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Early this year, over one of our many coffee chats, I asked my father to tell me his top 5 life highlights and what made them stand out. He gave me a strange look and admitted he had never really thought of that before. He had lived a full life, but stopping and reflecting on the highlights of his life was something he had not done.

Listing your highlights is one of the most powerful questions you can ask someone – whether in a performance review with a team member focussed on last year’s highlights, kids on their birthday to help them see how far they have come, yourself to celebrate your successes or your elderly parent to help them find meaning in their life.

But the greatest depth in the conversation comes from the question, “Why is that important to you?

When someone tells you their highlights, their voice deepens with emotion, they re-live the memory in their mind, and their eyes take on a faraway look. When answering the “why” question, they share their values and give you a window into what makes them tick and what gives them joy.

Knowing their responses helps build connection, develops an appreciation for what they have experienced and helps you to tailor more experiences that deliver joy for them in the future.

Too often in life, we look at what didn’t work and what we need to improve. We focus on the next thing, rather than stopping to reflect and celebrate on where we have been. And yet without that reflection, we don’t know when we have “won”.

So, when I asked my elderly dad about his highlights, he went away for a few days to mull it over. When he came back, he had written out his list so he wouldn’t forget anything. His list was unique to him and fully reflected the richness and diversity of his life. The things he had chosen included things I had never realised were important to him.

We talked in depth about his list. And to make the conversation even richer, I filmed our discussion so my girls and my brother could hear and see his stories in years to come.

Tomorrow is my birthday. And as is my annual birthday habit, I will be reflecting on my life highlights for the past year. One of the key highlights for me was that single conversation with my father. Talking about his life list helped him gain closure and a sense of a life well lived. It helped to ensure there was nothing left unsaid when he finally passed just over a week ago.

That single conversation was a definite “win” in my life. Most of the time, winning has nothing to do with money or fake success. Winning is simply how you personally choose to define it. So how do you define winning? What are some of your life highlights?

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