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Weekly 3: Useful Guesswork, “Endless Newbies” & Flexible Expertise


Idea Journal Weekly 3

January 28 · Issue #19 · View online

We combine 3 ideas to help you think differently and be more creative.

Summary: Educated guesses about the future. Embrace your inner newbie. Expertise for the long haul. (~5 min read)

#1. Make your business plans more effective by calling them what they really are.
Jason Fried and David Heinemeier Hansson write in their book Rework that “Unless you’re a fortune teller, long-term business planning is a fantasy.”
That’s because there are too many factors outside of your control – from market conditions and competitors, to customers and the overall economy.
In this context, Fried and Heinemeier Hansson write that plans are problematic for at least 3 reasons:
  1. They let the past drive the future.
  2. They put blinders on you: “This is where we’re going because, well, that’s where we said we were going.”
  3. They are “inconsistent with improvisation.”
Instead, they suggest calling plans what they really are: guesses.
From this perspective, business plans become business guesses, financial plans become financial guesses, and strategic plans become strategic guesses.
“Working without a plan may seem scary. But blindly following a plan that has no relationship with reality is even scarier.”
#2. To increase your odds of success in a rapidly advancing technological environment, learn how to learn.
Kevin Kelly, author and oracle of digital culture, writes in his book The Inevitable that “technological life in the future will be a series of endless upgrades,” and that the cycle of enhancements will itself continue to increase.
Every person, even the youngest and most technologically-savvy, will be an “endless newbie” because you won’t have time to master the commands and logic of a given tool before it is displaced.
Discussing this trend on the Waking Up podcast, Kelly suggests that learning how to learn will be the most important meta skill in such a dynamic environment. 
As a bonus, if you can optimize your own personal learning style to understand how you learn best, then that will be “the superpower you’ll want.” 
Kelly admits that getting to this point of self-awareness can take a lifetime, but he cites author and “human guinea pig” Tim Ferriss, as an example of someone who’s successfully pushed himself down this path.
#3. Believe in change to become better at predicting it.
Entrepreneur and investor Paul Graham writes in his essay How to Be an Expert in a Changing World that when experts are wrong, “it’s often because they’re experts in an earlier version of the world.” 
If the world were static, then we could have increasing confidence in those beliefs that survived more experiences over time.
But the world isn’t static.
Graham recommends two ways to help protect yourself against obsolete beliefs:
Have an explicit belief in change: Beliefs about the future are “so rarely correct that they usually aren’t worth the extra rigidity they impose, and that the best strategy is simply to be aggressively open-minded.” It’s OK to have working hypotheses, but you should be disciplined enough to ensure they don’t “harden into anything more.”
Bet on people over ideas: Predicting the nature of future discoveries is hard. Predicting the kind of people who will make them is easier – good new ideas come from those who are earnest, energetic, and independent-minded. “If you want to notice quickly when your beliefs become obsolete, you can’t do better than to be friends with the people whose discoveries will make them so.”
Quote of the Week
“You see, one thing is, I can live with doubt and uncertainty and not knowing. I think it’s much more interesting to live not knowing than to have answers which might be wrong.”
- Physicist Richard Feynman in his book The Pleasure of Findings Things Out
Idea Journal
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