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What does it take to turn a junior golf mindset into a career of meaningful leadership? We sit down with Chief Legal Officer Jessica Monson to trace the winding path from Fargo fairways to the Caribou Coffee C-suite—and the life lessons gathered along the way. Jessica shares how biking to Edgewood with a bag over her shoulder, ASU golf camp, and playing with top junior boys taught her “think box vs play box,” a mental model she still applies to decisions, risk, and resilience at work.

The story doesn’t smooth out; it gets honest. We unpack recruiting pressures, the move to Santa Clara, homesickness, the transfer back to NDSU, and a London trip colliding with the 2005 bombings. Jessica opens up about choosing law over the PGA track, going in-house at Life Time, and learning to build businesses rather than win arguments. Mentors and a “glass ball” reminder—protect family, health, and spirit—reshaped how she manages energy, teams, and trade-offs. We talk grief and gratitude through “Live Like Rach,” a family mantra that turned loss into action, generosity, and daily courage.

There’s joy, too: a manifest-it hole-in-one for a Rolex she couldn’t accept, later echoed by a gift from her dad; joining Hazeltine and giving back through the U.S. Amateur and KPMG Women’s PGA; and growing women’s golf by pairing visibility with opportunity. We dive into wandering with eyes open, short meditations, walking to think, and how to bring “play box” focus into meetings, hiring, and big bets. If you’re balancing ambition with purpose—or searching for permission to try, fail, and try again—this conversation offers practical tools, heartfelt stories, and a nudge to keep swimming.

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