Let’s start this off with a disclaimer. There are a lot of very wonderful people who mean the world to me in this story. Few of them are named, because the work is ultimately deeply personal. If you are one of those people and would like to be named, feel free to let me know!
Imagine knowing nothing of a career, not even dreaming it would exist, and then standing on its most sacred ground five years later. It’s awe-inspiring. Hana is the epicenter of life planning, brought into existence by George Kinder. With the goal of connecting the mental side of money with the meaning that we are looking for in our lives, life planning is an incredible way to work with clients. If you missed the previous blog post in this series, please go read or listen to Journey to Hana. That blog post lays the foundation for this one, focused on my three challenges in Hana, and my Journey Home which I will be releasing in the future.
Arriving in Hawaii was full of emotion. I was exhausted and annoyed because long flights and little sleep do that to a person. I was also overjoyed, because my wife rented me a convertible Camaro as a surprise. Finally, I was hopeful. I hoped that I would learn something that would allow me to serve my clients better and propel my business forward. I know that most conferences and retreats leave me filled with inspiration, and I didn’t expect this one to fall short.
The ride from Kahului to Hana is a true sight. I was used to winding mountain roads, having graduated from App State, but I was not used to seeing the ocean along winding mountain roads. Some of the overlooks gave a stunning view of waves crashing on rocks, waterfalls, and small communities down on the coast. All of it was incredible. I was beginning to understand why George spends a lot of his days in this part of the world.
Our little home-away-from-home was simple, but perfect. A suite-style apartment attached to the home of a lovely couple. We had this amazing view of the coast across a grassy field (pictured below) and I jokingly called it my office to a few clients I corresponded with the next morning. I could have worked from that porch for the whole week and the trip would have been worth it.

Before the workshop started we took one little adventure. Waioka Pond (pictured below) was less than a mile from our front door, so we decided to go on a hike.


It is a sight to behold! The pond is actually more a lagoon, an intersection of a stream, a spring, and the sea. The water level is pretty consistent and the pool is deep. We witnessed several travelers jumping off the high rock into the pool, laughing and having a great time. That’s when the first challenge of the trip set in for me. I wish I could do that. I’m afraid of heights.
Ten minutes went by. Rebecca and I took pictures of the pond. The same travellers went back to the top of the rock and jumped off half a dozen times. They were fine. I can do that. “H-hey…Becca…I think I’m going to do that.”
After deliberating for a moment, Rebecca promised to film me. I went to the top of the rocks, my heart pounding in my chest. I looked off the edge of the rock and took a deep breath. Why can’t I move? My legs were frozen in place. My chest was tight. Maybe I can’t do this.Then the simplest, easiest solution presented itself. The path was obvious. One of the travelers who had done it before walked up behind me, clearly impatient for his turn. “Can you count me off? I’m nervous.”
“Sure. Three…two…one…”
It was actually that simple. Much like life planning, overcoming a fear is all about having a partner to talk through your obstacles with. The stranger didn’t provide the solution, I did. But him being there was necessary. It made me have to do it.
And did it feel good! The water was refreshing and cool. My adrenaline surged and laughter spilled forth from me. Joy was abundant at that moment.
Rebecca joined me in the pool, though in a more gingerly fashion. She didn’t want to jump, and I don’t blame her. It was my goal, not hers.
That evening, after a shower, we found ourselves at the opening evening for the 5-Day. It was amazing for an entirely different reason, because now I was face-to-face with so many people I knew (or knew of.) People I loved, people I admired, people I hoped to know were filling that room. I knew I’d be paired with one of these people eventually to practice with. Someone in this room was MY life planner!
Making a room of people comfortable with that notion is hard work. But, the lead trainer set in on it with a smile. We worked through some surprisingly non-painful exercises in sharing. It was all about us too. The activities required us to open up about ourselves and receive praise, smiles, laughs, and consolation from our peers. All of which were working toward the greater goal of making it easier to select a life planner to work with, and the secret goal of making it easier to share in front of people this week.
So then the next morning came, and so did the selection of our partner. This was the one thing about the training I was dreading. We were instructed to “Just feel where in the room you were pulled to.” and go to that person. It brought back flashbacks of something traumatic from my childhood, being the worst athlete I knew. Great. It’s like being picked last for kickball. Anxiety and fear bubbled up, barely contained within my calm outer demeanor.
It’s a great reminder that in a room full of people, it’s entirely possible to feel alone.
Then I locked eyes with my partner, grinned, and sat back down immediately. Meg Bartelt, someone I admired greatly, had chosen me. A kindred spirit, someone who stayed glued to the exact spot they stood up in. I could not have been happier to have that awkwardness behind me. I happen to know very keenly that a number of my colleagues were feeling the same emotions, partly because of an aside I had with one of them where tears were shed. But, the torrent of emotion was behind us. Kinda.
The next three days were full of sessions exploring the Kinder methodology, known as EVOKE, and becoming deeply familiar with the emotions of our partner. What were the things that made up their ideal life? What were the emotions driving them to want or need those things? How could we bring those things into reality soon? Not five years from now.
Whereas the selection of our partners brought forth a torrent of emotion, I would call these three days a slow burn. Imagine always feeling strong emotion, so much so that your eyes are a little sore every day. It’s not that you’re denying yourself tears, it’s just that the tears don’t need to be shed. There’s a fair mix of positive and negative in life planning.
Someone needs to get a divorce, but their life will be better on the other side.
Another person needs to leave the career they’ve had for the last 30 years, the one that’s supported their family. But, their new work is more meaningful, and leaves more time for their spouse and children.
These things provide the full range of emotion. Joy, happiness, and excitement, but never without anxiety, longing, and change.
As one trainer said about life planning “Emotion is energy.” This is true whether it’s positive or negative. Emotion provides motivation for us. Life planning is mostly concentrated on the aspirational emotions, but it does not ignore the negative. It breathes, sits with that emotion, then smiles and asks “How would you like it to be instead?” Life planning is about the present and the future.
My second challenge for the week presented itself in the form of my partner. Throughout the three days, some aspects of Meg’s personality stood out in particular – hard-edged skepticism, discomfort, unease in this space. What I would later learn is that this was a transformation my partner was going through, compared to me she was new to the world of life planning and had not fully embraced the potential results. I can imagine that being told what you’ve been doing for years is only a part of the bigger picture is jarring, and that’s what I imagine she was feeling.
Yet the amazing thing about life planning still stood true, as we removed the focus from the workshop and focused on her and our conversations, some wonderful emotions blossomed forth. Meg had a deep caring for her family and getting to see them more often. There was a reading chair, a sanctuary in which she could relax and be herself. Lastly, there was a longing for an adventure with her children, something very particular and beautiful. All of that was unpacked through our work, which showed me the whole person as opposed to the image we so carefully cultivate and show to the wider world.
All of that was stunning and wondrous, but also nerve-wracking in a way. It’s incredible to work with someone on their ideal life (not perfect, nothing is perfect and life changes always), but it’s also challenging to be there with someone emotionally as they discover what really matters to them. You have to practice it, both staying calm yourself and mirroring the other person so that they know you’re listening. That’s how you become a truly great life planner. So while I got over the speed bump on that challenge, there’s still a long way for me to go.
It would be dishonest for me to end this post here, despite the fact that my written posts are in danger of becoming small books. I’ve already pointed the lense at my partner, but now let’s talk about myself. Pointing the lense at myself was my third challenge. Being life planned was an emotional journey.
What I realized, both in private conversation with my amazing partner, and in the demo session we did in front of the whole workshop full of people, was that my old enemy had returned to me in a way. I often hold myself back from success with self-limiting belief. I’m too young. I need a bigger practice. I need more time. I can’t do this.
These mantras are insidious. They don’t show up visibly in my life often, but they’re just under the surface, directing me toward self-doubt at inopportune moments. They slow down my growth, both as a person and in business.
It was obvious to me, tears welling up in front of all of my peers, that I don’t have to let this happen. The pathway forward was clear. It all crystallized in the moment she asked me “How can you make sure this happens?” My partner and I worked together to set deadlines, a pathway toward the life and business that I want for myself and my wife. I smiled, and breathed out, with no more tears sitting just behind my eyes.
Having those deadlines has already done incredible things for me.
Since Hana, just under a month ago, I’ve:
-Published My Life Planning Story (My highest performing piece of content ever)
-Gotten A Spot at a 100+ Person Conference to Speak (About life planning and my journey)
-Signed Contracts with Two Wonderful Clients
-Rebuilt All of My Firm’s Processes (To focus on life planning and serving clients better)
-Hired and Begun Training an Associate Planner
-Scheduled My Wife’s Dream Trip (With the family, to Belize!)
-Rebuilt My Calendar (To focus on giving me time back with my wife)
I’ve also done plenty of other things that aren’t mentioned here, but that have renewed my vigor for my business and life.
Where I would like to end this post is on a high note. The journey is emotional, certainly, and the work is challenging. But, the reward is great. Life planning is incredible. We should all do more of it and help ourselves and our clients live into their dreams. The world will be better for it.