It has been a month since I executed my deliberate choice to step away from the structure of traditional W-2 employment. Since then, my wife and I took my mom on her first cruise; I haven’t missed a single workout; I’ve caught up with close friends; we made a trip to visit extended family; and I continue to explore interests as they unfold. Along the way, I’ve noticed a curious pattern in the conversations that follow me sharing that I have stepped away from traditional work. When people hear the news, well-meaning as they are, the most common question is: “So, what are you going to do with your time?”
It’s an understandable default. It’s simple and polite, even if it feels a bit misplaced. I hadn’t been asked that question since I retired from the Navy. Society rarely questions how we spend our hours when we hold a conventional job; the assumption is that filling a calendar with scheduled meetings and tasks is inherently productive and responsible. Structured busyness is often assumed to be meaningful, purposeful, and fulfilling. The moment we remove that external framework, others worry about how we will manufacture structure, maintain meaning, find new purpose, and enjoy continued fulfillment.
Last week, I attended the funeral of a dear friend’s mother. She lived a very full 83 years, surrounded by family, rich stories, and lasting impact. While catching up with people there, the topic of my recent transition came up. The reaction couldn’t have been more different than what I experienced until that point, partly due to the solemnity of the event, and partly because many in attendance had the gift of age and perspective.
Nobody asked what I was going to do next. Instead, they simply celebrated the choice and endorsed the decision.
In a space where the brevity of life is front and center, there is no confusion about the value of personal freedom. They understood instinctively that time is our most precious, non-renewable resource. They recognized that stepping away from a defined track to pursue emerging interests, invest in relationships, and intentionally own your day isn’t an aimless retreat – it’s an act of deliberate living. It’s something many of them had wished they had done earlier in life.
It was both refreshing and validating. Yet, it also left me pondering a broader question: why do so many of us wait until the end of life to celebrate such autonomy, while in the middle of it, we treat external routine as a, if not the, primary measure of worth?
Who we are is never defined by a tax form, a title, or a pre-packaged schedule. When we stop measuring our contribution solely by the hours we sell, we make room for the impact we are truly called to create.
For me, seeing peers on social media celebrate a new job title or promotion can sometimes stir a mixed reaction. While my default should always be celebration, I occasionally catch myself wondering why so many remain locked into the climb, or what they might be burying beneath the noise of work. But asking those questions of others is just as unfair as them asking me how I’ll fill my hours.
So, I continue to celebrate colleagues in their pursuits. And for anyone wondering what I’m doing with my time, the answer is simple:
Investing it in the people who matter most, pursuing emerging interests, and owning my days in favor of renting them out.
- How much of your daily schedule reflects your core values versus external expectations?
- If a traditional definition of productivity didn’t constrain you, what interests or relationships would you prioritize today?
- How can you bring a greater sense of intentionality and ownership to the time you have right now?
