
When Success Stops Serving Your Life
Our lives often revolve around focusing on a number.
Top-line revenue in practice. Percentage of EBITDA. X millions to retire.
If it is purely a financial metric, focusing on a number is hollow. Is that what will do it for you, really? Life doesn’t happen inside a financial vacuum. The problem with pursuing these metrics is that the goalposts always move.
What price will you pay for a full-bore focus on a number? More importantly, who else is and will pay that price?
This is the problem with “empire building.” To what end? It is a shallow goal and will leave many with regrets.
Retirement Planning, Or Enjoyment Planning?
Is it really “retirement planning” that you believe you are doing? Or should you instead be doing “enjoyment planning” so you can fully live today and not always be future-focused toward some mystical “someday” when you have finally “made it”?
What exactly does that destination look like?
Where does the scarcity mindset come from? Prior experiences? Failures? Expectations let down? The chase for security? Fear of the threat of all of this ending?
How much is enough? How will you know?
The problem is that you don’t. Neither does your financial advisor, CPA, tax attorney, or best friend. Most of us have never tried to have this conversation with those close to us—our spouse, partner, or family members.
We have relinquished so much control and definition of our lives to others and society at large.
Identifying our non-negotiables, defining “enough” and understanding how to utilize assets to provide cash-flow income, changes everything.
The Price of Focusing on an Accumulation Number
The real questions one must answer along the journey are, “Do I have enough?” “Am I enough?” and “How will I know?”
Without answers, the hamster wheel turns without an exit in sight.
And how resilient is that number?
Life was going great, and then in one day everything turned upside down for me: Jenna’s health crisis, subsequent divorce, a practice-sale failure, and a partnership in a legal morass.
Not exactly what I had signed up for.
I felt deep down in a hole. How did I get here—and so quickly? What really matters?
Entrepreneurship is not for everyone. Most are not cut out for the:
- Stress
- Long hours
- Sacrifices
- Financial risk
Starting a business is not a magic bullet. Thousands of “entrepreneurs” own very costly jobs. The journey begins with a desire to create outcomes that owning a business would afford: freedom, control, direction, momentum, and agency.
But starting a business does not guarantee any of them.
Inflection Points: You Are Closer Than You Think
I often find myself saying, “You are closer than you think.”
Those who have achieved a level of success often have the resources and ability to create the life they want. The challenge is that what got you here—your thinking and mindset—will not necessarily get you where you want to go.
Many successful owners are still living as though they are trying to become successful. They have accumulated resources, skills, relationships, and options—but their life still operates according to rules they created twenty years ago.
Those of us who survived the rigors of dental school and private practice are willing to embrace hard work. It becomes a way of life.
“I don’t know what I would do or who I would be without my work.”
Identity. Purpose. Respect.
We see a sort of virtue in grinding. We claim to do it for our family—but are we really serving our families? How are we measuring quality of life?
Working for work’s sake is a hollow victory.
You reached where you are today by embracing new ways of thinking and new ideas. When did that stop?
What if the primary obstacle between your present circumstances and the desires for tomorrow is an elevation in thinking? What beliefs/understandings of the world are holding you back? Are you willing to face that reality?
Traditional thinking:
- Postponing “life” until a distant someday
- Accumulation-based planning (the goalposts move)
- Tying identity to “what I do”
- Trying to create a bubble of control
- Lifestyle acceleration too fast, too soon
What mindset shifts would elevate your game? Could you be closer than you think?
How To Do What You Love
The problem with financial goals is that the goalposts continue to move.
True fulfillment begins when we face the reality that the mountain many of us chose to climb was chosen by society more than by us. Then we can discover our mountain—the one we were meant to climb.
Can you enjoy the process, the people, and the impact you can produce? Or are you grinding toward some false god that has promised the richness of a full life once you get “there”?
Have you found something you would do for free?
The essence of my Freedom philosophy is this:
“The most efficient route to achieving financial freedom is to advance one’s lifestyle solely through the acquisition or creation of cash-flow-producing assets, rather than relying on increasing active income to elevate one’s standard of living.”
There is a huge difference between owning and operating a business and investing your money with two or three degrees of separation.
The difference is measured in freedom of time.
Reaching the Freedom Number opens the door to the other four freedoms: time freedom, relationship freedom, health freedom, and the freedom to pursue our real purpose in life.
These four freedoms are what we really want. Financial freedom provides the permission to explore them fully without fear.
So what is the goal of financial freedom?
To explore one’s unique gifts and creativity—and to be able to do that as early in life as possible.
Materialism versus freedom. Wealth versus fulfillment. Status versus joy.
It is a choice.
The key is to focus on what really matters.
Simply stated, freedom is being able to do the work you enjoy, without constraint, and to do that work with whom, where, when, and how you want to do it.
That is not really “work” in my book.
Your life’s story is yours to write.
Make it a story you would love to tell.



