This coaching regrets exercise is useful to help a client think about making life decisions—with the outcome that they will look back over their life and have no regrets about the decisions made. When we think of pursuing our dreams, we usually have some idea of the costs and risks required to reach them. However, few people examine the cost of not taking the risk to pursue a dream. This exercise helps you weigh the price of both courses of action.

Coaching Regrets Step 1: Get Into the Dream:

This is an emotive exercise, and for it to work you have to really get into the dream. Visualize yourself living it. What would be different in your life? How would it change you? What would it be worth to reach it?

Coaching Regrets Step 2: Look Back:

Now, imagine that you are 75, looking back on what you’ve done in life. If you had never pursued this dream—the risk seemed too big, or you couldn’t find the time or money—how would you feel about that?

What would you lose? 

What would you think of yourself for making that choice? 

Would you be profoundly disappointed, or would it not be that big of a deal?

Coaching Regrets Step 3: Compare:

Once you’ve gotten in touch with the cost of not pursuing your dream, compare it to the cost of going for it. How does this change the equation? What’s the best long-term choice?

Coaching Tip: Here are a few typical questions a coach might use with regrets:

• “We often think about what it will cost to follow a dream. What would it cost you if you didn’t pursue this?”

• “Imagine you are 80 years old, sitting on the porch and talking to your grandkids about this decision. What would you want to be able to tell them, and why?”

• “What, if anything, would you miss out on if you just put this on the back burner for five years?”

• “How does reflecting on regrets change your sense of urgency about this dream?”

A pioneer in Christian leadership coaching, Tony Stoltzfus has trained thousands of coaches, founded several leadership- and coaching schools and created a wide range of leadership resources used around the world.