The tough decision checklist: Finish it and sleep soundly tonight

Stop second-guessing yourself and get out a pen. After you go coolly through this checklist point by point, you’ll be ready to stand up and make that difficult call—no hesitation, and no regrets.

  • I’ve done all the research and legwork I possibly can about this issue. I know the math, the history and the precedents.
  • I’ve done everything I can to remove the risk factor, taking steps to stabilize the circumstances that I can control.
  • I have examined the worst-case scenario that might occur if I go ahead with the decision—and I’ve even thought of some truly unlikely consequences, the “black swans.”
  • I fully understand the point of view of those who are likely to disagree most strongly with my decision.
  • I have visualized opening up the newspaper tomorrow and seeing news of my decision splashed across the front page, and I know what the headline would likely be.
  • I have put this decision into the context of my entire career to make sure it’s not something that could impact it irreversibly.
  • I have thought about what a much younger, more idealistic version of me might have done in this case, and I’ve explained my reasoning to that imaginary person.
  • I’ve taken the time to look at the issue through both very optimistic lenses and very pessimistic ones.
  • I have talked to the one person I trust most in the world to get their view on what I should do.
  • I have talked to someone utterly impartial, with no knowledge of the situation, to get their gut feel for what I should do.
  • I have identified and discarded all the information which might sway me emotionally, but has no place in making a logical decision.
  • When I look at the list I’ve made of the positive and negative consequences, the positive do outweigh the negative.
  • I have determined that no matter what the outcome, there is a way to fix it if things go haywire.
  • I am prepared to be turned against, and I will neither overreact to inevitable arguments or let valuable relationships suffer.
  • I have reminded myself that even if I make the wrong decision, carrying it out will change the circumstances to the point where unexpected opportunities and situations will arise—giving me yet another chance to act, make things better and be a strong leader.