Case Study: From Quiet Survival to Bold Revival — Jerald’s Rewilding Journey

When Jerald first met Laurel in Mexico City, he was standing at the edge of something new. He had just completed a 5-month Remote Year program—a leap of faith into adventure he had long dreamed of. After years of grief following the loss of his wife, Cesily, and the quiet acceptance that life might not hold much more joy , something had shifted. Surrounded by a vibrant group of travelers, Jerald reconnected with a part of himself that had been dormant for years : the dreamer, the explorer, the man who once imagined a life of movement and meaning.

But as the program neared its end, Jerald knew that continuing this lifestyle—and building a business that could support it—would require more than momentum. He needed support from someone who had walked a similar path, someone who understood the internal rewiring that comes with turning your life inside out. That’s when he began working with Laurel.

Together, they navigated the very human complexities of reinvention: balancing the freedom of travel with the grounding pull of family back home; rebuilding his professional identity after decades in accounting and consulting; learning to sell his services not through ego, but through genuine value. They worked through the stops and starts, the fear of not being enough, the grief that still lingered, and the longing to live life fully—not in spite of the loss, but because of it.

And slowly, things began to take shape.

He traveled more and more. He built a business as a Fractional CFO—work that truly lit him up. And perhaps most unexpectedly, he began to open his heart to love again.

Today, Jerald is living closer to his teenage dreams than ever before. The road hasn’t been linear. Life has thrown its fair share of wrenches. But through every twist, he’s stayed connected to his vision—and to the version of himself he always hoped would emerge: alive, in motion, and deeply at home in the world.

Jerald’s coaching journey didn’t follow a strict blueprint. It couldn’t—because Jerald’s life was in flux. He was splitting time between travel and Seattle. There were financial tensions, emotional pulls, and unexpected detours. He was trying to build a new business while straddling two worlds: the one he had built over decades, and the one he was beginning to create for himself.

What made the difference was the space he and Laurel created together—one where everything could be brought to the table. One week they’d talk strategy, refining Jerald’s offer as he transitioned from consulting into CEO-level strategic advisory. Another week, they’d process the complex emotions of dating again after loss, navigating uncharted relational territory with an open but still-tender heart.

Through it all, Jerald kept showing up—for himself, for the vision, for the version of life he was slowly building.

He let go of needing everything to be figured out. He learned to trust his intuition more. He stopped seeing business as something to prove, and started seeing it as a fun challenge, a way to support his new digital nomad community, and a vehicle to support the life he wanted to live. He began traveling more spontaneously—sometimes arriving in a new country without a place booked, trusting that it would all work out.