Sisyphus is THE archetype of a person engaged in an ennobling struggle. Camus was the main culprit behind the dumb argument that Sisyphus had a meaningful life, rolling that rock repeatedly up the hill, only to have it roll down again. Today, you see people engaged in any sort of struggle with symptoms of pointlessness making similar arguments. There is a whole painful genre of entrepreneurial motivational commentary based on fetishizing the pain, blood and sweat of certain kinds of struggle into something sacred and noble. This is smarmy bullshit. You should not avoid hard work where it is the only path, but you SHOULD use every available trick and hack to mitigate the need for Sisyphean efforts.
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This is not a happy guy. Illustration by Grace Witherell.
1/ The Gods decided to punish Sisyphus by having him repeatedly roll a rock up a hill, only to have it roll right back down again, for all eternity.

2/ Could Sisyphus have been happy and fulfilled in his fate? Camus thought so. So do certain kinds of entrepreneurs apparently.

3/ For anyone not equipped with the masochistic genius of a gloomy French intellectual, Sisyphus' fate is obviously hellish.

4/ I call a project Sisyphean if it feels like a mighty, pointless, ugly, arbitrary and unpleasant struggle, with little reward.

5/ Neither the means (a brute-force struggle), nor the rewards (just slightly higher than the effort... if you're lucky) can justify it.

6/ The ONLY thing that can justify such a struggle is a philosophically convoluted fetishization of pain as some sort of meaning.

7/ If you poke at the psychology behind this masochism, you invariably find a lack of imagination and a suspicion of ideas.

8/ Classic signs: "ideas don't matter, only execution does." Or "hard work trumps talent" or "1% inspiration, 99% perspiration"

9/ There is more to this than dislike of blithe-spirit types who coast through life on the strength of ideas. There is shame and guilt.

10/ Ideas are cheats. They add leverage to hard work. Being suspicious of ideas is about a perverted sense of what counts as honest labor.

11/ In businesses, you see this in sales-driven people who are suspicious of marketing; operations people who distrust elegant designs.

12/ To Sisypheans, if effort feels beautiful and flowing, or god forbid, actually fun, it must be morally "wrong". ESPECIALLY if it works.

13/ Another sign: compartmentalizing fun into required "partying." When work is not allowed to be fun, fun turns into work.

14/ Elegant marketing and engineering are not just fun to do, they turn adjacent Sisyphean efforts  into fun non-Sisyphean ones.

15/ They do this through the spillover power of ideas: compressed insights into the nature of the world that create leverage. 

16/ Through marketing/engineering network efforts, ideas unleash what Einstein called the most powerful force in the universe: compound interest. 

17/ By analogy, cold-call sales is perhaps the weakest force in the universe, and the perfect embodiment of Sisyphean grinding.

18/ You cannot entirely avoid it, but you need not fetishize it or make it your first and preferred form of effort out of a masochistic work ethic. 

19/ Sisyphean grinding is how you backstop effort shortfalls once you've exhausted the idea-potential of marketing and engineering.

20/ Drucker got this: he said marketing and innovation (he meant it in the sense we use "engineering" today) are the only two essential functions.

21/ He also said that the job of marketing was to make sales unnecessary. In practice you can rarely get 100% there, but you should be trying.

22/ Something similar could be said of design engineering versus production operations. The job of the former is to make the latter unnecessary.

23/ Far from diminishing the importance of sales and operations, this is about making both more fun, leveraged and meaningful.

24/ A good analogy is sail warfare: to the extent you can maneuver to be upwind, you win easily and minimize tough hand-to-hand melee combat on enemy decks.

25/ You can also keep a military wisecrack in mind: the point is not to die for your country, but to make the other guy die for his.

26/ Mutatis mutandis: the point is not to undertake a Sisyphean struggle for your idea, but to make the competition undertake one for theirs.

27/ Creating clever positioning, engineering lucky breaks, replacing "hard" with "smart": these are winning behaviors, not immoral ones.

28/ Marketing and engineering put the smart in "work smart, not hard." You should only work hard where you cannot work smart.

29/ The dangers of avoiding hard, painful work are widely recognized. Armchair idea people are reliable villains in advice to entrepreneurs.

30/ But the dangers of avoiding easy and enjoyable work not only go unrecognized, we actively valorize Sisyphean masochism as "heroism".

31/ But there are more masochistic Sisypehans than armchair idea people out there, preaching the virtues of bleeding and having no fun.

32/ They are actually more dangerous. Idle idea-people just create hot air. Anti-idea types burden us with awful, inelegant solutions to problems.

33/ As a professional idea-person-for-hire who works out of an armchair, you might argue that of course I'd say that.

34/ Don't take my word for it. Look around. Anywhere you see awful things built with Sisyphean efforts and weak ideas, you'll see broken, miserable "winners." 

35/ On the other hand, anywhere you see things built around powerful ideas/insights, you'll see happy, fulfilled winners, enjoying their huge "unfair" victories more.

36/ Bottomline: without beautiful, imaginative and powerful ideas for leverage, no undertaking is worth it. Idleness is better than Sisyphean winning.
Check out Breaking Smart Season 1 for the deeper context behind this newsletter. If you're interested in bringing the Season 1 workshop to your organization, get in touch. You can follow me on Twitter @vgr

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