Leadership Lessons
From Landing Pages to Life Lessons.
My co-worker logged on expecting a simple conversation — a check-in on Jake Perry Coaching’s website and a roadmap to support an upcoming relaunch. What she got instead was a window into what happens when you blend strategy with humanity, content planning with connection, and yes, even web design with a stuffed elephant named Stuffy.
Their meeting began like many others — a little tech hiccup, a few light jokes, and a shared sigh about how tired they both felt. But almost immediately, she found herself pulled into something deeper. As Jake vulnerably reflected on his own fears around finances, purpose, and identity, she was reminded why she had signed on to help in the first place.
She spoke about a recent chat with a friend — a moment of real talk about finances, pressure, and how even the wealthiest people are often carrying silent burdens. “Even the richest people are the most in debt,” a financial advisor had said. It stuck with her. And it made Jake’s honesty even more refreshing.
Then came the stories that sealed the day.
There was her toddler son, who had recently hidden her phone. Once in his toy dump truck. Another time, in a similar kid-like fashion, the thermometer mysteriously vanished during a feverish week… only to be discovered weeks later under the toy chest. Jake reframed those moments not as frustrations, but as gifts — reminders that our children are here to teach us, not the other way around. That maybe our phones are just grown-up versions of our childhood stuffed animals.
Speaking of which, my co-worker shared a memory of her own — her childhood elephant named Stuffy. No frills, no fancy names. Just “Stuffy.” And in that moment, her phone got a new name too.
But perhaps the most hilarious story came near the end — the tragic fate of an Elf on the Shelf. In a well-intentioned stepmom moment, she bought an expensive elf to surprise her stepson, only to return home and find it decapitated, torn apart by the dogs in a full-blown tug-of-war. “The elf’s head was looking at me sideways,” she laughed. “They loved it.”
What began as a strategy call to map out landing pages, content cadence, and design tweaks evolved into something much richer: a reminder that stories are what connect people to brands — not just polished taglines or professional bios. And it reminded her that her job isn’t just about building websites. It’s about making sure that those websites feel like the people behind them.
By the end of the conversation, she walked away not just clearer on the branding direction, but with a deeper understanding of Jake’s mission: to lead with realness, empower through vulnerability, and remind people that coaching isn’t about performance. It’s about becoming who you already are — in full color. And yes, Stuffy still lives on… this time as a metaphor for all the little things we carry, lose, and rediscover.
From Pause to Practice: Put the Love Back in the Story
Some conversations don’t set out to fix anything. They exist to remind us who we are, what we carry, and how faith shows up in the ordinary. On September 12, I sat down with my friend and peer, Pamela, for one of those hours. We called it The Pam & Jake Show, but beneath the playful title was a serious check-in on where I’m at these days – naming depression honestly, reframing money with meaning, and discovering again that the truest identity isn’t “burden”, but “beloved”.
Where the Story Starts Today
This wasn’t a coaching ‘problem-solve’. It was a power check-in – two peers holding space for truth, faith, and the gentle third voice. The session opened with Jake’s morning message: “I put the love story back in life – through Him, with Him, forever and ever. Amen.” That line set the tone: presence over performance, intimacy over image.
Naming What’s Real (and letting it been seen)
Jake described recent weeks. Navigating a depressive dip, talking candidly with a doctor, and choosing to look directly at difficult thoughts so they lose their power. Pamela mirrored with her own experience: how naming the ‘exact nature’ of our harms with God and one trusted witness can turn the tide. The theme under the theme: vulnerability as intimacy, not an emergency.
Pam invited me to let the most authentic parts of me be known to those I care about most.
The Love Song (and the silence after)
Jake shared a long-held longing: to write and play a love song for Katie. After years of half-melodies, the song arrived quickly this summer. He finally played it for her at the campground – imperfect, honest, whole. Silence followed. No eye contact. And yet, he knew it had landed. Sometimes receiving is the harder courage.
Money, Meaning, and Responsibility
The conversation turned to money. Underneath the numbers, a deeper why emerged. At first: “I want money so people don’t worry about me.” Reframed with Pam’s help: “I need money because I am a responsible father, husband, and steward of what we’ve built.” Service first; money as support for responsibilities – not as proof of worth.
From ‘Burden’ to ‘Beloved’
Pam asked, “Are you a burden?” Jake answered. “No, I’m a gift.” If I’m not a burden, then what am I? Love. God working through me. This became the hinge of the hour – exchanging an old identity for a truer one.
Pam’s Parallel: Surrender and the Real Estate ‘Two-by-Four’.
Pam shared her own surrender story: letting go of a fantasy ‘magic million’ attached to a home development and choosing a path that creates real freedom – housing security in 10 years, energetic relief now. The spiritual two-by
Practices We’re Keeping
- Tell the truth early: name the exact thing (with God and one trusted person).
- Move toward intimacy: share the vulnerable piece at home, not just in public.
- Serve first: let money support responsibilities, not identity.
- Listen for the third voice: write it down. (it arrives fast).
- Share the melody with another person: imperfect performance counts as love.
Gratitude for the Shared Space
Two friends, one hour, and a handful of sentences that might change a life:
“I’m not a burden.”
“I’m a gift.”
“I’m love.”
The pause did the work; we simply made room for it.