I’ve started weaving a new question into almost every conversation I have.

“What are you wrestling with at this stage of life and leadership?” 

The responses have been diverse and insightful. Here is a sampling:

• -Managing my time and tasks in order to do more that aligns with my unique abilities.

• -Entrusting responsibilities to the next generation of leaders.

• -Handling disappointment.

• -Decision fatigue.

• -The loneliness of leadership.

• -Developing resilience.

• -Finishing well.

• -Combating busyness that leads to lukewarmness and quick reactions.

• -Learning to trust in God’s provision more than my own grit.

What do you notice about those statements?

I’ll tell you what I notice – none of them talked about the outer work of strategy, budgets, policies, and the other visible mechanics of leadership. Rather, what was top of mind for each person was the inner work of leadership. These are the invisible dynamics that determine whether a leader can sustain the outer work with integrity and clarity. Richard Rohr would call these second-half-of-life questions.

Early in our careers, we do the important and necessary work of acquiring skills, making connections, and hustling. We are concerned with building a strong sense of identity, growing in competency, and position. But as we reach mid-career, a transition needs to happen.

Sometimes this shift is triggered by an external factor like illness, being fired, the death of a loved one, or a major failure – whether your own or someone you admire. Sometimes it comes from an internal conflict…the realization that success, achievements, and wealth don’t satisfy. In fact, they leave you feeling emptier.

That’s what I love about the people who responded to my question. Each one is a driven Christian leader who is accelerating into their most productive and influential years. They’ve proven that they can lead people and companies. They’ve reached mid-career with extraordinary capacity. They know that they are at an intersection of reexamining their approach. The grit and hustle that served them in the first half will only lead to running on fumes and frustration in this next season.

How would you answer that question if we were having coffee? “What are you wrestling with at this stage of life and leadership?” It’s not an academic question. What is your initial reaction?

I am genuinely interested in hearing your response because we at Workmatters want to do a better job of serving you as your career grows. Please help us develop products, events, and content that will address second-half-of-life questions. I invite you to drop me a line or connect with me as soon as you can: DHarvey@workmatters.org