The Second Harvest: Recasting Midlife As The Start of Your Best Years

Waking up and starting life over at the midst of a midlife crisis

Update: Along with Devon MacDonald and Bernhard Schluga, I’ll be hosting a 5-day retreat at the I AM ESCAPE Retreat and hotel, in Austria on 7th-13th July, 2025. Entitled, Second Harvest, this retreat is for individuals and couples navigating a major life shift, whether personal or professional (or both), who are ready to leverage their experiences, wisdom, and resources to create a life of deeper meaning, fulfillment, and alignment. You can learn more or apply here or join one of our informational calls.

Midlife, for most of us, carries the weight of cultural stereotypes — a time of crisis, of diminishing returns, of existential dread. For many it is the beginning of the end. It certainly was for me.

What I didn’t expect was that instead of being the end, it became the start of the best part of my life.

After losing my wife, Kristy, to cancer, I found myself standing at a crossroads that would define the second half of my life. To add insult to injury, I found myself unemployed and in the depths of the COVID pandemic. At 51 years old I was widowed, jobless and left with a young family to take care of. This was a midlife crisis of epic proportions.

But as I began to grapple with my grief and search for meaning, I realized midlife could be something far greater. It could be a second harvest — a chance to draw from the rich soil of past experiences and plant seeds for a deeply fulfilling future.

From Loss to Possibility

When Kristy passed away, the pain of loss was undeniable, but it also became an accelerant for change. Her death served as a very uncomfortable and vivid reminder that life is fragile and finite. Even as this unthinkable situation surrounded me, I recognized that I was not at the end of something but at the beginning of a profound transformation.

Kristy’s passing propelled me to reexamine my choices. I had already spent decades building a career, raising a family, and collecting accomplishments that look impressive on the surface. But there was a gnawing sense that my greatest work — and my greatest joy — still lay ahead. I didn’t want midlife to be a gradual decline; I wanted it to be an ignition point.

The Concept of the Second Harvest

The idea of a second harvest comes from one of the themes in my business life: agriculture. My longest running business was called Fresh Tilled Soil in honor of the careful nurturing farmers do to keep their land rich and rewarding. Well cared for fields yield an often richer bounty after the first harvest. In our lives, this second harvest is a metaphor for the opportunity to leverage the wisdom, networks, and resilience we’ve built in our earlier years.

It wasn’t until my midlife crisis that it even occurred to me that the years after 50 might be the most creative, loving, energetic and rewarding. It felt counterintuitive to think this way but the pull from deep inside me made me trust what was happening.

Designing a Second Harvest Life

To be clear, it’s not an easy switch to make. The transition wasn’t obvious. I had to move through profound grief and embrace the discomfort of unanswered questions. Could I raise my children without their mother? Could I love again? Who would love an older, widower with emotional baggage? Could I redefine my identity? How could I support my family financially, emotionally, and how could I simple stay alive long enought o raise my boys?

The answers didn’t come overnight. They came through experiments — what I call “thin-sliced retirements” — moments of exploration, reflection, and trial. Each question became a hypothesis. Each hypothesis became a journey of discovery. How might I do these things?

In my career as a product designer, I’ve used design thinking to solve complex problems. After Kristy’s death, I began applying the same principles to my life. Instead of treating my grief as something to overcome, I treated it as something to integrate. This led me to design a life centered on connection, creativity, and intentionality.

Experimentation and Renewal

I approached this phase of life as a series of experiments. Some were metal exercises, while others required a commitment to rolling the dice and seeing what answers emerged. Here are some of the experiments I ran with my family:

• Spending three months in Europe to test whether living abroad felt right.
• Embracing single parenthood and celibacy for two years to recalibrate my emotional foundation.
• Reimagining work through fractional executive roles to find balance between professional fulfillment and personal freedom.

Each experiment yielded answers (and some more questions). Some questions found resolution, while others became new starting points. The goal wasn’t perfection — it was discovery.

The Role of Creativity

Creativity became my anchor. It wasn’t just about producing work; it was about how I approached challenges, relationships, and possibilities. Creativity is at the heart of my latest experiment, Second Harvest, the personal growth initiative I’ve created to help others navigate this journey. By tapping into our inherent creativity, we can transform fear into courage, setbacks into opportunities, and our past into a platform for renewal.

The core mission of Second Harvest is to help individuals reclaim and nurture their creativity, drawing from their life experiences to create a balanced, fulfilling, and financially rewarding life. It’s about guiding people through a process of personal growth and self-discovery, enabling them to harvest the creative potential they’ve cultivated over time and transform it into meaningful work.

Midlife as a Beginning

Through this journey, I’ve reframed what it means to be in the middle of life. Rather than seeing midlife as a plateau or decline, I see it as a springboard. The first half of life provides the building blocks or resources — skills, connections, resilience — that can power an extraordinary second act. Recognizing that what made us who we are needs to be honored but also redefined or reframed so it’s not a burden in the next chapter of our lives.

This perspective isn’t about denying the challenges of aging, grief, or uncertainty. It’s about expanding your experience of life so those challenges become smaller in comparison to the possibilities ahead. If grief or loss is the biggest piece of furniture in the room, you’ll keep bruising your shins as you try get around it. But if you expand the room and open up the spaces for growth, the furniture can exist without becoming a painful obstacle.

What’s Next?

For me, this second harvest is still unfolding. I’m focused on building a life that balances creative projects with meaningful relationships and personal growth. I’m still experimenting and opening new doors. There are more lessons to learn but I’ve learned that the journey is less about reaching a destination and more about embracing the process.

The second harvest is a mindset — a recognition that our lives can bear new fruit even after the hardest of seasons. It’s an opportunity to take stock of where we’ve been, what we’ve learned, and how we can channel that wisdom into the future. For those navigating midlife, I invite you to think not of what’s ending but of what’s beginning. The best chapters of your life may be the ones you haven’t written yet.

Second Harvest is going to be running events in 2025 to empower individuals to reap their creative potential and align their passions with purposeful, sustainable success. Through these events, I hope to help people reconnect with their true creative selves, turning their experiences into seeds for growth — both personally and financially. If it goes as planned, we’ll all leave with a renewed sense of personal agency and creative empowerment, clarity about how to align their creative passions with meaningful work that contributes to their financial well-being and find a balanced, calm way to pursue our personal and professional lives with purpose. Find me here if you’d like to know more.