Possibly the single most difficult idea to grasp in the breaking smart philosophy is that goal-setting is very dangerous in creative work, and that it is possible (and even necessary sometimes) to work without goals. The key to this idea is that the very act of setting a goal can destroy your ability to achieve it, a phenomenon called the objective paradox. Why is this, what can you do about it, and what can you do instead? And is there any role for goals at all in complex situations?
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The Objective Paradox. Illustration by Grace Witherell.
1/ Many simple situations have clear goals, like traveling to a destination or assembling a piece of furniture.

2/ In these situations you are usually reusing one or more canned, proven plans rather than inventing one.

3/ At the other extreme are situations that seem to defy goal-setting and planning, like "revive the economy."

4/ Such "goals" are usually ill-posed in a "life, the universe and everything" way.

5/ Such situations usually resolve themselves in unexpected emergent ways or lead to inevitable collapse.

6/ Usually, we don't understand what happened till decades or centuries later, if ever.

7/ We still don't grok how Europe achieved the "goal" of getting out of the Dark Ages via a renaissance. Nobody planned it.

8/ Emergent resolutions, unlike planned solutions, usually occur despite authoritarian goals and plans, not because of them.

9/ Between reused canned solutions and illegible emergent resolutions of "situations" lie the tricky cases.

10/ In this middle, we have 
creativity-demanding situations that also seem to allow clear goals and determinate planning.

11/ Examples include things like getting to Mars or proving an important theorem.

12/ The apparent clarity of "obvious" goals and plans is deceptive. Critical enabling breakthroughs are usually unplanned.

13/ Proving a theorem, for instance, may involve spotting an unexpected connection to a seemingly unrelated math problem.

14/ Getting to Mars may rely on an unplanned technical breakthrough in a field not even considered in the plan.

15/ Without such creative breakthroughs, complex goals leads to failure or pyrrhic victories.

16/ The research described in this fivethirtyeight article gets at why this happens.

17/ Setting a goal closes off thinking to the unexpected insights that might create extreme leverage.

18/ To work without goals, the key is to devote energy and attention to capability expansion through tinkering.

19/ Tinkering with a sufficiently open mind and playful attitude reveals unexpected capabilities.

20/ These unexpected capabilities suggest unplanned possibilities. The medium suggests the message.

21/ You may not achieve the goal you set, but whatever you do achieve will be a highly leveraged victory.

22/ In other words, you'll know what you want when you find it, so long as you are expanding capabilities.

23/ Complex achievements depend on a cascade of such leveraged breakthroughs fueling serendipitous momentum.

24/ From beginning to end, it may feel like a goal is being set and achieved, but that's usually a hindsight narrative.

25/ Is there any need for goal-setting in complex situations? Perhaps. Goal-setting is fundamentally about analysis..

26/ In material effect terms, analysis is destruction, synthesis is creation.

27/ Destruction (not always a bad thing) of any sort may work well with goal-setting.

28/ Why? Because when you are destroying, entropy and uncertainty work with you, instead of against you.

29/ Examples include war-time goals, placing a complex short-selling bet or taking a machine apart to see how it works.

30/ You can "plan" for destruction in a way you cannot plan for creation. And the process can generate creation insights too.

31/ Of course complex achievements involve creative-destruction, so you need a bit of both.

32/ Plan your destruction with goals, your creation through tinkering and capability expansion.

33/ In conclusion, there IS a best way to achieve any goal: by accident. So try and get lucky, punk.
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

And don't forget to share this newsletter to people who might find it useful.
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