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  • Writer's pictureLisa Blair Fratzke

The Fifth Time Is the Charm

Updated: Apr 24, 2020

One of my favorite podcasts these days is by Tim Ferris. If you haven’t listened to it before, it’s a long form podcast and can be anywhere between 60 minutes to two hours in length. It’s pretty much unedited – just two people talking, Tim and his guest.

Because of how popular the podcast has become and Tim’s overall network as an entrepreneur, angel investor and author, his guest list is pretty fascinating. It’s made up of people that you’d like to listen to for over an hour.

Each episode is filled with insightful thoughts about life from people who are just trying to do their best – and making a difference in the process.

All of this to say that in the last episode I listened to he interviewed a man who is a New York Times bestselling author, boutique hotelier in San Francisco and worked for Airbnb as the head of global strategy and hospitality. His name is Chip Conley and his latest venture is a Modern Elder Academy to help those in their middle years calibrate and reassess their lives in order to find maximum fulfillment.

He shared that one of the exercises he had the leadership team do at Airbnb to define their purpose and mission was to get into pairs of two and ask each other five times: “What do we do?” They had to answer that same question five different ways. That’s how they drilled down to the core of what Airbnb is as a company – a collection of people with a mission to help others "belong anywhere."

He says that this same exercise can be applied to us and our personal lives. According to Chip:

“The question would be: ‘What mastery can you offer?’ So have a friend of yours ask that question of you five times, and you’ll be sort of surprised at, by the fifth time you get asked that question, and you’ve had to come up with four other answers before that, what kind of revelation you may have in this archaeological dig.”

There’s something to this idea. It forces us to dig deep and answer questions in specific terms when we are asked to answer the same question in five different ways. The first way is likely the most generic. The second a little less so, until the fourth or fifth answer gives way to a truth that is unique to us.

Because most of us aren’t willing to admit that we offer a mastery. Most of us aren’t willing to look at what we have to offer and call it worthwhile. But the hard and

sometimes unrecognizable truth is that it is – and this world needs who you are and who you are created to be.

It’s okay to acknowledge that there are things we excel at and gifting that we can use for the benefit of others. To not acknowledge that would be to miss an opportunity to make this world a little better, a little bolder and a little brighter.

So, my question to you on this Monday morning is this: “What mastery can you offer?”

Answer this question on repeat five times – and you may find the answer sheds new light on the path that you were made to follow.


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