I’m currently tucked away amongst the aspen trees in the beautiful mountains of Telluride. I’ve been here the past week alongside some incredible leaders discussing legacy, the meaning of life, and how this inspires the actions of our present day.

The group is an eclectic mix of individuals ranging from those who are just getting started in their careers to those who have already retired. The majority are much wiser in age and find themselves in transition periods for what comes next.

Despite the age gap, there’s a lot I can relate with. For the first time in my life I’ve created margin — with career, finances, and free time. I think this is what many would describe as the entrepreneurial dream, this so-called freedom to be the “master of my fate: the captain of my soul.”

And yet as I sit here writing this in the middle of the woods, overlooking the quaint town of Telluride, I can’t help but wonder if this is it. 

Freedom becomes lackluster when it becomes the end goal. You realize life is best lived with certain levels of constraints, limitations, and there’s a shock factor in realizing being free of responsibility really isn’t all that freeing.

I don’t know. Emotions are hard for me and I’m more confused than I am certain of anything. I can’t help but think of peers my age, who are just getting settled into their careers and are beginning to lay roots through marriage, kids, buying first homes. And if I’m being honest, I find myself, again, alone in a season where I’m seeking guidance in what my pursuits need to be. The ever-present pressure to do more still remains engrained in my DNA.


A lot of this week has been discussing and processing two books: The Sun Also Rises by Ernest Hemingway and Living Life Backwards by David Gibson. The theme has revolved around the book of Ecclesiastes — both everything is meaningless and how does death reveal how we should live.

What I have found to be the most comforting aspect of this group is their transparency and openness in sharing their struggles. There has been solace in realizing even the retired folks are still asking the same questions: what’s next, how can I be more obedient, generous, and servant-hearted?

I’m still processing specifics and it will require additional prayer and contemplation, but I want to begin with this group and why, even though we’ve only known each other for a short few days, there’s been significant progress in finding the solution to these questions.

What Makes This Group Special

Generosity begets generosity –

I have never met a group more kind and generous in their finances, insights, and willingness to give to one another. If anything, the biggest struggle for many in this group is learning how to receive. It takes humility for certain individuals, myself included, to be on the receiving end. But the gift of grace can only be given when it has first and foremost been received and so it’s been both humbling and delightful to be present with heads bowed and hands open.

Transparency expedites trust – 

Relationships take time. The best relationships take a long time. And yet it hasn’t even been a week and I look to these people as peers, mentors, and brothers and sisters who have shared their pains and struggles with me. It’s a responsibility I don’t take lightly and because of it, a mutual level of trust has been established in a very short period of time. You have my back and I have yours. I’m still learning how I can get better at opening up, but this group has challenged me to continue striving for a more transparent and authentic lifestyle; I have a long ways to go.

Laughter is the best medicine –

Only those secure enough in their identities are strong enough to laugh at themselves – and each other. My time here has been full of friendly prodding, trash talk and testing the bounds of how much each of us can take. From corn hole to boardgames to hiking, the jest in this group runs strong and I may have to visit the doctor to get my jaw realigned from all the laughter. Regardless of age, one is never too old to add a fresh wrinkle formed by humor. I may only hope I may be full of them one day.

The Encouragement of Death –

There are many who came into this trip in a state of grieving: death of a loved one or arriving at the end of a previous season. Yet each of us has been challenged to keep death at the forefront of our minds. Every man dies. Not every man really lives. With that understanding has been learning to better celebrate the gift of today. Each breath feels fresher, each conversation ruminates deeper, and each laugh resonates longer. Death can be a celebration if the life lived matched its full potential.

Coming back

I go home tomorrow. Part of me will miss this place and these people, but I’m ready. The scenery’s been beautiful, the weather perfect, but this isn’t my permanent reality. My reality is with my people – the entrepreneurs, the marginalized, my parents, my little brother, my coworkers, the one’s I’m called to love and serve and learn from. 

God’s given me presence of mind to remember He’s given me all of these things to steward. So may I be humble enough to accept the gifts and bold enough to give them away. May my ego die at the altar of self-worth and may what remain be what transcends this life and into the next.

While I live, may my life be exemplary, and when I die may my end be peace.