Have you asked yourself the tombstone question? The yellow brick road is a path to so much more than just work success. Is the one you’re following leading you to fulfilment in every aspect of your life?

What do I want my path to look like when it’s all over, and why?

This is the question that’s been at the forefront of my thoughts and reflection recently.

Here are the answers I’ve been seeking:

  • What will the lines on my tombstone read?
  • What will people say at my funeral?
  • What will be the most important achievements of my life when I’m tucked away under the soil?
  • What legacy will I leave that can transcend my time on earth?

Thoughtful answers to these questions aren’t something you write off-the-cuff. This is a heavy ask, and it’s nearly impossible to get right without putting in a ton of emotional and cognitive effort.

I’ve pondered this extensively, and know these answers aren’t set in stone. This will be a living document I hold in my mind every day for the rest of my life.


For the person I am today, these are the lines I’d want carved on my tombstone:

“Bryan crafted a pathway for himself to belong in this world. He dedicated his life to helping others do the same.” 

I want this to be my legacy. I hope the people at my funeral echo this same sentiment.

How did I come to this conclusion, you might ask?

How do you do it for yourself?

I know the prospect is daunting, so the easiest way I found was to define my pathways that lead to belonging.

For me, this all goes back to one of the most important lessons I’ve ever learned. It’s probably not somewhere you’d expect:

Middle school basketball.


When I was in middle school, I felt like my whole life depended on making the freshman basketball team when I started high school. At the time, basketball was an outlet for me that extended far beyond the sport itself.

Basketball was a place where I could find progression in and build great friendships. It was a community I wanted to belong to, and a place where I could feel like I belonged.

I trained every day to improve my game, practicing as much as I could independently, and testing those skills in scrimmages. Being on the basketball team felt like the best path to pursue in high school.

There was just one problem. When I brought my hours of hard work to the court, where it counted the most, my progress seemed to vanish. As I endlessly replayed every misstep, mistouch, and every other mistake you can think of, my confidence evaporated.

I could envision myself making the team so vividly, but I had neither the structure nor patience to get me there.

Why did I stop “being Bryan” the moment I stepped on the court?

Why did I lose myself the second a game started?

Why couldn’t I ever  perform to the best of my ability during games?

What was I so afraid of?

Before I could block shots, I had to find what was blocking me.

My mother saw the depths of my pain, and decided it was time we found a sports performance coach. Dr. Neal Bowes described what lay at the core of all my problems on the court. I vividly remember him saying,

“Bryan, your confidence is like the water in an open water bottle. When you play a bad game, all the water flies out, and it’s depleted.”

Imagine this image for your goals in life and the set of paths you’re pursuing that will make you finally feel like you belong. You make great progress, set a direction, and then suddenly have a misstep. You lose all of your confidence in one fell swoop. Your momentum is crushed under the force of pressure. All this effort and achievement seem to crumble, and you find yourself having to turn around and start from empty.

Constant depletion can never build consistent, sustainable high performance. After our first meeting, Neal thought he could help me. I immediately trusted that he could, too.

Dr. Neal went on to share how Olympic athletes perform at a high level so consistently by building their foundation on a variety of water bottles (as their tombstone might say, Olympic Gold Medalist).

Each water bottle represents a different foundation with goals, systems, measurements, and skill-sets required.

Each foundation represented a different aspect of both the game and also my life at the time.

Here are mine, for context:

  • Physical: Conditioning, Speed & Agility, Nutrition, Weight Lifting, Recovery, etc.
  • Technical: Ball Handling, Shooting, Defensive Angles, etc.
  • Recovery: What did I do for fun, time away from the game?
  • Mental Preparation: What was I going to tell myself before or during the game? How would situations trigger specific responses so I could mentally “rebound” if I made a mistake?
  • Physically, I worked to get my mile time under 6 minutes.
  • Nutritionally, I cut all soda and fatty foods from my diet, started lifting weights 4-5x per week, and took downtime for my body to recover and heal.
  • Technically, I worked on my right hand, put up 500-1000 jump shots per week. I focused on my defensive speed because I had slow lateral movement.
  • Socially, I built in time in my schedule to recover, rest, and recharge, so I could come back stronger.

In combination, these foundations, daily habits, and systems helped me achieve peak performance consistently, game-in and game-out. Even though some games are never going to be as good as others, I finally understood the process that went into a good one.

Reviewing my performance taught me how to tweak the systems in each foundation. For continuous improvement, I steadily build upon them all, one by one.

All these water bottles contain the processes, tools, and tactics I need to fully succeed, find belonging, and stand out on my own terms. These lessons empower me to live the life I want, and I learned them all  through a high school sport.


What does a meaningful life look like to you? It all starts with forethought, intentionality, and reflection on where you have been.

  • Figuring this out meant asking myself some fundamental questions:
    What are the water bottles that make up my path centered around belonging and helping others belong?
  • How am I filling them?
  • What would my life look like if I were to work backward?
  • Am I creating a process to think far in advance without feeling overwhelmed?
  • Do I have the right people in my corner to help me get “there,” whatever “there” might be?

The “Tombstone answer” is built on the foundation of crafting a pathway to belonging. How will you fill the right “water bottles,” and what systems and processes will that require?

The water bottles I’ve defined that make up BELONGING for me include the following:

  • A father and husband with a family who could always be relied upon
  • A leader and executor of ideas that transcended my inner orbit to reach the people around me
  • A person who realized strong and sustainable health made his goals attainable
  • A good friend to those he cared about and who cared about him

Remember, these tombstone lines might be different for you. If that is the case, you’ll need different tactics and strategies to carve a path to get there.

The most important step is defining your tombstone [aka your purpose] as early as you can. Knowing where you want to end up, and how you want to be remembered, will help you create a life with more meaning and intentionality.

Choosing the Correct Water Bottles for You

After asking myself the hard questions, the answers gave me clues I could use to start working backward (thanks to Dr. Neal).

Ask yourself:

  • Why are these bottles important foundations to build around?
  • How they can help me Belong in the world on my own terms as I navigate my path forward

1. A Father and Husband My Family Can always Rely On

Why I Care: To me, a successful life stems beyond work. Work helps lay the foundation to set up a successful personal life and is why I’ve put more of a focus on it earlier in life.

How I’ll Become This PersonPersonally,  I’ve always felt like if I could put in the right habits first with work, and get aligned professionally, it would be easier to build a family on top of that than going in the reverse order. This strategy and sequence will enable me to be a better guide for my future children as I help them chart their own path forward.

2. A Leader & Executor of Ideas that Transcend My Inner Orbit to Reach People and Resonate

Why I Care: I come alive and feel like I belong in the world when I am pursuing the ideas that matter most to me within my career.

How I’ll Become This Person: To continue feeling this way, I need to keep building paths that push my ideas forward while helping others do the same.

3. A Person Who Realizes Strong and Sustainable Health Make His Goals Attainable

Why I Care: I realize I can’t walk down the paths for myself that make me feel like I belong without sustainable health.

How I’ll Become This Person: Eating, nutrition, exercise, sleep are the bedrock for achieving the other goals of my life.

4. A Person Who Learns About the World by Furthering His Education and Interests

Why I Care: In my 27 years on earth, I’ve learned that being well rounded is paramount. It’s easy to get more stuck/focused on one water bottle.

How I’ll Become This Person: Learning new things about the world around me will help me become more dynamic and relatable in conversations.

Here are just a few ways I plan to do so:

  • Traveling
  • Reading books on diverse topics
  • Trying new hobbies and skills like improv
  • Getting out of my comfort zone

With aspirations I have, walking into a lot of different environments, being able to talk about things outside of work will be fundamental.

5: A Person Who Has Strong Financial Systems

Why I Care: Without the means to support my vision, the way I belong in the world won’t align.

How I’ll Become This Person: To support my family, business dreams, health, and learning experiences, it will be incredibly important to set myself up financially to have the means to support these endeavors.

No one’s path forward in life is one dimensional. I never focus on just one water bottle at a time. I define all the bottles early that allow me to belong on my path, then pick a focus within one. At any given time, I prioritize some of the bottles over the others and tweak my focus along the way by using the right systems and processes.

What Does This Look Like in Action?

Let me manifest 1 of these “Belonging Bottles” for a second…

Health: I want to be remembered as a person who realized strong and sustainable health made his goals attainable. This has more practical guidance and value than you might think, and it sounds a lot like relationship advice.

Why this is important to me: At the foundation of everything we do, our health is what takes us forward. After going through two injuries being in pain for a year at a time, I’m the first to tell you, life is no fun when you’re in pain. It takes the joy away from positive experiences, it creates angst, worry, and more. To live life and be strong and healthy supports the mind beyond measure.

Structurally, I consider:

  • What does a strong health system look like?
  • Nutrition
  • How many times a week do I work out?
  • What muscle groups and why?
  • What kind of “fit” is important to me as I head into my 30s, 40s, 50s?
  • What is sustainable health?

Skillsets Required:

  • Knowledge of how the body works at a fundamental level
  • How to combine different exercises to produce results
  • Nutritional Education
  • Understanding which types of exercises, like yoga and meditation, impact the mind and breathing

From there, I reflect on my life and begin thinking about some of these questions within this bucket more deeply.

  1. If I can sustain active health to prevent serious injuries or setbacks like a heart attack from work stress? What will this allow me to do that I otherwise couldn’t?
  2. How will I establish strong health systems that will support me when I’m older, and give me longer to live with the most important and closest people in my life?
  3. Which parts of my life do I need to think about as I age, what does healthy aging look like, and why?
  4. When in my life should I make changes to my health, eating habits, and exercise habits to avoid pain and strengthen my body?
  5. To achieve success, what do I need to be doing now that I’m not already? What will I need to do over the next 3-5 years?
  6. What people are doing all of these things right now that I can emulate, speak too, and gain insight and perspective from so I don’t make (as many) mistakes?

There’s no perfect way to do this, but here are the most important steps:

  • Defining the vision for where you want to go
  • Selecting the structures/containers/buckets you want to operate within
  • Developing the skills you will need to succeed
  • Building a measurable gameplan around your goal
  • Deciding how you will track your progress

Why Does all of This Matter?

Ultimately, when you get really clear on the tombstone question, I’ve found it becomes easier to understand the path you want to take in life and why you’re on it. Prioritizing the areas I deemed worthwhile will help me belong in the world.

When it’s all said and done, I hope people at my funeral will echo the same verse that’s inscribed across my tombstone.