solicit your thoughts regarding a particularly powerful piece of writing on leadership that I recently read and also hopefully kickstart a conversation. I am curious about your answers to two questions:

  1. What does being a leader mean, in your opinion?

  2. What are some of the most difficult aspects of leadership to learn or develop?

But first, I want to share the piece on leadership. It’s a bit long, but I assure you it’s worth the read.

Excerpt From Up, Simba by David Foster Wallace:

“It is all but impossible to talk about the really important stuff in politics using terms that have become such awful cliches they make your eyes glaze over and are difficult to even hear. One such term is ‘leaders,’ which all the big candidates use all the time – as in ‘providing leadership,’ ‘a proven leader,’ ‘a new leader for a new country,’ etc. – and have reduced to such a platitude that it’s hard to try and think about what ‘leader’ really means….The weird thing is that the word ‘leader’ itself is cliche and boring, but when you come across somebody who is a real leader, that person isn’t boring at all; in fact he’s the opposite of boring.

Obviously, a real leader isn’t just somebody who has ideas you agree with, nor is it just somebody you happen to believe is a good guy. A real leader is somebody who, because of his own particular power and charism and example, is able to inspire people, with ‘inspire’ being used here in a serious and noncliche way. A real leader can somehow get us to do certain things that deep down we think are good and want to be able to do but usually can’t get ourselves to do on our own. It’s a mysterious quality, hard to define, but we always know it when we see it, even as kids. You can probably remember seeing it in certain really great coaches, or teachers, or some extremely cool older kid you ‘looked up to’ and wanted to be like…

If you’ve ever spent time in the military, you know how incredibly easy it is to tell which of your superiors are real leaders and which aren’t and how little rank has to do with it. A leader’s true authority is a power you voluntarily give him, and you grant him this authority not in a resigned or resentful way but happily; it feels right. Deep down, you find yourself working harder and pushing yourself and thinking in ways you wouldn’t be able to if there wasn’t this person you respected and believed in and wanted to please.

In other words, a real leader is somebody who can help us overcome the limitations of our own individual laziness and selfishness and weakness and fear and get us to do bettter, harder things than we can get ourselves to do on our own…

Now you have to pay close attention to something that’s going to seem obvious at first. There is a difference between a great leader and great salesman. There are also similarities, of course. A great salesman is usually charismatic and likable, and he can often get us to do things (buy things, agree to things) that we might not go for on our own, and to feel good about it. Plus a lot of salesman are basically decent people with plenty about them to admire. But even a truly great salesman isn’t a leader. This is because a salesman’s ultimate, overriding motivations is self-interest – if you buy what he’s selling, the salesman profits.

So even though the salesman may have a very powerful, charismatic, admirable personality, and might even persuade you that buying is in your interests (and it really might be) – still, a part of you always knows that what the salesman ultimately after is something for himself. And this awareness is painful…although admitted it’s a tiny pain, more like a twinge, and often unconscious. But if you’re subjected to great salesman and sales pitches and marketing concepts for long enough – like from your earliest Saturday-morning cartoons, let’s say – it is only a matter of time before you start believing deep down that everything is sales and marketing, and that whenever somebody seems like they care about you or about some noble idea or cause, that person is a salesman and really ultimately doesn’t give a shit about you or some cause but really wants something for himself.

Some people believe that President Ronald W. Reagan (1981 - 89) was our last real leader. But not many of them are Young Voters. Even in the 80s, most younger Americans, who could smell a marketer a mile away, know that what Reagan really was was a great salesman. What he was selling was the idea of himself as a leader. And if you’re under, say, 35, this is what pretty much every US president you’ve grown up with has been: a very talented salesman, surrounded by smart, expensive political strategists and media consultants and spinmasters who manage his ‘campaign’ (as in also ‘advertising campaign’) and help him sell us on the idea that it’s in our interests to vote for him.

But the real interests that drove these guys were their own. They wanted, above all, To Be President, wanted the mind-bending power and prominence, the historical immortality – you could smell it on them. And that is why these guys weren’t real leaders: because it was obvious that their deepest, most elemental motives were selfish, there was no chance of them ever inspiring us to transcend our own selfishness.

Instead, they usually helped reinforce our market-conditioned belief that everybody’s ultimately out for himself and that life is about selling and profit and that words and phrases like ‘service’ and ‘justice’ and ‘community’ and ‘patriotism’ and ‘duty’ and ‘give government back to the people’ and ‘I feel your pain’ and ‘Compassionate Conservatism’ are just the politics industry’s proven sales pitches, exactly the same way ‘Anti-Tartar’ and ‘Fresher Breath’ are the toothpaste industry’s pitches.

We may vote for them, the same way we may go and buy toothpaste. But we’re not inspired. They’re not the real thing.

It’s not just a matter of lying or not lying, either. Everyone knows that the best marketing uses the truth – i.e., sometimes a brand of toothpaste really is better. That’s not the point. The point, leader-wise, is the difference between merely believing somebody and believing in him.”

Anyways, I really enjoyed and resonated with this piece, and as an aspiring leader (used here in the noncliche way), I’m very interested in figuring out how to be an authentic leader that elevates people.

And my response:

Thanks for the interesting read. Love Wallace. In response to your point, while Wallace doesn’t touch on this I’d like to make my observation that perhaps the very thing that separates leaders from salesman is that they don’t want to be leaders. In fact, the best leaders possibly couldn’t care less if anyone at all followed them per se - perhaps what they’re driven by are causes, and they push so nobly and virtuously at those causes that people are naturally drawn to them.

Some examples of real leaders that come to mind are people like Washington, Lincoln, Martin Luther King. The following observations are largely based on vague facts and tidbits contributing to a general attitude I have on each person, but I believe they’re by and large true and at least serve to aid my point.

Taking Washington, he had no particular desire to be president. He legitimately did everything he did not out of a personal desire for the attainment of the status of leader, but rather out of what he perceived to be his duty and obligation to help build this dream of a better nation the founding fathers held. And it’s for this reason exactly that probably everyone gravitated to him unanimously without doubt as the only possible option for leader - he won 100% of the electoral votes and no one’s ever done that since. He preferred the title Mr. President to eschew himself from traditional royalty. He only reluctantly, under pressure, served another term - what other president can that be said for? He refused to serve a third term, and thus established the informal precedent for a two-term limit. He probably could have served forever if he wanted to, precisely because he didn’t want to, and would only be doing it if he truly believed it was the best thing for the nation.

Same thing with Lincoln, though to a lesser extent as he seems like a much more pragmatic person in several regards. But there’s a reason he’s often regarded as the greatest President we’ve ever had - he deeply cared about for the Union and held its interests above all. It’s almost unbelievable that he managed to pull the nation together in the midst of such overwhelming turbulence. Poor guy. I truly consider his presidency to have been a personal sacrifice to preserve the nation - it ended abruptly in his assassination, but even if it hadn’t I can’t imagine he would have lived much longer after being subjected to so much tragedy, turmoil, stress, and anguish.

Same thing with Martin Luther. Guy was definitely doing what he was doing because of the cause, not because he wanted to be a leader. He got shot too.

Thus in answer to your two questions:

  1. Being a leader means leading for a cause, a purpose, an aim. The central point of focus is not the process of leading, but the end goal, the vision. It starts from there and works its way back. It doesn’t start from a desire to lead to the end point. Kind of like Simon Sinek’s TED talk on “Start With Why”

  2. For someone who wants to be a leader per se, the hardest part may perhaps be divesting oneself from that desire and committing more fully to the cause that demands leadership.

More difficult done than said. It’s really a question of values - and how does one change their values? I guess you have to care deeply about other people if you are to lead them, and like Wallace says, really have our interests either directly or indirectly (through advancement of a cause) centrally at heart. Can one be truly selfless? Perhaps it’s possible, but even so there’s a second question. Can one who is presently selfish become, through some sort of desire and exercise, selfless?

I’d have to imagine it’s rather difficult for a primarily selfish person to develop a desire to become selfless, unless that desire is truly driven by some underlying ulterior ultimately selfish motivation. But this is coming from me as a moral nihilist, who views most things as inherently selfish (say, donating money to some homeless guy on the street may be ultimately selfish, if we are doing it for the personal feeling of satisfaction and happiness we derive from the act - then it’d be for the same underlying motivation that drives many to rape. Clearly, the means to the end [personal satisfaction] is different, though the end is the same. So If we uphold those means, I suppose the challenge is in engineering ourselves to truly believe that what is best for us is what is best for others/the advancement of a particular cause. But how do we do that? And is it, truly?)

So ultimately my question for you would be - why do you want to be a leader?

A little raw, but I think the general gist of the point I’m trying to get at in the email is captured well enough. Both of us would love to hear more opinions on the subject, so send them over if you’ve got them.


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