Cultivating Confidence: My Chat with Cannabis Grower Jack
Back in our very first episode of the podcast, I interviewed my mom and uncovered a gold mine of life lessons, including what it takes to instill strong values in our kids. Then, in episode number two, we dove into the power of being honest with ourselves and our partners. Now, in this third episode, I recently found myself in a totally unplanned conversation with a fascinating fellow, Jack, right after we both wrapped up a product photo shoot. The moment felt right, so I hit that record button, and here we are.
Jack grew up on a family farm outside of Portland—an old-school operation that produced berries, grains, and a whole lot of early mornings spent crisping in the Oregon sun. Sounds like the standard farmer’s life, right? Well, add a dash of Bible-study Wednesdays, Sunday church, and the same last name on a county road sign, and you’ve got an idea of just how generational it all was. Then Jack went and did something wild: he steered his green thumb toward cannabis.
In our chat, Jack opened up about going against family expectations, pushing past repeated failure, and finding meaning in his work—even when it meant stepping outside those traditional lines decorated with rows of blueberries. Below, I break down some takeaways from our conversation, from the final-boss challenge of parental disapproval to the triumphant moment of forging your own path.
1. A Farm Kid at Heart
As a kid, Jack helped churn up farmland, load up firewood, and pick berries, all with a strict daily schedule that left little time for messing around. The structure was relentless—work on the farm six days a week, Sunday for church, rinse, repeat. But that routine also planted seeds of discipline and consistency in him.
On top of that, Jack’s parents took their farm and faith seriously, so it’s no shock that his decision to grow cannabis was met with, shall we say, a lukewarm reception. Picture Luke Skywalker telling Darth Vader, “I’m dropping out of Jedi school to become a professional interpretive dancer.” (Okay, maybe not that extreme, but you get the idea.)
2. Where Purpose Takes Root
Jack’s pivot to cannabis actually started from a compassionate angle, helping a friend’s mother who was dealing with chronic pain and found little relief in the heavy opioids that doctors kept prescribing. The woman was open to trying cannabis, and Jack became her grower. Just like that, he was fulfilling a need she never imagined would help—and found his own calling in the process.
Watching her health and spirits improve provided Jack with something money couldn’t buy: a sense of mission. What began as a single plant in a closet grew into an entire greenhouse operation. Before anyone could say “holy hemp,” he was nurturing rows of cannabis plants—both the psychoactive kind (high-THC) and the non-psychoactive varieties (CBD-rich). Some people call that living on the edge; I call it being driven by purpose.
3. Embracing Failure—Or at Least Waving at It
We’ve all heard the old adage: “Fail faster.” That might work if you’re a tech startup in someone’s garage, but in farming—cannabis or otherwise—the margins for error can be painfully slim. Jack admitted he’s had more than a few flops. Plants get moldy, the weather refuses to cooperate, or some complex building step needed to happen earlier in the season. There’s always a next time, but losing a crop can feel like losing a chunk of your soul.
He told me his biggest breakthroughs came from leaning into his mistakes. It’s not that he sets out to fail (that would be like complimenting your boss’s haircut when you secretly hate it—pointless and painful). Instead, each misstep is a chance to learn and adapt. The more he confronted those problems head-on, the quicker he found solutions and prevented repeat catastrophes down the line.
4. Going Against the Grain (and the Parents)
Speaking of catastrophes: telling your parents, “I want to be a cannabis grower,” can be like telling them you’re setting sail for Mars using a paper boat. If any moment deserves dramatic background music, it’s that one. Jack opened up about being turned down by his parents when he first asked for help to get his operation off the ground.
In their eyes, cannabis simply didn’t belong in the family’s proud tradition of blueberries and wheat. Over time, though, they began to see the value—especially when they themselves tried growing hemp outdoors (with only moderate success). They saw their son’s passion, recognized that hemp and cannabis are industries here to stay, and eventually came around. Ironically, it was the same values of dedication and thoroughness they taught him that fueled Jack’s journey to begin with.
5. The Final Boss: Yourself
Jack doesn’t just credit family pushback for lighting a fire under him—he points out that sometimes the biggest obstacle is right in your mirror. Between doubts about having enough money, resources, know-how, or connections, there’s no shortage of excuses to stay in your comfort zone. But you only level up by trying.
He eventually saved up a bit, pulled that trigger to move, and started his greenhouse in an area with conditions that worked for cannabis. It was a crash course in business, self-belief, and humility (ask him about the first time he discovered an entire row of plants turning sour—oof!). Yet each lesson propelled him further toward the dream.
6. Honoring Your Roots While Growing Your Own Branches
When I asked Jack if he felt a sense of fulfillment in this new calling, his answer was a resounding yes. He’s still got big dreams—warehouses of healthy plants, a strong customer base, maybe a cameo in a rap video—but he’s already seeing meaningful impact from each harvest. He’s also found that bridging the gap between old-school farming wisdom and innovative cannabis cultivation has brought him closer to his family. They might shake their heads from time to time, but they also brag a little about their son who’s thriving in a brand-new field. (No pun intended. Well, maybe a tiny pun intended.)
7. Parting Thoughts: Failure, Faith, and Farming
I love talking to guests like Jack because he’s proof that with enough resilience and optimism, we can transform our so-called “final boss” of parental disapproval into an unlikely ally. Sometimes the real boss is the negativity we churn up in our own minds—telling ourselves we can’t do something because it’s “too hard” or “no one in my family understands it.”
If there’s one thing you can use from Jack’s story today, it’s to face those personal doubts head-on. Learn from the mistakes, treat fear as just a friend who’s comically late to the party, and never forget: if your heart is set on that dream, the only person who can truly stop you is you.
Thanks for tuning in to Episode 3 of the podcast. Stay inspired, keep your eyes peeled for unplanned moments of insight, and never forget that the road to success might be bumpy—but hey, so is a good potting soil.