Hope for the best, prepare for the worst

Hope for the best, prepare for the worst is the practical mindset adopted by successful entrepreneurs. They plan for a range of outcomes.

Hope for the best, prepare for the worst

Some thoughts on the value of preparing for a range of outcomes from your current course of action.  I think the most famous version of this advice comes from a song by Mel Brooks.

Hope for the best, expect the worst
The world’s a stage, we’re unrehearsed

Mel Brooks lyrics to The Twelve Chairs, “Hope for the Best, Expect the Worst” (1970)

I think the best version comes from Zig Ziglar, urging a flexible response to a range of outcomes.

“Expect the best.
Prepare for the worst.
Capitalize on what comes.”
Zig Ziglar

The oldest versions I could find come from Benjamin Disraeli and Mary M. Bell, but this may have been a proverb in circulation in the 19th century.

“Hope for the best,
prepare for the worst,
and take what God sends.”
Mary M. Bell in “Seven to Seventeen; or, Veronica Gordon” (1873)

“I am prepared for the worst, but hope for the best.”
Benjamin Disraeli in “The Wondrous Tale of Alroy” (1845)

Tony Hsieh offers a more tactical prescription in his book “Delivering Happiness” that also applies to cash management for bootstrappers:

  • Always be prepared for the worst possible scenario.
  • Play only with what you can afford to lose.
  • Make sure your bankroll is large enough for the game you’re playing and the risks you’re taking.
  • Remember it’s a long term game. You will win or lose individual sessions, but it’s what happens in the long term that matters.

Tony Hsieh in his book “Delivering Happiness” in the chapter on “Poker”

I used this in Texas Hold’Em as a Model for Technology Startups.

“What you prepare for, what you hope for, and what you expect are often three different things.”
John D. Cook (@JohnDCook)

Make affordable loss bets

“Look at the Underside First: Legions of people are paid large sums to promote the positive aspects of commercially available products. Very few people earn their daily bread by pointing out malfunctions, bugs, screw-ups, design failures, side-effects and the whole sad galaxy of trade-offs and failings that are inherent in any technological artifact. To counteract this gross social imbalance, a wise designer and a wise critic will make it a matter of principle to look at the underside first.”  Bruce Sterling in Viridian Design Principles (1998)

There is much more at the Viridian Design Site. In “Constructive Pessimism,” I observed that you have to be willing to acknowledge the possibility of problems and look for them to be able to prevent or at least manage them. Many entrepreneurs who are naturally optimistic make a serious mistake in discouraging pessimistic thinking instead of putting it to good use. The clever utilization of constructive pessimism is one of the keys to success.

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