Optimize to Minimize Regret

Optimize to minimize regret.

When you see regret in the mans eyes its fucking painful... It [talking to retirees that have regret] will make you want to do shit every minute of your life. Because when you are 90, and you are tired, and its over. You can't do it. You can't build the company you wanted. You can't spend that time with your kid. It's regret. And it fucking drives the shit out of me. - - Gary-Vaynerchuk (video)

The biggest poison in us is Regret. - Gary-Vaynerchuk (video)

Great for making big decisions: Look at the decision as if you were already 80 years old and look back at this decision.

  • Minimize number of regrets that you have when you are 80.
  • Lots of times we will regret more never having tried.

Regret Minimization Framework Video

AVOID: living the future or past.

“Do not regret what you have done.” — Miyamoto Musashi, Dokkōdō#6

“Of all sad words of tongue or pen, the saddest are these, ‘It might have been’”— John Greenleaf Whittier

“Throughout our lives, we are mostly worried about things that won’t happen anyway. We are afraid of failure when in reality the regret about not having tried can be by far more painful than failure in itself. The question you have to ask yourself is whether you prefer to laugh at all the awkward failures you’ve experienced or to regret all the missed opportunities you rejected out of fear of failure. To me, failure is an inevitable aspect of my life. A “challenge” if you so want that I will have to face every once in a while. With it comes the realization and wisdom that the only fool-proof way to avoid any kind of failure is to not try at all. The attempt to avoid failure at any cost – by not trying – is an irreversible mistake, which I regard as the worst failure of all.” — Steve Mueller

Do not play what if game

You should analyze the past. But never sink down to extrapolating what if I have done X and now would be at Y. Well what if you have done X and because of it you were hit by a bus the next day.

The only path that you know for sure kept you alive is the path you have traveled. All other paths from the past could have lead to death by now.

“Be not ashamed of mistakes and thus make them crimes.” — Confucius

TIM FERRIS: “What advice would you give to Marc, the 20-something, at Netscape?”

MARC ANDREESSEN: I’ve never for a moment even thought about that. I don’t do replays well. The question I’ll never answer is, ‘What would you have done differently had you known X?’ I never, ever play that game because you didn’t know X.’

DoNot Compare yourself with others

Your life is your life. Their life is their life.

Clarification: it’s encouraged to model other’s desired qualities. It’s the unproductive comparison of where someone else is or what they are doing without a healthy goal of modeling that must be avoided.

“When you are content to be simply yourself and don't compare or compete, everybody will respect you.” — Lao Tzu

”I'm Too Busy Working on my Own Grass To Notice If Yours Is Any Greener” — David Peplinski

“Comparison Is A Thief Of Joy” — Theodore Roosovelt

“The more you know what you really want, and where you’re really going, the more what everybody else is doing starts to diminish. The moments when your own path is at its most ambiguous, [that’s when] the voices of others, the distracting chaos in which we live, the social media static start to loom large and become very threatening.” — Alain De Botton, TOTs pg. 487


Instead DO:

Overcome yourself of yesterday

“Determine that today you will overcome your self of the day before, tomorrow you will win over those of lesser skill, and later you will win over those of greater skill.” — Miyamoto Musashi

“Don't compare yourself with other people; compare yourself with who you were yesterday.” — Jordan-Peterson

Compare yourself with your own potential.