iirecently spoke at a conference in Silicon Valley and I was pleased to stay for the rest of the event afterwards. The final speaker, Connie Podesta, said something which struck my curiosity. She said, “I am going to share the two most important questions you will ever answer. If you answer no to either of them I will know some things about you. I will know you are more stressed than you need to be. I will know you are unhappier than you need to be.” She had my attention. Here are the two questions:

  1. Are you proud of the choices you are making at home?
  2. Are you proud of the choices you are making at work?

We might feel tempted to push these questions aside as being overly simplistic. Yet, as Oliver Wendell Holmes is credited with saying, “I wouldn’t give a fig for simplicity on this side of complexity but I’d give my right arm for simplicity on the other side of complexity.”

One reason these questions strike me as simplicity on the other side of complexity is they remind us to pay attention to our current choices rather than our current results. Our results, whether we are currently experiencing success or failure, can be misleading because they happen after the fact. They are lag indicators. Consider how these questions can help:

In Times of Failure

There are clearly times when things are not going as we want them at work or at home. We could complain about this. We could make a fuss. We could become discouraged. Yet, if we ask these two questions every morning we can focus our energy on the choices we can make. Messed up something? Fine. We can get back on track. We can ask whether we are proud of the choices we are making now.

In Times of Success

Success can be a poor teacher. It can teach us to under invest in the things which generated the success in the first place. I have argued this more fully in a piece for Harvard Business Review where I intentionally overstate the case in order to make it: success can be a catalyst for failure. We can begin to coast along and in the very moment of our greatest outward achievements we can make choices which undermine our future success.

In Rudyard Kipling’s beautiful poem “If” he brings together both of these scenarios when he penned counsel to his son:

“If you can meet with Triumph and Disaster
And treat those two impostors just the same…”

Kipling cautions his son to distrust both success (triumph) and failure (disaster) as imposters. He warns him both are deceptive.

Asking these two questions and becoming more deliberate in our choices can seem like a small thing in the moment. Sometimes we feel we are too busy living to really think about life. Yet failure to reflect on these questions could contribute to a life of regrets. Indeed, an Australian nurse, Bronnie Ware, cared for people in the last 12 weeks of their lives and she recorded the most often-discussed regrets. At the top of the list:

  • “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”
  • Next on the list: “I wish I hadn’t worked so hard” and “I wish I’d had the courage to express my feelings.”

I am not sure these are the most important two questions we will ever ask, but surely we will have fewer regrets if we spend a moment every morning asking them.

Closing Remarks

Jason Pries QuestionNow, I’d love to hear from you.

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