The questions we ask ourselves shape the lives we live. They set the terms of our self-talk, filter our view of the world, and quietly shift our compass. Ready to change course? Turning 60 has created a natural landing for me to ask some tough questions. Here are 3 for those willing to join me in the journey forward:
Are there any leaks in my boat? The Foundational Four of Time, Money, Health, and Purpose are not intended to take the stage in our lives but they do SET the stage for what matters most. Notable gaps in any of these four can cause us to take on water and never get out of the harbor. Reflect honestly: packed schedules, mounting debt, dwindling fitness, a fading sense of purpose. Do any of these deserve a closer look and a committed response?
Are my current peers anchors pulling me under? Or launchpads moving me forward? Our 3 (now adult) kids grew up hearing their dad reminding them that we become the five people with whom we spend the most time. It’s a cheat code for living that holds true across almost every aspect of life. A Kellogg/Harvard Business School working paper on toxic workers found that sitting near a high performer notably elevated performance. Similarly, sitting near a negative employee not only dragged down performance but also increased likelihood of quitting.
Have I been settling? When was the last time I took on a new challenge? Stepped outside my proverbial comfort zone? Moved beyond society’s pull toward status quo mediocrity? Gravity is a powerful force and the 4-letter f-word (”fine”) is a readily available escape clause to remaining on the couch. But life - fully living - involves leaning into who we are ever free to become. It’s a life which was never available from the couch, in spite of the Sirens’ song calling from our screens.
Taking these questions seriously creates tension. But it’s in that tension where we move, stretch, and grow. Like the dragons of legend, the felt tension signals we are nearing the gold - and reminds us we are not... done... yet!


