Goodbye Old Hello Bold Read & Reflection Questions

1. (The book cover through the end of the introduction p.17) Let’s start with the title. Goodbye Old, Hello Bold—got it. But what about the subtitle? A Joyful Leap into a World of New Possibilities as We Age. A joyful leap—really? Or is it more like a sudden unwanted push, a painfully slow slide, or has it been an easy breezy stroll in the park? Write or draw what geJng older is like for you. 

2. (p.8-62) Swedish folks call it death cleaning. Most of us call it downsizing. The idea is the same. To move forward and make room for new things in our lives, something has to go. In the book I said that all great journeys begin by going “away,” and that can include moving away from relationships, places, things, activities, ideas, dreams, even our self-image. 

3. What in your life may have outgrown its original value and needs to be tossed, tweaked, or re-purposed to clear space for the “highest and best you” from here on in? 

4. (pp.63-100) Once you’ve cleared off your metaphorical plate, what’s next? Some people are loaded with great ideas already and can’t wait to get going now that they have the time and opportunity, but some of us don’t have a clue, or at least not a clue that works with creaky knees, uncooperative relatives, and a retirement account that turned out to be too small. That’s why I’ve listed dozens of possibilities to prime your creative pump. 

5. What’s next for you? Choose an assortment, or focus on one big idea, like the wildly successful yak farmer. What is so appealing to you about the things you chose? 

6. (pp.101-112) Going back home after hearing a rousing motivational speech, or closing an inspirational book, and trying out some of those wonderful new ideas on your family and friends, can be daunting or even disappointing. Life can quickly burst our enthusiasm bubbles. 

7. Think about the people in your current circle of friends and family. Which ones might be interested in hearing your new thoughts, or willing and able to provide support for exploring new possibilities? 

8. (pp.113-117) Poor Bony Tony. Wait, wait, and wait some more. It never seemed to be the right time for him to get a move on and create the life he wanted. Lucky for us, we’re nothing like Tony—ok, maybe sometimes just a little. So, what are you waiting for? We’ve all heard that it’s supposedly never too late for something to be possible, but, in my experience, it can be too late for something to be plausible. 

9. What first steps would you need to take right now in order to transform your getting- older journey into a more joyful, meaningful, rewarding, and exciting one? 

Final thoughts: We can’t help getting older, but we can help thinking, playing, eating, feeling, dressing, or talking that way. Be bold! What have you got to lose? One of the perks of having lived a bit longer is that the phrase “now or never” has taken on a whole new meaning, and being bold and stepping out into the unknown might even be a bit easier to do than it was back when we were overloaded with responsibilities. 

Most of us have had to be very bold many times in our lives, whether we wanted to or not. That means looking back over a lifetime is the perfect vantage point for making some new powerful, positive choices. 

What does saying “goodbye” to old and “hello” to bold mean for you?