The Importance of Saying “Oops”

I just finished read­ing a his­tory of En­ron’s down­fall, The Smartest Guys in the Room, which hereby wins my award for “Least Ap­pro­pri­ate Book Ti­tle.”

An un­sur­pris­ing fea­ture of En­ron’s slow rot and abrupt col­lapse was that the ex­ec­u­tive play­ers never ad­mit­ted to hav­ing made a large mis­take. When catas­tro­phe #247 grew to such an ex­tent that it re­quired an ac­tual policy change, they would say, “Too bad that didn’t work out—it was such a good idea—how are we go­ing to hide the prob­lem on our bal­ance sheet?” As op­posed to, “It now seems ob­vi­ous in ret­ro­spect that it was a mis­take from the be­gin­ning.” As op­posed to, “I’ve been stupid.” There was never a wa­ter­shed mo­ment, a mo­ment of hum­bling re­al­iza­tion, of ac­knowl­edg­ing a fun­da­men­tal prob­lem. After the bankruptcy, Jeff Skil­ling, the former COO and brief CEO of En­ron, de­clined his own lawyers’ ad­vice to take the Fifth Amend­ment; he tes­tified be­fore Congress that En­ron had been a great com­pany.

Not ev­ery change is an im­prove­ment, but ev­ery im­prove­ment is nec­es­sar­ily a change. If we only ad­mit small lo­cal er­rors, we will only make small lo­cal changes. The mo­ti­va­tion for a big change comes from ac­knowl­edg­ing a big mis­take.

As a child I was raised on equal parts sci­ence and sci­ence fic­tion, and from Hein­lein to Feyn­man I learned the tropes of Tra­di­tional Ra­tion­al­ity: the­o­ries must be bold and ex­pose them­selves to falsifi­ca­tion; be will­ing to com­mit the heroic sac­ri­fice of giv­ing up your own ideas when con­fronted with con­trary ev­i­dence; play nice in your ar­gu­ments; try not to de­ceive your­self; and other fuzzy ver­bal­isms.

A tra­di­tional ra­tio­nal­ist up­bring­ing tries to pro­duce ar­guers who will con­cede to con­trary ev­i­dence even­tu­ally—there should be some moun­tain of ev­i­dence suffi­cient to move you. This is not triv­ial; it dis­t­in­guishes sci­ence from re­li­gion. But there is less fo­cus on speed, on giv­ing up the fight as quickly as pos­si­ble, in­te­grat­ing ev­i­dence effi­ciently so that it only takes a min­i­mum of con­trary ev­i­dence to de­stroy your cher­ished be­lief.

I was raised in Tra­di­tional Ra­tion­al­ity, and thought my­self quite the ra­tio­nal­ist. I switched to Bayescraft (Laplace /​ Jaynes /​ Tver­sky /​ Kah­ne­man) in the af­ter­math of . . . well, it’s a long story. Roughly, I switched be­cause I re­al­ized that Tra­di­tional Ra­tion­al­ity’s fuzzy ver­bal tropes had been in­suffi­cient to pre­vent me from mak­ing a large mis­take.

After I had fi­nally and fully ad­mit­ted my mis­take, I looked back upon the path that had led me to my Awful Real­iza­tion. And I saw that I had made a se­ries of small con­ces­sions, min­i­mal con­ces­sions, grudg­ingly con­ced­ing each mil­lime­ter of ground, re­al­iz­ing as lit­tle as pos­si­ble of my mis­take on each oc­ca­sion, ad­mit­ting failure only in small tol­er­able nib­bles. I could have moved so much faster, I re­al­ized, if I had sim­ply screamed “OOPS!

And I thought: I must raise the level of my game.

There is a pow­er­ful ad­van­tage to ad­mit­ting you have made a large mis­take. It’s painful. It can also change your whole life.

It is im­por­tant to have the wa­ter­shed mo­ment, the mo­ment of hum­bling re­al­iza­tion. To ac­knowl­edge a fun­da­men­tal prob­lem, not di­vide it into palat­able bite-size mis­takes.

Do not in­dulge in drama and be­come proud of ad­mit­ting er­rors. It is surely su­pe­rior to get it right the first time. But if you do make an er­ror, bet­ter by far to see it all at once. Even he­do­nically, it is bet­ter to take one large loss than many small ones. The al­ter­na­tive is stretch­ing out the bat­tle with your­self over years. The al­ter­na­tive is En­ron.

Since then I have watched oth­ers mak­ing their own se­ries of min­i­mal con­ces­sions, grudg­ingly con­ced­ing each mil­lime­ter of ground; never con­fess­ing a global mis­take where a lo­cal one will do; always learn­ing as lit­tle as pos­si­ble from each er­ror. What they could fix in one fell swoop vol­un­tar­ily, they trans­form into tiny lo­cal patches they must be ar­gued into. Never do they say, af­ter con­fess­ing one mis­take, I’ve been a fool. They do their best to min­i­mize their em­bar­rass­ment by say­ing I was right in prin­ci­ple, or It could have worked, or I still want to em­brace the true essence of what­ever-I’m-at­tached-to. Defend­ing their pride in this pass­ing mo­ment, they en­sure they will again make the same mis­take, and again need to defend their pride.

Bet­ter to swal­low the en­tire bit­ter pill in one ter­rible gulp.