top of page

It's Questionable

During a friend's 70th birthday party, I was talking to a local sailing guru and was prompted to ask what I consider the most important question of my life. What astonishes me is not how few people ask this question, but that by my mid-50s, I had never asked it...

One model of human behavior holds that we steer to the questions we ask, and that we tend to have dominant questions that rule our lives. Asking questions like

How do I get a bigger piece of the pie?

How can I get more people to like me?

or worse,

Why don’t people like me?

lead us to very different lives compared to asking questions like:

How can I make the biggest contribution?


What can I do to make people’s lives better?

These are questions we ask of ourselves, that, for the most part, we don’t even realize we are asking. But if we can start asking ourselves questions with intention, it can profoundly impact our lives. Here are some great questions that are worth asking:

What are my values?

What are my beliefs?

What are my limiting beliefs?

What are my strengths and weaknesses?

What are the most important things for me to focus on?

What are my triggers?

What things am I doing that are not in my best interest?

What are the best ways for me to grow and improve?

These questions have transformative potential, if considered and acted upon. If we turn our question-asking attention outward, we again find opportunities for breakthroughs. Here are some outward-oriented questions worth asking:

What can I learn from the people around me?

Where is our common ground?

What is the best way to connect with people?

How would I interact if I were modeling someone I really admire?

There are also questions we ask of others. These can be to gain information, to connect with people, or to benefit from their knowledge and wisdom. Asking open-ended questions in these situations usually draws out richer, more interesting answers, compared to closed-ended questions. There are also questions to prefer and avoid. Questions starting with why tend to come across as challenges and might receive pushback. Questions starting with what are usually more neutral, and questions that start with how tend to be collaborative and good at moving toward mutually agreeable solutions.

With the birthday party, I was at a stage in life where I had accomplished most of my major goals. I was looking ahead and saying,

I have some cash in the bank and some gas in tank. How do I want to spend my life?

I use the word spend like life is money, which is intentional because our lives do have worth. With that perspective, it might be unsurprising that the answer that came back was:

I want to spend my life doing something worthwhile, which means doing something to leave the world a better place for my having been here.


bottom of page